Systems and compounds for imaging of bacteria

Abstract

Systems and compounds for imaging of bacteria can comprise a conjugate of maltodextrin and a near-infrared heptamethine dye. The conjugate of maltodextrin and a near-infrared heptamethine dye can further comprise a linker. The conjugate of maltodextrin and a near-infrared heptamethine dye can be utilized to detect and monitor a bacterial infection in vivo.

Description

SYSTEMS AND COMPOUNDS FOR IMAGING OF BACTERIACROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application claims benefit to U. S. Provisional Appl. No. 63 / 646,302, entitled “Systems and Compounds for Imaging of Bacteria”, filed May 13, 2024, the disclosure of which is hereby incorporated by reference in its entirety.TECHNICAL FIELD

[0002] The disclosure is generally directed to systems and compounds for imaging of bacteria, including systems that comprise a maltodextrin and a heptamethine dye.BACKGROUND

[0003] The number of bacterial infections is increasing worldwide and are the second largest cause of death globally. Bacterial infections are a great health burden and with increasing use of antibiotics, becoming more difficult to treat due to resistance. Additionally, the higher life expectancy of humans leads to more necessary medical procedures including implants, which can often be a source of infection. It is therefore ideal to identify, localize, and assess bacterial infections in order to optimally diagnose and treat an infection. Unfortunately, identification, localization, and assessment of bacterial infection is difficult due to the scarcity of effective imaging probes for bacteria. There is a critical need for better bacterial imaging probes to improve diagnostic capabilities.SUMMARY

[0004] Several embodiments of the disclosure are directed towards systems and compounds for imaging of bacteria. In some embodiments, a probe system comprises a maltodextrin sugar in connection a heptamethine dye, and optionally a linker for providing the connection between the maltodextrin sugar and the heptamethine dye. In some embodiments, the heptamethine dye of the probe system is a near infrared emitting fluorescent dye. In some embodiments, the maltodextrin sugar of the probe system is maltotriose. In some embodiments, the probe system comprises an amide linker or adibenzocyclooctin (DBCO) linker for providing the connection between the maltodextrin sugar and the heptamethine dye. In some embodiments, the probe system is water soluble and capable of being utilized in vivo.

[0005] Many embodiments of the disclosure are directed to the use of a probe system for detection of bacteria, in some embodiments, the probe system comprises a maltodextrin sugar such that the probe is capable of interacting with and detecting gram¬ positive and gram-negative bacteria. In some embodiments, the probe system is administered to a recipient via intravenous administration, intratissue injection, intracerebroventricular injection, intrathecal administration, oral ingestion, intranasal administration, ocular administration, otic administration, topically applied, pulmonary administration, vaginal administration, rectal administration, intraurethral administration, intralymphatic administration, or another means to reach a potential site of bacterial infection. In some embodiments, upon administration of the probe system, the heptamethine dye is visible when concentrated at a bacterial infection via fluorescence imaging or photoacoustic imaging. In some embodiments, the heptamethine dye is visible within an hour (or less) upon administration. In some embodiments, the probe system is utilized to monitor bacterial colony growth, bacterial spread, and / or treatment response.BRIEF DESCRIPTION OF THE DRAWINGS

[0006] The description and claims will be more fully understood with reference to the following figures and data graphs, which are presented as exemplary embodiments and should not be construed as a complete recitation of the scope of the disclosure.

[0007] Figure 1A provides a structural formula of maltodextrin.

[0008] Figure 1B provides a structural formula of maltotriose.

[0009] Figure 2A provides a structural formula of a near-infrared fluorescent heptamethine dye.

[0010] Figure 2B provides a structural formula of a sNIR dye with a carboxylic acid linker.

[0011] Figure 2C provides a structural formula of a sNIR dye with a NHS linker.

[0012] Figure 2D provides a structural formula of a sNIR dye with a DBCO linker.

[0013] Figure 2E provides a structural formula of a sNIR dye with an alkyne linker.

[0014] Figure 3A provides a structural formula of a conjugate of maltodextrin with a near-infrared fluorescent heptamethine dye.

[0015] Figure 3B provides a structural formula of a maltotriose-amide-sNIR conjugate.

[0016] Figure 3C provides a structural formula of a maltotriose-DBCO-sNIR conjugate.

[0017] Figure 3D provides a structural formula of a maltotriose-triazol-C3-sNIR conjugate.

[0018] Figure 3E provides a structural formula of a maltotriose-triazol-C5-sNIR conjugate.

[0019] Figure 3F provides a structural formula of a maltotriose-triazol-C6-sNIR conjugate.

[0020] Figure 3G provides a structural formula of a maltohexose-triazol-C3-sNIR conjugate.

[0021] Figure 4A provides an image of mice infected with E. coli in the left thigh.

[0022] Figure 4B provides time-course imaging of a mouse infected with E. coli in the left thigh and systemically administered maltotriose-DBCO-sNIR.

[0023] Figure 4C provides time-course imaging of a mouse infected with E. coli in the left thigh and systemically administered maltotriose-amide-sNIR.

[0024] Figure 4D provides ventral images of a mouse infected with E. coli in the left thigh and systemically administered maltotriose-DBCO-sNIR.

[0025] Figure 5A provides bright-field and fluorescent images of uninfected rabbit corneas topically administered with malto-sNIR.

[0026] Figure 5B provides bright-field and fluorescent images of bacterially infected rabbit corneas topically administered with malto-sNIR.

[0027] Figures 6A provides a schematic for synthesizing a maltotriose compound with linker.

[0028] Figure 6B provides a schematic for synthesizing a maltohexose-triazol-C3- sNIR probe.

[0029] Figure 7A provides optical data of sNIR in phosphate buffered solution (PBS) and serum.

[0030] Figure 7B provides emission data of sNIR in the short-wavelength infrared (SWIR) spectrum.

[0031] Figure 8A provides liquid chromatography data and mass spectral data of the maltotriose-amide-sNIR conjugate.

[0032] Figure 8B provides liquid chromatography data and mass spectral data of the maltotriose-DBCO-sNIR conjugate.

[0033] Figure 8C provides liquid chromatography data and mass spectral data of the maltotriose-triazol-C3-sNIR conjugate conjugate.

[0034] Figure 8D provides liquid chromatography data and mass spectral data of the maltotriose-triazol-C5-sNIR conjugate.

[0035] Figure 8E provides liquid chromatography data and mass spectral data of the maltotriose-triazol-C6-sNIR conjugate.

[0036] Figure 8F provides liquid chromatography data and mass spectral data of the maltohexose-triazol-C3-sNIR conjugate.DETAILED DESCRIPTION

[0037] The various embodiments of the disclosure are directed to probe systems utilizing a near-infrared dye for imaging and detection of biological entities. In many embodiments, a probe system is utilized to image and detect bacteria, including detecting pathogenic or microbiomic bacteria (or other microbes). In several embodiments, a probe system comprises a carbohydrate moiety connected with a near-infrared (NIR) heptamethine dye. In some embodiments, the carbohydrate moiety is a maltodextrin. In many embodiments, the probe system comprises a linker for connection the maltodextrin to the NIR dye. In some particular embodiments, the probe system comprises sNIR, a heptamethine dye found to have great properties including increased photostability, allowing for extended excitation and monitoring. By conjugating maltotriose with sNIR, it has been found that the probe is capable of being systemically administered within a subject to detect a bacterial infection within an hour. It has further been found that the maltotriose-sNIR conjugate clears from the host body fairly quickly and does not significantly accumulate within the liver.

[0038] The maltodextrin-dye conjugates of the disclosure provide enhanced properties that allow for greatly improved identification, localization, and assessment of bacterial infections, yielding surprising diagnostic capabilities never before achieved. In severalembodiments, systemic and / or localized administration of the maltodextrin-dye conjugate within a subject can provide rapid detection of a bacterial infection within an hour, utilizing fluorescent imaging and / or photoacoustic imaging. In many embodiments, the signal provided by the maltodextrin-dye conjugate precisely targets to the bacteria, allowing for very accurate localization of the infection such that targeted medical procedures (e.g., surgery) can be performed. In several embodiments, the signal provided by the maltodextrin-dye conjugate allows for quantitative assessment of a bacterial infection such that the growth and / or decline of a bacterial colony can be monitored. Further, in many embodiments, the advancement and spread of a bacterial infection within a host is monitored via the maltodextrin-dye conjugate. And in several embodiments, a patient is administered a treatment for bacterial infection and the treatment effect on the bacteria is monitored.Terms of Art

[0039] The term "alkyl" refers in context of the present invention to a monoradical of a saturated unbranched or branched hydrocarbon. Preferably, the alkyl group comprises from 1 to 10 carbon atoms, i.e., 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, carbon atoms, more preferably 1 to 8 carbon atoms, such as 1 to 6 or 1 to 4 carbon atoms. Exemplary alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, iso-butyl, tert-butyl, n-pentyl, iso¬ pentyl, sec-pentyl, neo-pentyl, 1,2-dimethylpropyl, iso-amyl, n-hexyl, iso-hexyl, sec-hexyl, n-heptyl, iso-heptyl, n-octyl, 2-ethyl-hexyl, n-nonyl, n-decyl, and the like.

[0040] The term "cycloalkyl" or "cycloaliphatic" represents cyclic non-aromatic versions of "alkyl" and "alkenyl" with preferably 3 to 14 carbon atoms, such as 3 to 10 carbon atoms, i.e., 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms, more preferably 3 to 6 carbon atoms, even more preferably 6 carbon atoms. Exemplary cycloalkyl groups include cyclopropyl, cyclopropenyl, cyclobutyl, cyclobutenyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, cycloheptenyl, cyclooctyl, cyclooctenyl, cyclononyl, cyclononenyl, cyclodecyl, and adamantyl. The term "cycloalkyl" is also meant to include bicyclic and tricyclic versions thereof. If bicyclic rings are formed it is preferred that the respective rings are connected to each other at two adjacent carbon atoms, however, alternatively the two rings are connected via the same carbon atom, i.e., they form a spiroring system or they form "bridged” ring systems. Preferred examples of cycloalkyl include C3-C8-cycloalkyl, in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, spiro[3,3]heptyl, spiro[3,4]octyl, spiro[4,3]octyl, bicyclo[4.1.0]heptyl, bicyclo[3.2.0]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[5.1.0]octyl, and bicycle[ 4.2. O]octyl.

[0041] The term "cycloalkylene" means a cycloalkyl group as defined above in which one hydrogen atom has been removed resulting in a diradical. The cycloalkylene may link two atoms or moieties via the same carbon atom (1, 1 -cycloalkylene, i.e., a geminal diradical) or via two carbon atoms (1,2-cycloalkylene).

