367 results about "BODIPY" patented technology

Methods and materials for the imaging of cells containing active proteases such as cathepsin are disclosed. The present materials include activity based probes that bind to an enzyme and are subsequently cleaved. Cleavage results in a fluorescent signal due to removal of a quenching group which, when present on the probe causes altered or no fluorescence. The probes employ an acyloxymethyl ketone reactive group, one or more amino acids for determining specificity, a fluorophore and a quencher. The probes are cell permeable and may use, for example, a QSY7 (diarylyrhodamine) quencher and a BODIPY (bora-diaza-indecene) dye.

The invention discloses a fluorine-boron fluorescent dye as well as a preparation method and application thereof, wherein the structure of the fluorine-boron fluorescent dye is shown as a formula (I) or a formula (II), in the formula (I) and the formula (II), R1 is H or halogen; R2 is CN; R3, R4, R5 and R6 are independently selected from H, halogen, C1-C6 alkyl or C1-C6 alkoxy; V, W, X, Y and Z are independently CH or N, and when V, W, X, Y or Z is N, N has no substituent group. According to the fluorine-boron fluorescent dye and the preparation method thereof, the maximal fluorescence emission wavelength of the fluorine-boron fluorescent dye is 518-600nm, and the fluorine-boron fluorescent dye also has excellent fluorescence quantum yield and Stokes shift, which shows that the fluorine-boron fluorescent dye has good application prospect in the bioanalysis fields of fluorescence labeling, bioimaging and so on; meanwhile, the preparation method is simple in steps, and raw materials can be obtained easily.

The invention relates to a fluorescent ion probe (I) with high selectivity and high sensitivity in detection and the application of the fluorescent ion probe in identifying and detecting heavy metal ion and transition metal ion, wherein, the Y is an organic conjugate group with fluorescence transmitting function such as pyrene, naphthalene, 4-amidogen-1, 8-naphthyl imide, Dan sulfonamide, anthracene, carbazole, benzimidazoins, benzoxazoles, boron fluoride bipyrrole (BODIPY), fluorescein, 3, 4, 9, 10-perylenetetracarboxylic diimide or rhodamine B; the X is acylamino group, sulfoamino group or ester group. The fluorescent ion probe uses the fluorescence peak of fluorescence chromophore aggregate as the response signal to identify metal ion, thereby effectively avoiding the quenching effect of transition metal ion and heavy metal ion on fluorophore; moreover, the fluorescent ion probe realizes selective identification of heavy metal ion and transition metal ion in various solvents and aqueous solution in particular.

The invention discloses a fluorescent probe for detecting a biologic thiol and a preparation method and a usage method thereof. The fluorescent probe for detecting the biologic thiol consists of two parts: namely, a 2, 4-bi-nitrobenzene sulfonyl group which is a recognizing group and a boron difluoride-dipyrryl methane (BODIPY) derivative which is an information reporting functional group. The molecule of the probe can simply and quickly enter a living cell, generates a specificity reaction with the thiol in the cell, and causes to obviously enhance fluorescence intensity, so that the fluorescent probe further can be used for the fluorescence detection and the imaging of the active thiol in the living cell. The fluorescent probe has good stability, can be stored and used for a long time, is applicable to various environments in which the living cell grows, and has higher detection sensitivity for the thiol, strong anti-interference capability, excellent selectivity and no action on other common biologic interfering molecules. The fluorescent probe can simply enter the living cell and a living tissue; the single recognition of the thiol in a biologic system can be achieved effectively; and therefore, the fluorescent probe can be used for the fluorescence imaging of the living cell.

Provided are azido-BODIPY compounds of formula (I), cyclooctyne-based fluorogenic probes of formula (IV), and activity-based probes of formula (VI). These compounds undergo azide alkyne cycloadditions (AAC) with to form triazolyl products. The provided compounds are useful for detection and imaging of alkyne-, or azide-containing molecules. Methods for detection and imaging biomolecules using compounds of the present disclosure are disclosed.

