Application of aggregation-induced emission photosensitizer in preparation of antiviral products

Abstract

The invention discloses an application of an aggregation-induced emission (AIE) photosensitizer in preparation of an antiviral product. The AIE photosensitizer has efficient active oxygen generation capability, and the AIE photosensitizer and the prepared fiber material show strong killing activity on various viruses; particularly, the photosensitizer and the fiber material prepared from the photosensitizer can quickly and efficiently kill viruses under the irradiation of extremely low power density white light, and can still keep an excellent virus inactivation effect under the condition of no light, so that the strong dependence of the traditional photosensitizer on a light source is broken through. Meanwhile, the AIE photosensitizer has excellent photobleaching resistance, good biocompatibility and efficient pathogen capturing capacity, can be widely applied to preparation of anti-virus products such as textile raw materials and medical functional materials, and provides a novel solution for virus prevention and control in clinical and daily scenes.

Description

Technical Field

[0001] This invention relates to the field of biomedical technology, specifically to the application of a class of aggregation-induced emission photosensitizers in the preparation of antiviral products, which are particularly suitable for combating various RNA viruses. Background Technology

[0002] Viral infections pose a serious threat to human health. Common pathogenic viruses include SARS-CoV-2 and H1N1 influenza A virus, which are characterized by rapid transmission, high mutation rates, and strong pathogenicity. Existing antiviral drugs, such as nucleoside analogs and protease inhibitors, are prone to drug resistance due to viral mutations, have poor broad-spectrum activity, and some have significant toxic side effects. Besides chemical drugs, nucleic acid drugs have shown some potential in the antiviral field; however, unmodified nucleic acid drugs are easily degraded, have high immunogenicity, and insufficient targeting, requiring complex modification or delivery systems to achieve effective in vivo delivery, resulting in high drug development costs and significant challenges in clinical translation. While vaccines can prevent viral infections, their development cycles are long and cannot keep pace with the rate of viral mutation, failing to meet clinical needs. Therefore, there is an urgent need to develop novel antiviral agents with broad-spectrum antiviral activity, low susceptibility to drug resistance, and low toxicity.

[0003] Photodynamic therapy (PDT) is a novel technology that uses a specific wavelength of light to excite a photosensitizer to generate reactive oxygen species (ROS), thereby destroying the target biological structure (such as viral envelopes, proteins, and nucleic acids) to achieve therapeutic goals. Compared to traditional chemical drugs, PDT has significant advantages such as a unique mechanism of action, low susceptibility to inducing drug resistance, excellent targeting, and low toxicity. However, traditional photosensitizers (such as porphyrins and phthalocyanines) generally suffer from the "aggregation-induced quenching" (ACQ) effect: these photosensitizers are prone to molecular aggregation in vivo, which not only significantly reduces ROS generation efficiency and therapeutic efficacy but may also cause non-specific toxicity, severely limiting their clinical application. In contrast, AIE photosensitizers stand out due to their unique properties. In the aggregated state, the intramolecular motion of these photosensitizers is significantly restricted, and their fluorescence intensity and ROS generation efficiency are simultaneously and significantly improved, fundamentally overcoming the ACQ defect of traditional photosensitizers and possessing both higher photodynamic therapeutic efficacy and biosafety.

[0004] Currently, AIE photosensitizers have been the subject of a series of studies and have made phased progress in fields such as anti-tumor therapy, bioimaging, and bacterial detection. However, their application in the antiviral field is still in the exploratory stage, especially with no reports of systematic research on RNA viruses. Furthermore, in the existing technological system, AIE photosensitizers with broad-spectrum antiviral activity are still lacking, making it difficult to meet the treatment needs of mixed viral infections in reality. Summary of the Invention

[0005] Purpose of the invention: The technical problem to be solved by the present invention is to address the shortcomings of the prior art by providing a class of aggregation-induced emission photosensitizers for use in antiviral applications.

