Meta-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods and pharmaceutical uses

Abstract

This invention belongs to the field of pharmaceutical synthesis technology, and relates to meta-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and pharmaceutical uses, specifically meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and applications. The compounds of this invention, through photosensitization efficiency and in vitro and in vivo antibacterial activity tests, demonstrate good antibacterial activity and can be used to prepare novel pyridine quaternary ammonium salt-containing fluoroboron dipyrrole (BODIPY) photosensitizers, and further to prepare new antibacterial drugs.

Description

Technical Field

[0001] This invention belongs to the field of pharmaceutical synthesis technology, and relates to meta-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and pharmaceutical uses, specifically meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and applications. The meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compounds can be used to prepare novel pyridine quaternary ammonium salt-containing fluoroboron dipyrrole (BODIPY) photosensitizers. Background Technology

[0002] Existing technology has revealed that antibiotics have saved countless lives from deadly infections and extreme cold for decades. However, due to overuse or misuse in practice, some antibiotics are rapidly losing their effectiveness, a phenomenon known as antibiotic resistance. Industry experts believe that without urgent international action, the world will enter a "post-antibiotic era," and many infectious diseases may become uncontrollable. One specific example is the common methicillin-resistant Staphylococcus aureus (MRSA). MRSA has been reported to be resistant not only to methicillin but also to other aminoglycosides, macrolides, tetracyclines, chloramphenicol, and lincosamides. However, an even more serious threat comes from "pan-drug-resistant" Gram-negative bacteria. Their low-permeability outer membrane barrier and highly efficient multidrug efflux pumps make these Gram-negative pathogens resistant to virtually all available antibiotics. Compared to the number of antibiotics available for bacteria, the number of drugs available to treat fungal infections is much more limited, and with long-term drug exposure, drug-resistant fungi continue to emerge and infections persist after treatment.

[0003] In recent years, a series of new antibacterial methods have been developed. Antimicrobial photodynamic therapy (aPDT) is considered a promising and innovative approach to treating infections caused by Gram-positive and Gram-negative bacteria, fungi, mycoplasma, and parasitic protozoa. Photodynamic antibacterial therapy has advantages over antibiotics or other antibacterial strategies due to its mechanism: firstly, it is phototargeting, producing cytotoxicity only at the site of light irradiation; secondly, its unique oxidative damage mechanism makes it less likely to induce drug resistance in microorganisms; and thirdly, it theoretically has the potential for broad-spectrum antibacterial activity, with a wide range of therapeutic applications. However, limited by the optical window wavelength of human tissue and the depth to which light can penetrate tissues, photodynamic antibacterial therapy is generally only applied to local infections, such as those in the oral cavity and skin.

[0004] Mechanistically, photodynamic antibacterial agents should possess good broad-spectrum antibacterial capabilities. However, actual studies have found that different microorganisms exhibit completely different sensitivities to photosensitizers, primarily due to differences in microbial cell structures. The envelope structure of Gram-positive bacteria consists of a high-charge-density outer wall zone (OWZ) and an inner membrane (IM). Gram-negative bacteria have a more complex structure than Gram-positive bacteria. The cell wall of Gram-negative bacteria consists of an outer membrane (OM), a peptidoglycan layer, and an inner membrane (IM). Compared to Gram-positive bacteria, the peptidoglycan layer of Gram-negative bacteria is thinner and denser, and it contains an outer membrane structure absent in Gram-positive bacteria. Fungal cell envelopes are mainly composed of covalently linked β-glucans, chitin, and mannoproteins. The presence of a highly organized outer membrane (OM) hinders the application of photosensitizers in antibacterial agents. In particular, neutral or negatively charged photosensitizers exhibit very poor activity against Gram-negative bacteria because the outer membrane of Gram-negative bacteria is a highly complex multilayered structure, with its outer surface covered by Mg... 2+ and Ca 2+ Neutralized polyanions. Therefore, antibacterial photosensitizers are often positively charged, interacting closely with the negatively charged sites on the surface of polyanions, thereby improving the efficiency of the photoinactivation process.

