Multi-rotor near-infrared second-region cyanine molecule as well as preparation method and application thereof

Abstract

The invention discloses a multi-rotor near-infrared second-region cyanine molecule as well as a preparation method and application thereof, and belongs to the technical field of organic luminescent materials in the field of organic synthesis. The compound provided by the invention has a structural formula as shown in a structural formula (I): # imgabs0 #. The compound provided by the invention can realize near-infrared second-region tumor fluorescence imaging and high-resolution angiography by utilizing the penetration advantage of a near-infrared second region, and can realize near-infrared second-region photothermal immunotherapy by activating tumor immunogenic cell death.

Description

Technical Field

[0001] The present invention belongs to the field of fluorescent biodiagnosis and treatment technology; specifically, it relates to a multi-rotor near-infrared second-zone cyanine compound with high photothermal conversion efficiency and high fluorescence quantum yield. The present invention also relates to a method for synthesizing the compound and its application in the diagnosis and treatment of deep tumors. Background Art

[0002] In 1856, cyanine dyes were first synthesized by Willimas, and subsequently, cyanine molecules were extensively studied and rapidly developed. Cyanine dyes can be classified by conjugated chain length into monomethine cyanine (Cy1), trimethine cyanine (Cy3), pentamethine cyanine (Cy5), and heptamethine cyanine (Cy7). As the conjugated chain lengthens, the absorption and emission of cyanine molecules also red-shift. When heptamethine cyanine is reached, the absorption and emission of the molecule enter the near-infrared region I (NIR-I, 700-900nm). Although various strategies have been used to modify the structure of cyanine molecules to enable them to reach the near-infrared region II (NIR-II, 1000-1700nm), there are still deficiencies. For example, the modified cyanine dyes may have poor photostability, poor water solubility, low fluorescence quantum yield, or low photothermal conversion efficiency. This greatly limits the clinical application of NIR-II cyanine dyes.

[0003] Malignant tumors are a major disease that threatens human health, and their treatment strategies have always faced the dual challenges of efficacy and safety. Traditional treatment methods such as surgical resection, radiotherapy and chemotherapy drugs are widely used in clinical practice, but they are limited by problems such as tumor heterogeneity, metastasis and recurrence, and systemic toxicity, making it difficult to achieve precise treatment. In recent years, although tumor immunotherapy represented by immune checkpoint inhibitors (ICIs) has made breakthrough progress, the response rate of single drugs is generally less than 30%, and it is easy to induce immune-related adverse reactions. In this context, the development of synergistic therapies that can locally kill tumors and activate systemic anti-tumor immunity has become an important direction to break through the existing treatment bottleneck.

[0004] Photothermal therapy (PTT) converts near-infrared light energy into thermal energy through photothermal conversion materials, and can induce local tumor cell ablation under spatiotemporally controllable conditions. Local hyperthermia can induce tumor cell necrosis or apoptosis, release tumor-associated antigens (TAAs) and damage-associated molecular patterns (DAMPs), activate dendritic cells (DCs), and promote antigen presentation. Traditional NIR-I light sources are limited by tissue scattering and absorption, and their penetration depth is low, making it difficult to effectively treat deep or large tumors. This has prompted researchers to increase the depth of PTT and combine it with immunotherapy, by inducing immunogenic cell death (ICD) to release tumor antigens, reshape the immunosuppressive microenvironment, and stimulate systemic anti-tumor immune responses, thereby providing more possibilities for building an integrated "diagnosis and treatment-thermal ablation-immune activation" system. Summary of the Invention

[0005] The technical problem to be solved by the present invention is to overcome the defects and shortcomings of existing cyanine dyes, such as imbalance in photothermal and fluorescence properties, poor photothermal stability, low absorption band, and low molar extinction coefficient, and to provide a near-infrared second-zone cyanine compound with high penetrability, coordinated fluorescence and photothermal properties, and to use it for the diagnosis and treatment of deep tumors.

[0006] The second object of the present invention is to provide a method for preparing a multi-rotor near-infrared second-zone cyanine compound.

[0007] The third object of the present invention is to provide an application of multi-rotor near-infrared second-zone cyanine compounds.