The invention relates to a near infrared BODIPY fluorescence dye and a preparation method thereof. A BODIPY derivative and 2-aldotruxene undergo a Knoevenagel condensation reaction under the catalysis action of p-toluenesulfonic acid and piperidine to synthesize the dye, and the maximal absorption wavelength and the maximal emission wavelength of the dye in an organic solvent are 650nm or above respectively. The preparation method has the advantages of simple reaction steps, mild reaction conditions and good selectivity. Like fluorescence dyes have the advantages of high molar extinction coefficient, good solubility and light stability, excellent photophysical performances, and good application prospect in cell imaging and biological marking.

The invention discloses a four-color fluorescence labeling reversible terminal and a use thereof in DNA (Deoxyribonucleic Acid) sequencing. The structural formula of the reversible terminal is as shown in a formula (I) in the specification, wherein R1 is triphosphate; R2 is H or OH; the basic group is U, C, A, G or derivatives thereof; the connecting unit is a bifunctional compound which is breakable under a mild condition; the fluorescence group is one selected from a combination of BODIPY, fluorescein, rhodamine, coumarin, xanthene, cyanin, pyrene, phthalocyanine, alexa, squarene dye and an energy transferring dye, and derivatives thereof. The reversible terminal provided by the invention can be used for DNA single-molecule sequencing; simultaneously, raw materials required by the synthesis of the reversible terminal provided by the invention are simple and easy to get and the synthesis process of the reversible terminal is completely involved with conventional chemical reactions, so that the four-color fluorescence labeling reversible terminal can be popularized and utilized to a large scale; biological evaluation results indicate that the reversible terminal is capable of completely meeting the biochemical reaction requirements of high-flux sequencing and has a good practical prospect.

The invention provides a preparation method of a long wavelength BODIPY dye and a derivative thereof, belonging to the organic chemical industry and the fine chemical industry technology field. Bromine or iodo-BODIPY and substituted alenyle boric acid are used as the raw material with the mol ratio around 1 to between 2 and 10 in the preparation method of the long wavelength BODIPY dye and the derivative thereof, palladium carbon or zero-valent palladium is used as a catalyst, the mol ratio of bromine or iodo-BODIPY to the catalyst is 1 to between 0.01 and 0.20. Allowing the bromine or iodo-BODIPY and the substituted alenyle boric as well as the catalyst to react in an organic solvent for one to seventy-two hours at a temperature of between forty and one hundred and sixty DEG C with the protection and stirring of argon or nitrogen, then the bromine or iodine on the raw material is substituted, conjugated double bond BODIPY derivative is generated and the boric acid and conjugated double bond BODIPY derivative is substituted, and after the introduction of conjugated double bond groups in different numbers, the optical property of the BODIPY is changed to absorb and emit spectrum and Einstein shift occurs.

The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.

The invention belongs to the technical field of analysis chemistry and relates to a copper ion fluorescence probe and a synthetic method of the copper ion fluorescence probe. The copper ion fluorescence probe disclosed by the invention has a chemical name of 8-[di(2-picolyl)amine-3-benzyl]-4, 4-difluoro-1,3,5,7-tetramethyl-4-boron-3a, 4a-dipyrrole (called BODIPY-DPA for short). The synthetic method of the copper ion fluorescence probe comprises the steps of: mixing 2, 4-dimethylpyrrole with 3-chloromethyl benzoyl chloride, then adding CH2Cl2 into the mixture, then adding boron trifluoride for reaction, and then orderly adding di(2-picoly)amine and triethylamine for reaction, at last, obtaining the copper ion fluorescence probe. The BODIPY-DPA shows light yellow in the solution, has high fluorescence emission at 590 nm, can enter HepG-2 to show green fluorescence imaging, and has a lowest limit of detection of 2.78 muM on copper ions in water solution. The copper ion fluorescence probe prepared by the synthetic method is characterized in low toxicity and the inhibition rate of 100 muM of HepG-2 is smaller than 10%, so the copper ion fluorescence probe can be used for detection of living cell imaging and copper irons in the cell, and has a very good application prospect in environment monitoring and detection of copper irons in a biologic system.