[0042] The term "heterocyclyl" means a cycloalkyl group as defined above in which from 1, 2, 3, or 4 carbon atoms in the cycloalkyl group are replaced by heteroatoms of 0, S, or N. Preferably, in each ring of the heterocyclyl group the maximum number of O atoms is 1, the maximum number of S atoms is 1. and the maximum total number of O and S atoms is 2. The term "heterocyclyl" is also meant to encompass partially or completely hydrogenated forms (such as dihydro, tetrahydro or perhydro forms) of the above-mentioned heteroaryl groups. Exemplary heterocyclyl groups include morpholino, isochromanyl, chromanyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, indolinyl, isoindolinyl, di- and tetrahydrofuranyl, di- and tetrahydrothienyl, di- and tetrahydrooxazolyl, di- and tetrahydroisoxazolyl, di- and tetrahydrooxadiazolyl (1,2,5- and 1,2,3-), dihydropyrrolyl, dihydroimidazolyl, dihydropyrazolyl, di- and tetrahydrotriazolyl (1,2,3- and 1,2,4-), di- and tetrahydrothiazolyl, di- and tetrahydrothiazolyl, di- and tetrahydrothiadiazolyl (1,2,3- and 1,2,5-), di- and tetrahydropyridyl, di- and tetrahydropyrimidinyl, di- and tetrahydropyrazinyl, di- and tetrahydrotriazinyl (1,2,3-, 1,2,4-, and 1,3,5-), di- and tetrahydrobenzofuranyl (1- and 2-), di- and tetrahydroindolyl, di- and tetrahydroisoindolyl, di- and tetrahydrobenzothienyl (1-and 2), di- and tetrahydro-1 H-indazolyl, di- and tetrahydrobenzimidazolyl, di- and tetrahydrobenzoxazolyl, di- and tetrahydroindoxazinyl, di- and tetrahydrobenzisoxazolyl, di- and tetrahydrobenzothiazolyl, di- and tetrahydrobenzisothiazolyl, di- and tetrahydrobenzotriazolyl, di- and tetrahydroquinolinyl, di- and tetrahydroisoquinolinyl, di-and tetrahydrobenzodiazinyl, di- and tetrahydroquinoxalinyl, di- and tetrahydroquinazolinyl, di- and tetrahydrobenzotriazinyl (1,2,3- and 1,2,4-), di- andtetrahydropyridazinyl, di- and tetrahydrophenoxazinyl, di- and tetrahydrothiazolopyridinyl (such as 4,5,6-7-tetrahydro[1,3]thiazolo[5,4-c]pyridinyl or 4, 5,6-7-tetrahydro[1,3]thiazolo[4,5-c]pyridinyl, e.g., 4,5,6-7-tetrahydro[1,3]thiazolo[5,4-c]pyridin- 2-yl or 4,5,6-7~tetrahydro[1,3]thiazolo[4,5-c]pyridin-2-yl), di- and tetrahydropyrrolothiazolyl (such as 5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazolyl), di- and tetrahydrophenothiazinyl, di- and tetrahydroisobenzofuranyl, di- and tetrahydrochromenyl, di- and tetrahydroxanthenyl, di- and tetrahydrophenoxathiinyl, di-and tetrahydropyrrolizinyl, di- and tetrahydroindolizinyl, di- and tetrahydroindazolyl, di- and tetrahydropurinyl, di- and tetrahydroquinolizinyl, di- and tetrahydrophthalazinyl, di- and tetrahydronaphthyridinyl (1,5-, 1,6-, 1,7-, 1,8-, and 2,6-), di- and tetrahydrocinnolinyl, di- and tetrahydropteridinyl, di- and tetrahydrocarbazolyl, di- and tetrahydrophenanthridinyl, di- and tetrahydroacridinyl, di- and tetrahydroperimidinyl, di- and tetrahydrophenanthrolinyl (1,7-, 1,8-, 1,10- 3,8-, and 4,7-), di- and tetrahydrophenazinyl, di- and tetrahydrooxazolopyridinyl, di- and tetrahydroisoxazolopyridinyl, di- and tetrahydropyrrolooxazolyl, and di- and tetrahydropyrrolopyrrolyl. Exemplary 5- or 6-membered heterocyclyl groups include morpholino, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, di- and tetrahydrofuranyl, di- and tetrahydrothienyl, di- and tetrahydrooxazolyl, di- and tetrahydroisoxazolyl, di- and tetrahydrooxadiazolyl (1,2,5- and 1,2,3-), dihydropyrrolyl, dihydroimidazolyl, dihydropyrazolyl, di- and tetrahydrotriazolyl (1,2,3- and 1,2,4-), di- and tetrahydrothiazolyl, di- and tetrahydroisothiazolyl, di- and tetrahydrothiadiazolyl (1,2,3-and 1,2,5-), di- and tetrahydropyridyl, di- and tetrahydropyrimidinyl, di- and tetrahydropyrazinyl, diand tetrahydrotriazinyl (1,2,3-, 1,2,4-, and 1,3,5-), and di- and tetrahydropyridazinyl.

[0043] The term "heterocycloalkylene" as used herein means a heterocyclyl group as defined above and in which one hydrogen atom has been removed from a nitrogen atom, the same carbon atom or different carbon atoms, resulting in a diradical. The heterocycloalkylene may link two atoms or moieties via the same carbon atom or via two carbon atoms.

[0044] The term “near infrared (NIR)” as used herein is defined as light having a range of wavelengths between 700 to 1000 nanometers (nm). The term “small-wavelengthinfrared (SWIR)” as used herein is defined as light having a range of wavelengths between 1000 to 2000 nanometers (nm). Various NIR probes described herein can be illuminated by NIR light, resulting in emission of NIR and / or SWIR light.Compound Formulae

[0045] Compounds in accordance with embodiments described herein are based on conjugates of maltodextrins and NIR heptamethine dyes. Provided in Fig. 1A is a structural formula of digestive maltodextrin, which is a polysaccharide having two or more glucose monomers linked via a-1,4 glycosidic bonds. It is noted that resistant maltodextrin (which can include a-1,2 and / or a-1,3 glycosidic bonds) can be utilized as well within a dye conjugate. Provided in Fig. 1 B is example of maltotriose, a maltodextrin having 3 glucose monomers linked via a-1,4 glycosidic bonds. The number of glucose monomers of a maltodextrin for conjugating with a NIR can vary. In various embodiments, the maltodextrin has between 2 and 30 glucose monomers, between 2 and 20 glucose monomers, between 2 and 10 glucose monomers, or between 2 and 4 glucose monomers.

[0046] Provided in Fig. 2A is structural formula of NIR heptamethine dyes (compounds of Formula I). In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, and R21are each independently: H or (Ci-Cs alkyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is H. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is (Ci-Ce)alkyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R2is methyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is ethyl. In some embodiments, R1, R2, R8, R7, R14, R15, R6, R17, R15, or R2is propyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is butyl. n some embodiments, R1, R2, R6, R7, R14R15, R16, R17, R18or R2’ is pentyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is hexyl.

[0047] In some embodiments, R3is -SO3X3or COOH. In some embodiments, R3is - SO3X3In some embodiments, R3is COOH. In some embodiments, X3is a cation, a proton, or absent. In some embodiments, X3is a cation. In some embodiments, X3is a proton. In some embodiments, X3is absent (i.e., R3is -SO3⁻). in some embodiments, X3is a cation, in which the cation is Na+, K+, or NH4+. In some embodiments, X3is Na+. In some embodiments, X3is K+. In some embodiments, X3is NH.

[0048] In some embodiments, R4is -ethinyl, -azide,-1^ HCF3-COOH, NH2, Cl, Br, I, -OSO2CF3, -COSO2CH3, -OH, vinyl, or -SH. In some embodiments, R4is -ethinyl. Insome embodiments, R4is -azide. In some embodiments, R4isl' In someembodiments, R4is In some embodiments, R4is In someembodiments, R4is(f. In some embodiments, R4isn someembodiments, R4isIn some embodiments, R4isCF=. In some embodiments, R4is -COOH. In some embodiments, R4is NH2. In some embodiments, R4is Cl. In some embodiments, R is Br. n some embodiments, R4is I. In some embodiments, R4is -OSO2CF3. In some embodiments, R4is -COSO2CH3. In some embodiments, R4is -OH. In some embodiments, R4is vinyl. In some embodiments, R4is -SH.

[0049] In some embodiments, R5is -SO3X4. In some embodiments, X4is a cation, a proton, or absent. In some embodiments, X is a cation. In some embodiments, X4is a proton. In some embodiments, X4is absent (i.e., R5is -SO3 ). In some embodiments, X4is a cation, in which the cation is Na+, K+, or NH In some embodiments, X4is Na*. In some embodiments, X4is K*. In some embodiments, X4is NH.

[0050] n some embodiments, R8, R9, R10, R11, R12, and R13are each independently: H, CN, -COO(C1-C6)alkyl, -CONH(C1-C6)alkyl, Cl, Br, I, F, -CF3, -O(C1-C6)alkyl, -NR14R15, -NHC(O)(C1-C6)alkyl, -NHC(O)NH (Ci-C6)alkyl, -SO3H. -SO2NH2, or (Ci-Cs)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is H. n some embodiments, R8, R9, R10, R11, R12, or R13is CN. In some embodiments, R8, R9, R10, R11, R12, or R13is -COO(C1-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -CONH(C1-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is Cl In some embodiments, R8, R9, R10, R11, R12, or R13is Br. In some embodiments, R8, R9, R10, R11, R12, or R13is I. In some embodiments, R8R9, R10, R11, R12, or R13is F. In some embodiments, R8, R9, R10, R11, R12, or R13is -CF3. In some embodiments, R8, R9, R10, R11, R12, or R13is -O(C1-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -NR14R15, -NHC(O)(C1-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -NHC(O)NH (Ci-Ce)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -SO3H. In some embodiments, R8, R9, R10, R11, R12, or R13is -SO2NH2. n some embodiments, R8, R9, R10R11, R12, or R13is (C1- Cejalkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is methyl. In some embodiments, R8, R9, R10, R11, R12, or R13is ethyl. IIn some embodiments, R8, R9, R10, R11, R12, or R13is propyl. In some embodiments, R8, R9, R10, R11, R12, or R13is butyl. In some embodiments, R8, R9, R10, R11, R12, or R13is pentyl. In some embodiments, R8, R9, R10, R11, R12, or R13is hexyl.

[0051] In some embodiments, R19and R20are each independently: H, (Ci-C6)alkyl, -O(Ci-C6)alkyl, Cl, F, Br, CN, C(O)NH2. n some embodiments, R19or R20is H. In some embodiments, R19or R20is (C1-C6)alkyl. In some embodiments, R19or R20is methyl. In some embodiments, R19or R20is ethyl. In some embodiments, R19or R20is propyl. In some embodiments, R19or R20is butyl. In some embodiments, R19or R20is pentyl. In some embodiments, R19or R20is hexyl. In some embodiments, R19or R20is CL In some embodiments, R19or R20is F. In some embodiments, R19or R20is Br. In some embodiments, R19or R20is CN. In some embodiments, R19or R20is C(O)NH2.

[0052] In some embodiments, L is one or more of: -(CH2)ni-, -(Ci-C6)cycloalkylene-, - (Ci-C6)heterocycloalkylene-, -O-, -NR16-, -NH-, -NHC(O)-, -C(O)NR17, -CH(OH)-, and - CH(OR18)-. In some embodiments, ni is an integer between 1 to 30. In some embodiments, ni is an integer between 1 to 20. In some embodiments, ni is an integerbetween 1 to 10. In some embodiments,niis 1. In some embodiments, ni is 2. In some embodiments, ni is 3. In some embodiments,niis 4. In some embodiments, M is 5. In some embodiments, ni is 6. In some embodiments, ni is 7. In some embodiments, ni is 8. In some embodiments,niis 9. In some embodiments, ni is 10. In some embodiments, ni is 11. In some embodiments, ni is 12. In some embodiments, ni is 13. In some embodiments, ni is 14. In some embodiments, ni is 15. In some embodiments, ni is 16. In some embodiments, ni is 17. In some embodiments, ni is 18. In some embodiments, ni is 19. in some embodiments, ni is 20. In some embodiments, ni is 21. In some embodiments, ni is 22. In some embodiments, ni is 23. In some embodiments, ni is 24. In some embodiments, ni is 25. In some embodiments, ni is 26. In some embodiments, ni is 27. In some embodiments, ni is 28. In some embodiments, ni is 29. In some embodiments, ni is 30.

[0053] In some embodiments, X1and X2are each independently: a cation, a proton, or absent. In some embodiments, X1or X2is a cation. In some embodiments, X1or X2is a proton. In some embodiments, X1or X2is absent (i.e., -SO3'). In some embodiments, X1orX2is a cation, in which the cation is Na+, K+, or NH4+. In some embodiments, X1or X2is Na+. In some embodiments, X1orX2is K+. In some embodiments, X1orX2is NH4+.

[0054] In some embodiments, Q is -(CH2)n2- In some embodiments, Q is -(CH2)n2-, wherein any H is optionally replaced with (C1-C6)alkyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with methyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with ethyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with propyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with butyl, in some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with pentyl. In some embodiments, Q is - (CH2)n2~, wherein any H is optionally replaced with hexyl. In some embodiments, n2 is an integer between 1 to 10. In some embodiments, n2 is an integer between 1 to 8. In some embodiments, n2 is an integer between 1 to 6. In some embodiments, n2 is an integer between 1 to 4. In some embodiments, n2 is 1. In some embodiments, n2 is 2. In some embodiments, n2 is 3. In some embodiments,n2 is 4. In some embodiments, n2 is 5. In some embodiments, n2 is 6. In some embodiments, n2 is 7. In some embodiments, n2 is 8. In some embodiments,n2 is 9. In some embodiments, n2 is 10.