[0005] Fluoroboropyrrole (BODIPY) photosensitizers have become a research hotspot in photodynamic therapy (PDT) in recent years due to their high molar extinction coefficient, high singlet oxygen yield, resistance to photobleaching, and high light-to-dark toxicity ratio. With appropriate modification, the maximum absorption peak of BODIPY photosensitizers can be tuned to the near-infrared region, effectively increasing tissue penetration in PDT. Heavy atoms can enhance spin-orbit coupling, thereby facilitating intersystem crossings and increasing the yield of singlet oxygen; this is known as the "heavy atom effect." Furthermore, iodine atoms exhibit a more effective heavy atom effect than other halogens.

[0006]

[0007] Studies have also reported on antibacterial photosensitizers A and B with a meso-position 4-pyridine quaternary ammonium salt BODIPY structure. The structural difference between the two lies in the quaternary ammonium salt group. Through photodynamic activity tests on Staphylococcus xylose and Escherichia coli, researchers found that both A and B exhibit strong photodynamic antibacterial activity, capable of killing bacteria under low light doses and low photosensitizer concentrations. Overall, photosensitizer A shows stronger activity than B, and in subsequent reports, A has been widely used in research related to various antimicrobial agents.

[0008]

[0009] While reported BODIPY photosensitizers A and B exhibit excellent antimicrobial activity, the BODIPY backbone tends to aggregate in physiological environments. Furthermore, photosensitizer A suffers from a low singlet oxygen yield due to the photo-induced electron transfer (PET) effect. These properties limit its application as an antibacterial photosensitizer to some extent.

[0010] Based on the current state of the technology, the inventors of this application intend to provide a method for preparing and using a meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY photosensitizer. Compared with photosensitizer A, which has been widely studied and applied, the meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY photosensitizer provided in this application has the advantages of enhanced solubility in the physiological environment, increased singlet oxygen production, and enhanced antibacterial phototoxicity. Furthermore, in vivo studies have shown that the prepared photosensitizer can effectively kill microorganisms on infected wounds and accelerate wound healing, and is expected to develop into a novel antibacterial treatment method. Summary of the Invention

[0011] The purpose of this invention is to provide a meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY photosensitizer with good microbial cell killing effect, based on the current state of the technology. Its main advantages include good solubility in the physiological environment, high singlet oxygen production rate, and strong binding ability to microbial cells.

[0012] Specifically, this invention provides meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compounds, their preparation methods, and their use in the preparation of novel fluoroboron dipyrrole (BODIPY) photosensitizers containing pyridine quaternary ammonium salts.

[0013] The meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compound of the present invention has the structure shown in the following formula:

[0014] in:

[0015] R is independently selected from C1-12 alkyl, C1-12 alkyl-substituted phenyl, C1-12 alkoxy-substituted benzyl, halogen-substituted benzyl, and hydroxyl-substituted benzyl.

[0016] In this invention, the compounds have the structures of compounds 1, 2, and 3 as described below:

[0017]

[0018] A further object of the present invention is to provide a method for preparing the above-mentioned meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compound.

[0019] The compounds of the present invention are prepared by the following process:

[0020]

[0021] The results of in vitro photosensitization efficiency tests showed that compounds 1, 2, and 3 all had good singlet oxygen yields. Numerical results showed that the singlet oxygen yield of compounds 1, 2, and 3 substituted with 3-pyridine quaternary ammonium salt was about three times that of compound A substituted with 4-pyridine quaternary ammonium salt.

[0022] In this invention, the solubility test results of photosensitizers in physiological saline showed that 3-methylpyridine quaternary ammonium salt substituted compound 1 had the best solubility in the physiological environment and no obvious aggregation behavior was found in the concentration range of 4–24 μM, while 4-methylpyridine quaternary ammonium salt substituted compound A showed obvious aggregation.

[0023] In this invention, the results of the microbial cell uptake test showed that S. aureus, E. coli and C. albicans all achieved good uptake of the compounds of this invention within 15 minutes, especially for compounds 2 and 3, the uptake results were better than those for compound A.