[0008] The above-mentioned purpose of the present invention is achieved through the following technical solutions:

[0009] A multi-rotor near-infrared second-zone cyanine compound, the structure of which is shown in formula (I):

[0010]

[0011] Wherein R can be any one of the following groups:

[0012]

[0013] X - Cl - Br - , I - PF6 - 、BF4 - .

[0014] The present invention introduces benzene rings into cyanine dyes to construct cyanine molecules containing different numbers of "benzene rotors". The conjugated and rotor properties of the benzene rings are used to red-shift the absorption and emission spectra and achieve coordinated regulation of photothermal and fluorescence properties.

[0015] The present invention also provides a method for preparing a multi-rotor near-infrared second-zone cyanine compound, comprising the following steps:

[0016] S1: dissolving 6-bromo-1-ethylbenz[cd]indol-2(1H)-one in an organic solvent, heating the mixture in the presence of a catalyst, and post-treating the mixture to obtain a compound represented by formula (III);

[0017] S2: dissolving the compound represented by formula (III) and methylmagnesium chloride in an organic solvent, heating for reaction, and adding the corresponding salt of X during post-treatment to obtain formula (IV);

[0018] S3: dissolving the compound represented by formula (Ⅳ) and 2-chloro-1-formyl-3-hydroxymethylenecyclohexene in an organic solvent, heating for reaction, and post-treating to obtain the product;

[0019] The structures of the compounds of formula (II), formula (III) and formula (IV) are as follows:

[0020]

[0021] Wherein R can be any one of the following groups:

[0022]

[0023] X - Cl - Br - , I - PF6 - 、BF4 - .

[0024] The specific synthetic route is as follows:

[0025]

[0026] Preferably, in step S1, the temperature of the heating reaction is 30-100°C; in step S2, the temperature of the heating reaction is 20-100°C; and in step S3, the temperature of the heating reaction is 30-110°C.

[0027] Preferably, in step S1, the reaction time is 4 to 24 hours; in step S2, the reaction time is 0.5 to 12 hours; in step S3, the reaction time is 0.5 to 12 hours.

[0028] Preferably, in step S1, the molar ratio of 6-bromo-1-ethylbenzo[cd]indole-2(1H)-one and the compound of formula (II) is 1:1 to 1:5; in step S2, the molar ratio of the compound of formula (III) and methylmagnesium chloride is 1:1 to 1:5; in step S3, the molar ratio of the compound of formula (IV) and 2-chloro-1-formyl-3-hydroxymethylenecyclohexene is 2:1 to 4:1.

[0029] Preferably, the organic solvent is one or more of anhydrous acetonitrile, anhydrous toluene, anhydrous dimethylformamide, anhydrous tetrahydrofuran, anhydrous ethanol, acetic acid or acetic anhydride.

[0030] More preferably, in step S1, the organic solvent is one of anhydrous dimethylformamide, anhydrous toluene or anhydrous tetrahydrofuran; in step S2, the organic solvent is one of anhydrous acetonitrile, anhydrous ethanol or anhydrous tetrahydrofuran; in step S3, the organic solvent is one or more of anhydrous toluene, anhydrous ethanol, acetic acid or acetic anhydride.

[0031] Preferably, the catalyst is one of tetrakis(triphenylphosphine)palladium, palladium acetate, tris(dibenzylideneacetone)dipalladium or tris(dibenzylideneacetone)dipalladium(0)chloroform adduct.

[0032] The present invention also provides the use of the multi-rotor near-infrared second-zone cyanine compound as a preparation of deep anti-tumor drugs.

[0033] The present invention also provides the use of the multi-rotor near-infrared second-zone cyanine compound as a preparation of angiographic contrast agents.

[0034] The present invention also provides the use of the multi-rotor near-infrared second-zone cyanine compound as a preparation of an organic light-emitting material.

[0035] The present invention also provides the use of the multi-rotor near-infrared second-zone cyanine compound in organic luminescent materials, wherein the organic luminescent material is a fluorescent probe, a biological imaging material, or a material for diagnosing and treating deep or recurrent tumors.

[0036] More preferably, the bioimaging applications include fluorescence imaging, angiography and photothermal imaging.

[0037] More preferably, the diagnosis and treatment of deep tumors (breast cancer, brain glioma, liver cancer, lung cancer, etc.) includes the application of imaging diagnosis and photothermal immunotherapy of deep tumors (breast cancer, brain glioma, liver cancer, lung cancer, etc.).