[0055] In some embodiments, A is –(CH2)n3- In some embodiments, A is –(CH2)n3-, wherein any H is optionally replaced with (Ci-C6)alkyl. In some embodiments, A is -(CH2)n3-, wherein any H is optionally replaced with methyl. In some embodiments, A is –(CH2)n3-, wherein any H is optionally replaced with ethyl. In some embodiments, A is - CH2)n3-, wherein any H is optionally replaced with propyl. In some embodiments, A is -(CH2)n3-, wherein any H is optionally replaced with butyl. In some embodiments, A is - (CH2)n3-, wherein any H is optionally replaced with pentyl. In some embodiments, A is - CH2)n3~, wherein any H is optionally replaced with hexyl. In some embodiments, n3 is an integer between 1 to 10. In some embodiments, n3 is an integer between 1 to 8. In some embodiments,n3 is an integer between 1 to 6. In some embodiments, n3 is an integer between 1 to 4. In some embodiments,n3 is 1. In some embodiments, n3 is 2. In some embodiments, n3 is 3. In some embodiments,n3 is 4. In some embodiments, n3 is 5. In some embodiments, n3 is 6. In some embodiments,n3 is 7. In some embodiments, n3 is 8. In some embodiments, n3 is 9. In some embodiments, n3 is 10.

[0056] The various compounds within Fig. 2A can also be related to pharmaceutically acceptable salts. A “pharmaceutically acceptable salt” retains the desirable biological activity of the compound without unacceptable toxicological effects. Salts can be salts with a suitable acid, including, but not limited to, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, nitric acid and the like; acetic acid, oxalic acid, tartaric acid, succinic acid, malic acid, benzoic acid, pamoic acid, alginic acid, methanesulfonic acid, naphthalenesulfonic acid, and the like. Also, incorporated cations can include ammonium, sodium, potassium, lithium, zinc, copper, barium, bismuth, calcium, and the like; or organic cations such as tetraalkylammonium and trialkylammonium cations. Also useful are combinations of acidic and cationic salts. A pharmaceutical salt can be a salt with an acetic acid, such as salts with trifluoroacetic acid, chloroacetic acid, or trichloroacetic acid.

[0057] Provided in Fig. 2B is a structural formula of sNIR with a carboxyl appendage that can be used for linkage. Provided in Fig. 2C is a structural formula of sNIR with an NHS appendage that can be used for linkage. Provided in Fig. 2D is a structural formula of sNIR with an DBCO appendage that can be used for linkage. Provided in Fig. 2E is a structural formula of sNIR with an alkyne appendage that can be used for linkage.

[0058] Provided in Fig. 3A is structural formula of maltodextrin NIR heptamethine dye conjugates (compounds of Formula II). In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, and R21are each independently: H or (Ci-C6)alkyl. In some embodiments, R1, R2, R6, R7, R14R15, R16, R17, R18, or R21is H. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is (C1-C6)alkyl. In some embodiments, R1, R2, R6, R7, R14R15, R16, R17, R18, or R21is methyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is ethyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is propyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is butyl. In some embodiments, R1, R2, R6, R7, R14R15, R16, R17, R18, or R21is pentyl. In some embodiments, R1, R2, R6, R7, R14, R15, R16, R17, R18, or R21is hexyl.

[0059] In some embodiments, R3is -SO3X3or COOH. In some embodiments, R3is - SO3X3. In some embodiments, R3is COOH. In some embodiments, X3is a cation, a proton, or absent. In some embodiments, X3is a cation. In some embodiments, X3is a proton. In some embodiments, X3is absent (i.e., R3is -SO3'). In some embodiments, X3is a cation, in which the cation is Na+, K+, or NH4+. In some embodiments, X3is Na+. In some embodiments, X3is K+. In some embodiments, X3is NH4+.

[0060] In some embodiments, R5is -SO3X4. In some embodiments, X4is a cation, a proton, or absent. In some embodiments, X4is a cation. In some embodiments, X4is a proton. In some embodiments, X4is absent (i.e., R5is -SO3 ). in some embodiments, X4is a cation, in which the cation is Na*, K*, or NH4*. In some embodiments, X4is Na*. In some embodiments, X4is K*. In some embodiments, X4is NH4*.

[0061] In some embodiments, R8, R9, R10, R11, R12, and R13are each independently: H, CN, -COO(Ci-C6)alkyl, -CONH(Ci-C6)alkyl, Cl, Br, I, F, -CF3, -O(Ci-C6)alkyl, -NR14R15, -NHC(O)(Ci-C6)alkyl, -NHC(O)NH (Ci-C6)alkyl, -SO3H, -SO2NH2, or (Ci-C6)alkyl. In some embodiments, R8, R9R10, R11, R12, or R13is H. In some embodiments, R8, R9, R10, R11, R12, or R13is CN. In some embodiments, R8, R9, R10, R11, R12, or R13is -COO(Ci-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -CONH(Ci-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12or R13is Cl. In some embodiments, R8, R9, R, R11, R12, or R13is Br. In some embodiments, R8, R9, R10, R11, R12, or R13is I. In some embodiments, R8, R9, R10, R11, R12, or R13is F. In some embodiments, R8, R9, R10, R11, R12, or R13is -CF3. In some embodiments, R8, R9, R10, R11, R12, or R13is -O(Ci-C6)alkyl.In some embodiments, R8, R9, R10, Ri1, R12, or R13is -NR14R15, -NHC(O)(Ci-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -NHC(O)NH (Ci-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is -SO3H. In some embodiments, R8, R9, R10, R11, R12, or R13is -SO2NH2. In some embodiments, R8, R9, R10, R11, R12, or R13is (C1-C6)alkyl. In some embodiments, R8, R9, R10, R11, R12, or R13is methyl. In some embodiments, R8, R9, R10, R11, R12, or R13is ethyl. In some embodiments, R8, R9, R10, R11, R12, or R13is propyl. In some embodiments, R8, R9, R10, R11, R12, or R13is butyl. In some embodiments, R8, R9, R10, R11, R12, or R13is pentyl. In some embodiments, R8, R9, R10, R11, R12, or R13is hexyl.

[0062] In some embodiments, R19and R20are each independently: H, (Ci-C6)alkyl, -O(Ci-C6)alkyl, Cl, F, Br, CN, C(O)NH2. In some embodiments, R19or R20is H. In some embodiments, R19or R20is (Ci-C6)alkyl. In some embodiments, R19or R20is methyl. In some embodiments, R19or R20is ethyl. In some embodiments, R19or R20is propyl. In some embodiments, R19or R20is butyl. In some embodiments, R19or R20is pentyl. In some embodiments, R19or R20is hexyl. In some embodiments, R19or R20is Cl. In some embodiments, R19or R20is F. In some embodiments, R19or R20is Br. In some embodiments, R19or R20is CN. In some embodiments, R19or R20is C(O)NH22.

[0063] In some embodiments, L is one or more of: -(CH2)ni~, -(Ci-C6)cycloalkylene-, - (Ci-C6)heterocycloalkylene-, -O-, -NR16-, -NH-, -NHC(O)-, -C(O)NR17, -CH(OH)-, and - CH(OR18)-. In some embodiments,niis an integer between 1 to 30. In some embodiments, ni is an integer between 1 to 20. In some embodiments, ni is an integer between 1 to 10. In some embodiments, ni is 1. In some embodiments, ni is 2. In some embodiments, ni is 3. In some embodiments, ni is 4. In some embodiments, ni is 5. In some embodiments, ni is 6. In some embodiments, ni is 7. In some embodiments, ni is 8. In some embodiments,niis 9. In some embodiments, ni is 10. In some embodiments, ni is 11. In some embodiments, ni is 12. In some embodiments, ni is 13. In some embodiments, ni is 14. In some embodiments, ni is 15. In some embodiments, ni is 16. In some embodiments, ni is 17. In some embodiments, ni is 18. In some embodiments, ni is 19. In some embodiments, ni is 20. In some embodiments,niis 21. In some embodiments, ni is 22. In some embodiments, ni is 23. In some embodiments, ni is 24. In some embodiments, ni is 25. In some embodiments, ni is 26. In some embodiments, ni is 27. Insome embodiments, ni is 28. In some embodiments, ni is 29. In some embodiments, ni is

[0064] In some embodiments, Li is a suitable linking moiety. In some embodiments,Li is. In some embodiments, Li isCOMHIn some embodiments, Li is. In some embodiments, Li is -CO-.

[0065] In some embodiments, L2 is one or more of: -(CH2)ni-, -(Ci-C6)cycloalkylene-, -(Ci-C6)heterocycloalkylene-, -O-, -NR16-, -NH-, -NHC(O)-, -C(O)NR17, -CH(OH)-, and -CH(OR18)-. n some embodiments, ni is an integer between 1 to 30. In some embodiments, ni is an integer between 1 to 20. In some embodiments, ni is an integer between 1 to 10. In some embodiments,niis 1. In some embodiments, ni is 2. In some embodiments,niis 3. In some embodiments, ni is 4. In some embodiments,niis 5. In some embodiments, ni is 6. In some embodiments, ni is 7. In some embodiments, ni is 8. In some embodiments,niis 9. In some embodiments, ni is 10. In some embodiments, ni is 11. In some embodiments, ni is 12. In some embodiments, ni is 13. In some embodiments, ni is 14. In some embodiments, ni is 15. In some embodiments, ni is 16. In some embodiments, ni is 17. In some embodiments, ni is 18. In some embodiments,niis 19. In some embodiments, ni is 20. In some embodiments, ni is 21. In some embodiments, ni is 22. In some embodiments, ni is 23. In some embodiments, ni is 24. In some embodiments, ni is 25. In some embodiments, ni is 26. In some embodiments, ni is 27. In some embodiments, ni is 28. In some embodiments, ni is 29. In some embodiments, ni is 30.

[0066] In some embodiments, X1and X2are each independently: a cation, a proton, or absent. In some embodiments, X1or X2is a cation. In some embodiments, X1or X2is a proton. In some embodiments, X1or X2is absent (i.e., -SO3-). In some embodiments, X1or X2is a cation, in which the cation is Na+, K+, or NH4+. In some embodiments, X1or X2is Na+. In some embodiments, X1orX2is K+. In some embodiments, X1or X2is NH4+.

[0067] In some embodiments, Q is –(CH2)n2- In some embodiments, Q is -(CH2)n2-, wherein any H is optionally replaced with (Ci-C6)alkyl. In some embodiments, Q is -(CH2)n2-, wherein any H is optionally replaced with methyl. In some embodiments, Q is -(CH2)n2-, wherein any H is optionally replaced with ethyl. In some embodiments, Q is -(CH2)n2-, wherein any H is optionally replaced with propyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with butyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with pentyl. In some embodiments, Q is - (CH2)n2-, wherein any H is optionally replaced with hexyl. In some embodiments, n2 is an integer between 1 to 10. In some embodiments, n2 is an integer between 1 to 8. n some embodiments,n2 is an integer between 1 to 6. In some embodiments, n2 is an integer between 1 to 4. In some embodiments, n2 is 1. In some embodiments, n2 is 2. In some embodiments, n2 is 3. In some embodiments, n2 is 4. In some embodiments, n2 is 5. In some embodiments, n2 is 6. In some embodiments,n2 is 7. In some embodiments,n2 is 8. In some embodiments, n2 is 9. In some embodiments, n2 is 10.

[0068] In some embodiments, Y is -(CH2)n3- In some embodiments, Y is -(CH2)n3-, wherein any H is optionally replaced with (Ci-C6)alkyl. In some embodiments, Y is - (CH2)n3-, wherein any H is optionally replaced with methyl. In some embodiments, Y is - (CH2)n3-, wherein any H is optionally replaced with ethyl. In some embodiments, Y is - (CH2)n3-, wherein any H is optionally replaced with propyl. In some embodiments, Y is - (CH2)n3~, wherein any H is optionally replaced with butyl. In some embodiments, Y is - (CH2)n3~, wherein any H is optionally replaced with pentyl. In some embodiments, Y is - (CH2)n3~, wherein any H is optionally replaced with hexyl. In some embodiments, n3 is an integer between 1 to 10. In some embodiments, n3 is an integer between 1 to 8. In some embodiments,n3 is an integer between 1 to 6. In some embodiments, n3 is an integer between 1 to 4. In some embodiments, n3 is 1. In some embodiments, n3 is 2. In some embodiments, n3 is 3. In some embodiments, n3 is 4. In some embodiments,n3 is 5. Insome embodiments, n3 is 6. In some embodiments, n3 is 7. In some embodiments,n3 is 8. In some embodiments, n3 is 9. In some embodiments,n3 is 10.