[0024] In this invention, in vitro cell-level test results showed that the compounds of this invention exhibited good antibacterial activity against microbial cells S. aureus, E. coli, C. albicans, and MRSA (methicillin-resistant Staphylococcus aureus). In particular, compound 1 had a lower minimum inhibitory concentration (MIC) than compound A, which was substituted with 4-pyridine quaternary ammonium salt.

[0025] The meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compounds of the present invention can be used to prepare novel antibacterial photosensitizers of the fluoroboron dipyrrole (BODIPY) class containing pyridine quaternary ammonium salts.

[0026] Based on in vitro experimental results, compound 1 was used for in vivo testing. In a mouse S. aureus-infected wound model, photodynamic therapy with compound 1 as a photosensitizer showed that almost all microorganisms in the mouse wound were killed, and wound healing was accelerated.

[0027] The meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY compound of the present invention can be further developed into a novel meso-position 3-pyridine quaternary ammonium salt-substituted BODIPY antimicrobial infection drug. The microbial infection is a non-specific, widespread infection, and the types of microorganisms include bacteria, fungi, viruses, mycoplasma, and chlamydia infections, with infection sites including human skin, oral cavity, respiratory tract, intestines, and reproductive tract. Attached Figure Description

[0028] Figure 1 Aggregation of the compound in physiological saline (containing 0.2% DMSO).

[0029] Figure 2 Antibacterial dose-dependent experimental results of compound 1.

[0030] Figure 3 : Wound healing status of experimental animals.

[0031] Figure 4 Microbial counts in experimental animal wounds. Detailed Implementation

[0032] Example 1: Synthesis of Compound 1

[0033] 1) Synthesis of 1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroboron dipyrrole

[0034] 470 mg of 3-pyridinecarboxaldehyde and 920 mg of 2,4-dimethylpyrrole were dissolved in 250 mL of dry DCM. A catalytic amount of TFA was added, and the mixture was stirred at room temperature for 24 hours under argon protection. Part of the DCM was evaporated under reduced pressure to a final volume of 70 mL. 1.5 g of 2,3-dichloro-5,6-dicyanobenzoquinone was added, and the mixture was stirred at room temperature for 2 hours under argon protection. 7 mL of triethylamine and 7 mL of boron trifluoride diethyl ether solution were added, and the mixture was stirred overnight at room temperature under argon protection. The solvent was removed under reduced pressure, and the remaining solid was dissolved in 150 mL of DCM. The solid was washed three times with water, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Column chromatography was used to purify the solid (DCM / PE = 1 / 3) to give 328 mg of an orange-yellow solid. Yield: 23%. 1 HNMR (600MHz, CDCl3) δ8.77(d,J=4.8Hz,1H),8.59(s,1H),7.67(d,J=7.7Hz,1H),7.48(dd,J=7.6,5.0Hz,1H),6.03(s,2H),2.58(s,6H),1.40(s,6H). 13 C NMR (151MHz, CDCl3) δ155.75,149.58,147.89,142.16,136.64,135.39,130.87,130.67,123.11,121.15,14.37,14.02. MS(ESI)m / z([M+H] + ):326.2.

[0035] 2) Synthesis of 2,6-diiodo-1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroboron dipyrrole

[0036] Compound 1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroboron dipyrrole (100 mg) was placed in a 25 mL round-bottom flask and dissolved in 6 mL of HOAc / DCM = 1 / 3. 340 mg of N-iodosuccinimide was added, and the mixture was stirred at room temperature for 1 h. The reaction was monitored by TLC until complete. The mixture was washed with 20 mL of saturated sodium thiosulfate solution, 20 mL of water, and 20 mL of saturated NaHCO3 aqueous solution. After drying with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the mixture was subjected to column chromatography (PE:EA = 1:1) to give 161 mg of a brown solid. Yield: 91%. 1 HNMR (400MHz, CDCl3) δ8.83 (d, J = 3.3 Hz, 1H), 8.56 (s, 1H), 7.65 (d, J = 8.0 Hz, 1H), 7.52 (t, J = 8.4 Hz, 1H), 2.66 (s, 6H), 1.40 (s, 6H). 13 C NMR (151MHz, CDCl3) δ157.31,149.33,146.96,144.23,136.07,135.74,130.94,130.69,123.63,85.84,17.03,15.54. MS(ESI)m / z([M+H] + ):578.0.