[0006] To solve the above-mentioned technical problems, the present invention discloses the following technical solution:

[0007] In a first aspect, the present invention discloses the application of an aggregation-induced emission photosensitizer of Formula I with high ROS yield in the preparation of antiviral products.

[0008]

[0009] Formula I

[0010] in,

[0011] R is selected from 2,2'-(benzo[1,2-D:4,5-D']bis(thiazolyl)-2,6-diyl)diacetonitrile (TPBI), terephthalic acid acetonitrile (TPCI), hex-3-enidiazolyl (TPEI), 3-cyanophenylacetonitrile (JPCI), 2,2',2''-(benzyl-1,3,5-triacyl)triacetonitrile, p-benzothiadiazolyl, p-benzoselenodiazolyl, 6,7-diphenyl-benzo[C][1,2,5]thiadiazolo[3,4-G]quinoxaline or benzothiazolyl.

[0012] In some embodiments, the virus includes enveloped RNA viruses and non-enveloped RNA viruses; such as any one or more of the following: SARS-CoV-2, influenza A virus (H1N1), porcine epidemic diarrhea virus (PEDV), and enterovirus 71 (EV-71).

[0013] In some embodiments, the antiviral treatment includes antiviral treatment in the presence of darkness or light; the light is white light; in some embodiments, the light intensity is 2.0-20 mW / cm². 2 Irradiation conditions, in some embodiments 3.5, 5.5, 6, 7.5, 16, or 20 mW / cm². 2 Illumination under certain conditions; in some embodiments, illumination is 1 min or more, in some embodiments it is 1-50 min, and in some embodiments it is 1, 10, 20, 30, or 40 min.

[0014] In some embodiments, the antiviral product is a spray, coating material, or dye.

[0015] In some embodiments, the antiviral product includes antiviral medical materials, which in some embodiments are antiviral fabrics, in some embodiments are antiviral fibers, and in some embodiments are antiviral polyester fibers.

[0016] In some embodiments, the antiviral product is used to inhibit, inactivate, or remove viruses, such as for treating air, liquid, or solid surfaces contaminated with viruses or at risk of viral contamination.

[0017] In a second aspect, the present invention discloses an antiviral product comprising an aggregation-induced emission photosensitizer as shown in Formula I.

[0018]

[0019] Formula I

[0020] in,

[0021] R is selected from 2,2'-(benzo[1,2-D:4,5-D']bis(thiazolyl)-2,6-diyl)diacetonitrile (TPBI), terephthalic acid acetonitrile (TPCI), hex-3-enidiazolyl (TPEI), 3-cyanophenylacetonitrile (JPCI), 2,2',2''-(benzyl-1,3,5-triacyl)triacetonitrile, p-benzothiadiazolyl, p-benzoselenodiazolyl, 6,7-diphenyl-benzo[C][1,2,5]thiadiazolo[3,4-G]quinoxaline or benzothiazolyl.

[0022] In some embodiments, the virus includes enveloped RNA viruses and non-enveloped RNA viruses; such as any one or more of the following: SARS-CoV-2, influenza A virus (H1N1), porcine epidemic diarrhea virus (PEDV), and enterovirus 71 (EV-71).

[0023] In some embodiments, the antiviral treatment includes antiviral treatment in the presence of darkness or light; the light is white light; in some embodiments, the light intensity is 2.0-20 mW / cm². 2 Irradiation conditions, in some embodiments 3.5, 5.5, 6, 7.5, 16, or 20 mW / cm². 2 Illumination under certain conditions; in some embodiments, illumination is 1 min or more, in some embodiments it is 1-50 min, and in some embodiments it is 1, 10, 20, 30, or 40 min.

[0024] In some embodiments, the antiviral product is a spray, coating material, or dye.

[0025] In some embodiments, the antiviral product includes antiviral medical materials, which in some embodiments are antiviral fabrics, in some embodiments are antiviral fibers, and in some embodiments are antiviral polyester fibers.