[0069] In some embodiments, Z is a maltodextrin polysaccharide. In some embodiments, Z is a digestible maltodextrin polysaccharide. In some embodiments, Z is a resistant maltodextrin polysaccharide. In some embodiments, Z is a maltodextrin polysaccharide having between 2 and 30 glucose monomers. In some embodiments, Z is a maltodextrin polysaccharide having between 2 and 20 glucose monomers. In some embodiments, Z is a maltodextrin polysaccharide having between 2 and 10 glucose monomers. In some embodiments, Z is a maltodextrin polysaccharide having between 2 and 8 glucose monomers. In some embodiments, Z is a maltodextrin polysaccharide having between 2 and 6 glucose monomers. In some embodiments, Z is a maltodextrin polysaccharide having between 2 and 4 glucose monomers. In some embodiments, Z is a maltohexaose, having six glucose monomers. In some embodiments, Z is a maltotriose, having three glucose monomers. In some embodiments, Z is a maltose.

[0070] Provided in Fig. 3B is a structural formula of maltotriose-amide-sNIR conjugate. Provided in Fig. 3C is a structural formula of maltotriose-DBCO-sNIR conjugate. Provided in Fig. 3D is a structural formula of maltotriose-triazol-C3-sNIR conjugate. Provided in Fig.3E is a structural formula of maltotriose-triazol-C5-sNIR conjugate. Provided in Fig. 3F is a structural formula of maltotriose-triazol-C6~sN! R conjugate. Provided in Fig. 3G is a structural formula of maltohexose-triazol-C3~sNIR conjugate.

[0071] The various compounds within Fig. 3A can also be related to pharmaceutically acceptable salts. A “pharmaceutically acceptable salt” retains the desirable biological activity of the compound without unacceptable toxicological effects. Salts can be salts with a suitable acid, including, but not limited to, hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, nitric acid and the like; acetic acid, oxalic acid, tartaric acid, succinic acid, malic acid, benzoic acid, pamoic acid, alginic acid, methanesulfonic acid, naphthalenesulfonic acid, and the like. Also, incorporated cations can include ammonium, sodium, potassium, lithium, zinc, copper, barium, bismuth, calcium, and the like; or organic cations such as tetraalkylammonium and trialkylammonium cations. Also useful are combinations of acidic and cationic salts. A pharmaceutical salt can be a salt with an acetic acid, such as salts with trifluoroacetic acid, chloroacetic acid, or trichloroacetic acid.Modes of Use

[0072] The various maltodextrin with NIR dye conjugate probes of the disclosure have several beneficial properties allowing for enhanced or novel methodologies of bacterial detection and monitoring. Many of the benefits improve use for in vivo applications. For example, the probes of the disclosure have been shown to shown to be capable of detecting and localizing a bacterial infection within an hour of systemic administration, several hours prior to other probes such as those that use indocyanine green (ICG) (see Figs. 4A to 4C and accompanying description). When systemically administered, the probes are preferentially processed and cleared via the kidneys and urinary systems over the liver, ensuring safe use for in vivo applications. The probe has very low non-specific binding in vivo and thus provides great signal to background ratio, allowing for precise detection and various medical techniques (e.g., surgical extraction or localized drug delivery). The signal provided by the probes correlates well with the amount of specific interaction with bacteria, and thus the probes are good for estimating and / or monitoring the relative count of bacteria present. And importantly, the probes interact with bacteria via maltodextrin, a fairly universal sugar metabolized and utilized by both gram-positive and gram-negative bacteria, and thus the probe can be utilized for virtually all pathogenic or microbiomic bacteria species that would be of interest.

[0073] The maltodextrin with NIR dye conjugate probes can be detected by various in vivo clinical and preclinical imaging modalities, including fluorescent imaging modalities and photoacoustic imaging modalities. These imaging modalities can be noninvasive, partially invasive, or invasive, allowing for a variety of medical techniques to be performed.

[0074] A fluorescent imaging modality can illuminate NIR light via an emission source to impinge upon and induce NIR fluorescence of the probe, which can be captured by a camera system. The illumination source can be a pulsed laser, a continuous wave laser, a laser diode, a light emitting diode, a mercury argon lamp, etc., and various sources may be desired for various purposes. Fluorescent imaging can be deep penetrating imaging (up to 5 cm) if resolution is less important, but may be better suited for shallower imaging (0.1 mm to 1 cm) where resolution is greater. For various high-resolution applications,fluorescent imaging can be suitable for topical imaging, near skin imaging, and scope- guided internal imaging (e.g. for scope-guided procedures such as scope-guided surgery). The light imaging modality can emit NIR light between 700 and 900 nm, and preferably between 770 and 810 nm, in accordance with the absorbance of the NIR dye conjugate probes. Various examples of imaging described herein have utilized a 785 nm laser for illumination. Detection systems (i.e., cameras or other light detection sensors) having sensitivity to detect NIR and / or SWIR emission can be utilized. In some embodiments, detection is performed within the wavelength range of 700 and 1700 nm. In some embodiments, detection is performed within the NIR wavelength range of 700 to 1000 nm. In some embodiments, detection is performed in the wavelength range of 800 to 840 nm. In some embodiments, detection is performed in the wavelength range of 790 and 810 nm, where many of NIR probes of the disclosure have peak emission. In some embodiments, detection is performed within the SWIR wavelength range of 1000 and 2000 nm, where the NIR probes of the disclosure were found to have a tail of emission. In some embodiments, detection is performed within the range of 1000 and 1700 nm, as quantum efficiency of the InGaAs sensors drops at about 1700 nm. In some embodiments, detection is performed within the range of 1000 and 1200 nm. In some embodiments, detection is performed within the range of 1200 and 1400 nm. Detection of light in the longer IR wavelengths have various benefits, such as less autofluorescence, more contrast due water absorption, and deeper penetration of tissue. Because the emission is lower, the recording by the detection system may need to be longer to capture the emission signal. It has been found that using LPs specified as high as 1300 nm were able to record emission signal, and in theory can record up to about 1700 nm based on quantum efficiency of sensors. Examples of clinical and preclinical systems that can be utilized in include EleVision (Medtronic), IC-Flow (Diagnostic Green), and I VIS Spectrum series (Revvity).

[0075] A photoacoustic imaging modality can illuminate NIR light via an emission source to impinge upon and induce heat and thermoelastic expansion resulting in emission of acoustic waves, which can be detected via sonography. The emission source can be a pulsed laser, a continuous wave laser, a laser diode, a light emitting diode, a mercury argon lamp, etc., and various sources may be desired for various purposes. Oneadvantage of photoacoustic imaging is that it can stimulate acoustic waves via diffused photons of pulsed or continuous wave lasers allowing for high-resolution deep penetrating techniques (up to 7 cm deep), such as deep noninvasive imaging of inner tissue. The light imaging modality can emit NIR light between 700 and 900 nm, and preferably between 770 and 810 nm, in accordance with the absorbance of the NIR dye conjugate probes. Various examples of imaging described herein have utilized a 785 nm laser for illumination. Acoustic transducer systems can detect the acoustic waves produced by the stimulation of the NIR dye conjugate probes. Several groups are translating preclinical photoacoustic imaging systems, such as the Vevo F2 LAZR-X system (FujiFilm) into clinical systems, many of which are currently seeking approval at various regulatory agencies across the globe.

[0076] The maltodextrin with NIR dye conjugate probes can be utilized in a number of methods that can be performed on recipients in order to detect, assess, and monitor bacterial infections. The probes can be formulated for administration into recipient (e.g., human) and can be administered via various routes, such as intravenous administration, intratissue injection, intracerebroventricular injection, intrathecal administration, oral ingestion, intranasal administration, ocular administration, otic administration, topically applied, pulmonary administration, vaginal administration, or another means to reach a bacterial site of infection.

[0077] A recipient can be any animal capable of being infected by bacteria or having microbiomic bacteria, but especially humans, research animals, livestock, and domesticated animals. Examples of research animals include mice, rats, rabbits, and macaques. Examples of livestock include cattle, bison, pigs, boars, horses, donkeys, goats, sheep, chickens, turkeys, and ducks. Examples of domesticated animals include dogs and cats.

[0078] Various types of bacterial infections and / or microbiomes can be detected. Generally, any pathogenic bacteria or microbiomic bacteria capable of infecting or otherwise persisting in a recipient can be detected, inclusive of both gram-positive and gram-negative bacteria. Examples of infectious bacteria that can be detected include Actinomyces israelii, Bacillus anthracis, Bacteroidesfragilis, Bordetella pertussis, Borrelia burgdorferi, Borrelia garinii, Borrelia afzelii, Borrelia recurrentis, Brucella abortus, Brucellacanis, Brucella melitensis, Brucella suis, Campylobacter jejuni, Chlamydia pneumoniae, Chlamydia trachomatis, Chlamydophila psittaci, Clostridium botulinum, Clostridium difficile, Clostridium perfringens, Clostridium tetani, Corynebacterium diphtheriae, Escherichia coli, Francisella tularensis, Haemophilus influenzae, Helicobacter pylori, Klebsiella pneumoniae, Legionella pneumophila, Leptospira interrogans, Listeria monocytogenes, Mycobacterium leprae, Mycobacterium tuberculosis, Mycoplasma pneumoniae, Neisseria gonorrhoeae, Neisseria meningitidis, Pseudomonas aeruginosa, Nocardia asteroides, Rickettsia rickettsia, Salmonella bongori, Salmonella enterica, Salmonella typhi, Shigella sonnei, Shigella dysenteriae, Staphylococcus aureus, Staphylococcus epidermidis, Staphylococcus saprophyticus, Streptococcus agalactiae, Streptococcus pneumoniae, Streptococcus pyogenes, Streptococcus viridans, Treponema pallidum, Vibrio cholerae, and Yersinia pestis,

[0079] In one example, a method of using a maltodextrin with NIR dye conjugate probe is for detecting a bacterial infection. The method can comprise:* Administer a maltodextrin with NIR dye conjugate probe to a recipient* Image recipient to detect infectionIn some implementations, the method further comprises determining or diagnosing that the individual may have or has a bacterial infection. In some implementations, the probe is administered systemically. In some implementations, the probe is administered locally where the bacterial infection has likelihood of being located. In some implementations, the imaging is performed within one hour of administering the probe. In some implementations, the imaging is performed within two hours of administering the probe. In some implementations, the imaging is performed within three hours of administering the probe. In some implementations, the imaging is performed within four hours of administering the probe. In some implementations, imaging comprises deep-tissue imaging (e.g., > 5 cm). In some implementations, imaging comprises a systemic scan (e.g., scan of the whole body). In some implementations, imaging is repeated, or probe administration and imaging is repeated to monitor bacterial colony growth, bacterial spread, and / or bacterial clearance.

[0080] In one example, a method of using a maltodextrin with NIR dye conjugate probe is for performing surgery upon infected tissue. The method can comprise:« Administer a maltodextrin with NIR dye conjugate probe to a recipient • Image recipient to determine infection location and boundaries® Surgically remove infected tissueIn some implementations, the method further comprises determining or diagnosing that the individual may have a bacterial infection. In some implementations, the probe is administered systemically. In some implementations, the probe is administered locally where the bacterial infection has likelihood of being located. In some implementations, the imaging and surgery is performed within one hour of administering the probe. In some implementations, the imaging is performed within two hours of administering the probe. In some implementations, the imaging is performed within three hours of administering the probe. In some implementations, the imaging is performed within four hours of administering the probe. In some implementations, imaging is performed using a scope. In some implementations, probe administration and imaging are repeated post-operation to detect any residual infection.

[0081] In one example, a method of using a maltodextrin with NIR dye conjugate probe is for assessing an implant. The method comprises:« Install an implant into a recipient• Administer a maltodextrin with NIR dye conjugate probe to a recipient• Image recipient at implant location to determine if infection occurredIn some implementations, the probe is administered systemically. In some implementations, the probe is administered locally where the implant was installed. In some implementations, the imaging is performed within one hour of administering the probe. In some implementations, the imaging is performed within two hours of administering the probe. In some implementations, the imaging is performed within three hours of administering the probe. In some implementations, the imaging is performed within four hours of administering the probe. In some implementations, imaging comprises deep-tissue imaging (e.g., > 5 cm). In some implementations, imaging is performed noninvasively.