[0038] Compared with the prior art, the present invention has the following beneficial effects:

[0039] The compound provided by the present invention has stable fluorescence and coordinated photothermal and fluorescence properties. It not only has high photothermal conversion efficiency and photothermal stability in solution, but can also achieve near-infrared zone II photothermal therapy, photothermal imaging, near-infrared zone II fluorescence imaging, and angiography in mice, and has obvious advantages over the FDA-approved near-infrared zone ICG dye. BRIEF DESCRIPTION OF THE DRAWINGS

[0040] Figure 1 1HNMR spectrum of the compound (PH-CyA) in Example 1 of the present invention.

[0041] Figure 2 This is the 1H NMR spectrum of the compound (TBE-CyA) in Example 2 of the present invention.

[0042] Figure 3 This is the 1H NMR spectrum of the compound (TPE-CyA) in Example 3 of the present invention.

[0043] Figure 4 is the photothermal conversion efficiency of the compound (TPE-CyA) in Example 3 of the present invention.

[0044] Figure 5 The photothermal stability of the compound (TPE-CyA) and ICG in Example 3 of the present invention

[0045] Figure 6 The toxicity and photothermal toxicity of TPE-CyA-incubated mouse breast cancer cells (4T1) in Example 3 of the present invention were determined by MTT method.

[0046] Figure 7 This is a thermal imaging diagram of the temperature change of TPE-CyA of the compound in Example 3 of the present invention after intravenous administration to 4T1 tumor-bearing Balb / c female mice and irradiation with 1064 nm laser (1).

[0047] Figure 8 These are near-infrared second-zone fluorescence imaging images of TPE-CyA of the compound in Example 3 of the present invention at different times after intravenous administration to 4T1 tumor-bearing Balb / c female mice. DETAILED DESCRIPTION

[0048] The present invention is further described below with reference to the accompanying drawings and specific examples. Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art.

[0049] Unless otherwise specified, the reagents and materials used in the following examples were commercially available.

[0050] Example 1 Preparation of PH-CyA Compound

[0051] S1. 2 mmol of 6-bromo-1-ethylbenz[cd]indol-2(1H)-one, 10 mmol of 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (CAS No. 24388-23-6, designated as Compound II-PH), and 3 mmol of sodium tert-butoxide were dissolved in 20 mL of anhydrous toluene. 0.1 mmol of palladium catalyst was added under a nitrogen atmosphere, and the mixture was reacted at 30°C for 12 h. After the reaction, 15 mL of acetone was added for dilution, and the mixture was filtered. The crude product was purified by silica gel chromatography using petroleum ether / ethyl acetate (v / v = 5:1) as the eluent and dried under vacuum at 30°C at 10 Pa to obtain Compound III-PH.

[0052] The structural formula of the compound II-PH is as follows:

[0053]

[0054] The structural formula of the compound III-PH is as follows

[0055]

[0056] S2. Weigh 2 mmol of compound III-PH prepared in S1 and dissolve it in anhydrous tetrahydrofuran. Add 2 mmol of methylmagnesium chloride solution (CAS No. 676-58-4) dropwise, and react at 20°C for 4 hours. After the reaction, pour the reaction mixture into 5 mL of 20 wt% aqueous fluoroboric acid. Extract with 10 mL of dichloromethane. The crude product is purified by silica gel chromatography using dichloromethane / methanol (v / v = 10:1) as the eluent and dry in a vacuum at 30°C at 10 Pa to obtain compound IV-PH.

[0057] The structural formula of the compound IV-PH is as follows:

[0058]

[0059] S3. Weigh 2 mmol of IV-PH prepared in S2 and 1 mmol of 2-chloro-1-formyl-3-hydroxymethylenecyclohexene, add 0.5 mL of triethylamine, 0.5 mL of acetic anhydride, and 0.5 mL of acetic acid, respectively, and react at 30°C for 4 hours. After cooling, add 5 mL of deionized water and extract with 10 mL of dichloromethane. The crude product is purified by silica gel chromatography using dichloromethane / methanol (v / v = 10:1) as the eluent and dried in a vacuum at 30°C and 10 Pa to obtain the target compound PH-CyA.