[0026] In some embodiments, the antiviral product is used to inhibit, inactivate, or remove viruses, such as for treating air, liquid, or solid surfaces contaminated with viruses or at risk of viral contamination.

[0027] Existing AIE photosensitizers generally lack pathogen adsorption capacity, and their research and application in the antiviral field remain significantly insufficient. To address these issues, this invention provides a novel AIE photosensitizer possessing both highly efficient antiviral activity and excellent pathogen capture capability, as well as antiviral functional products constructed based on this photosensitizer. The high-performance antiviral material described in this invention can be flexibly adapted and applied in multiple scenarios: it can be prepared as a spray to directly disinfect pathogens in the environment; it can also be processed into a coating material to coat various media surfaces and interfaces, constructing a protective barrier to block pathogen transmission; and it can also be compounded as a functional component into carriers such as clothing and protective equipment (e.g., masks, protective suits), thereby effectively addressing the risk of virus transmission in complex environments and comprehensively meeting diverse infection control needs.

[0028] Beneficial effects: Compared with the prior art, the present invention has the following advantages:

[0029] This invention proposes a class of aggregation-induced emission photosensitizers with highly efficient antiviral activity. Its molecular structure design is significantly innovative: the four methylpyridine iodide groups introduced into the molecular backbone endow the photosensitizer with a positive charge, enabling it to efficiently capture negatively charged viruses through electrostatic interactions, laying the foundation for broad-spectrum and highly efficient antiviral efficacy. Furthermore, the iodide ions themselves possess inherent antiviral activity, allowing this type of photosensitizer to exert basic pathogen inhibition and killing effects even in the absence of light, fundamentally breaking through the absolute dependence of traditional photosensitizers on light. In addition, the AIE photosensitizer prepared by this invention achieves highly efficient antiviral activity under mild conditions of extremely low working concentration and low-intensity white light irradiation; and maintains good pathogen killing effects even in the absence of light. Crucially, this photosensitizer effectively avoids the development of viral resistance and possesses excellent biocompatibility, fundamentally overcoming the problems commonly found in traditional antiviral drugs, such as frequent drug resistance, limited broad-spectrum activity, and significant toxic side effects. Furthermore, this invention has simple operating conditions and low preparation cost in terms of antiviral treatment, and is suitable for various pathogen control scenarios. Attached Figure Description

[0030] Figure 1 Photostability study of different AIE photosensitizers and RB under continuous LED white light illumination: A0 is the initial maximum absorbance, and A is the maximum absorbance of the sample after continuous irradiation at a specified time interval.

[0031] Figure 2(A) Fluorescence emission spectra of different AIE photosensitizers in glycerol / water mixed solutions of different ratios. (B) Changes in fluorescence intensity of the maximum emission peak of different AIE photosensitizers in glycerol / water mixed solutions of different ratios. The photosensitizer concentration was 10 μM, and the excitation wavelength was 430 nm.

[0032] Figure 3 The graph shows the changes in fluorescence intensity of mixed solutions containing different photosensitizers and DCFH, as well as the control group, as a function of illumination time. The excitation wavelength was 485 nm.

[0033] Figure 4 The results of cell viability after 24 h of treatment with different photosensitizers on normal tissue cells.

[0034] Figure 5 The graph shows the results of the ability of photosensitizer of general formula I to inactivate PEDV virus.

[0035] Figure 6 (A) Fluorescence of AIE photosensitizer TPBI against SARS-CoV-2 virus; (B, C) Inactivation ability of AIE photosensitizer TPBI against different RNA viruses under dark and light conditions; (D) Inactivation ability of commercial photosensitizer RB against H1N1 virus under no light conditions (* P < 0.05, ** P < 0.01, *** P < 0.001, **** P < 0.0001).

