Aromatic diamine derivative, method for preparing the same, and method for improving active oxygen generation ability thereof

Abstract

The application discloses a kind of aromatic diamine derivatives and its preparation method and the method for improving its active oxygen generation capacity, belong to organic synthesis and biological medicine technical field, the aromatic diamine derivative is with thiophene unit as acceptor, contain oxygen heterocycle and aryl or its derivative as donor, development reactive donor-acceptor interaction structure system, its preparation method is simple, with NO response, can start photodynamic therapy in the tumor microenvironment of high expression NO, and the aromatic diamine derivative and NO or NO donor electron transfer oxidation reaction generation triazole derivative after active oxygen generation capacity improves, by targeting endoplasmic reticulum, further improve the killing effect on tumor cell, it has good application prospect in tumor treatment.

Description

TECHNICAL FIELD

[0001] The present application belongs to the field of organic synthesis and biomedicine, and particularly relates to an aromatic diamine derivative, a preparation method thereof and a method for improving the active oxygen generation capacity thereof. BACKGROUND

[0002] Cancer has long been a major problem that seriously endangers human health and life safety. Chemotherapy is one of the important means for treating cancer at present, but the traditional chemotherapy strategy has problems such as poor targeting and strong side effects. After the chemotherapy drug enters the patient's body, it is often difficult to accurately and correctly act only on the cancer cells, but will affect the normal cells of the body indiscriminately. In order to improve the targeting and treatment effect of tumor treatment, many new anti-tumor strategies have been developed, and photodynamic therapy, immunotherapy, gene therapy and targeted therapy have gradually become research hotspots. Among them, photodynamic therapy (PDT) is a light-activated treatment of tumor using photosensitive drugs, which sensitizes the active oxygen by irradiating the tissue-uptaken photosensitizer with a specific wavelength of light, and causes irreversible damage to tumor cells, ultimately leading to cancer cell death. PDT has the advantages of small side effects, small trauma, good selectivity, repeatable treatment, good adaptability and less drug resistance, and has been applied to the treatment of superficial tumors and intracavitary tumors.

[0003] A photodynamic therapy-based AIE-type heat-activated delayed fluorescence photosensitizer is disclosed in Chinese patent document CN118255762A, which is composed of a indolizine acceptor unit and two identical heteroaromatic amines as donor units. It has obvious triplet exciton activity and good photodynamic therapy effect. Chinese patent document CN115232145A discloses an AIE-type organic photosensitizer, which uses triphenylamine as an electron donor, pyridine salt as an electron acceptor, and thiophene as an electron π bridge. The photosensitizer shows strong phototoxicity under the irradiation of an LED white light lamp.

[0004] However, photodynamic therapy is limited by the characteristics of photosensitizer drugs and the complexity of tumor microenvironment. The photosensitizer drugs currently used have defects such as poor tissue penetration, low active oxygen ROS generation efficiency, and poor stability. On the other hand, the hypoxic environment in tumor tissue limits the generation of active oxygen, which in turn affects the treatment effect of photosensitizer. Therefore, it is particularly important to develop new photo-functional materials based on the tumor microenvironment to realize photodynamic therapy initiated by the tumor microenvironment. SUMMARY

[0005] The present application provides an aromatic diamine derivative, which has a simple preparation method, NO responsiveness, and can initiate photodynamic therapy in a tumor microenvironment with high NO expression, and has good tumor inhibition effect.

[0006] The specific technical solutions are as follows:

[0007] An aromatic diamine derivative, a structural formula of which is as shown in the following formula:

[0008]

[0009] In the formula, R1 and R2 are electron-donating groups, and R1 and R2 can be the same or different;

[0010] R1 and R2 are each independently selected from an oxygen-containing heterocyclic aryl group or an oxygen-containing heterocyclic aryl derivative;

[0011] The aromatic diamine derivative has NO responsiveness (can undergo single-electron transfer oxidation reaction with NO to generate a triazole derivative) and photodynamic antitumor effect.

[0012] The present application is based on a reactive molecular donor-acceptor (D-A) strategy to construct an intelligent photosensitive functional material, which has NO responsiveness and photodynamic generation capacity, and in combination with the high expression of NO in the tumor microenvironment, has good application prospect in tumor treatment.

