CN113061128B - Photosensitizer with aggregation-induced light emission and broad-spectrum absorption characteristics and preparation method and application thereof - Google Patents
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Abstract
The invention provides a photosensitizer with aggregation-induced light emission and broad-spectrum absorption characteristics and a preparation method thereof. The photosensitizer has a structure shown in a formula I. In addition, the invention also provides the application of the photosensitizer in killing cancer cells and bacteria under the condition of illumination. Tests show that the photosensitizer provided by the invention has the advantages of wide absorption spectrum, strong active oxygen generation capacity, good biocompatibility in darkness, good effect of killing cancer cells and bacteria in illumination and the like
Description
Technical Field
The invention belongs to the field of biochemistry, and particularly relates to a photosensitizer with aggregation-induced luminescence and broad-spectrum absorption characteristics, a preparation method thereof and application thereof in killing cancer cells and bacteria.
Background
Photodynamic therapy (PDT) is an emerging therapeutic modality that has been applied clinically. Photodynamic therapy has been used in cancer therapy, treatment of bacterial and fungal infections because of the advantages of being non-invasive, the area of treatment can be controlled by light, and there is no resistance to drug development. The working principle is that the photosensitizer can be excited to a singlet excited state under the irradiation of light with proper wavelength, the singlet excited state passes through gaps to a triplet excited state, and when the photosensitizer returns to a ground state from the triplet excited state, the photosensitizer can sensitize surrounding triplet oxygen molecules to generate active oxygen. Reactive oxygen species can destroy cells, bacteria, fungi, etc. in diseased tissues (adv. Funct. Mater.2018, 28, 1804632). Light, photosensitizers and oxygen molecules are three elements of photodynamic therapy, where photosensitizers play a crucial role, and the development of high efficiency photosensitizers is essential.
Conventional photosensitizers (such as those containing tetrapyrrole structures) suffer from substantial reduction in both photosensitizing efficiency and fluorescence intensity in the aggregated state due to pi-pi stacking, among other things (adv. Mater.2018, 30, 1801350). The discovery of aggregation-induced emission (AIE) provides a new idea for the development of photosensitizers. The distorted spatial configuration allows the AIE molecules to reduce Π - Π stacking effect when in an aggregated state. Due to the principle of intramolecular motion limitation (RIM), the AIE molecules in the aggregate state minimize energy loss from vibration and rotation. Thus, AIE photosensitizers typically exhibit dual enhancements in photosensitizing efficiency and fluorescence intensity in the aggregated state. In addition, better biocompatibility is another great advantage of AIE photosensitizers. AIE photosensitizers have become the focus of research (Nanoscale, 2019, 11, 19241) and are expected to replace traditional photosensitizers.
Disclosure of Invention
The invention aims to provide a photosensitizer with aggregation-induced light emission and broad-spectrum absorption characteristics. The dye has aggregation-induced emission fluorophore and carbazole group, and has the advantages of wide absorption spectrum, strong active oxygen generating capacity, good biocompatibility in dark and capability of effectively killing cancer cells and bacteria in light.
The purpose of the invention is realized by the following scheme:
a photosensitizer with aggregation-induced emission and broad-spectrum absorption characteristics has a structure shown in formula I:
in the formula I, the compound is shown in the specification,
R 1 independently selected from: c 1 ～C 12 Any one of alkyl, phenyl or group shown in formula II (wherein the marked position of the curve is a substituted position, the same applies below; in the formula II, n is an integer of 0-10);
r2 is independently selected from: any one of a pyridine group, a group represented by formula III or a group represented by formula IV.
In another aspect, the present invention further provides a method for preparing the photosensitizer with aggregation-induced emission and broad-spectrum absorption characteristics, which mainly comprises the following steps: in the presence of a basic catalyst (piperidine), a compound with a structure shown in a formula V and a compound with a structure shown in a formula VI or a formula VII are subjected to reflux reaction in an organic solvent (acetonitrile) for 10-12h, and the photosensitizer with a structure shown in a formula I is generated through Knoevenagel condensation.
Wherein R is 1 The substituents are the same as described above.
In a preferred embodiment of the present invention:
R 1 each independently selected from: c 1 ～C 12 Any one of a straight chain or branched alkyl group of (1), a phenyl group or a group represented by the formula II (n is an integer of 0 to 10);
r2 is any one of a pyridine group, a group shown in a formula III or a group shown in a formula IV.
Further preferred R 1 Is any one of ethyl, phenyl or a group of formula II (wherein n = 4); r 2 Is any one of a pyridine group, a group shown in a formula III or a group shown in a formula IV.
Further preferred R 1 Is phenyl. R 2 Is any one of a pyridine group, a group shown in a formula III or a group shown in a formula IV.