The invention relates to a novel red BODIPY fluorescent dye with the chemical formula of C10+mH7+nBF2N2+xOy, wherein m, n, x and y are integers from 0 to 100. The preparation method comprises the following steps: dissolving pyrrole with substituent groups R1, R2 and R3 in an organic solution; adding ethyl glyoxylate together with nitrogen to the organic solution for a chemical reaction by using trifluoroacetic acid or toluenesulfonic acid as a catalyst; adding 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidative dehydrogenation; and adding organic amine and a boron trifluoride diethyl ether solution for another reaction. After the reaction solution is concentrated, chromatography is performed with a silicagel column to obtain the fluorescent dye. The fluorescent dye can be used for cell imaging, fluorescent probe or laser dye. The fluorescent dye has the advantages that the ultraviolet-visible absorption spectrum and the fluorescence emission spectrum of the fluorescent dye are narrow; fluorescent quanta has high efficiency and good light stability; and the fluorescent dye has simple molecular structure and can be synthesized easily, so as to facilitate popularization and application.

The invention relates to a compound for detecting secondary amine, and preparation and application thereof. The compound contains boron ester and a BODIPY structure unit in conjugate connection with the boron ester. The compound has a structural general formula shown as in (I), wherein R1 and R2 are independently selected from the group consisting of benzene, naphthalene, anthracene, pyrene, carbazole, triphenylamine, binaphthalene, thiophene, quinoline, imidazole and rhodamine. The preparation method has the advantages of simpleness, high yield, easy separation and high purity. The compound provided by the invention has a novel structure and rapid and sensitive detection of secondary amine; and when the compound reacts with secondary amine, the film turns into purple from red, and the fluorescence is quenched. The test paper and film prepared from the compound react with secondary amine, and significant changes of the color and fluorescence take place in a few minutes and are visible to the naked eyes, so as to conveniently identify secondary amine.

The invention discloses a fluorescent probe for detecting a cyanide ion and a synthesis and application method thereof. A cyanide ion fluorescent probe takes boron fluoride dipyrrole (BODIPY) as a fluorescent signal group and hemicyanine as a recognition site, and the probe is obtained by carrying out Knoevenagel condensation reaction on 1,3,5,6-tetramethyl 8-(4(formylphenyl)) boron fluoride dipyrrole and 1,2,3,3-tetramethyl-3H-indolium iodide. Ultraviolet absorption and fluorescence emission spectroscopy research finds that the probe can solely identify the cyanide ion, the lowest detection limit can reach 59 nM, the identification process is not interfered by other negative ions, and response speed is high. The fluorescent probe disclosed by the invention can be used for detection of the actual water sample, and relative standard deviation is less than 5%. Besides, the fluorescent probe is simple in synthesis method and relatively low in cost and has a good application prospect in cyanide ion detection.

The invention discloses a preparation method and an application of a boron-dipyrromethene (BODIPY) based fluorescent probe for determining cysteine (Cys). The structural formula of the probe is shown in the specification. The preparation method of the BODIPY derivative based Cys fluorescent probe with a simple structure is provided, and the BODIPY derivative based Cys fluorescent probe is used for directly measuring Cys concentration. In the system, the fluorescent probe shows good selectivity and is not interfered with other biological thiols (Hcy and GSH) and other 19 amino acids. The probe shows quite high sensitivity to Cys, and the fluorescence intensity is enhanced by 23 times when 3 equivalents of Cys are added. When the pH is between 6.0 and 8.0, determination of Cys by the fluorescent probe is not affected by pH. The fluorescence probe and Cys act quickly, and the response time is within 6 minutes. In addition, the probe can also be used in cell imaging to detect intracellular Cys.