[0013] Preferably, R1 and R2 are the same; the structure of the oxygen-containing heterocyclic aryl group or the oxygen-containing heterocyclic aryl derivative is any one of the structures shown in formula (I):

[0014]

[0015] In formula (I), X is an oxygen element, and R3 is hydrogen, a substituted or unsubstituted straight-chain, branched-chain or cyclic alkyl chain having 1-20 carbon atoms.

[0016] Further preferably, the structure of the aromatic diamine derivative is:

[0017]

[0018] The aromatic diamine derivative corresponding to the structure has good tumor inhibition effect, and through targeting the endoplasmic reticulum, initiates photodynamic therapy after NO reaction, and realizes efficient inhibition of tumor cells.

[0019] The present application also provides a preparation method of the aromatic diamine derivative, which specifically comprises the following steps:

[0020] (1) In an inert gas atmosphere, using compound 2,5-dibromo-3,4-dinitrothiophene as a raw material, 2,5-dibromo-3,4-dinitrothiophene and a donor compound are reacted to prepare an intermediate; the donor compound contains R1 and / or R2 groups, and the definitions of R1 and R2 are the same as above;

[0021] (2) the intermediate is subjected to a reduction reaction to convert the nitro group into an amino group, so as to prepare the aromatic diamine derivative.

[0022] Further, in step (1), the molar ratio of 2,5-dibromo-3,4-dinitrothiophene to the donor compound is 1:2.5-3; and the palladium catalyst and phosphine ligand are added during the reaction.

[0023] Further, in step (2), the reaction system is constructed to include the intermediate, zinc powder and ammonium chloride, and the reduction reaction is carried out under an inert gas atmosphere, so as to prepare the aromatic diamine derivative.

[0024] Preferably, the molar ratio of the intermediate, zinc powder and ammonium chloride is 1:30-35:10-12. Correspondingly, the reaction system can be subjected to the reduction reaction at room temperature, and the reaction condition is mild and easy to implement. Under the above preferred conditions, the reduction reaction is facilitated, and the yield is improved.

[0025] The application further provides application of the aromatic diamine derivative in preparation of a tumor treatment product. The aromatic diamine derivative has a killing effect on tumor cells and a solid tumor inhibiting effect, can be used for photodynamic anti-tumor, and has a wide application prospect in tumor treatment.

[0026] Further, the tumor treatment product is a NO-initiated tumor treatment product.

[0027] The application further provides a method for improving the active oxygen generation capacity of the aromatic diamine derivative, which comprises: subjecting the aromatic diamine derivative to a single electron transfer oxidation reaction with NO or a NO donor to generate a triazole derivative, so as to improve the active oxygen generation capacity thereof.

[0028] The inventors have found through a large number of experiments that the aromatic diamine derivative can spontaneously and efficiently react with NO to generate a triazole derivative, which leads to an increase in the donor-acceptor interaction of the molecule, a decrease in the energy difference between the singlet state and the triplet state, an improvement in the photosensitivity, and an application in photodynamic therapy initiated by a tumor microenvironment, a reduction in phototoxicity and other toxic side effects.

[0029] Further, the molar ratio of the aromatic diamine derivative to NO or a NO donor is 1:0.1-1000, and the reaction is carried out at a certain temperature (the temperature is higher than 4℃) or under white light irradiation (20-40 mW / cm 2 ).

[0030] Compared with the prior art, the application has the following beneficial effects:

[0031] 1. The aromatic diamine derivative in the application has good biocompatibility, low dark toxicity, good endoplasmic reticulum targeting ability and excellent NO response capacity.

[0032] 2. The aromatic diamine derivative in this invention reacts with NO in the tumor microenvironment to generate triazole derivative, which enhances the ability to generate reactive oxygen species. Under light conditions, it can induce cell death, thereby achieving highly efficient inhibition of tumor cells and solid tumors.

[0033] 3. The aromatic diamine derivatives in this invention are simple and efficient to prepare. Attached Figure Description

[0034] Figure 1 The graph shows the changes in absorbance of four compounds under NO donor BNN6 and light conditions.

[0035] Figure 2 This is a characterization diagram showing the enhanced reactive oxygen species production capacity of the compound TA-DTO in the examples after reacting with NO to generate TT-DTO.

[0036] Figure 3 Figure 1 shows the results of colocalization imaging experiments of compounds TA-DPA, TA-TPA, TA-TPAMO, TA-DTO, and TN-DTO with cells.