[0037] 3) Synthesis of compound 1

[0038] 58 mg of compound 2,6-diiodo-1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroboron dipyrrole was dissolved in 3 mL of iodomethane and refluxed for 10 h. After the reaction was complete, the solvent was evaporated under reduced pressure, and the crude product was dissolved in an appropriate amount of methanol. Recrystallization was performed using diethyl ether as a poor solvent to give 62 mg of a brown compound, with a yield of 86%. 1 H NMR (600MHz, DMSO) δ9.29 (s, 1H), 9.24 (d, J = 6.2Hz, 1H), 8.85 (d, J = 8.0Hz, 1H), 8.40-8.33 (m, 1H), 4.43 (s, 3H), 2.59 (s, 6H), 1.43 (s, 6H). 13 C NMR(151MHz,DMSO)δ157.78,146.95,145.44,144.85,144.72,132.85,131.93,130.45,128.24,88.27,48.45,18.00,15.87.HRMS(ESI)m / z([MI] - ):591.9722.

[0039] Example 2: Synthesis of Compound 2

[0040] Compound 2,6-diiodo-1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroboron dipyrrole (58 mg, 0.1 mmol) and benzyl bromide (240 μL, 2 mmol) were dissolved in 5 mL of acetonitrile and refluxed in a sealed tube at 90 °C. After 12 h, the solvent was removed by vacuum distillation, and the solution was purified by silica gel column chromatography using DCM / MeOH (10:1, v / v) as eluent to give 61 mg of a reddish-brown compound, in 81% yield. 1 H NMR (600MHz, DMSO) δ9.60 (s, 1H), 9.55 (d, J = 5.4Hz, 1H), 8.89 (d, J = 7.8Hz, 1H), 8.43 (t ,J=7.0Hz,1H),7.66-7.60(m,2H),7.47(m,3H),5.94(s,2H),2.58(s,6H),1.22(s,6H). 13 C NMR (151MHz, DMSO) δ157.79,146.29,146.03,144.37,144.14,133.98,133.65,131.74,13 0.45,129.54,129.30,129.13,129.02,88.28,64.08,17.58,15.86.HRMS(ESI)m / z([M-Br] - ):668.0042.

[0041] Example 3: Synthesis of compound 3

[0042] Compound 2,6-diiodo-1,3,5,7-tetramethyl-8-(3-pyridyl)-4,4'-difluoroboron dipyrrole (58 mg, 0.1 mmol) and 1-iodoheptane (330 μL, 2 mmol) were dissolved in 5 mL of acetonitrile and refluxed in a sealed tube at 90 °C. After 24 hours, the solvent was removed by vacuum distillation, and DCM and Et₂O were added to precipitate the product. Filtration yielded 30 mg of a reddish-brown compound, with a yield of 37%. 1 H NMR (600MHz, DMSO) δ9.44(s,1H),9.40(d,J=6.1Hz,1H),8.89(d,J=8.0Hz,1H),8.45-8.39(m,1H),4.71( t,J=7.3Hz,2H),2.59(s,6H),1.99(m,2H),1.40(s,6H),1.32(m,2H),1.26(m,6H),0.86(t,J=6.9Hz,3H). 13C NMR (151MHz, DMSO) δ157.78,146.20,145.90,144.58,143.95,133.36,131.89,130.48,128.8 3,88.31,61.39,30.83,30.25,27.77,25.23,21.75,17.84,15.87,13.77.HRMS(ESI)m / z([MI] - ):676.0686.

[0043] Example 4: Singlet oxygen yield test

[0044] Compounds 1, 2, 3, A, and Rose Bengal were prepared into 2 mL isopropanol solutions (5 μM). 2 mL of the singlet oxygen probe DPBF in isopropanol solution (100 μM) was added to each of the five different compound solutions to prepare a 4 mL mixture. Based on the UV-Vis absorption spectra, a suitable cutoff wavelength filter (450 nm) was selected. A halogen lamp was placed 30 cm away from the solution, and UV-Vis scans were performed at irradiation times of 10, 20, 30, 40, and 50 s, recording the absorbance change at 411 nm (the maximum absorption wavelength of DPBF). Specific results are shown in Table 1. The results indicate that compounds 1, 2, and 3 in this invention all exhibit good singlet oxygen yields. Using Rose Bengal's singlet oxygen yield of 0.76 in alcohol solution as a reference, the singlet oxygen yield of the compounds in this invention is approximately four times that of compound A.