[0082] In one example, a method of using a maltodextrin with NIR dye conjugate probe is for assessing a wound. The method comprises:« Identify a wound on a recipient« Administer a maltodextrin with NIR dye conjugate probe to a recipient • Image recipient at wound location to determine if infection occurredIn some implementations, the probe is administered systemically. In some implementations, the probe is administered locally where the wound is located. In some implementations, the imaging is performed within one hour of administering the probe, in some implementations, the imaging is performed within two hours of administering the probe. In some implementations, the imaging is performed within three hours of administering the probe. In some implementations, the imaging is performed within four hours of administering the probe. In some implementations, imaging is performed noninvasively.

[0083] In one example, a method of using a maltodextrin with NIR dye conjugate probe is for assessing treatment efficacy. The method comprises:* Administer a treatment for a bacterial infection to a recipient® Administer a maltodextrin with NIR dye conjugate probe to a recipient» Image recipient to detect infectionIn some implementations, the method further comprises determining or diagnosing that the individual may have or has a bacterial infection. In some implementations, the treatment comprises an antibiotic. In some implementations, the treatment comprises an antibody. In some implementations, the probe is administered systemically. In some implementations, the probe is administered locally where the bacterial infection has a likelihood of being located. In some implementations, the imaging is performed within one hour of administering the probe. In some implementations, the imaging is performed within two hours of administering the probe. In some implementations, the imaging is performed within three hours of administering the probe. In some implementations, the imaging is performed within four hours of administering the probe. In some implementations, imaging comprises deep-tissue imaging (e.g., > 5 cm). In some implementations, imaging comprises a systemic scan (e.g., scan of the whole body). In some implementations, imaging is repeated, or probe administration and imaging is repeated to monitor treatment efficacy over a time course.EXAMPLES AND DATA

[0084] Biological data supports the use of the aforementioned probe systems comprising a maltodextrin NIR heptamethine dye conjugate. It is noted that embodiments of the compounds described herein, in accordance with the disclosure, are capable of detecting bacterial infections in vivo. Accordingly, various embodiments are directed to utilizing these compounds to monitor bacterial colony growth, bacterial spread, and / or treatment response.Treatment of Bacterial infections in Animal Models

[0085] Provided in Figs. 4A to 4D are results of an experiment of assessing bacterial infection in mice using the maltotriose-amide-sNIR probe (see Fig. 3B) and the maltotriose-DBCO-sNIR probe (see Fig. 3C). Mice were infected with 1 x 106CFUs of E. coli in the left thigh via subcutaneous injection. Mice were then systemically administered 10nanomoles of the maltotriose-amide-sNIR probe or the maltotriose-DBCO-sNIR probe. Mice were imaged via fluorescent imaging by impinging 798 nm laser light upon the mouse and capturing the fluorescent light via a short wavelength infrared camera. Imaging was repeated over a time course of 24 hours.

[0086] Provided in Fig. 4A is bioluminescent imaging of the bacteria at the site of infection. Provided in Fig. 4B are the images captured with a mouse that was administered the maltotriose-DBCO-sNIR probe. Notably, the bacterial infection is detectable at 1 hour and remains detectable up to 24 hours, but the probe is being cleared. Provided in Fig.4C are the images captured with a mouse that was administered the maltotriose-amide- sNIR probe. Again, the bacterial infection is detectable at 1 hour. Provided in Fig. 4D are ventral images of the mouse receiving the maltotriose-DBCO-sNIR probe, which shows that the probe is being cleared via the kidneys and urinary system.

[0087] Provided in Figs. 5A and 5B are results of bioluminescent imaging of a rabbit corneal ulcer infection model. Maltotriose-sNIR (10 µL of 10 µM) was topically administered in control uninfected corneas (Fig. 5A) and corneas infected with S. Aureus (Fig. 5B). Following washing with 1 ml PBS x 2, corneas were illuminated with 800 nm light and fluorescence intensities of emitted light were measured using fluorescent imaging.Compound Synthesis and Data

[0088] Synthesis of a maltotriose compound with linker for conjugation is provided in Fig. 6A. Synthesis of a maltohexose-C3-sNIR probe is provided in Fig. 6B

[0089] Optical properties of sNIR are provided in Fig. 7A. Capture of emission of the sNIR probe at various SWIR wavelengths is provided in Fig. 7B. A 2.5 µM solution of sNIR-amide in FBS was transferred to a mini cap (Code-Nr: 9000110, V 10 µL, d = 0.0652 cm), and sealed with wax. The inclusion of bubbles was avoided. Absorbance over the capillary was 0.04. It was placed on a capillary holder made from acryl and imaged with longpass filters at the detection site. Using Image! a linear region of interest was placed over the capillary and its plotprofile was extracted. Illumination was performed with a 785 nm laser, roughly 69 mW / cm², FESH0800, and engineered diffuser. For SWIR detection, various long pass filters (FELH1000, FELH1100, FELH1200, FELH1300), then colored glass around 830 nm, Acktar black tube, FELH0850, Computar HyperAPO lens, Goldeye G-032 with same cooling temperature and gain, and with a camera pointing down.Liquid Chromatography-Mass Spectrometry Methods

[0090] Method 1: An ultra-high-performance liquid chromatography (UHPLC) system coupled to a single quadrupole mass spectrometer with an integrated UV detector was used for analysis. The system was equipped with a Nucleodur PFP column (50 x 2.0 mm, 3.0 pm particle size) and a matching precolumn cartridge. The chromatographic runs followed a gradient elution program (5-95% over 13 minutes) after a 5-minute equilibration period (table) with a flow rate of 0.3 mL / min. Electrospray ionization (ESI) was employed for negative ionization, and mass detection was performed in the m / z range of 100-1250. Data acquisition and processing were carried out using Chromeleon Chromatography Data System (CDS) software.Solvent Gradient for UHPLC Systemt [min] Water + 0.1% FA MeCN + 0.1% FA[mm]-5 95 50 95 58 5 9513 5 95

[0091] Method 2: A 2795 separation module connected to an LCT Premier mass spectrometer, a 1050 UV multiwavelength detector, and a widepore XB-C18 column (50 x 2.1 mm, particle size: 3.6 pm. Runs (5-95% over 5 minutes) employed a standard gradient as listed at a flow rate of 0.6 mL / min, the used solvents contained 0.1% formic acid (FA). Electrospray ionization (ESI) was used for ionization, and the m / z range of 100-2500 was detected. MassLynx 4.1 software was used for analysis.Solvent Gradient for composite HPLC systemt [min] Water + 0.1% MeCN + 0.1%FA FA[mm]0.00 95 54.00 10 9090

[0092] Synthesis of 3-azidopropan-1 -ol:

[0093] 3-bromopropan-1 -ol (1.0 g, 7.14 mmol, 1.0 eq) was dissolved in 15 ml of water and sodium azide (1.0 g, 15.72 mmol, 2.2 eq) was added. The mixture was stirred at 60 °C overnight and the completion monitored with TLC. The organic phases were extracted with CH2CI2 (3 x 50 ml), dried over anhydrous Na₂SO₄ and the solvent removed in vacuo. The product was obtained as a light-yellow oil (650.0 mg, 6.43 mmol, 90%).¹H-NMR (400 MHz, CDCl₃) 5 = 3.76 (t, J = 5.9 Hz, 2H), 3.46 (t, J = 6.6 Hz, 2H), 1.89 - 1.76 (m, 2H). ¹³C-NMR (101 MHz, CDCl₃) 5 = 60.09, 48.64, 31.57. Rf(PE / EA, 1:1) = 0.5.

[0094] Synthesis of 5-azidopentan-1 -ol:

[0095] 5-hydroxypentyltosylate (300.0 mg, 1.16 mmol 1.0 eq), sodium azide (166.2 mg, 2.56 mmol, 2.2 eq) were dissolved in water (2.3 ml) and stirred for 24 h at 55 °C. The reaction was monitored with TLC. After cooling to room temperature, the mixture was extracted with EtOAc (3 x 15 ml). The organic fractions were combined and dried over anhydrous Na2SO4 and evaporated to dryness. The crude was purified by flash column chromatography (PE / EA = 0-100% EA) and the product was obtained as a light yellow oil (122.5 mg, 0.95 mmol, 82%).¹H-NMR (400 MHz, CDCl₃) 5 = 3.66 (t, J = 6.4 Hz, 2H), 3.29 (t, J = 6.8 Hz, 2H), 1.72 - 1.53 (m, 4H), 1.46 (m, J = 12.5, 7.4, 5.5, 2.4 Hz, 4H). ¹³C NMR (101 MHz, CDCl₃) 5 = 62.77, 51.52, 32.30, 28.79, 23.13. Rf (PE / EA = 3:1): 0.46.

[0096] Synthesis of 6-azidohexan-1 -ol:

[0097] Tosyl-hexanol (300 mg, 1.10 mmol, 1.0 eq) was dissolved in 1.5 ml DMF and sodium azide (122 mg, 1.9 mmol, 1.7 eq) was added. The mixture was stirred at 55 °C for 17 h. After completion of the reaction the mixture was diluted with water (10 ml) and extracted with CH2CI2 (3x20 ml) and washed with brine once. The combined organic phases were dried over anhydrous Na2SO4 and the solvent removed in vacuo. The crude was purified by silica column chromatography (PE / EtOAc gradient) to obtain the product as a colorless oil (85 mg, 0.6 mmol, 54%).1H NMR (400 MHz, CDCb) 5 = 3.65 (t, J = 6.5 Hz, 2H), 3.27 (t, J = 6.9 Hz, 2H), 1.68 - 1.53 (m, 4H), 1.44 - 1.35 (m, 4H).

[0098] Synthesis of 3R,5R,6R)-6-(acetoxymethyl)-5-(((2R,3R,5R,6R)-3,4-diacetoxy- 6-(acetoxymethyl)-5-(((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran~2-yl)oxy)tetrahydro-2H-pyran~2,3,4-triyl triacetate:OAc

[0099] Inert gas conditions, Schlenk technique. Maltotriose (1.0 g, 1.98 mmol, 1 eq) was dissolved in 80 ml of pyridine and acetic anhydride (40 ml) was added. The reaction mixture was stirred for 24 h at rt. After completion of the reaction, the solvent was removed in vacuo and coevaporated with toluene (2x100 mi). The crude was dissolved in EtOAc (250ml) and washed with aqueous sat. NaHCO₃ solution (2x50ml), 1M HCl (2x50ml) and brine (2x50ml). The combined organic phases were dried over anhydrous Na₂SO₄ and the solvent removed in vacuo. The crude was dissolved in CH2CI2 and purified over a silica pad (2CV 2:1 PE: EtOAc, 5CV 1:2 PE: EtOAc) to obtain the product as a colorless foam. HRMS: m / z calculated for [C₄₀H₅₄O₂₇+H⁺]: 989.2750, found: 989.2718. Rf (PE / EtOAc, 1:1) = 0.23

[0100] Synthesis of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6~(((2R,3R,5R,6R)-4,5- diacetoxy-2-(acetoxymethyl)-6-(((2R,3R,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(3- azidopropoxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate:

[0101] Ac-Maltotriose (800 mg, 0.83 mmol, 1.0 eq) was dissolved in 8 ml anhydrous CH2CI2 and cooled down to -70 °C. Then BF₃·Et₂O (511 µl, 4.14 mmol, 5.0 eq) were added and stirred for 15 min before the addition of 3-azido-1-propanol (228 µl, 2.48 mmol, 3.0 eq). The mixture was stirred at -70 °C for 45 min and then let to warm up to rt and stirred overnight. After completion of the reaction (TLC, LCMS), it was quenched with freshly distilled Et₃N (5.0 eq, 70 µl) and the solvent removed in vacuo. The residue was dissolved in EtOAc (50 ml), washed with brine (3x50ml) and the combined organic phases dried over anhydrous Na2SO4 and the solvent removed in vacuo. The crude was purified by flash column chromatography (silica, PE: EtOAc gradient, main separation at 60% EtOAc) to obtain the product as a colorless foam (215 mg, 0.22 mmol, 26%).¹H-NMR (400 MHz, CDCl₃) 6 = 5.44 - 5.30 (m, 3H), 5.30 - 5.21 (m, 2H), 5.06 (t, J = 9.9 Hz, 1 H), 4.89 - 4.76 (m, 2H), 4.73 (dd, J = 10.3, 4.1 Hz, 1H), 4.52 (d, J = 7.9 Hz, 1H), 4.52 -4.41 (m, 2H), 4.35-4.14 (m, 3H), 4.09-4.01 (m, 1H), 4.00- 3.87 (m, 5H), 3.76 (t, J = 6.0 Hz, 2H), 3.73 - 3.68 (m, 1 H), 3.63 - 3.57 (m, 1 H), 3.45 (t, J = 6.6 Hz, 2H), 3.39 - 3.30 (m, 2H). 2.17 (s, 3H), 2.15 (s, 3H), 2.09 (s, 3H), 2.05 (s, 3H), 2.04 - 1.96 (m, 18H), 1.87 - 1.77 (m, 2H). ¹³C-NMR (101 MHz, CDCl₃) 5 - 170.78, 170.73, 170.69, 170.64, 170.52, 170.26, 170.00, 169.86, 169.84, 169.59, 100.38, 95.87, 95.80, 75.40, 73.91, 72.59, 72.29,72.24, 71.88, 70.58, 70.19, 69.49, 69.04, 68.63, 68.01, 66.60, 63.03, 62.44, 61.50, 60.08, 48.64, 48.09, 31.57, 29.09, 21.05, 21.02, 20.95, 20.82, 20.79, 20.74, 20.72, 20.70. HRMS: calculated for [C₄₅H₆₂N₃O₂₆+Na⁺] = 1030.3128, found 1030.3120. Rf (PE / EtOAc, 1:2, MOPS stain) = 0.51.

