CN105412924A - Sugar-containing photodynamic therapy nano particles with blood stability and target ability and preparing method of sugar-containing photodynamic therapy nano particles - Google Patents
Sugar-containing photodynamic therapy nano particles with blood stability and target ability and preparing method of sugar-containing photodynamic therapy nano particles Download PDFInfo
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Abstract
The invention discloses sugar-containing photodynamic therapy nano particles with blood stability and target ability and a preparing method of the sugar-containing photodynamic therapy nano particles. The nano particles are formed by wrapping photosensitizer micromolecules with a synthesized copolymer of DMA and DMAEMA, and wrapping the outer layers of nano particles with glycopolymer layers, wherein the average particle size of the nano particles ranges from 180 nm to 300 nm. The preparing method of the sugar-containing photodynamic therapy nano particles comprises the steps that the copolymer of DMA and DMAEMA is subjected to self-assemblage in water to wrap the photosensitizer micromolecules to form the nano particles, the nano particles are mixed with a glycopolymer solution with an end group serving as carboxyl, and the glycopolymer is aggregated on the surfaces of the nano particles through electrostatic interaction to form the sugar-containing photodynamic therapy nano particles. According to the method, operation is easy and convenient, and various photodynamic reagents can be wrapped. The adopted polymer shows electropositivity and can be combined with various glucide polymers with negative electricity, meanwhile, the glycopolymer is aggregated on the surfaces of the nano particles, and thus blood stability, target ability and biocompatibility are achieved.
Description
Technical field
The present invention relates to a kind of nanoparticle of polymer wrapped photosensitizer, be specifically related to a kind of to there is sugary photodynamic therapy nanoparticle of blood stability and targeting and preparation method thereof.
Background technology
Photosensitizer (photosensitizer, PS) be the material that a class has absorption, transmission, conversion light energy, if this kind of material is enriched in the cell surface or cell that will act on, excites at specific wavelength light source and just can produce photodynamic effect thus kill cell down.Based on the understanding to photosensitizer, people have invented a kind of brand-new Therapeutic Method for tumor, i.e. photodynamic therapy (photodynamictherapy, PDI).The ultimate principle of this treatment technology is sensitiser absorption photon energy, and by ground state transition to excited state, its physics de excitation process produces fluorescence, can carry out medical diagnosis on disease by spectrofluorimetry; Its chemical de excitation process can produce some active oxygen species (ROS), wherein most importantly singlet oxygen.Active oxygen species can with cell membrane and intracellular multiple interaction of biomacromolecules, when active oxygen species reaches certain value, cell injury or death will be caused, thus produce therapeutical effect.Micromolecule photosensitizer due to water solublity generally poor, not there is targeting, limit its application.
Glycan molecule has good hydrophilic, bio-identification and biological degradability, and this makes sugary polymer tool in biological, medical etc. have been widely used.Cancerous cell and normal cell significant difference are exactly that endocellular sugar metabolism is vigorous, the cell membrane of cancerous cell usually exists some and with sugar, the albumen of specific effect can occur, such as glucose transporter (GlucoseTransporters, GLUT) be almost be present in the hypotype in all cancerous cell lines, and found all have process LAN in many human tumors.Based on the understanding to cancerous cell this respect, prepare sugary smooth power nanoparticle and targeted therapy is carried out to cancer have broad application prospects.
Summary of the invention
The present invention seeks to: provide a kind of and there is sugary photodynamic therapy nanoparticle of blood stability and targeting and preparation method thereof, it utilizes the method for active free radical polymerization, prepare the controlled dopamine polymer of compound with regular structure and the end group sugar-containing polymer with carboxyl, use the self assembly in water of dopamine polymer that photosensitizer parcel is wherein formed nanoparticle, sugar is made to be gathered in nanoparticle surface in utilization electrostatic effect, synthetic method economy, be convenient to extensive synthesis, and the sugar prepared parcel nanoparticle has good blood stability, strong fluorescence, good killing action is had to cancerous cell.
Technical scheme of the present invention is:
A kind of sugary photodynamic therapy nanoparticle with blood stability and targeting, it is characterized in that, described nanoparticle wraps up photosensitizer micromolecule by DMA and DMAEMA synthetic copolymer, its outer layer covers one deck sugar-containing polymer forms, wherein DMA is N-3,4-dihydroxy benzenes ethyl methacrylamide, and DMAEMA is N, N-dimethylamino methyl ethyl acrylate, described nanoparticle mean diameter is 180nm ~ 300nm.
Further, preferably, described photosensitizer is phthalocyanine Zn, phthalocyanine Si, porphyrin and based on phthalocyanine Zn, the one in the derivant of phthalocyanine Si or porphyrin.