The invention provides a fluorescent silk fiber based on BODIPY dyes and a preparation method of the fluorescent silk fiber. The preparation method comprises the following steps: swollen silk fibers are immersed in a zeolite-containing aqueous solution and are pretreated, then are repeatedly immersed in hydrophilic BODIPY fluorescent dyes and a low molecular chitosan solution, and finally are steamed, heated and cured to obtain the fluorescent silk fiber. The fluorescent silk fiber based on BODIPY dyes prepared according to the method is stable in fluorescence, high in strength and uniform in color, can be produced in large scale, has excellent mechanical properties and high flexibility, and is applicable to the textile, bio-medical treatment, anti-counterfeiting and many other fields.

The invention discloses a kind of near infrared boron dipyrromethene compounds (BODIPY) based on duplex thiophene pyrrole groups. The near infrared boron dipyrromethene compounds have the following structure: FORMULA, wherein the group at meso site is changed to obtain a series of hydroxyl radical probes. The BODIPY hydroxyl radical probes based on 3,5-(diphenyl phosphate styryl) are synthesized for the first time in the invention, the 3,5 site groups of the BODIPY are introduced into the group, so that the absorption spectrum red shift of the probe reaches 630nm, the emission peak reaches 650nm and is located within the range (650-900nm) of a biological window, and meanwhile, the fluorescence quantum efficiency of the probe is high. Moreover, the kind of probes can be used for efficiently and quickly detecting hydroxyl radicals and can be successfully applied in biological imaging. Therefore, the probes have a brilliant application prospect of detecting the hydroxyl radicals in biological systems.

The invention provides synthesis of a platinum-based bodipy compound and a new application thereof in pharmacy, and particularly relates to the synthesis of platinum-based bodipy molecules and derivatives thereof, preparation of a nano-scale medicament, and an application to anti-tumor photosensitive medicament in photodynamics and photothermal therapy. Self-assembling nano-particles with photodynamic and photothermal dual activities are constructed by taking bodipy dye molecules as parent nuclei, introducing divalent platinum ions in a covalent coordination mode, and performing modifying through a polymer hydrophilic chain. Under light conditions, a self-assembling nano-scale medicament shows good photodynamic and photothermal therapeutic effects. The platinum-based bodipy compound confirms dual effects of the photodynamics and photothermal therapy at cell and animal levels, and the light induction of tumor ablation is realized.

The invention discloses a structure and a preparation method of a truxene-based star-like compound (TBP-C60). The preparation method is implemented by the following steps: by taking 7,12-dibromo-truxene-aldehyde derivative as a raw material and taking tetrahydrofuran as a solvent, performing Suzuki reaction on the raw material, the solvent and a BODIPY borate derivative under the catalysis action of tetra(triphenylphosphine) palladium, thus obtaining a truxene-BODIPY binary system compound TB; then by taking the TB and a porphyrin borate derivative as raw materials, performing reaction under the catalysis action of the tetra(triphenylphosphine) palladium, thus obtaining a BODIPY-truxene-porphyrin ternary system compound TBP; then performing cycloaddition reaction on the TBP, sarcosine and fullerene through 1,3-dipole, thus obtaining the star-like compound TBP-C60 in which the truxene is used as a core and the porphyrin, the BODIPY and the fullerene are used as arms. The preparation method of the star-like compound is simple, mild in reaction condition and easy and convenient to operate, shows excellent energy transfer efficiency and high heat stability and can be used for a light absorption antenna, a solar panel, light-simulated biological photosynthesis and other aspects.

The invention relates to development of a BODIPY fluorescent dye with a novel structure and excellent photochemical properties and provides a BODIPY fluorescent dye, and a preparation method and application thereof, belonging to the field of organic chemistry. The BODIPY fluorescent dye has high fluorescence quantum yield (0.99), good photostability and other excellent photochemical properties; and the preparation method is simple, uses easily available raw materials, has low requirements on equipment and is easy for industrial production.