[0037] Figure 4 This is a statistical graph showing the cytotoxicity test results. In the graph, A represents the dark toxicity test results of TA-DPA, TA-TPA, TA-TPAMO, and TA-DTO under no white light; B represents the cytotoxicity test results of TA-DPA, TA-TPA, TA-TPAMO, and TA-DTO under white light (18 mW / cm²). 2 Phototoxicity test at 15 minutes.

[0038] Figure 5 The images show the in vivo treatment effects of TA-DTO. In the images, A is a statistical chart of the body weight of 4T1 tumor mice under different treatment methods, B is a statistical chart of the relative change in the volume of the primary tumor in 4T1 tumor mice under different treatment methods, C is a typical photograph of 4T1 tumor mice after tumor resection at the end of different treatments, I is the PBS group, II is the PBS + light irradiation group, III is the TA-DTO NPs group, and IV is the TA-DTO NPs + light irradiation group. Detailed Implementation

[0039] To make the objectives, features, and advantages of this invention more apparent and understandable, a detailed description is provided below through specific embodiments. Many specific details are set forth in the following description to provide a thorough understanding of the invention. However, the invention can be practiced in many other ways different from those described herein, and those skilled in the art can make similar modifications without departing from the spirit of the invention. Therefore, the invention is not limited to the specific embodiments disclosed below. Technical features in various embodiments of the invention can be combined appropriately without mutual conflict.

[0040] The methods of operation used in the following examples, where not otherwise expressly indicated, are typically in accordance with conventional methods or as otherwise described herein. The description herein of materials, which are not specifically prepared, is believed to be present in the art. The experimental materials used in the following examples, unless otherwise specified, are commercially available from a conventional biochemical reagent company.

[0041] Comparative Example 1

[0042] Compound TA-DPA was synthesized according to the following synthetic route:

[0043]

[0044] Synthesis of compound TN-DPA: Compound 1 (2,5-dibromo-3,4-dinitrothiophene, 1.66 g, 5.0 mmol), compound 2 (5.26 g, 12.5 mmol) and Pd(PPh3)4(0.57 g, 0.50 mmol) were dissolved in 120 mL tetrahydrofuran (THF) and 120 mL toluene, then purged under argon atmosphere. After the mixture was stirred at 50 °C for 10 min, 80 mL degassed K2CO3(2 M) aqueous solution was added, then refluxed overnight. The reaction was stopped, brought to room temperature, and THF, toluene were removed by rotary evaporation. The residual solid was dissolved in dichloromethane, and washed with water (3 x 100 mL). The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated by rotary evaporation. Purification was performed by column chromatography (silica gel) using petroleum ether / dichloromethane (8 / 1, v / v) as eluent to give orange solid TN-DPA, yield: 2.5 g (65.78% yield).

[0045] The1H NMR data of compound TN-DPA is as follows: 1 H NMR (500 MHz, Methylene Chloride-d2) δ 7.93 (s, 4H), 7.86 (s, 2H), 7.52 (s, 4H), 7.41 (s, 4H), 7.29 (s, 7H), 7.22 (s, 4H), 7.08 (s, 3H), 6.93 (s, 4H).

[0046]

[0047] Synthesis of compound TA-DPA: In a 50 mL two-necked flask, compound TN-DPA (1 g, 1.31 mmol), zinc powder (2.7 g, 41.3 mmol) and ammonium chloride (0.703 g, 13.1 mmol) were weighed separately, degassed, purged with nitrogen, purged with dichloromethane (7 mL) and 90% degassed methanol solution (13 mL), and reacted at room temperature for 4 hours. After the reaction was completed, the reaction solution was filtered with celite, and then extracted with dichloromethane and saturated brine. The organic phase was collected in three portions. It was dried with anhydrous magnesium sulfate, filtered, and the dried organic phase was concentrated by rotary evaporation to obtain black powder compound TA-DPA, yield: 0.46 g (yield 50.5%).

[0048] The nuclear magnetic hydrogen spectrum data of compound TA-DPA is: 1 H NMR (500 MHz, Methylene Chloride-d2) δ 7.94 (s, 4H), 7.81 (s, 2H), 7.50 (d, J = 8.4 Hz, 4H), 7.34 (d, J = 29.5 Hz, 8H), 7.21 (s, 4H), 7.03 (s, 8H), 6.95 (s, 2H), 3.62 (s, 4H).