[0102] Synthesis of (2R,3R54S,5RJ6R)-2-(acetoxymethy!)-6-(((2RJ3R,5R,6R)-4,5- diacetoxy-2~(acetoxymethyl)-6-(((2R)3RJ5R!6R)-4,5-diacetoxy-2~(acetoxymethyl)-6-( 3-ammopropoxy [tetrahy dro-2H -pyran -3~y )oxy)tetrahydro-2H -pyran -3- ynoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate:OAc

[0103] The prior product (100 mg, 97.0 pmol, 1.0 eq) was dissolved in THF (0.01 M) and the flask flushed with nitrogen. Then Pd / C (10 wt% Pd, 20 mg) was added and the mixture stirred in a hydrogen atmosphere at rt overnight. After completion of the reaction, the mixture was diluted with EtOAc and filtered over syringe filter. The filtrate was concentrated under reduced pressure to obtain the crude product which was purified with column chromatography (silica, Cf- Ch / MeOH, main separation at 10% MeOH) The product was obtained as a colorless solid (62 mg, 64.0 pmol, 66%). H NMR (400 MHz, CDCb) 5 = 5.43 - 5.26 (m, 5H), 5.07 (t, J - 9.9 Hz, 1H), 4.85 (dd,10.5, 4.0 Hz, 1H), 4.81 - 4.67 (m, 3H), 4.56 - 4.51 (m, 1 H), 4.50 - 4.44 (m, 1H), 4.29 -4.16 (m, 3H), 4.07 - 3.87 (m, 6H), 3.79 - 3.69 (m, 2H), 3.25 - 3.06 (m, 2H), 2.25 - 1.98 (m, 30H), 1.82 - 1.78 (m, 4H). ¹³C NMR (101 MHz, CDCl₃) 5 = 171.27, 170.98, 170.71, 170.64, 170.48, 170.08, 169.97, 169.78, 169.55, 100.33, 95.81, 95.71, 74.78, 73.50, 72.53, 72.44, 72.15, 71.84, 70.57, 70.13, 69.44, 69.04, 68.58, 68.00, 67.61, 62.58, 62.38, 61.45, 60.49, 38.04, 27.09, 21.15, 20.99, 20.95, 20.94, 20.92, 20.77, 20.68, 20.66, 14.28. HRMS: calculated for [C₄₁H₅₉NO₂₆+Na⁺] = 1004.3223, found 1004.3242. Rf (CH₂Cl₂ / MeOH 9:1, Ninhydrin stain) = 0.3.

[0104] Synthesis of (2R,3R(4S,5R,6R)-2-(acetoxymethyl)-6-(((2R,3R,5R,6R)-4?5- diacetoxy-2-(acetoxymethy )-6-(((2RJ3R,5R!6R)-4,5-diacetoxy-2-(acetoxymethy )-6-((5-az§dopentyl)oxy)tetrahydro-2H"pyran"3-yl)oxy)tetrahydro-2H-pyran-3- yl)oxy)tetrahydro-2H"pyran~3,4,5-triyl triacetate:OAc

[0105] Ac-Maltotriose (200 mg, 0.21 mmol, 1.0 eq) was dissolved in 2 ml anhydrous CH2CI2 and cooled down to -70 °C. Then BF₃·Et₂O (128 µl, 1.03 mmol, 5.0 eq) were added and stirred for 15 min before the addition of 3-azido-1-propanol (72.9 µl, 0.62 mmol, 3.0 eq). The mixture was stirred at -70 °C for 45 min and then let to warm up to rt and stirred overnight After completion of the reaction, it was quenched with freshly distilled Et₃N (70 µl) and the solvent removed in vacuo. The residue was dissolved in EtOAc (30 ml), washed with brine (3x30ml) and the combined organic phases dried over anhydrous Na₂SO₄ and the solvent removed in vacuo. The crude was purified by flash column chromatography (silica, PE: EtOAc gradient, main separation at 60% EtOAc) to obtain the product as a colorless foam (22.5 mg, 0.02 mmol, 11%).¹H-NMR (400 MHz, CDCl₃) 5 = 5.43 - 5.31 (m, 3H), 5.30 - 5.21 (m, 2H), 5.06 (t, 1 H), 4.88 - 4.70 (m, 3H), 4.53 - 4.40 (m, 3H), 4.34 - 4.14 (m, 3H), 4.04 (dd, J = 12.5, 2.4 Hz, 1 H), 4.01 - 3.89 (m, 4H), 3.85 (dt, J = 9.7, 6.2 Hz, 1 H), 3.73 - 3.65 (m, 1 H), 3.48 (m, 1 H), 3.25 (t, J = 6.8 Hz, 2H), 2.20 - 1.94 (m, 30H), 1.64 - 1.54 (m, 3H), 1.45 - 1.35 (m, 2H), 1.25 - 1.23 (m, 1 H).¹³C-NMR (101 MHz, CDCl₃) 5- 170.60, 170.56, 170.51, 170.46, 170.34, 170.13, 169.82, 169.70, 169.63, 169.42, 100.18, 95.69, 95.65, 75.32, 73.85, 72.49, 72.21, 72.03, 71.74, 70.43, 70.04, 69.63, 69.34, 68.86, 68.48, 67.87, 62.97, 62.32, 61.35, 51.31, 28.90, 28.49, 23.12, 20.88, 20.87, 20.86, 20.78, 20.65, 20.60, 20.56, 20.55, 20.53. HRMS: calculated for [C₄₃H₅₁N₃O₂₆+Na⁺] = 1058.3441, found 1058.3486. Rf (PE / EtOAc = 1:1): 0.35.

[0106] Synthesis of (2R,3Rs4SJ5R,6R)-2-(acetoxymethyl)-6-(((2R,3RJ5R56R)-4J5- d§acetoxy~2“(acetoxymethyl)-6"(((2Rs3R!5R,6R)~4,5~d§acetoxy~2“(acetoxymethyl)~6" ((6-az dohexy )oxy)tetrahydro-2H-pyran-3“yl)oxy)tetrahydro-2H-pyran-3" yl)oxy)tetrahydro-2H-pyran-3,4,5-triy triacetate:OAc

[0107] Ac-Maltotriose (146.3 mg, 0.15 mmol, 1.0 eq) was dissolved in 1.5 ml anhydrous CH2CI2 and cooled down to -70 °C. Then BFs-Et20 (93 pl, 0.76 mmol, 5.0 eq) were added and stirred for 15 min before the addition of 3-azido-1 -propanol (65.0 mg, 0.45 mmol, 3.0 eq). The mixture was stirred at -70 °C for 45 min and then let to warm up to rt and stirred overnight. After completion of the reaction, it was quenched with freshly distilled Et₃N (70 µl) and the solvent removed in vacuo. The residue was dissolved in EtOAc (30 ml), washed with brine (3x30ml) and the combined organic phases dried over anhydrous Na2SO4 and the solvent removed in vacuo. The crude was purified by flash column chromatography (silica, PE: EtOAc gradient, main separation at 60% EtOAc) to obtain the product as a colorless foam (37.9 mg, 0.04 mmol, 24%).1H-NMR (400 MHz, CDCl3) 6 = 5.44 - 5.20 (m, 4H), 5.11 - 5.01 (m, 1 H), 4.90 - 4.68 (m, 3H), 4.50 (d, J = 7.9 Hz, 1H), 4.45 (dt, J = 12.3, 3.1 Hz, 2H), 4.35 - 4.13 (m, 3H), 4.04 (dd, J = 12.5, 2.4 Hz, 1 H), 3.94 (tdd, J = 9.7, 7.5, 4.2 Hz, 3H), 3.84 (dt, J = 9.6, 6.3 Hz, 1H), 3.74 - 3.62 (m, 2H), 3.47 (dt, J - 9.9, 6.7 Hz, 1H), 3.31 - 3.21 (m, 3H), 2.18 - 2.13 (m, 5H), 2.11 - 1.91 (m, 21 H), 1.68 - 1.52 (m, 7H), 1.49 - 1.30 (m, 3H).13C-NMR (101 MHz, CDCl3) 5 = 170.76, 170.71, 170.67, 170.64, 170.51, 170.29, 169.98, 169.86, 169.77, 169.58, 100.35, 95.84, 95.80, 75.48, 74.02, 72.65, 72.38, 72.17, 71.89, 70.59, 70.20, 69.98, 69.50, 69.01, 68.63, 68.02, 63.16, 62.74, 62.48, 61.51, 51.51, 51.46, 32.29, 29.37, 28.89, 28.78, 26.51, 25.54, 23.13, 21.03, 21.02, 20.95, 20.93, 20.80, 20.78, 20.72, 20.71, 20.68. HRMS: calculated for [C44H63N3O26+Na+] = 1072.3597, found 1072.3568. Rf(PE / EtOAc = 1:1): 0.34.

[0108] Synthesis of sodium 2-((1E,3Z,5E)-4-((7-((3-(((2R,3R,5S,6R)-5- (((2RJ3R,5S,6R)-354-dshydroxy-6-(hydroxymethyl)-5-(((2RJ3RJ4S,5S!6R)-3J4,5- trihydroxy~6"(hydroxymethyl)tetrahydro-2H"pyran-2”yl)oxy)tetrahydro-2H-pyran"2- yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2- yl)oxy)propyl)amino)-7“Oxoheptyl)carbamoyl)“7”((E)-3,3"dimethyl~5“Sulfonato-1"(4”sulfonatobutyl)indolin-2~yiidene)hepta-,3,5-trien-l -yl)"3,3-dimethyl-1 -(4- sulfonatobutyl)-3H-mdol-1-ium-5-suifonate ( alto-Amide-sNIR; Fig. 3B):

[0109] The sNIR-NHS (1 eq, 0.013 mmol, 15 mg) was dissolved in 900 pl DMF and Maito-C3~amine (1.1 eq, 0.014 mmol 14.1 mg) and DIPEA (6 eq, 0.078 mmol, 14 pl) were added. The mixture was stirred for 90 min at rt. Then 200 pl of NaOMe in MeOH solution (25%wt) were added and the mixture stirred for 5 min at rt. After completion of the reaction (LCMS). the mixture was quenched with 50 pl acetic acid and the solvent removed in vacuo. The crude was purified using reverse phase column chromatography (C-18 gradient of H2O / MeCN, 0.05% TEA, product at 20% MeCN). The product was obtained as a green solid(2.2 mg, 1.38 pmol, 11%). Liquid chromatography data and mass spectrometry data are provided in Fig. 8A. LC-MS (05~95__13 min): tR = 5.3 min, m / z calc, for [C64H94N4O30S4 - 2H+ 2“= 762.85 [M-2H; found 762.34.