[0036] Figure 7 Figure 1 shows the results of anti-SARS-CoV-2 virus activity of polycarbonate fiber with AIE photosensitizer TPBI under light and dark conditions (*** P < 0.001). Detailed Implementation

[0037] The present invention can be better understood from the following embodiments. However, those skilled in the art will readily understand that the descriptions in the embodiments are for illustrative purposes only and should not, and will not, limit the invention as detailed in the claims.

[0038] Unless otherwise specified, the experimental methods described in the following examples are conventional methods; the reagents and materials described are commercially available unless otherwise specified.

[0039] This invention provides a class of aggregation-induced emission photosensitizers, including TPBI, TPCI, TPEI, and JPCI, which can be prepared according to Chinese Invention No. 202510587583.0, and their specific chemical structural formulas are as follows:

[0040] .

[0041] The TPEI synthesis route is as follows:

[0042]

[0043] Compound 1 (216 mg), (E)-hexyl-3-enadionitrile (25.3 mg), and potassium tert-butoxide (286 mg) were dissolved in 15 mL of methanol. The mixture was heated to 70 °C and refluxed under nitrogen protection for 11 h with stirring. After cooling to room temperature, the solvent was removed under reduced pressure, and the product was purified by silica gel column chromatography. The residue after rotary evaporation was dissolved in dichloromethane and loaded onto the sample using a mobile phase of dichloromethane:methanol = 40:1 to obtain the product TPE. 1 H NMR (400 MHz, CDCl3) δ 8.67 (d, J = 5.3 Hz, 8H), 7.80 (d,J = 8.4 Hz, 3H), 7.63 (d, J = 8.2 Hz, 9H), 7.52 (d, J = 5.2 Hz, 8H), 7.29 (d,J = 8.2 Hz, 9H), 7.23 – 7.08 (m, 7H).

[0044] TPE (67.6 mg) was added to a flask containing 20 mL of acetonitrile and dissolved. Then, 1 mL of iodomethane was injected using a syringe. The mixture was reacted at 40 °C for 1 h, then heated to 80 °C and refluxed for 12 h. After the reaction was completed, the mixture was cooled to room temperature, and an appropriate amount of anhydrous diethyl ether was added. The mixture was allowed to stand for 20 min and then filtered to obtain a red powdery solid TPEI. 1 H NMR (400 MHz, DMSO) δ 8.97 (t, J= 5.6 Hz, 8H), 8.51 – 8.41 (m, 8H), 8.18 – 8.08 (m, 9H), 7.91 (dd, J = 10.2,7.5 Hz, 5H), 7.38 – 7.14 (m, 13H), 4.31 (d, J = 5.5 Hz, 12H).

[0045] The JPCI synthesis route is as follows:

[0046]

[0047] Compound 1 (427 mg), 1,3-phenyleneacetonitrile (55.5 mg), and potassium tert-butoxide (573.5 mg) were dissolved in 30 mL of methanol. The mixture was heated to 70 °C and refluxed under nitrogen protection for 24 h with stirring. After cooling to room temperature, the solvent was removed under reduced pressure. The mixture was extracted three times with dichloromethane and water. The organic layer was collected, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography. The residue after rotary evaporation was dissolved in dichloromethane and loaded onto the sample. The mobile phase was dichloromethane:anhydrous ethanol = 20:1 to give product JPC. 1 H NMR (400 MHz, CDCl3) δ 8.70 – 8.60 (m, 8H), 7.94 – 7.84 (m, 4H), 7.73 – 7.61 (m, 9H), 7.61 – 7.42 (m, 12H), 7.37 – 7.25 (m, 9H), 7.25 – 7.17 (m,4H).