[0045] Table 1 shows the singlet oxygen yield test results of the compounds of this invention.

[0046] Table 1

[0047]

[0048] Example 5: Physiological Environment Aggregation Test

[0049] Compounds 1, 2, 3, and A were prepared into physiological saline solutions (containing 0.2% DMSO) with concentrations of 24, 20, 16, 12, 8, and 4 μM, respectively, and their UV-Vis spectra were recorded. The absorbance values ​​at the maximum wavelength were fitted to the concentration; a correlation coefficient closer to 1 indicated a better adherence to Beer-Lambert law within the tested concentration range, thus representing better solubility. The results showed that compound 1, substituted with 3-methylpyridine quaternary ammonium salt, exhibited the best solubility in the physiological environment, with no significant aggregation observed in the concentration range of 4–24 μM. In contrast, compound A, substituted with 4-methylpyridine quaternary ammonium salt, showed significant aggregation behavior.

[0050] Implementation Example 7: Cellular Uptake Test

[0051] Bacterial cells were prepared at a density of 10-1.9 CFU / mL, fungal cell density was 10 7 A microbial cell suspension of CFU / mL was incubated with 10 μM of the test compound. After incubation at 37°C in the dark for 15 min, 3 mL of the suspension was removed, and the remaining suspension was incubated for another 15 min. The removed sample was centrifuged at 12000 rpm for 3 min, and the UV-Vis absorption spectrum of the supernatant was recorded. The above procedure was repeated every 30 and 60 minutes. The remaining photosensitizer in the supernatant indicated that these molecules did not bind to the microbial cells. The results showed that *S. aureus*, *E. coli*, and *C. albicans* cells all achieved good uptake of the compounds of this invention within 15 min. In particular, the uptake of compounds 2 and 3 was better than that of compound A.

[0052] Table 2 shows the microbial cell uptake results of the compounds of this invention (incubated for 15 min).

[0053] Table 2

[0054]

[0055] Implementation Example 8: In Vitro Antibacterial Activity Test

[0056] Resuscitation and Culture: Staphylococcus aureus (ATCC25923), Escherichia coli (ATCC25922), Candida albicans (ATCC90028), and methicillin-resistant Staphylococcus aureus (MRSA, ATCC43300) were used in the experiment. CAMHB broth was used as the culture medium. Frozen bacteria and fungi were added dropwise to CAMHB liquid medium and shaken at 37°C and 180 rpm / min for 18 hours on a shaker. The bacterial suspension was then inoculated onto MHA plates and incubated at 37°C for 24 hours (fungal culture temperature was 28°C). Preparation of Test Compound Solutions: In a dark room, the compound was accurately weighed and dissolved in a small amount of DMSO. Serial dilutions were made with CAMHB liquid medium to concentrations ranging from 80 to 0.31 μM. 50 μL of each concentration gradient was placed in a 96-well plate, with three replicates per concentration. Preparation of bacterial suspension: Colonies were picked from MHA plates and dispersed in PBS buffer until suspended. The optical density was measured using a turbidimeter until it reached 0.5 McF. The bacterial suspension was then diluted 1000-fold with CAMHB liquid medium. 50 μL of the bacterial suspension was placed in each well of a 96-well plate containing the added compound. Separately, 50 μL of the bacterial suspension was placed in each well of a 96-well plate containing 50 μL of CAMHB liquid medium as a blank control. Incubation: The 96-well plates were incubated at 37°C for 15 min. Illumination: After incubation, the light group was placed in a 90 mW / cm² incubator. 2Under a halogen lamp light source, a cooling device was used for heat insulation, and a filter with a cutoff wavelength of 450 nm was placed for 15 minutes of irradiation. MIC determination: After irradiation, the 96-well plate was placed in a 37°C constant temperature incubator (28°C for fungi). After 24 hours, the clarity of the 96-well plate was observed, and the minimum photosensitizer concentration corresponding to the clear pore size was taken as the minimum inhibitory concentration. Specific results are shown in Table 2. The results show that the compounds in this invention exhibit good antibacterial activity. Compound 1, under the experimental conditions, showed minimum inhibitory concentrations of 0.63, 1.25, 0.63, and 0.63 μM against four microorganisms: *S. aureus*, *E. coli*, *C. albicans*, and MRSA, respectively. The compounds of this invention can be further developed into antibacterial photosensitizers as novel anti-infective drugs.