[0110] Synthesis of sodium 2-((1EJ3Z,5E)-4-((7-((3-(1-(3-(((2R!3Rs5S,6R)-5-(((2R,3R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(((2R,3R,4S,5S,6R)-3,4,5- trihydroxy-6-(hydroxymefhyi)tetrahydrO“2H~pyran-2-yl)oxy)tetrahydro"2H"pyran-2- ynoxy)-3,4~dihydroxy~6-(hydroxymethyl)tetrahydro~2H"pyran-2-yl)oxy)propyl)"1,9~ djhydro-8H-dibenzo[b,fl[1,2l3]triazolo[4s5-d]a ocin-8-yl)-3-oxopropyl)am o)-7- oxoheptyl)carbamoyi)-7"((E -3?3-dimethyl-5-sulfonato~1-(4”Sulfonatobutyi)indoiin~ 2-ylidene)hepta-1,3,5-trien-1 -yl)-3s3-dimethyl-1 ”(4-sulfonatobutyl)-3H- dol-1 -ium- 5-suifonate (Malto-DBCO-sNIR; Fig. 3C):Molecular Weight: 1895.3763

[0111] The sNIR-DBCO (1eq, 0.004 mmol, 4.7 mg) was dissolved in 0.5 ml DMF and Maltotriose-C3-azide (1.1, eq, 0.004 mmol, 4.0 mg) was added. The reaction mixture was stirred at rt for 45 min. After completion of the reaction, 100 pl NaOMe in MeOH solution (25wt%) were added and stirred at rt for 30 min. After complete deprotection, the reaction was quenched with 50 pl of acetic acid. The mixture was added to ice cold Et20 and the precipitate obtained via centrifugation (2x at 4500 rpm for 3 min). The precipitate was dissolved in water and purified with reverse phase flash column chromatography (C-18, gradient of H2O / MeCN, 0.05% TFA, product at 20% MeCN). The product was obtained as a green solid. Liquid chromatography data and mass spectral data are provided in Fig.8B. LC- S (05-95 3 min): tR= 6.0 min, m / z calc, for [C82H108N8O31S4 - 3H+]3'= 609.01 M-2H*]3’; found 609.26.

[0112] Synthesis of sodium 2-((1E,3Z,5E)~4-((4-(1~(3-(((2Rs3R!5S,6R)-5~ (((2Rs3R,5S!6R)-3,4-dihydroxy-6-(^ydroj(:ym^hyl)-5"(((2R!3R!4Ss5S,6R)-3!4s5- trihydroxy"6~(hydroxymethyl)tetrahydTO~2H~pyran~2"ynoxy)tetrahydro-2H-pyran-2- yl)oxy)"3s4-dihydroxy-6-(^ydroxymethyi)tetrahydro-2H"pyran"2-yi)oxy)propyi)" H" 1s2,3-triazol-4-yl)butyl)carbamoyl)-7-((E)-3i3-dimethyl-5-s lfonato-1-(4- sulfonatobutyl)indolin-2"ylidene)hepta~,3,5-trien-1 "yl)~3,3“dimethyl-1 -(4- suifonatobutyl)-3H-indol-1-ium-5" Sulfonate ( alto-C3-sNiR; Fig. 3D):

[0113] The solvents used were degassed for 15 min in a sonication bath prior to use. The 3-azidopropoxy maltotriose compound (10.6 mg, 0.01 mmol, 1.0 eq) and sNIR-alkyne (10 mg, 0.01 mmol, 0.95 eq) were dissolved in 0.3 ml of water and 0.1 ml of tBuOH. Then the catalyst solution containing copper sulfate pentahydrate (10.5 mg, 0.04 mmol, 4.0 eq), THPTA (18.3 mg, 0.04 mmol, 4.0 eq) and sodium ascorbate (10.4 mg, 0.05 mmol, 5.0 eq) in 0.4 ml water were added. The mixture was stirred for 1 h at rt. After the completeness of the reaction, the crude was directly purified via column chromatography (C18, H2O / MeCN (TFA 0,05 %) to obtain the acetylated product. For deprotection, the acetylated compound was dissolved in 1 ml MeOH and NaOMe / MeOH (25 w%) was added until pH 9 was reached. The mixture was stirred for 2 h at rt and after complete deprotection, Amberlite IR 120 resin was added. The solvent was removed in vacuo and the crude purified via column chromatography (C18, HaO / MeCN (TFA 0.05 %) to obtain the product as a green solid (1.5 mg, 0.9 pmol, 9 %). Liquid chromatography data and mass spectral data are provided in Fig. 8C. LC-MS (05-95__13 min): tR= 5.1 min, m / z calc, for [C63H90N6O29S4 - 3H+]3- 506.84 [M-2H; found 506.61.

[0114] Synthesis of sodium 2-((1E53Z,5E)-4-((4-(1~(5-(((2R,3R,5S,6R)-5- (((2R,3R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyi)-5-(((2R,3R,4SJ5S,6R)-3,4J5- trihydroxy-6-(hydroxymethyi)tetrahydro“2H~pyran-2-yl)oxy)tetrahydro"2H~pyran-2- ynoxy)-3,4-dlhydroxy-6-(hydroxymethy )tetrahydro-2H-pyran-2~yl)oxy)pentyl)-1H- 1s2J3-triazol-4-yl)butyncarbamoy )-7-((E)-3)3-dimethyl-5-sulfonato"1-(4- su fonatob tyl)mdo ~2-y dene)hepta~,3,5-trien-1 -y )-3,3-dimethyl~1 -(4- su fonatobuty )-3H-mdol-14um-5-suifonate ( aho-CS-sNIR F g. 3E):

[0115] The solvents used were degassed for 15 min in a sonication bath prior to use. The 5-azidopentaloxy maltotriose compound (6.3 mg, 6.1 pmol, 1.0 eq) and sNIR-alkyne (5.8 mg, 5.8 pmol, 0.95 eq) were dissolved in 0.3 ml of water and 0.1 ml of tBuOH. Then the catalyst solution containing copper sulfate pentahydrate (6.1 mg, 0.02 mmol, 4.0 eq), THPTA (10.6 mg, 0.02 mmol, 4.0 eq) and sodium ascorbate (6.0 mg, 0.03 mmol, 5.0 eq) in 0.4 ml water were added. The mixture was stirred for 1 h at rt. After the completeness of the reaction, the crude was directly purified via column chromatography (C18, H2O / MeCN (TFA 0,05 %) to obtain the acetylated product. For deprotection, the acetylated compound was dissolved in 1 ml MeOH and NaOMe / MeOH (25 w%) was added until pH 9 was reached. The mixture was stirred for 1 h at rt and after complete deprotection, Amberlite IR 120 resin was added. The solvent was removed in vacuo and the crude purified via column chromatography (C18, H2O / MeCN (TFA 0.05 %) to obtain the product as a green solid (2.4 mg, 1.5 pmol. 26 %). Liquid chromatography data and mass spectral data are provided in Fig. 8D. LC-MS (05-95__13 min): tR= 5.1 min, m / z calc,for [C65H94N6O29S4 - 516.24 [M-2H ]3"; found 516.22.

[0116] Synthesis of sodium 2-((1E,3Z,5E)-4-((4-(1-(6-(((2R,3R,5S,6R)-5- (((2R,3R,5S,6R)-3)4-dihydroxy-6-(hydroxymethyn-5-(((2RJ3RJ4Ss5S,6R)-3>4s5- trihydraxy-6-(hydroxymethyl)tetrahydi"o-2H-pyran-2-yl)oxy)tetrahydTO-2H"pyran-2- ynoxy)"3s4-dihydroxy-6-(hydroxymethyi)tetrahydro-2H-pyran"2-yl)oxy)hexyl)-1H" 1,2,3"triazol~4”ynbutyncarbamoyl)~7~((E)-3i3~d!methyF5" S lfonato"1~(4~ sulfonatobutyl)indoiin-2-yiidene)hepta-1,3s5-trien-1 -yl)-3,3-dimethyi-1 -(4- suifonatobutyl)-3H"indol-1-mm~5-sulfonate ( alto-C6-sNiR; Fig. 3F):

[0117] The solvents used were degassed for 15 min in a sonication bath prior to use. The 6-azidohexyloxy maltotriose compound (4.2 mg, 4.0 pmol, 1.0 eq) and sNIR-alkyne (3.8 mg, 3.8 pmol, 0.95 eq) were dissolved in 0.3 ml of water and 0.1 ml of tBuOH. Then the catalyst solution containing copper sulfate pentahydrate (4.0 mg, 0.16 mmol, 4.0 eq), THPTA (7.0 mg, 0.16 mmol, 4.0 eq) and sodium ascorbate (4.0 mg, 0.02 mmol, 5.0 eq) in 0.4 ml water were added. The mixture was stirred for 1 h at rt. After the completeness of the reaction, the crude was directly purified via column chromatography (C18, H2O / MeCN (TFA 0.05 %) to obtain the acetylated product. For deprotection, the acetylated compound was dissolved in 1 ml MeOH and NaOMe / MeOH (25 w%) was added until pH 9 was reached. The mixture was stirred for 1 h at rt and after complete deprotection, Amberlite IR 120 resin was added. The solvent was removed in vacuo and the crude purified via column chromatography (C18, HaO / MeCN (TFA 0,05 %) to obtain the product Malto-C6-sNIR (C6.3.016) as a green solid (2.8 mg, 1.72 pmol, 45 %). Liquid chromatography data and mass spectral data are provided in Fig. 8E. LC-MS (05-95_13 min): tR= 5.3 min, m / z calc, for [C66H97N6O29S4 - 3H+p = 521.25 M-2H; found 521.39.

[0118] Synthesis of Hexakis(2,3s6"tri"0-acety )-a--cyclodextrin:Chemical Formula: C72H96O48Exaci Mass. 1728.5071Molecular Weight: 1729.5120

[0119] To a solution of a-cyclodextrin (2.0 g, 2.1 mmol, 1.0 equiv.) in anhydrous pyridine (25.0 mL), AC2O (25.0 mL) and DMAP (25 mg, 206 pmol, 0.1 equiv.) weresuccessively added at 0 °C and under an inert nitrogen atmosphere. The solution was stirred at room temperature overnight when TLC (EtOAc) shows formation of a single fast-moving spot. The mixture was concentrated under reduced pressure, dissolved in EtOAc (75 mL). and washed with H2O (2 * 100 mL) and brine (1 * 100 mL). The organic phase was dried over anhydrous MgSC, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Heptanes / EtOAc 70:30 — > 0:100) to yield hexakis(2,3,6-tri-O-acetyl)-a-cyclodextrin as a white solid with a yield of 99% (3.53 g, 2.0 mmol).1H NMR (400 MHz, CDCl3) δ 5.55 (6H, dd, J = 10.3, 8.6 Hz, 6xH-3), 5.05 (6H, d, J = 3.6 Hz, 6xH-1 ), 4.76 (6H, dd, J = 10.3, 3.5 Hz, 6*H-2), 4.41 (12H, d, J - 3.4 Hz, 6xCH2-6), 4.18 (6H, dt, J = 9.4, 3.7, 3.1 Hz, 6*H- 5), 3.79 (6H, dd, J ■= 9.4, 8.7 Hz, 6xH-4), 2.17 (18H, s, 6xOAc), 2.06 (18H, s, 6xOAc), 2.05 (18H, s, 6xOAc) ppm. MS: (ESI) m / z calcd C72H96O48Na, 1751.2 [M+Na]+: found 1751.2. MS: (ESI) m / z calcd C72H97O48, 1729.2 [M+H]+; found 1729.2.= 0.29 (EtOAc).

[0120] Synthesis of 2,3,456-Tetra" O"acetyl-a-d-glucopyranosyL(1 >4)-2.3,6"t i-O- acetyl-a-d-glucopyranosyb(T *4)-2,3,6"t i-0-acetyl-a“d"glucopyranosyl-(1 >4)- 2,3!6-tri-O-acetyha-d-glucopyranosy -(1— >4)”2s3,6~tri-0-acetyl-a~d-glucopyranosyl- (1>4)-152J3.6-tetra-O’acetyha-d-glucopyranose / Icosa-O-acetyl-a-maltohexaose:OA.cExact Mass: 1830.5388Molecular Weight: 1831.6010

[0121] Hexakis(2,3,6-tri-O-acetyl)-a-cyclodextrin (3.56 g, 2.0 mmol) was dissolved in 50 mL of AC2O / H2SO4 mixture (49:1) and the mixture was stirred at 60 °C overnight when TLC (EtOAc) shows approximately 50% conversion, while formation of one main product (Rf = 0.60) and several faster-moving byproducts (shorter oligosaccharides) was observed. To prevent further cleavage of the main product, the reaction mixture was poured into a separatory funnel containing H2O (100 mL) and the solution was extractedwith CH2CI2 (300 mL). The organic phase was successively washed with sat. NaHCCh (100 mL) and brine (100 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Heptanes / EtOAc 80:20 — » 0:100) to yield icosa-O-acetyl-o-maltohexaose (a / p 7:1) as a yellowish foam with a yield of 41 % (1.56 g, 854 pmol).