[0049] Comparative Example 2

[0050] Compound TA-TPA was synthesized according to the following synthesis route:

[0051]

[0052] Synthesis of compound TN-TPA: Compound 1 (2,5-dibromo-3,4-dinitrothiophene, 1.66 g, 5.0 mmol), compound 3 (4-(diphenylamino)phenylboronic acid, 3.6 g, 12.5 mmol) and Pd(PPh3)4(0.57 g, 0.50 mmol) were dissolved in 120 mL of tetrahydrofuran (THF) and 120 mL of toluene, and then purged under an argon atmosphere. After the resulting mixture was stirred at 50°C for 10 minutes, 80 mL of a degassed K2CO3(2M) aqueous solution was added, and then refluxed overnight. The reaction was stopped, returned to room temperature, and THF and toluene were removed by rotary evaporation. The residual solid was dissolved in dichloromethane and washed with water (3 x 100 mL). The organic layer was separated by extraction, and dried with anhydrous sodium sulfate, and the organic layer was concentrated by rotary evaporation. Eluent petroleum ether / dichloromethane (6 / 1, v / v) was used for purification by column chromatography (silica gel) to obtain orange solid TN-TPA, yield: 2.54 g (yield 76.96%).

[0053] The nuclear magnetic hydrogen spectrum data of compound TN-TPA is: 1H NMR (500 MHz, Methylene Chloride-d2) δ 7.40 - 7.28 (m, 12H), 7.14 (dd, J = 15.2, 7.7 Hz, 12H), 7.02 (d, J = 8.5 Hz, 4H).

[0054]

[0055] Synthesis of compound TA-TPA: In a 50 mL two necked flask, compound TN-TPA (1 g, 1.51 mmol), zinc powder (3.11 g, 47.56 mmol) and ammonium chloride (0.807 g, 15.1 mmol) were weighed separately, degassed, purged with nitrogen, purged with dichloromethane (7 mL) and 90% degassed methanol solution (13 mL) and allowed to react for 4 hours at room temperature. After completion of the reaction, the reaction solution was filtered through celite and then extracted with dichloromethane and saturated brine. The organic phase was collected in three portions. The organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent was removed by rotary evaporation to obtain black colored powder compound TA-TPA, yield: 0.4 gram (yield 44.44%).

[0056] NMR data of compound TA-TPA: 1 H NMR (500 MHz, Methylene Chloride-d2) δ 7.40 - 7.28 (m, 12H), 7.14 (dd, J = 15.2, 7.7 Hz, 12H), 7.02 (d, J = 8.5 Hz, 4H).

[0057] Example 1

[0058] Compound TA-DTO was synthesized following the below synthesis route:

[0059]

[0060] Synthesis of compound TN-DTO: Pd2(dba)3(0.366 g, 0.4 mmol) and P(o-tol)3(0.365 g, 1.2 mmol) were added to a solution of compound 1 (2,5-dibromo-3,4-dinitrothiophene, 1.6 g, 5.0 mmol) and compound 5 (5.39 g, 12.5 mmol) in anhydrous toluene (30 mL) under anhydrous and deoxygenated conditions. The mixture was refluxed at 110 °C under nitrogen for 24 hours. After cooling to room temperature, the solvent was removed by rotary evaporation and the crude was purified by column chromatography (PE / DCM) to obtain the product brown red solid TN-DTO, yield: 1.5 gram (yield 68%).

[0061] The nuclear magnetic hydrogen spectrum data of compound TN-DTO is: 1 H NMR (500 MHz, Chloroform-d) δ 6.31 (s, 2H), 4.34 - 4.29 (m, 4H), 4.27 - 4.22 (m, 4H).

[0062]

[0063] Synthesis of compound TA-DTO: In a 50 mL two-necked flask, compound TN-DTO (0.5 g, 1.1 mmol), zinc powder (2.262 g, 34.6 mmol) and ammonium chloride (0.588 g, 11.0 mmol) were weighed respectively. After degassing, nitrogen was injected, dichloromethane (7 mL) and 90% degassed methanol solution (13 mL) were injected, and the reaction was carried out at room temperature for 4 hours. After the reaction was completed, the reaction solution was filtered with diatomite, and then extracted with dichloromethane and saturated brine. The organic phase was collected in three times. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation to obtain black powder compound TA-DTO, yield: 0.26 grams (yield 59%).