Even more excellentSelected R 1 Is phenyl. R 2 Is a group of the formula III (wherein the anion is PF) 6 -)
Use of a photosensitizer having aggregation-induced emission and broad-spectrum absorption properties of the present invention for killing cancer cells or bacteria.
Drawings
FIG. 1 is a graph of the absorption and fluorescence spectra of photosensitizer I-6 (10 μ M concentration) in water, with wavelength (nm) on the abscissa and normalized absorbance or fluorescence intensity on the ordinate.
FIG. 2 comparison of the active oxygen generating abilities of photosensitizers I-2 and I-3 with commercial photosensitizer chlorin e6 under the same light conditions
FIG. 3 comparison of the capacity of photosensitizers I-4 and I-6 to produce active oxygen with the commercial photosensitizer chlorin e6 under the same light conditions.
FIG. 4. Toxicity of photosensitizer I-6 to HeLa cells under dark or light conditions.
FIG. 5 toxicity of photosensitizer I-6 to E.coli under dark or light conditions.
Detailed Description
The invention is further illustrated by the following examples, which are intended only for a better understanding of the contents of the invention. The examples given therefore do not limit the scope of protection of the invention:
example 1
(1) Synthesis of photosensitizer I-1
To a 50mL two-necked flask, compound V-1 (100mg, 0.24mmol), compound VI (403mg, 1.45mmol), acetonitrile (15 mL), and piperidine (0.5 mL) were sequentially added. Refluxing at 95 deg.C for 12h under nitrogen protection. The solvent was removed by rotary evaporation and column chromatography (dichloromethane: methanol =100 = 1) gave 52mg of an orange-red solid (photosensitizer I-1) in 23% yield.
1 H NMR(400MHz，DMSO-d 6 ，ppm)，δ：11.99(s，1H)，8.26(d，4H，J＝7.72Hz)，7.77-7.70(m，1H)，7.70-7.56(m，10H)，7.56-7.47(m，6H)，7.37(t，4H，J=7.40Hz)，7.26-7.10(m，4H)，7.05(s，2H)，4.37(t，2H，J=7.12Hz)，2.15(t，2H，J＝7.20Hz)，1.76-1.61(m，2H)，1.56-1.43(m，2H)，1.36-1.25(m，2H).
Mass spectrometry(ESI negative ion mode for[M-H]-)：Calcd.for C 59 H 41 N 6 O 2 S 2 ：929.2732，found：929.2752.
(2) Synthesis of photosensitizer I-2
To a 50mL two-necked flask, compound V-2 (200mg, 0.61mmol), compound VI (1020mg, 3.68mmol), acetonitrile (15 mL), and piperidine (0.75 mL) were sequentially added. Refluxing at 95 deg.C for 12h under nitrogen protection. The solvent was removed by rotary evaporation and column chromatography (dichloromethane: methanol = 400: 1) gave 201mg of red solid (photosensitizer I-2) in 39% yield.
1 H NMR(400MHz，DMSO-d 6 ，ppm)：8.26(d，4H，J＝7.72Hz)，7.75-7.70(m，1H)，7.68(d，2H，J＝3.92Hz)，7.66-7.55(m，8H)，7.55-7.48(m，6H)，7.40-7.33(m，4H)，7.30-7.00(m，6H)，4.42(q，2H，J＝6.84Hz)，1.31(t，3H，J＝7.00Hz).
Mass spectrometry(ESI positive ion mode for[M+H] + )：Calcd.for C 55 H 37 N 6 S 2 ：845.2521；found：845.2517.
(3) Synthesis of photosensitizer I-3
A50 mL two-necked flask was charged with compound V-3 (150mg, 0.45mmol), compound VI (958mg, 3.45mmol), acetonitrile (15 mL), and piperidine (0.5 mL) in that order. Refluxing at 95 deg.C for 12h under nitrogen protection. The solvent was removed by rotary evaporation and column chromatography (dichloromethane: petroleum ether = 4: 1) gave 156mg of red solid (photosensitizer I-3) in 39% yield.
1 H NMR(400MHz，DMSO-d 6 ，ppm)：8.21(d，4H，J＝7.52Hz)，7.71-7.64(m，4H)，7.64-7.51(m，4H)，7.51-7.41(m，12H)，7.41-7.37(m，2H)，7.37-7.31(m，4H)，7.31-7.26(m，2H)，7.23(s，2H)，5.95(d，2H，J＝15.68Hz).
Mass spectrometry(ESI positive ion mode for [M+H] + )：Calcd.for C 59 H 37 N 6 S 2 ：893.2521；fbund：893.2512.