Present invention also offers the preparation method of above-mentioned nanoparticle, the method comprises the steps: simultaneously
(1) DMA and DMAEMA copolymer is prepared, this copolymer and a certain amount of photosensitizer are fully dissolved in a solvent, getting this mixed liquor is slowly added drop-wise in a small amount of water, fully be uniformly mixed, obtain blue settled solution, blue settled solution is transferred in bag filter, lucifuge dialysis 2-4 days, change water 6-12 time, obtain the micromolecular nano-particle solution of DMA and DMAEMA copolymer self assembly parcel photosensitizer of blue-tinted transparent;
(2) synthesizing end group is the glycopolymers of carboxyl, this glycopolymers is added step 1 by a certain percentage) in the nano-particle solution of synthesizing, fully be uniformly mixed, glycopolymers is made to be gathered in nanoparticle surface by electrostatic interaction, obtain sugary photodynamic therapy nanoparticle, described glycopolymers structural formula is as follows
Wherein, n span is 10-150, and wherein R, R' are phenyl ring, cyano group, or the structure such as the alkyl of no more than 10 C.
Further, the step preparing DMA and DMAEMA copolymer described in step (1) is as follows: adopt SET-RAFT polymerization, take a certain amount of DMA and DMAEMA, wherein DMA and DMAEMA mol ratio is 1:1 ~ 6, add a certain amount of initiator, chain-transferring agent, catalyst and part, be dissolved in solvent, under the condition of 20 ~ 40 DEG C of anaerobics, react 3h ~ 8h, coagulation in ether, obtains dark green solid, sucking filtration, is drying to obtain;
Further, synthesizing end group described in step (2) is that the step of the glycopolymers of carboxyl is as follows: take and have the good organic monomer of targeted cells affinity, chain-transferring agent and initiator, be dissolved in solvent, 20 ~ 24h is reacted under the condition of 60 ~ 80 DEG C of anaerobics, after cooling in methanol coagulation, obtain red precipitate, sucking filtration, is dissolved in water, and transfers in bag filter, dialyse 2 ~ 3 days, change water 6 ~ 10 times, lyophilizing obtains red solid, obtains water-soluble for red solid the glycopolymers solution that end group is carboxyl.
Further, preferably, in the step of described preparation DMA and DMAEMA copolymer, described initiator is 2-isobutyl ethyl bromide (EBIB), described chain-transferring agent is sulfo-esters RAFT agent, described catalyst is copper powder, and described part is pentamethyl-diethylenetriamine (PMEDTA), and wherein initiator, chain-transferring agent, catalyst, part mol ratio are 1:3:1:2 ~ 10;
Further, preferably, described synthesis end group is in the step of the glycopolymers of carboxyl, described initiator is AIBN, BPO or ACPA, described chain-transferring agent is the RAFT agent containing carboxyl end groups, described organic monomer is selected from galactose, glucose or mannose a kind of, and its Chain transfer agent, initiator mol ratio are 8 ~ 2:1.
Further, preferably, described in the described step preparing DMA and DMAEMA copolymer, chain-transferring agent is α-dithio naphthoic acid isopropyl cyanide ester.
Further, preferably, chain-transferring agent described in the step of the glycopolymers that described synthesis end group is carboxyl is 4-cyano group-4-(phenyl formyl sulfenyl) valeric acid, and described organic monomer is 2-(methacryl amido) Glucopyranose..
Further, described in the described step preparing DMA and DMAEMA copolymer, solvent is DMSO.
Further, described synthesis end group is in the step of the glycopolymers of carboxyl, and when described initiator and chain-transferring agent are oil-soluble, described solvent is DMF, DMAc or DMSO, and when described initiator and chain-transferring agent are water solublity, described solvent is water.
Further, described in step (1), photosensitizer is phthalocyanine Zn, phthalocyanine Si or porphyrin and based on and based on phthalocyanine Zn, the one in the derivant of phthalocyanine Si or porphyrin.；
Further, in step (1), copolymer and photosensitizer mol ratio are 1:1 ~ 20;
Further, described in step (1), solvent is DMF, DMAC or THF;
Further, 0.5 ~ 1mg/ml that in mixed liquor described in step (1), copolymer concentration is;
Further, described in step (1), mixed liquor and a small amount of water volume ratio are 1:3 ~ 8;
Further, the copolymer mol ratio in glycopolymers described in step (2) and mixed solution is 120 ~ 40:1.
Further, preferably, described in step (1), photosensitizer is phthalocyanine Zn.
Advantage of the present invention is:
1) adopt self assembly parcel light power reagent in polymer water, have easy and simple to handle, multiple photodynamic agents can be wrapped up.The polymer adopted shows electropositive, can combine with multiple electronegative polymer.
2) nanoparticle surface assembles sugar-containing polymer, has blood stability and targeting, biocompatibility.