[0060] The structural formula of the compound PH-CyA is as follows:

[0061]

[0062] PH-CyA1 H NMR spectrum reference Figure 1 .

[0063] Example 2 Preparation of TBE-CyA Compound

[0064] S1. 2 mmol of 6-bromo-1-ethylbenz[cd]indol-2(1H)-one, 8 mmol of 4,4,5,5-tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane (CAS No. 219488-97-8, referred to as Compound II-TBE), and 3 mmol of sodium tert-butoxide were dissolved in 20 mL of anhydrous tetrahydrofuran. Under a nitrogen atmosphere, 0.1 mmol of palladium catalyst was added and the mixture was reacted at 50°C for 18 h. After the reaction, 15 mL of acetone was added for dilution, and the mixture was filtered. The crude product was purified by silica gel chromatography using petroleum ether / ethyl acetate (v / v = 5:1) as the eluent and dried under vacuum at 30°C at 10 Pa to obtain Compound III-TBE.

[0065] The structural formula of the compound II-TBE is as follows:

[0066]

[0067] The structural formula of the compound III-TBE is as follows:

[0068]

[0069] S2. Weigh 2 mmol of III-TBE prepared in S1 and dissolve it in anhydrous acetonitrile. Add 4 mmol of methylmagnesium chloride solution dropwise, and react at 50°C for 8 hours. After the reaction, pour the reaction mixture into 5 mL of 20 wt% aqueous fluoroboric acid. Extract with 10 mL of dichloromethane. The crude product is purified by silica gel chromatography using dichloromethane / methanol (v / v = 10:1) as the eluent and dried under vacuum at 30°C at 10 Pa to obtain the target compound IV-TBE.

[0070] The structural formula of the compound IV-TBE is as follows:

[0071]

[0072] S3. Weigh 3 mmol of IV-TBE prepared in S2 and 1 mmol of 2-chloro-1-formyl-3-hydroxymethylenecyclohexene, add 0.5 mL of triethylamine, 0.5 mL of acetic anhydride, and 0.5 mL of acetic acid, respectively, and react at 40°C for 12 hours. After cooling, add 5 mL of deionized water and extract with 10 mL of dichloromethane. The crude product is purified by silica gel chromatography using dichloromethane / methanol (v / v = 10:1) as the eluent and dried in a vacuum at 30°C and 10 Pa to obtain compound TBE-CyA.

[0073] The compound TBE-CyA has the following structural formula:

[0074]

[0075] TBE-CyA 1 HNMR spectrum reference Figure 2 .

[0076] Example 3 Preparation of TPE-CyA Compound

[0077] S1. 2 mmol of 6-bromo-1-ethylbenz[cd]indol-2(1H)-one, 6 mmol of 4,4,5,5-tetramethyl-2-(4-(1,2,2-triphenylvinyl)phenyl)-1,3,2-dioxaborolane (CAS No. 1260865-91-5, referred to as Compound II-TPE), and 3 mmol of sodium tert-butoxide were dissolved in 20 mL of anhydrous dimethylformamide. 0.1 mmol of palladium catalyst was added under a nitrogen atmosphere, and the mixture was reacted at 100°C for 24 h. After the reaction, 15 mL of acetone was added for dilution, and the mixture was filtered. The crude product was purified by silica gel chromatography using petroleum ether / ethyl acetate (v / v = 5:1) as the eluent and dried under vacuum at 30°C and 10 Pa to obtain Compound III-TPE.

[0078] The structural formula of the compound II-TPE is as follows:

[0079]

[0080] The structural formula of the compound III-TPE is as follows:

[0081]

[0082] S2. Weigh 2 mmol of III-TPE and dissolve it in anhydrous ethanol. Add 10 mmol of methylmagnesium chloride solution dropwise, and then react at 90°C for 12 hours. After the reaction, pour the reaction mixture into 5 mL of 20 wt% aqueous fluoroboric acid. Extract with 10 mL of dichloromethane. The crude product is purified by silica gel chromatography using dichloromethane / methanol (v / v = 10:1) as the eluent and dried under vacuum at 30°C at 10 Pa to obtain compound IV-TPE.