(4) Synthesis of photosensitizer I-4
To a 50mL two-necked flask were added compound V-3 (1215mg, 3.25mmol), compound VI (300mg, 1.08mmol), acetonitrile (15 mL), and piperidine (0.5 mL) in that order. Refluxing at 95 deg.C for 12h under nitrogen protection. Column chromatography (dichloromethane: petroleum ether = 4: 1) gave 302mg (intermediate 1) of a red solid in 44% yield.
A50 mL two-necked flask was charged with intermediate 1 (50mg, 0.08mmol), 4-pyridinecarboxaldehyde (171mg, 1.60mmo 1), acetonitrile (12 mL), and piperidine (0.5 mL). Heating and refluxing at 95 ℃ for 12h under the protection of nitrogen. The solvent was removed by rotary evaporation and column chromatography (dichloromethane: methanol =100: 1) gave 28mg of a red solid (photosensitizer I-4) in 49% yield.
1 H NMR(400MHz，DMSO-d 6 ，ppm)，δ：8.54(d，2H，J＝5.96Hz)，8.23(d，2H，J＝7.72Hz)，7.78-7.70(m，1H)，7.70-7.57(m，7H)，7.54-7.43(m，7H)，7.41(d，1H，J＝3.88Hz)，7.38-7.30(m，3H)，7.28(s，1H)，7.23(d，2H，J＝5.96Hz)，7.19(s，1H)，6.97(d，1H，J=15.92Hz)，6.56(d，1H，J=16.04Hz)，5.97(d，1H，J=15.76Hz).
Mass spectrometry(ESI positive ion mode for[M+H] + )：Calcd.for C 48 H 31 N 6 S：723.2331；found：723.2330.
(5) Synthesis of photosensitizers I-5 and I-6
A50 mL two-necked flask was charged with photosensitizer I-4 (30mg, 0.04mmol), iodomethane (80mg, 0.56mmol), and methylene chloride (6 mL) in that order. Stirred at room temperature for 24h. The solvent was removed by rotary evaporation and column chromatography (dichloromethane: methanol = 15: 1) gave 23mg of a black solid (photosensitizer I-5) in 64% yield.
A50 mL two-necked flask was charged with photosensitizer I-5 (21mg, 0.024mmol) and acetone (5 mL). After the solid was dissolved, a saturated potassium hexafluorophosphate solution (5 mL) was added to the flask, and the mixture was stirred at room temperature overnight. A large amount of solid is separated out and filtered, and 14mg of black green solid (photosensitizer I-6) is obtained with the yield of 66 percent.
1 H NMR(400MHz，DMSO-d 6 ，ppm)，δ：8.85(d，2H，J＝5.32Hz)，8.24(d，2H，J=7.16Hz)，8.03(d，2H，J＝5.24Hz)，7.76-7.59(m，8H)，7.57-7.51(m，2H)，7.51-7.41(m，6H)，7.39-7.21(m，6H)，7.01(d，1H，J=15.96Hz)，5.97(d，1H，J=15.68Hz)，4.24(s，3H).
Mass spectrometry(ESI positive ion mode for[M-PF 6 ] + )：Calcd.for C 49 H 33 N 6 S：737.2487；found：737.2485.
Example 2
Absorption and fluorescence spectra of photosensitizer I-6 in Water
Photosensitizer I-6 synthesized in example 1 was dissolved in analytically pure dimethyl sulfoxide to give a concentration of 1.0X 10 -3 Stock solution of M (hereinafter referred to as stock solution of I-6). 30 μ L of the stock solution was added to 2970 μ L of ultrapure water, mixed well and transferred to a quartz cuvette (10X 10 mm) to test the absorption and fluorescence spectra. As shown in FIG. 1, photosensitizer I-6 exhibits a broad absorption peak at 350nm to 640nm, and has a maximum absorption wavelength of 512nm. With 520nm as excitation wavelength, photosensitizer I-6 has wide fluorescence emission peak at 600-800 nm, and maximum emission wavelengthAt 678nm.
Example 3
Ability of photosensitizers I-2 and I-3 to generate active oxygen in Water
The ability of photosensitizers I-2 and I-3 to generate active oxygen in water was tested using 9, 10-anthracenediyl-bis (methylene) dipropionic acid (ABDA, test concentration 50. Mu.M) as an active oxygen indicator, while the commercially available photosensitizer chlorin e6 (Ce 6) was used as a reference and the test concentration of photosensitizer was 10. Mu.M. As shown in FIG. 2, after white light irradiation, the photosensitizers I-2 and I-3 were able to cause a relatively rapid decrease in absorbance of the indicator at 378nm, while Ce 6 was able to cause a relatively slow decrease in absorbance of the indicator at 378 nm. In the absence of the photosensitizer, the absorbance of the indicator remains nearly unchanged after illumination. This indicates that the photosensitizers I-2 and I-3 are capable of rapidly generating reactive oxygen species under light irradiation.