[0064] The nuclear magnetic hydrogen spectrum data of compound TA-DTO is: 1 H NMR (500 MHz, Chloroform-d) δ 6.30 (s, 2H), 4.34 - 4.19 (m, 8H), 3.98 - 3.64 (m, 4H).

[0065] Comparative Example 3

[0066] Compound TA-TPAMO was synthesized according to the following synthetic route:

[0067]

[0068] Synthesis of compound TN-TPAMO: Compound 1 (2,5-dibromo-3,4-dinitrothiophene, 1.66 g, 5.0 mmol), compound 4 (5.39 g, 12.5 mmol) and Pd(PPh3)4(0.577 g, 0.50 mmol) were dissolved in 120 mL tetrahydrofuran (THF) and 120 mL toluene under argon atmosphere. After the resulting mixture was stirred at 50°C for 10 minutes, 80 mL of degassed K2CO3(2M) aqueous solution was added, and then refluxed overnight. The reaction was stopped, returned to room temperature, and the THF, toluene was removed by rotary evaporation. The residual solid was dissolved with dichloromethane, and washed with water (3 x 100 mL). The organic layer was separated by extraction, and dried with anhydrous sodium sulfate, and the organic layer was concentrated by rotary evaporation. Eluent petroleum ether / dichloromethane (1 / 8, v / v) was used for purification by column chromatography (silica gel) to obtain red solid TN-TPAMO, yield: 2.6 grams (yield 66.67%).

[0069] The nuclear magnetic hydrogen spectrum data of compound TN-TPAMO are as follows: 1 H NMR (500 MHz, Methylene Chloride-d2) δ 7.28 (d, J = 8.6 Hz, 4H), 7.13 (d, J = 8.6 Hz, 8H), 6.87 (dd, J = 19.7, 8.5 Hz, 12H), 3.80 (s, 12H).

[0070]

[0071] Synthesis of compound TA-TPAMO: In a 50 mL two-necked flask, compound TN-TPAMO (1 g, 1.28 mmol), zinc powder (2.632 g, 40.25 mmol) and ammonium chloride (0.685 g, 12.8 mmol) were weighed respectively, degassed, and nitrogen inert gas was injected, dichloromethane (7 mL) and 90% degassed methanol solution (13 mL) were injected, and the reaction was carried out at room temperature for 4 hours. After the reaction was completed, the reaction solution was filtered with diatomite, and then extracted with dichloromethane and saturated brine. The organic phase was collected in three times. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation to obtain black powder compound TA-TPAMO, yield: 0.4 g (yield 44.64%).

[0072] The nuclear magnetic hydrogen spectrum data of compound TA-TPAMO are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.30 (d, J = 8.4 Hz, 4H), 7.13-7.04 (m, 8H), 7.01-6.92 (m, 4H), 6.89-6.79 (m, 8H), 3.80 (s, 12H).

[0073] Sample analysis

[0074] (1) Study on the reaction ability of aromatic diamine derivatives with NO and the photo-promoted ring formation

[0075] After the reaction of aromatic diamine derivatives with NO, the red shift of the absorption spectrum was used to determine the reaction process. The product compounds prepared in the examples and comparative examples were mixed with NO donor BNN6 (TA-DPA, TA-TPA, TA-TPAMO and TA-DTO were dissolved in THF, the final concentration was 20 μM, and then BNN6 (20 μM) was added), and the change of absorption spectrum was detected by ultraviolet-visible light spectrometer. In order to further study the effect of light on the reaction, the change trend of absorption spectrum under light irradiation (white light irradiation (35 mW / cm 2 )) was studied, and the results are shown in Figure 1It can be seen that after the addition of BNN6, the TA-DTO absorption spectrum is obviously red-shifted with time, indicating that the reaction with NO is successful. Similar phenomenon can also be observed in the light, indicating that the light can also promote the reaction. The statistical results of the photophysical properties of the four compounds are shown in Table 1.

[0076] Table 1 Photophysical properties of four compounds

[0077]

[0078] In addition, from the results of Figure 2 , it can be seen that after the single electron transfer oxidation reaction of TA-DTO with NO or NO donor, the active oxygen production capacity is improved.