Accompanying drawing explanation
Below in conjunction with drawings and Examples, the invention will be further described:
Fig. 1 is the SEM figure of DMA and DMAEMA copolymer parcel phthalocyanine Zn nanoparticle in embodiment 1;
Fig. 2 is the SEM figure of sugary photodynamic therapy nanoparticle in embodiment 1;
Fig. 3 is DMA and DMAEMA copolymer parcel phthalocyanine Zn nanoparticle DLS figure in embodiment 1;
Fig. 4 is that in embodiment 1, sugary photodynamic therapy nanoparticle DLS schemes;
Fig. 5 is copolymer and phthalocyanine Zn mixed liquor and phthalocyanine Zn singlet oxygen comparison diagram in DMF phase in embodiment 1;
Fig. 6 is sugary photodynamic therapy nanoparticle aqueous phase singlet oxygen test pattern in embodiment 1;
Fig. 7 be in embodiment 1 sugary photodynamic therapy nanoparticle containing the stability in BSA, serum solution and with characteristic PROTEIN C onA action diagram.
Detailed description of the invention
Embodiment 1: preparation has the sugary photodynamic therapy nanoparticle of blood stability and targeting
Its step is as follows:
1) DMA and DMAEMA copolymer is synthesized: DMA and 1.0g (0.0064mol) DMAEMA taking 0.3g (0.0013) mol joins in ampere bottle, add 1.6 μ l (0.013mmol) EBIB, 10.8mg (0.039mmol) chain-transferring agent α-dithio naphthoic acid isopropyl cyanide ester and 2.5mg (0.013mmol) Cu powder, be dissolved in 2mlDMSO, logical 15minAr deaeration, add 8.3 μ l (0.039mmol) PMEDTA, tube sealing, 7h is reacted under the condition of 20 DEG C of anaerobics, reaction terminates rear 5mlTHF and dilutes, and crosses Al
2o
3chromatographic column removes unreacted Cu powder and Cu
2+, coagulation in ether, obtains dark green solid, and sucking filtration is drying to obtain copolymer.Above-mentioned obtained polymer molecular weight is 12300, and molecular weight distribution is about 1.32.
2) copolymer parcel photosensitizer nanoparticle is prepared: 10mg (0.000813mmol) copolymer and 2.0mg (0.0035mmol) the phthalocyanine Zn that get above-mentioned preparation are fully dissolved in 10ml solvent DMF, getting this mixed liquor 1ml is slowly added drop-wise in 6ml water, fully be uniformly mixed, obtain blue settled solution, blue settled solution is transferred in bag filter, lucifuge is dialysed 2 days, change water 6 times, the nano-particle solution obtaining DMA and the DMAEMA copolymer self assembly parcel photosensitizer molecule of blue-tinted transparent is about 15ml.
Fig. 1 is above-mentioned nanoparticle SEM photo, and Fig. 3 is the DLS figure of above-mentioned nanoparticle, and as can be seen from two figure all, the nano particle diameter that shown polymer self assembles is formed is at about 150nm.
3) synthesizing end group is the glycopolymers of carboxyl: take organic monomer 2-(methacryl amido) Glucopyranose. 0.5g (2mmol), RAFT agent 4-cyano group-4-(phenyl formyl sulfenyl) valeric acid 11mg (0.04mmol), initiator A IBN1.6mg (0.01mmol) joins in 5ml ampere bottle, add 2mlDMAc fully to dissolve, 24h is reacted under the condition of 70 DEG C of anaerobics, after cooling in methanol coagulation, obtain red precipitate, sucking filtration, be dissolved in water, transfer in bag filter, dialyse 3 days, change water 10 times, lyophilizing obtains red solid, obtained polymer molecular weight is about 6730, molecular weight distribution is about 1.2.Take above-mentioned red solid 0.003mmol to be dissolved in 10ml water and to obtain the glycopolymers solution that end group is carboxyl.
4) prepare sugary photodynamic therapy nanoparticle: get above-mentioned steps 3) the glycopolymers solution 1ml for preparing joins above-mentioned steps 2) in synthesis 1ml nano-particle solution in, fully be uniformly mixed, obtain sugary photodynamic therapy nanoparticle.
Fig. 2 is the SEM photo of the sugary photodynamic therapy nanoparticle of above-mentioned preparation, and Fig. 4 schemes for its DLS, as can be seen from two figure, step 1) after the nano-particle solution prepared mixes with sugar juice, DLS records nano particle diameter and becomes large.Due to DLS survey is hydration radius, and the nanoparticle radius surveyed than SEM is large.