Example 4
Ability of photosensitizers I-4 and I-6 to generate active oxygen in Water
The ability of photosensitizers I-4 and I-6 to generate active oxygen in water was tested using 2',7' -dichlorofluorescein diacetate (DCFH-DA, test concentration 40. Mu.M) as the active oxygen fluorescence indicator, while the commercially available photosensitizer chlorin e6 (Ce 6) was used as the reference and the test concentration of photosensitizer was 10. Mu.M. As shown in FIG. 3, after 30s of white light irradiation, the photosensitizers I-4 and I-6 can cause the fluorescence of the indicator to increase rapidly, while Ce 6 can cause the fluorescence of the indicator to increase more slowly. In the absence of the photosensitizer, the fluorescence of the indicator remains nearly unchanged after illumination. This indicates that the photosensitizers 1-4 and I-6 are capable of rapidly generating reactive oxygen species under light.
Example 5
Toxicity of photosensitizer I-6 to HeLa cells
HeLa cells were seeded in 96-well plates (10) 4 Cells/well) divided into two groups (dark and light), and cultured in a cell incubator for 12h. The stock solution of I-6 was diluted in DMEM medium to obtain media (10, 5,2.5,1, 0. Mu.M) containing different concentrations of I-6. Media containing different concentrations of I-6 were added to different wells. Incubating in cell incubator for 6 hr, and replacing culture medium containing photosensitizer with fresh culture mediumAnd (5) nutrient base. One set of cells was placed in the dark and the other set of cells was illuminated with white light for 15min. Both groups of cells were further incubated in the incubator for 12h in the dark, then 5mg/mLMTT (10. Mu.L/well) was added. After 4h, the supernatant liquid was carefully removed and 100 μ l of LDMSO was added to dissolve the solid, which was shaken up and read on a microplate reader. As shown in FIG. 4, the cell activity remained around 100% in the dark group at a photosensitizer concentration of 10. Mu.M, indicating that the photosensitizer has good biocompatibility under dark conditions. After 15min of illumination, the activity of the cells can be reduced to about 8% by 10 mu M of the photosensitizer I-6, which shows that the photosensitizer I-6 can obviously kill HeLa cells under the illumination condition.
Example 6
Toxicity of photosensitizer I-6 to Escherichia coli
E.coli cultures were diluted in PBS and divided into 3 groups on average. Group 1: the cells were incubated at 37 ℃ for 30min without adding photosensitizer I-6 and then placed in the dark. Group 2: a stock solution of photosensitizer I-6 (final photosensitizer concentration of 10. Mu.M) was added, incubated at 37 ℃ for 30min, and then placed in the dark. Group 3: stock solutions of photosensitizer I-6 (final photosensitizer concentration 10. Mu.M) were added and incubated at 37 ℃ for 30min, followed by white light illumination for 15min. mu.L of the treated bacterial solution was applied to a petri dish, incubated at 37 ℃ for 12 hours in the dark, and photographed. As a result, as shown in FIG. 5, in the presence of 10. Mu.M of the photosensitizer I-6, colonies in the dark group (group 2) were not significantly reduced compared to the control group (group 1), while colonies in the light group (group 3) were significantly reduced, indicating that the photosensitizer I-6 was able to significantly kill Escherichia coli in the light.
Claims (4)
1. A photosensitizer with aggregation-induced emission and broad-spectrum absorption characteristics has a structural formula shown as formula I:
in the formula I, the raw materials are shown in the specification,
the R is 1 Is any one of ethyl, phenyl or a group shown in a formula II; wherein n =4;
R 2 independent of each otherSelected from: any one of a pyridine group, a group shown as a formula III or a group shown as a formula IV;
2. the photosensitizer having aggregation-induced emission and broad-spectrum absorption properties according to claim 1, wherein R is 1 Is phenyl.
3. The photosensitizer having aggregation-induced emission and broad-spectrum absorption properties according to claim 1, wherein R is 2 A group of formula III; wherein the anion is PF 6 - 。
4. A method of preparing the photosensitizer having aggregation-induced emission and broad-spectrum absorption characteristics according to claim 1, comprising the steps of:
in the presence of a basic catalyst, carrying out reflux reaction on a compound with a structure shown in a formula V and a compound with a structure shown in a formula VI or a formula VII in an organic solvent for 10-12h, and carrying out Knoevenagel condensation to generate a photosensitizer with a structure shown in a formula I; the basic catalyst is piperidine; the organic solvent is acetonitrile;
wherein, in formula V:
the R is 1 Is any one of ethyl, phenyl or a group shown in a formula II; wherein n =4;
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