[0048] 100 mg of JPC was added to a flask containing 20 mL of acetonitrile and dissolved. Then, 1 mL of iodomethane was injected using a syringe. The mixture was reacted at 40 °C for 1 h, then heated to 80 °C and refluxed for 12 h. After the reaction was completed, the mixture was cooled to room temperature, and an appropriate amount of anhydrous diethyl ether was added. The mixture was allowed to stand for 20 min and then filtered to obtain an orange powdery solid JPCI. 1 H NMR (400 MHz, DMSO) δ 8.96 (t, J =7.6 Hz, 8H), 8.48 (d, J = 6.5 Hz, 8H), 8.22 – 8.09 (m, 10H), 8.10 – 8.03 (m,4H), 7.93 (s, 3H), 7.42 – 7.21 (m, 13H), 4.32 (s, 12H).

[0049] The embodiments of the present invention also relate to comparative AIE photosensitizers NC1 and NC2 containing only one or two pyridinium salts, and to commercially available comparative photosensitizers Bengal rose red (RB) and methylene blue (MB), whose chemical structural formulas are as follows:

[0050] .

[0051] Example 1: Evaluation of photostability and photobleaching resistance of AIE photosensitizer

[0052] Experimental Method: Using the commercially available photosensitizer Bengal Red (RB) as a control, 20 μL of a 1 mM dimethyl sulfoxide (DMSO) stock solution of different AIE photosensitizers and RB was added to 2 mL of ultrapure water and ultrasonically dispersed for 1 min to achieve a working concentration of 10 μM for all photosensitizers. The solution was then placed under an LED white light lamp (16 mW / cm²). 2 Irradiate the solution under light and record the changes in absorbance at the maximum absorption peak of different solutions as the irradiation time changes.

[0053] Experimental results: According to Figure 1 It can be seen that when the illumination time is 40 min, the degradation rate of the commercial photosensitizer RB is as high as 90%, while the degradation rate of the AIE photosensitizer is less than 20%; in particular, the degradation rates of TPCI and JPCI are less than 5%. The above results show that, compared with traditional commercial photosensitizers, the AIE photosensitizer of the present invention has better photostability and photobleaching resistance.

[0054] Example 2: Evaluation of AIE performance of different photosensitizers

[0055] Experimental method: The fluorescence intensity of AIE photosensitizers usually increases with the increase of environmental viscosity. By changing the viscosity of the system, the fluorescence change of the synthesized AIE photosensitizer can be studied, and its AIE performance can be evaluated.

[0056] The viscosity of the system can be adjusted by changing the ratio of glycerol to water, thus obtaining solvents with different viscosities. The photosensitizers (TPBI, TPCI, TPEI, and JPCI) from general formula I and the comparative AIE photosensitizers (NC1 and NC2) were added to solvents of different viscosities, all at a working concentration of 10 μM. Then, the fluorescence emission spectra of different photosensitizers in solvents of different viscosities and the changes in fluorescence intensity at the maximum emission peak were measured at an excitation wavelength of 430 nm.

[0057] Experimental results: According to Figure 2 It can be seen that the fluorescence intensity of the AIE photosensitizers (TPBI, TPCI, TPEI, JPCI) and the comparative AIE photosensitizers (NC1 and NC2) in synthetic general formula I gradually increases with the increase of solvent viscosity, indicating that the photosensitizers in synthetic general formula I and the comparative AIE photosensitizers all have good AIE performance.

[0058] Example 3: Evaluation of ROS generation capacity of AIE photosensitizer

[0059] 200 μL of a 5 mM DMSO solution of 2,7-dichlorofluorescein diacetate (H2DCFH-DA) was diluted with 800 μL of ethanol, followed by the addition of 4 mL of 0.01 M NaOH aqueous solution. The solution was then activated by incubating at room temperature in the dark for 30 min. Finally, 7.5 mL of 10 mM PBS (pH 7.4) was added. The resulting 80 μM DCFH solution was then placed on ice for later use. In the presence of ROS, DCFH is converted to 2,7-dichlorofluorescein (DCF) with a high quantum yield.