[0079] (2) Aromatic diamine derivatives for photodynamic antitumor

[0080] 4T1 cells were plated in cell culture dishes and incubated with culture medium mixed with TA-DPA, TA-TPA, TA-TPAMO, TA-DTO and TN-DTO respectively for 4 hours. After the interaction of the cells, imaging characterization was performed by laser confocal microscope, and the results are shown in Figure 3 From the results, it can be seen that TA-TPA and TA-DPA are mainly distributed in lysosomes, TA-TPAMO is distributed in lipid droplets, and TA-DTO is distributed in endoplasmic reticulum.

[0081] The dark toxicity group is: 4T1 cells are plated in 96-well plates and incubated for 24 hours, then incubated with culture medium solution containing different concentrations of product compounds of examples and comparative examples for 24 hours, then MTT is added and incubated for 4 hours, and the ultraviolet absorption intensity at 570 nm is measured. The light group is: 4T1 cells are plated in 96-well plates, first incubated with culture medium solution containing different concentrations of product compounds of examples and comparative examples for 4 hours, then white light irradiation for 20 minutes, then continue to incubate for 20 hours, then add MTT and incubate for 4 hours, then measure the ultraviolet absorption intensity at 570 nm, and the results are shown in Figure 4 A and B in . From the results, it can be seen that TA-DTO distributed in endoplasmic reticulum exhibits obvious tumor inhibition effect at a lower concentration.

[0082] SPF female BALB / c nude mice weighing 16-18g were selected, and 4T1 cells were inoculated subcutaneously on the right hind leg of each nude mouse, 100μL of physiological saline solution containing 5×10 6 cells was injected, and 7 days later, TA-DTO was injected into the tail vein, and white light irradiation was performed on the eighth day (light conditions: white light: 200mW / cm 2 , 20 minutes). The body weight and tumor size of the nude mice were recorded at any time after inoculation, and the results are shown in Figure 5 A-C in . From the results, it can be seen that TA-DTO has good tumor inhibition effect.

[0083] The above embodiments of the present application are described in detail, it should be understood that the above described are only specific embodiments of the present application, and not for limiting the present application, any modification, supplement or similar way of substitution, etc. made within the scope of the principles of the present application, should be included in the scope of the present application.

Claims

1. An aromatic diamine derivative, characterized in that, The structural formula is shown below: The aromatic diamine derivatives described above exhibit NO-responsive and photodynamic antitumor effects.

2. The method for preparing the aromatic diamine derivative according to claim 1, characterized in that, Specifically, the following steps are included: (1) Under an inert gas atmosphere, using compound 2,5-dibromo-3,4-dinitrothiophene as a raw material, an intermediate was prepared by reacting 2,5-dibromo-3,4-dinitrothiophene with a donor compound; the donor compound contains Group; (2) The intermediate undergoes a reduction reaction to convert the nitro group to an amino group, thereby preparing the aromatic diamine derivative.

3. The method for preparing the aromatic diamine derivative according to claim 2, characterized in that, In step (1), the molar ratio of 2,5-dibromo-3,4-dinitrothiophene to the donor compound is 1:2.5-3.

4. The method for preparing the aromatic diamine derivative according to claim 2, characterized in that, In step (2), a reaction system comprising an intermediate, zinc powder and ammonium chloride is constructed, and a reduction reaction is carried out under an inert gas atmosphere to prepare the aromatic diamine derivative.

5. The method for preparing the aromatic diamine derivative according to claim 4, characterized in that, The molar ratio of the intermediate, zinc powder and ammonium chloride is 1:30-35:10-12.

6. The application of the aromatic diamine derivative according to claim 1 in the preparation of tumor therapeutic products, characterized in that, The tumor treatment product mentioned is a NO-initiated tumor treatment product.

7. A method for improving the reactive oxygen species generation ability of aromatic diamine derivatives, characterized in that, include: The aromatic diamine derivative of claim 1 is subjected to a single-electron transfer oxidation reaction with NO or a NO donor to enhance its reactive oxygen species production capacity.

8. The method for improving the reactive oxygen species generation ability of aromatic diamine derivatives according to claim 7, characterized in that, The aromatic diamine derivative reacts with NO or NO donor in a molar ratio of 1:0.1 to 1000 at a certain temperature or under white light irradiation.

Images