[0083] The structural formula of the compound IV-TPE is as follows:

[0084]

[0085] S3. Weigh 4 mmol of IV-TPE and 1 mmol of 2-chloro-1-formyl-3-hydroxymethylenecyclohexene, add 0.5 mL of triethylamine, 0.5 mL of acetic anhydride, and 0.5 mL of acetic acid, respectively, and react at 110°C for 0.5 hour. After cooling, add 5 mL of deionized water and extract with 10 mL of dichloromethane. The crude product is purified by silica gel chromatography using dichloromethane / methanol (v / v = 10:1) as the eluent and dried in a vacuum at 30°C and 10 Pa to obtain the target compound TPE-CyA.

[0086] The structural formula of the compound TPE-CyA is as follows:

[0087]

[0088] IV-TPE 1 H NMR spectrum reference Figure 3 .

[0089] Experimental example:

[0090] The compound obtained in Example 3 (TPE-CyA) was prepared into a 20 mM stock solution with DMSO and stored in a refrigerator at 4° C. protected from light. Before use, the stock solution was diluted with the corresponding diluent to the target concentration.

[0091] Experimental Example 1

[0092] The compound (TPE-CyA) obtained in Example 3 was diluted to 20 μM with deionized water, and 200 μL was placed in a 1.5 mL centrifuge tube. The position and angle of the centrifuge tube were adjusted so that the laser beam with a wavelength of 1064 nm passed through the liquid surface and the laser focus was at the center of the liquid. The thermal imager was used to record the laser beam at 1.0 W / cm 2 The temperature changes with time during 10 minutes of laser power irradiation and 10 minutes after stopping irradiation, and the photothermal conversion efficiency is calculated through the cooling curve.

[0093] The results are as follows Figure 4 As shown, at 1064nm laser (1.0W / cm 2 ) irradiation, the photothermal conversion efficiency of the prepared TPE-CyA was 45.72%

[0094] Experimental Example 2

[0095] The compound (TPE-CyA) obtained in Example 3 was diluted to 20 M with deionized water. A 20 μM ICG solution was prepared at the same time. 200 μL of each solution was placed in a 1.5 mL centrifuge tube. The position and angle of the centrifuge tube were adjusted. Laser beams with wavelengths of 1064 nm and 808 nm were used to pass through the liquid surface, respectively, with the laser focus at the center of the liquid. The laser beams were recorded at 1.0 W / cm by a thermal imager. 2Temperature changes over time during four radiation-cooling cycles under different laser powers.

[0096] The results are as follows Figure 5 As shown, the compound (TPE-CyA) was compared with ICG, which proved that the compound had good photothermal stability.

[0097] Experimental Example 3

[0098] Mouse breast cancer 4T1 cells in the logarithmic growth phase were selected, digested with trypsin, and collected in serum-containing culture medium. The cell suspension was centrifuged, resuspended in culture medium, counted, and diluted to 50,000 cells / mL before inoculation into a 96-well plate. After culturing for 24 hours in a CO2 incubator at 37°C, 5% CO2 and 95% relative humidity, different concentrations (20 μM, 10 μM, 5 μM, 2.5 μM, 1.25 μM, 0 μM) of TPE-CyA were added and cultured for 24 hours. The supernatant (cell culture medium) was carefully aspirated and 0.5 mg / mL 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT, 100 μL per well) solution was added and cultured in the dark for 4 hours. The supernatant (cell culture medium) was aspirated and DMSO (150 μL) was added to dissolve the cells. After low-speed shaking on a shaker, the absorbance at a wavelength of 490 nm was measured using a multifunctional microplate reader, and the cell survival rate was calculated using the MTT method. At the same time, a photothermal toxicity experiment was conducted. After 4T1 cells were attached to the plate, the drug (TPE-CyA) was administered. After 4 hours of co-culture, the 1064 nm laser (1.0 W / cm 2 After 10 minutes of irradiation, cells were cultured for 12 hours. The OD values of the experimental and control groups were determined using the MTT assay. Cell viability was calculated using the following formula: Viability (%) = (average absorbance of the experimental group / average absorbance of the control group) * 100%.

[0099] The results are as follows Figure 6 As shown, in a dark environment, TPE-CyA has a slight toxicity to cancer cells, but exhibits a strong photothermal toxicity after laser irradiation, indicating that the present invention has a good in vitro anti-tumor ability.