The invention relates to preparation and an application of a fluorescent molecular probe for detecting hypochlorite ions, and belongs to the technical field of chemical fluorescent materials. The probe is a BODIPY derivative with the molecular formula of C26H23BF2N6O4. Firstly, an intermediate compound 2 is synthesized. Secondly, a certain quantity of 2,4-dinitrophenylhydrazine is added mixed with the intermediate compound, a certain quantity of ethanol and ethyl acetate mixed solvents are added and dissolved, and stirring reaction is performed at room temperature after acetic acid serving as a catalyst is dropped in. A crude product is recrystallized by ethanol and then purified by column chromatography to finally obtain a purple pure probe. The probe is used for detecting the hypochlorite ions under various conditions, ClO-fluorescent enhanced recognition is realized by the synthesized novel fluorescent probe, the probe is remarkable and good in effect, high in sensitivity and low in measuring detection limit, and hypochlorite can be effectively recognized even under interference of some other ions.

The invention discloses a triphenylamine-BODIPY derivative organic dye and a preparation method thereof. The triphenylamine-BODIPY derivative organic dye is prepared by that a triphenylamine-aldehyde compound is in reaction with pyrrole under the catalytic action of a catalyst, so as to synthetize dipyrromethane, and then a triphenylamine-BODIPY derivative is obtained through further oxidation and fluorine boronizing, and the general formula is shown in a structural formula I. The stokes displacement value of the triphenylamine-BODIPY derivative can reach 180 to 238 nm, and the fluorescence emission peak thereof locates in the near infrared region of 700 to 800 nm. The synthetic method of the compound is simple, the reaction is easy to control, the yield is high, common applicability is achieved, so that the BODIPY dye can be composited efficiently, and can be widely applied to the field of bioscience, analytic chemistry, environmental energy science and the like, and is particularly used as a near-infrared fluorescent dye and an organic solar cell material (refer to the description).

The invention relates to the field of optical functional materials, and more specifically relates to an infrared BODIPY fluorochrome. The fluorochrome has a structure shown in a formula (1), wherein R1 and R2 are mutually independent and selected from C1-C10 alkyl, aromatic bases or heterocyclic aromatic bases; R3 is one of H atom, C1-C10 alkyl or aromatic bases. The fluorochrome has the advantages of narrow ultraviolet visible absorption spectroscopy and fluorescence emission spectrum, high molar absorption coefficient, high fluorescence quantum efficiency, good light stability, trace detection, and high sensitivity; and the fluorochrome can be applied to cell imaging, fluorescence probe, laser dye, fluorescence sensor and near infrared dynamics, and different application fields with good practicality.

The invention provides a fluorescent detection method of 5-hydroxymethylcytosine based on FRET (Fluorescence Resonance Energy Transfer) principle with non-diagnostic purposes. The fluorescent detection method comprises the following steps of: firstly, oxidizing the 5-hydroxymethylcytosine in a DNA into 5-aldehyde cytosine by using potassium perruthenate; secondly, reacting a BODIPY (Boron Trifluoride Complex Dipyrromethene) compound with fluorescence with the 5-aldehyde cytosine in the DNA; and finally, adding a cationic fluorescent polymer, and measuring the content of the 5-hydroxymethylcytosine in the DNA through fluorescent detection. The detection method has the advantages of simpleness and rapidity, and low cost.

The invention discloses a novel conjugate microporous polymer based on a BODIPY derivative. The conjugate microporous polymer integrally forms a large conjugate skeleton and has high specific surface area, a good porous character, good heat stability and chemical stability and wide application prospects in the fields of gas separation, ion detection, gas absorption, catalysis and the like. The invention further discloses a preparation method of the conjugate microporous polymer. According to the method, 9-anthraldehyde and 2,4-dimethyl-1H-pyrrole serve as raw materials, BODIPY chromophore containing an anthracene group is obtained through multiple steps, then, the BODIPY chromophore containing the anthracene group and 1,3,5-triethynylbenzene are subjected to Sonogashira reaction under catalysis of tetrakis(triphenylphosphine)platinum and CuI, and the conjugate microporous polymer is obtained.