[0060] Add 1998 μL of activated DCFH solution and 10 μL of DMSO stock solution (1 mM) of AIE photosensitizer or commercial photosensitizers methylene blue (MB) or Bengal red (RB) to a transparent glass bottle. The final concentration of the photosensitizer is 5 μM or an equal volume of DMSO. After mixing thoroughly, irradiate the solution under an LED white light and record the changes with illumination time. When the excitation wavelength is set to 485 nm, record the change in fluorescence intensity of the mixed solution at 526 nm.

[0061] Experimental results: According to Figure 3 It was observed that only the DMSO-containing control solution showed a relatively constant fluorescence intensity at 526 nm over time, indicating that LED white light irradiation did not affect ROS generation. When photosensitizer molecules appeared, the fluorescence intensity of the mixed solution at 526 nm gradually increased with prolonged irradiation time, indicating the generation of more and more ROS. Notably, the AIE photosensitizers (TPCI, TPBI, and JPCI) synthesized in general formula I generated significantly more ROS than the commercial photosensitizers MB and RB; however, the ROS generation of the AIE photosensitizers was slightly lower than that of the commercial photosensitizers. These results indicate that the AIE photosensitizers (TPCI, TPBI, and JPCI) synthesized in general formula I possess stronger photodynamic effects.

[0062] Example 4: For the synthesized general formula Safety evaluation of AIE photosensitizer

[0063] Experimental methods: Normal tissue cells, such as mouse fibroblasts (NIH 3T3) and African green monkey kidney epithelial cells (Vero-E6), were incubated with different concentrations of the synthesized general formula I photosensitizer and commercial photosensitizers methylene blue (MB) and Bengal red (RB) in the dark for 24 h. Cell viability was then measured using the MTT assay.

[0064] Experimental results: According to Figure 4It is evident that the cytotoxicity of commercially available photosensitizers increases with increasing concentration. Furthermore, when the photosensitizer concentration is 30 μM, cell viability after MB and RB treatment is below 65% and 80%, respectively. However, the cell viability after treatment with the AIE photosensitizer remains as high as 95%. These results demonstrate that the AIE photosensitizer of this invention has no significant dark toxicity to normal tissue cells and exhibits good biocompatibility.

[0065] Example 5: Evaluation of the antiviral activity of different AIE photosensitizers

[0066] PEDV is a coronavirus that infects pigs. Plaque assays were used to verify the inhibitory effects of different AIE photosensitizers on PEDV. Experimental groups: virus + no light group (1), virus + AIE photosensitizer + no light group (2), virus + light group (3), virus + AIE photosensitizer + light group (4). Vero-E6 cells were seeded into 24-well plates at a seeding rate of 130,000 cells / well 12 h in advance. Appropriate amounts of PEDV virus solution were mixed with different concentrations of AIE photosensitizer to achieve final photosensitizer concentrations of 0.1, 1, and 10 μM, with a virus multiplicity of infection (MOI) of 0.1. The cells were incubated at room temperature for 30 min. The light group was incubated under an LED white light lamp (5.5 mW / cm²). 2 Irradiate under light for 10 min. Then add the mixture to the corresponding 24-well plates according to different treatment groups. After 2 h of infection, replace the medium with complete medium and continue culturing for 48 h.

[0067] Experimental results: Figure 5 It can be seen that under illumination, PEDV viral plaques were barely visible at 1 μM with different AIE photosensitizers; however, at 0.1 μM, only the TPBI group showed virtually no PEDV viral plaques. These results indicate that, under the same conditions, TPBI has a better antiviral effect.