[0057] Table 3 shows the results of the microbial cell inhibitory activity of the compounds of the present invention. (Unit: μM) Table 3

[0058]

[0059] Implementation Example 9: Concentration-dependent test

[0060] Concentration-dependent test: OD 600nm =1.0 microbial suspension was incubated with serially diluted compound 1 for 15 min. After incubation, the light group was placed in a 90 mW / cm² environment. 2 Under a halogen lamp light source, a cooling device was used for heat insulation, and a filter with a cutoff wavelength of 450 nm was placed inside for 15 minutes of irradiation. The control group received no light. The inhibition curve was then measured using the plate count method, and the results are as follows: Figure 2 As shown.

[0061] Example 9: In vivo antibacterial activity test in animals

[0062] Preparation of hydrogel containing compound 1: Dry carbomer 940 powder (0.3 g) was dispersed in 2 mL of water and equilibrated at room temperature for 16 h. Then, triethanolamine was added to adjust the pH of the gel to approximately 6.5. Finally, an aqueous solution (2 mL) of compound 1 (2 mg) and Tween 80 (20 mg) was added to the gel to obtain hydrogel containing compound 1.

[0063] In vivo activity test: Adult ICR mice (6-8 weeks old) were housed at a constant temperature for two days, with 12 hours of light and 12 hours of darkness each day. Mice were anesthetized by intraperitoneal injection of ketamine (80 mg / kg) and thiamethoxam (10 mg / kg), and then the hair on the back of the mice was removed using hair clippers and depilatory cream. After disinfection with 70% alcohol, a wound approximately 0.8 cm in diameter was made on the back of each mouse using sterile forceps and surgical scissors. On day 0, each wound was inoculated with a solution containing 10 mg / kg of ketamine. 7Mice were treated with a PBS solution containing CFU of Staphylococcus aureus, and then covered with a dressing (Tegaderm, 3M Health Care, USA) to create an infected wound. On day 2 post-infection, mice were randomly assigned to two groups, and the dressing was carefully removed for observation, including wound photography and bacterial count assessment. Subsequently, mice in the photodynamic therapy group received a 10 mg hydrogel containing compound 1, followed by treatment with 90 mW / cm² pressure. 2 The patient was irradiated under a halogen lamp light source, with heat insulation provided by a cooling device and a filter with a cutoff wavelength of 450nm. The treatment time was 15 minutes. The growth of microorganisms and wound healing were observed on the third and sixth days after treatment. The results are as follows: Figure 3 , Figure 4 As shown.

Claims

1. A kind meso BODIPY compounds substituted with a 3-pyridine quaternary ammonium salt at position 3, characterized in that... The compound is compound 1 having the following structure, 。 2. A meso A BODIPY compound substituted with a 3-pyridinium quaternary salt, characterized in that, The compound is compound 2 having the following structure, 。 3. A kind meso BODIPY compounds substituted with a 3-pyridine quaternary ammonium salt at position 3, characterized in that... The compound is compound 3 having the following structure, 。 4. The use according to any one of claims 1 to 3 meso Use of a BODIPY compound substituted with a 3-pyridinium quaternary salt for the preparation of an antibacterial photosensitizer.

5. The use according to any one of claims 1 to 3 meso meso Use of BODIPY compounds substituted with 3-pyridinium quaternary ammonium salts in the preparation of a medicament for the treatment of microbial infections, the microbial infections being non-specific, generalized infections, the microbial types including bacteria, fungi, and the infection sites including human skin, oral cavity, respiratory tract, intestinal tract, and genital tract.

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