[0100] Experimental Example 4

[0101] In vivo photothermal therapy: A mouse subcutaneous xenograft tumor model was established using 4T1. When the tumor volume reached approximately 100 mm 3 The TPE-CyA was encapsulated and intravenously administered to tumor-bearing mice. Twelve hours later, the tumor was illuminated by a 1064 nm laser (1.0 W / cm 2 , 10 minutes) and the temperature changes of the tumor area were recorded by thermal imaging. Figure 7 .

[0102] Experimental Example 5

[0103] In vivo angiography: Normal, tumor-free BALB / c female mice were selected and their back hair removed. TPE-CyA was encapsulated and intravenously administered. Images of the mouse leg vessels were recorded using a near-infrared two-zone in vivo imaging system using a 1064nm laser and 1150nm filter with an exposure time of 600ms. The results are shown in Figure 2. Figure 8 This indicates that the present invention has the potential for high-resolution imaging.

[0104] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be considered as equivalent replacement methods and are included in the scope of protection of the present invention.

Claims

1. A multi-rotor near-infrared second-zone cyanine molecule, characterized in that: It has the structural formula shown in formula (I): Wherein R can be any one of the following groups: X - Cl - Br - , I - PF6 - 、BF4 - .

2. The method for preparing the multi-rotor near-infrared second-zone cyanine compound according to claim 1, characterized in that: The steps include: S1: dissolving 6-bromo-1-ethylbenz[cd]indol-2(1H)-one in an organic solvent, then thoroughly mixing with the compound of formula (II) in the presence of a catalyst, heating to 30-100° C. and reacting for 4-24 hours, followed by post-treatment to obtain the compound of formula (III); The molar ratio of 6-bromo-1-ethylbenzo[cd]indol-2(1H)-one and formula II is 1:1 to 1:5; S2: dissolving the compound of formula (III) prepared in S1 and methylmagnesium chloride in an organic solvent, heating to 20-100°C for reaction for 0.5-12 hours, and adding the corresponding salt of X during post-treatment to obtain formula (IV); The molar ratio of the compound of formula (III) to methylmagnesium chloride is 1:1 to 1:5; S3: dissolving the compound of formula (IV) prepared in S2 and 2-chloro-1-formyl-3-hydroxymethylenecyclohexene in an organic solvent, heating to 30-110° C. for reaction for 0.5-12 hours, and post-treating to obtain the target product; The molar ratio of the compound of formula (IV) to 2-chloro-1-formyl-3-hydroxymethylenecyclohexene is 2:1 to 4:1; The structures of the compounds of formula (II), formula (III) and formula (IV) are as follows: Wherein R can be any one of the following groups: X - Cl - Br - , I - PF6 - 、BF4 - .

3. The method for preparing a multi-rotor near-infrared second-zone cyanine compound according to claim 2, characterized in that: In step S1, the organic solvent is one of anhydrous dimethylformamide, anhydrous toluene or anhydrous tetrahydrofuran.

4. The method for preparing a multi-rotor near-infrared second-zone cyanine compound according to claim 2, characterized in that: In step S2, the organic solvent is one of anhydrous acetonitrile, anhydrous ethanol or anhydrous tetrahydrofuran.

5. The method for preparing a multi-rotor near-infrared second-zone cyanine compound according to claim 2, characterized in that: In step S3, the organic solvent is one or more of anhydrous toluene, anhydrous ethanol, acetic acid or acetic anhydride.

6. The method for preparing a multi-rotor near-infrared second-zone cyanine compound according to claim 2, characterized in that: The catalyst in step S1 is one of tetrakis(triphenylphosphine)palladium, palladium acetate, tris(dibenzylideneacetone)dipalladium or tris(dibenzylideneacetone)dipalladium(0)chloroform adduct.

7. Use of the multi-rotor near-infrared second-zone cyanine compound according to claim 1 as a preparation of deep anti-tumor drugs.

8. Use of the multi-rotor near-infrared second-zone cyanine compound according to claim 1 in preparing a biological imaging agent.

9. Use of the multi-rotor near-infrared second-zone cyanine compound according to claim 1 as a preparation of an organic light-emitting material.

10. The use of the multi-rotor near-infrared second-zone cyanine compound in organic light-emitting materials according to claim 9, characterized in that: The organic luminescent material is a fluorescent probe material, a biological imaging material, or a material for diagnosing and treating deep or easily recurring tumors.

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