[0068] Example 6: Evaluation of the antiviral activity of AIE photosensitizer TPBI against different viruses

[0069] To verify whether the AIE photosensitizer TPBI can effectively inactivate viruses, enveloped viruses SARS-CoV-2, PEDV, and H1N1, and non-enveloped virus EV-71 were selected as models. The specific methods are as follows:

[0070] Experimental groups: Virus + no light group (1), Virus + 0.01 μM photosensitizer + no light group (2), Virus + 0.1 μM photosensitizer + no light group (3), Virus + 1 μM photosensitizer + no light group (4), Virus + 0.01 μM photosensitizer + light group (5), Virus + 0.1 μM photosensitizer + light group (6), Virus + 1 μM photosensitizer + light group (7), Virus + light group (8). Among them, SARS-CoV-2 infected Caco-2-N cells, PEDV infected Vero-E6 cells, H1N1 infected A549 cells, and EV-71 infected RD cells. Caco-2-N, Vero-E6, A549, and RD cells were seeded into 24-well plates at a seeding rate of 130,000 cells / well 12 h in advance. Appropriate amounts of virus solution were mixed with different concentrations of AIE photosensitizer to achieve final photosensitizer concentrations of 0.01, 0.1, and 1 μM, respectively, with a viral MOI of 0.1. The cells were incubated at room temperature for 5 min. The light group was placed under an LED white light lamp (5.5 mW / cm²). 2 The mixture was then exposed to light for 10 min. Subsequently, the mixture was added to the corresponding 24-well plates according to different treatment groups. After 2 h of infection, the medium was replaced with complete medium and cultured for another 48 h. The mRNA levels of different viruses were detected by RT-qPCR to verify the viral genome replication capacity.

[0071] Since SARS-CoV-2 is a pseudovirus constructed using reverse genetics, capable of mimicking the life cycle of a real virus, its nucleocapsid protein is replaced by a GFP reporter gene (SARS-CoV-2-GFP / ΔN trVLP). Therefore, the intensity of GFP can reflect the viral infection status. After treatment with the AIE photosensitizer TPBI, the inhibition of viral replication was verified by detecting the GFP fluorescence intensity, and the mRNA level of SARS-CoV-2 ORF was detected by RT-qPCR to verify the viral genome replication capacity. Figure 6 As shown in Figure A, treatment with the photosensitizer TPBI exhibits a strong antiviral effect even at relatively low concentrations; at a concentration of 1 μM, viral replication is almost completely inhibited. Figure 6 As shown in B and 6C, the ability to inhibit the virus increases with increasing concentration of the photosensitizer TPBI, achieving an inhibition rate exceeding 50% at 0.1 μM. EV-71 is a typical non-enveloped enterovirus. RT-qPCR detection results ( Figure 6 (B, 6C) shows that the photosensitizer TPBI in general formula I exhibits significant inhibitory activity against this non-enveloped virus, and its PDT antiviral effect is stable and independent of dosage. This result fully confirms that TPBI possesses potent and broad-spectrum antiviral activity, effectively blocking the invasion and replication processes of different types of viruses. Furthermore, combined with... Figure 6 Further analysis of C and 6D revealed that even under light-free conditions, TPBI at concentrations as low as 1 μM could effectively inhibit H1N1 virus replication; in stark contrast, commercially available photosensitizers showed no inhibitory activity under the same conditions. This characteristic may be closely related to the four iodopyridine groups contained in the TPBI molecule.

[0072] Example 7: Evaluation of the antiviral ability of polycarbonate fibers dyed with AIE photosensitizer as dye

[0073] Experimental Method: The photosensitizer TPBI was diluted 1 μM in 20 μL of PBS and dropped onto the polycarbonate fiber membrane of the Transwell chamber. The membrane was then dried in the dark. A solution containing SARS-CoV-2 virus was added to the Transwell chamber at an MOI of 1, at a concentration of 5.5 mW / cm². 2 After 10 min of white light exposure, the Transwell chambers were placed over the wells of a 24-well plate. After 8 h of infection, the viral infection intensity was detected by RT-qPCR. This test set up four groups: blank + no light group (1), pure virus + no light group (2), virus + TPBI coating + no light group (3), and virus + TPBI coating + light exposure (4).