[0122] Synthesis of 2,3,4,6-Tetra-O"acetyl"a-d”glucopyranosyi-(1-^4)-2,3,6~tri-O~ acetyLa-d-glucopyranosyh(1~ 4)-2,3,6-tri-0-acetyl-a-d-g ucopyranosyI--(1_>4)- 2,3!6-tri-0-acety -a-d-glucopyranosyb(1 »4)-2!3s6-tri-0-acetyl"a-d-g^ucopyranosyl" (1-_ 4)-1s2,3,6"tetra" O-acety ~p-d-glucopyranose / Icosa-O-acetyl-p-maltohexaose:Exact Mass: 1830.5388Molecular Weight: 1831.6010

[0123] Icosa-O-acetyl-a-maltohexaose (1.0 g, 546 pmol) was dissolved in anhydrous MeOH (22 ml.) and 10% NaOMe was added until pH > 10 and the reaction mixture was stirred overnight when precipitate was observed and LCMS showed only the product formed (m / z 991.2 [M+H] ). The reaction mixture was neutralized by the addition of Dowex 50W hydrogen form resulting in dissolving of the precipitate. The solution was filtered, and the solution was concentrated under reduced pressure. To the crude product, AC2O (12 mL) and NaOAc (400 mg) were successively added, and the suspension was refluxed (100 °C, oil bath) overnight resulting in a clear solution. The conversion of the reaction was checked by TLC (EtOAc) showing formation of a single product (Rf - 0.60). The reaction mixture was let cool down and subsequently poured into a separatory funnel (500 mL) containing sat. NaHCOs (100 mL) and CH2CI2 (100 mL). The two-phase mixture was shaken until no gas evolution. The aqueous phase was reextracted with CH2CI2 (100 mL) and the combined organic phases were dried over anhydrous MgSCh, filtered, and concentrated under reduced pressure. The residue was purified by columnchromatography on silica gel (Heptanes / EtOAc 80:20 ■■■■> 0:100) to yield icosa-O-acetyi- p-maltohexaose (a / p 1:3) as a yellowish foam with a yield of 89% (894 mg, 488 pmol).1H NMR (400 MHz, CDCl3) δ 6.23 (0.24H, d, J = 3.8 Hz, H-1a), 5.74 (0.76H, d, J = 8.1 Hz, H-1 ), 5.43 - 5.31 (6H, m), 5.29 - 5.25 (3H, m), 5.06 (1H, t,9.9, 9.9 Hz), 5.01 - 4.92 (1H, m), 4.85 (1H, dd, J = 10.5, 4.0 Hz), 4.78- 4.58 (3H, m), 4.60 -4.42 (4H, m), 4.40 -4.09 (6H, m), 4.09 - 3.82 (11 H, m), 2.24 - 1.92 (60H, set of singlets, 20 OAc) ppm. MS: (LCT-MS_5-95_5min) m / z calcd C74H99O49, 1771.5 [M-OAc-H2O+H]+; found 1771.2. Rf= 0.60 (EtOAc).

[0124] Synthesis of 3-Azidopropyl a"d-glucopyranosyh( -*4)~a-d~ glucopyranosyl-(1 4)-a-d-g ucopyranosyl-(1 >4)-a-d-g ucopyranosyl-(1 >4)-a-d-glucopyranosyl"(1-->4)~p~d”glucopyranoside / p-3-Azidopropyl maltohexaoside:OH-hemica! Formula: C3gH67N3O:.|Exact Mass: 1073.3759Moiecuiar Weight: 1073 9550

[0125] To a solution of icosa-O-acetyl-p-maltohexaose (100 mg, 546 pmol, 1.0 equiv.) in anhydrous CH2CI2 (550 pL), 3-azidopropan-l -al (22 mg, 218.4 pmol, 4.0 equiv.) and BFs OEt? (62 pL, 436.8 pmol, 8.0 equiv.) were added successively at room temperature. The mixture was stirred for 2 h (no reaction progress according to TLC - Rr = 0.66; EtOAc) at room temperature. Because of partial deacetylation, EtaN (1.5 mL), AC2O (1.0 mL), and DMAP (cat.) were successively added to the reaction mixture which was stirred for an additional 2 hours. The mixture was then poured into a separatory funnel containing CH2CI2 (50 mL) and a saturated solution of NaHCCh (50 mL). The two-phase mixture was shaken until no gas evolution. The aqueous phase was reextracted with CH2CI2 (50 mL) and the combined organic phases were dried over anhydrous MgSC, filtered, and concentrated under reduced pressure. The residue was purified by columnchromatography on silica gel (Heptanes / EtOAc 80:20 ■■■■■> 0:100) to yield per-O-acetylated p-3-azidopropyl maltohexaoside as a yellowish solid with a yield of 63% (64 mg, 34.2 pmol). The peracetate was directly dissolved in anhydrous MeOH (10 mL) and 10% NaOMe was added until pH > 10 and the reaction mixture was stirred for 2 hours LCMS showed only the product formed (m / z 1074.4 [M+H]+). The reaction mixture was neutralized by the addition of Dowex 50W hydrogen form resulting in dissolving of the precipitate. The solution was filtered, and the solution was concentrated under reduced pressure providing p-3-azidopropyl maltohexaoside as yellowish solid with a quantitative yield (36 mg, 33.5 pmol). LC-MS: m / z calcd C39H68N3O31, 1074.4found 1074.3. Rt = 0.63 min.

[0126] Synthesis of 2-((1E,3Z,5E)-7-((£)-3,3-d!methyl-5-sulfo~1-(4- ssj fobutyQindoHn-2-y idene)-4-((4-(1"(3-((a’d-g^copyranosy "( “^4)-a-d“ g ucopyranosyl-(1 ->4)-a-d-glucopyranosyi-(1 >4)-a-d-gtocopyranosyl-(1 4)-a-d-g ucopyranosyb(1~ 4)-p-d-g§ucopyranosyl)oxy)propyn-1H-5253-triazol-4- yl)buty )carbamoy )hepta-1,3!5-trien-1-yl)-3!3-dimethyh1-(4-sulfobuty )-3H-indol-1- ium-5-su fonate (MaHohexose-C3-s IR; Fig, 3G):OHChemical Formula: C8< H!,7N6Na3O,;4S,1Exact Mass: 2074 5678Molecular Weight: 2075 0343

[0127] The solvents used were degassed for 15 min in a sonication bath while being bubbled with N2 prior to use. The p-3-azidopropyl maltohexaoside (5.1 mg, 4.7 pmol, 1.0 equiv.) and sNIR-alkyne (4.5 mg, 4.5 pmol, 0.95 equiv.) were dissolved in 0.3 ml of deionized water. Then the catalyst solution containing CUSO4.5H2O (4.7 mg, 19.0 µmol,4.0 equiv.), THPTA (8.2 mg, 19.0 µmol, 4.0 equiv.), and sodium ascorbate (4.7 mg, 23.7 µmol, 5.0 equiv.) in 0.4 ml water was added. The mixture was stirred for 1 h at rt. After the completeness of the reaction (LCMS), the crude was directly purified via column chromatography (C18, H₂O / MeCN (TFA 0.05 %) to obtain the product as a green solid (3.33 mg, 1.60 µmol, 34 %) after lyophilization. Liquid chromatography data and mass spectral data are provided in Fig. 8F. LC-MS (05-95__13 min): tR ~ 4.9 min, m / z calc, for [C81H120N6O44S4– 3H+]3-669.03found 669.26.

Claims

WHAT IS CLAIMED IS:

1. A compound of formula:wherein:, R1, R2, R6, R7, R14, R15, R16, R17, and R18are each independently: H or (C1-C6)alkyl;R3is -SO3X3or COOH;R5is -SO3X4;R8, R9, R10, R11, R12, and R13are each independently: H, CN, -COO(Ci-C6)alkyl, -CONH(Ci-C6)alkyl, CL Br, I, F, -CF3, ~O(Ci-C6)alkyl, -NR14R15, -NHC(O)(Ci-C6)alkyi, -NHC(O)NH (Ci.-C6)alkyl, -SO3H, -SO2NH2, or (Ci-C6)alkyl;R19and R20are each independently: H, (Ci-C6)alkyl, -O(Ci-C6)alkyl, Cl, F, Br, CN, C(O)NH2;L is one or more of: -(CH2)ni-, -(Ci-C6)cycloalkylene~, ■-(C^Cs)heterocycloaikylene-, -0- -NR16-, -NH-, -NHC(O)-, -C(O)NR17, -CH(OH)-, and -CH(OR18)-;Li is a suitable linking moiety;L2 is one or more of: -(CH2)m-, -(Ci-Cejcycloalkylene-, -(Ci-Cejheterocycloalkylene-, -O- -NR16-, -NH-, -NHC(O)-, -C(O)NR17, -CH(OH)-, and -CH(OR18)-:X1, X2, X3, and X4are each independently: a cation, a proton, or absent;Q is -(CH2)n2- wherein any H is optionally replaced with (Ci~C6)alkyl;Y is -(CH2)n3-, wherein any H is optionally replaced with (Ci-C6)alkyl;Z is a maltodextrin polysaccharide;ni is an integer between 1 to 30:n2 and n3 are each independently an integer between 1 to 10.

2. The compound of claim 1, wherein the compound has the formula:

3. The compound of claim 1. wherein the compound has the formula:

4. The compound of claim 1, wherein the compound has the formula:

5. The compound of claim 1, wherein the compound has the formula:

6. The compound of claim 1, wherein the compound has the formula:

7. The compound of claim 1, wherein the compound has the formula:

8. The compound of claim 1:wherein the compound is a pharmaceutically acceptable salt.The compound of claim 1, wherein L1 is selected from:wherein R21is H or (Ci-C6)alkyl,, and -CO-.

10. The compound of claim 1, wherein the maltodextrin polysaccharide is between 2 and 30 glucose monomers.

11. The compound of claim 10, wherein the maltodextrin polysaccharide is 3 glucose monomers.

12. The compound of claim 10, wherein the maltodextrin polysaccharide is 6 glucose monomers.

13. The compound of claim 1, wherein the maltodextrin polysaccharide is digestible.

14. The compound of claim 1, wherein the maltodextrin polysaccharide is resistant.

15. The compound of claim 1, wherein the compound is formulated for administration into a human recipient.

16. A method of detecting bacteria in an animal, comprising:administering a maltodextrin with NIR dye conjugate probe to a recipient, wherein the maltodextrin with NIR dye conjugate probe is a compound of Formula II;illuminating small-wavelength infrared or near infrared light onto the recipient; detecting emission of the maltodextrin with NIR dye conjugate probe.

17. The method of claim 16, wherein illuminating small-wavelength infrared or near infrared light and the detecting emission of the maltodextrin with NIR dye conjugate probe is performed within one hour of administering the maltodextrin with NIR dye conjugate probe to the recipient.

18. The method of claim 16, wherein administering the maltodextrin with NIR dye conjugate probe to the recipient is a systemic administration.

19. The method of claim 16, wherein administering the maltodextrin with NIR dye conjugate probe to the recipient is a local administration.

20. The method of claim 16, wherein detecting emission of the maltodextrin with NIR dye conjugate probe comprises the use of a fluorescent imaging modality or a photoacoustic imaging modality.

21. The method of claim 16, wherein detecting emission of the maltodextrin with NIR dye conjugate probe comprises deep-tissue imaging or a systemic scan.

22. The method of claim 16 further comprising:monitoring one or more of: bacterial colony growth, bacterial spread, and bacterial clearance.

23. The method of claim 16 further comprising:surgically removing infected tissue, wherein a location and boundaries of the infected tissue is identified by the emission of the maltodextrin with NIR dye conjugate probe.

24. The method of claim 16, wherein the recipient comprises an installed implant; wherein illuminating small-wavelength infrared or near infrared light is directed at the position of at the installed implant.

25. The method of claim 16, wherein the recipient comprises a wound; wherein illuminating small-wavelength infrared or near infrared light is directed at the position of at the wound.

26. The method of claim 16, wherein the recipient has been administered a treatment for a bacterial infection; wherein detecting emission of the maltodextrin with NIR dye conjugate probe is to assess efficacy of the treatment.

27. The method of claim 16, wherein imaging illuminating small-wavelength infrared or near infrared light onto the recipient comprises one or more of: topical imaging, near skin imaging, and scope-guided internal procedures.

Images