[0074] Experimental results: Figure 7 A shows a schematic diagram of the Transwell assay after coating with the photosensitizer TPBI and the control group chamber virus inactivation test. The test results are as follows: Figure 7 As shown in Figure B, under these experimental conditions, the SARS-CoV-2 virus can infect cells normally. Under no-light conditions, the virus's infectivity is slightly reduced; under light conditions, the SARS-CoV-2 viral genome is almost undetectable, indicating that the virus has no replication ability and has been inactivated by TPBI photodynamic therapy.

[0075] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are specific and detailed, they should not be construed as limiting the scope of the present invention. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these modifications and improvements all fall within the scope of protection of the present invention. Therefore, the scope of protection of this patent should be determined by the appended claims.

Claims

1. The application of an aggregation-induced emission photosensitizer as shown in Formula I in the preparation of antiviral products; Formula I in, R is selected from 2,2'-(benzo[1,2-D:4,5-D']bis(thiazolyl)-2,6-diyl)diacetonitrile, terephthalic acid diacetonitrile, hex-3-enidiazolyl, 3-cyanophenylacetonitrile, 2,2',2''-(benzyl-1,3,5-triacyl)triacetonitrile, p-benzothiadiazolyl, p-benzoselenodiazolyl, 6,7-diphenyl-benzo[C][1,2,5]thiadiazolo[3,4-G]quinoxaline or benzothiazolyl.

2. The application according to claim 1, characterized in that, The viruses include enveloped RNA viruses and non-enveloped RNA viruses; optionally, any one or more of the following viruses: severe acute respiratory syndrome coronavirus type 2, influenza A virus, swine epidemic diarrhea virus, and enterovirus type 71.

3. The application according to claim 1, characterized in that, The antiviral treatment includes antiviral activity under either darkness or light conditions; the light is white light; optionally, at 2.0-20 mW / cm². 2 Under the given illumination conditions, the light intensity can be selected as 3.5, 5.5, 6, 7.5, 16, or 20 mW / cm². 2 Illumination under the following conditions; optionally, illumination for 1 min or more, optionally illumination for 1-50 min, optionally illumination for 1, 10, 20, 30, or 40 min.

4. The application according to claim 1, characterized in that, The antiviral product spray, coating material, or dye mentioned above.

5. The application according to claim 1, characterized in that, The antiviral products include antiviral medical materials, optionally antiviral fabrics, optionally antiviral fibers, and optionally antiviral polyester fibers.

6. An antiviral product, characterized in that, Including aggregation-induced emission photosensitizers as shown in Formula I; Formula I in, R is selected from 2,2'-(benzo[1,2-D:4,5-D']bis(thiazolyl)-2,6-diyl)diacetonitrile, terephthalic acid diacetonitrile, hex-3-enidiazolyl, 3-cyanophenylacetonitrile, 2,2',2''-(benzyl-1,3,5-triacyl)triacetonitrile, p-benzothiadiazolyl, p-benzoselenodiazolyl, 6,7-diphenyl-benzo[C][1,2,5]thiadiazolo[3,4-G]quinoxaline or benzothiazolyl.

7. The product according to claim 6, characterized in that, The viruses include enveloped RNA viruses and non-enveloped RNA viruses; optionally, any one or more of the following viruses: severe acute respiratory syndrome coronavirus type 2, influenza A virus, swine epidemic diarrhea virus, and enterovirus type 71.

8. The product according to claim 6, characterized in that, The antiviral treatment includes antiviral activity under either darkness or light conditions; the light is white light; optionally, at 2.0-20 mW / cm². 2 Under the given illumination conditions, the light intensity can be selected as 3.5, 5.5, 6, 7.5, 16, or 20 mW / cm². 2 Illumination under the following conditions; optionally, illumination for 1 min or more, optionally illumination for 1-50 min, optionally illumination for 1, 10, 20, 30, or 40 min.

9. The product according to claim 6, characterized in that, The antiviral product spray, coating material, or dye mentioned above.

10. The product according to claim 6, characterized in that, The antiviral products include antiviral medical materials, optionally antiviral fabrics, optionally antiviral fibers, and optionally antiviral polyester fibers.

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