Fig. 5 is concurrent mixture with phthalocyanine Zn in DMF phase and phthalocyanine Zn singlet oxygen comparison diagram, and wherein 1,3-diphenylisobenzofuran is agent for capturing, concurrent mixture and phthalocyanine Zn mixed liquor productive rate lower, illustrate that phthalocyanine Zn is wrapped up by concurrent mixture thus singlet oxygen productive rate is reduced.Fig. 6 is sugar parcel nanoparticle aqueous phase singlet oxygen test pattern, and spermine is agent for capturing, illustrates that nanoparticle still has good singlet oxygen productive rate in aqueous phase.
Fig. 7 be sugar parcel nanoparticle containing the stability in BSA, serum solution and with characteristic PROTEIN C onA action diagram, the nanoparticle prepared by explanation has specific recognition capability.
Embodiment 2: preparation has the sugary photodynamic therapy nanoparticle of blood stability and targeting
Its step is as follows:
1) DMA and DMAEMA copolymer is synthesized: DMA and 0.86g (0.0055mol) DMAEMA taking 0.5g (0.0022mol) joins in ampere bottle, add 1.6 μ l (0.013mmol) EBIB, 10.8mg (0.039mmol) chain-transferring agent α-dithio naphthoic acid isopropyl cyanide ester and 2.5mg (0.013mmol) Cu powder, be dissolved in 2mlDMSO, logical 15minAr deaeration, add 24.9 μ l (0.117mmol) PMEDTA, tube sealing, 6h is reacted under the condition of 20 DEG C of anaerobics, reaction terminates rear 5mlTHF and dilutes, and crosses Al
2o
3chromatographic column removes unreacted Cu powder and Cu
2+, coagulation in ether, obtains dark green solid, and sucking filtration is drying to obtain copolymer.
2) copolymer parcel photosensitizer nanoparticle is prepared: 10mg (0.000813mmol) copolymer and 1.0mg (0.0018mmol) the phthalocyanine Si that get above-mentioned preparation are fully dissolved in 10ml solvent THF, getting this mixed liquor 1ml is slowly added drop-wise in 5ml water, fully be uniformly mixed, obtain blue settled solution, blue settled solution is transferred in bag filter, lucifuge is dialysed 3 days, change water 8 times, the nano-particle solution obtaining DMA and the DMAEMA copolymer self assembly parcel photosensitizer molecule of blue-tinted transparent is about 15ml.
3) synthesizing end group is the glycopolymers of carboxyl: take organic monomer 2-(methacryl amido) Glucopyranose. 0.5g (2mmol) and RAFT agent 4-cyano group-4-(phenyl formyl sulfenyl) valeric acid 5mg (0.018mmol) and initiator A CPA0.8mg (0.0029mmol), be dissolved in DMF, 24h is reacted under the condition of 70 DEG C of anaerobics, after cooling in methanol coagulation, obtain red precipitate, sucking filtration, be dissolved in water, transfer in bag filter, dialyse 2 days, change water 8 times, lyophilizing obtains red solid.Take above-mentioned red solid 0.003mmol to be dissolved in 10ml water and to obtain the glycopolymers solution that end group is carboxyl.
4) prepare sugary photodynamic therapy nanoparticle: get above-mentioned steps 3) the glycopolymers solution 1.5ml for preparing joins above-mentioned steps 2) in synthesis 1ml nano-particle solution in, fully be uniformly mixed, obtain sugary photodynamic therapy nanoparticle.
Embodiment 3: preparation has the sugary photodynamic therapy nanoparticle of blood stability and targeting
Its step is as follows:
1) DMA and DMAEMA copolymer is synthesized: DMA and 0.60g (0.0038mol) DMAEMA taking 0.88g (0.0038mol) joins in ampere bottle, add 1.6 μ l (0.013mmol) EBIB, 10.8mg (0.039mmol) chain-transferring agent α-dithio naphthoic acid isopropyl cyanide ester and 2.5mg (0.013mmol) Cu powder, be dissolved in 2mlDMSO, logical 15minAr deaeration, add 8.3 μ l (0.039mmol) PMEDTA, tube sealing, 6h is reacted under the condition of 20 DEG C of anaerobics, reaction terminates rear 5mlTHF and dilutes, and crosses Al
2o
3chromatographic column removes unreacted Cu powder and Cu
2+, coagulation in ether, obtains dark green solid, and sucking filtration is drying to obtain copolymer.
2) copolymer parcel photosensitizer nanoparticle is prepared: 10mg (0.000813mmol) copolymer and 9.1mg (0.0162mmol) protoporphyrin of getting above-mentioned preparation are fully dissolved in 10ml solvent DMAc, getting this mixed liquor 1ml is slowly added drop-wise in 5ml water, fully be uniformly mixed, obtain blue settled solution, blue settled solution is transferred in bag filter, lucifuge is dialysed 2 days, change water 6 times, the nano-particle solution obtaining DMA and the DMAEMA copolymer self assembly parcel photosensitizer molecule of blue-tinted transparent is about 15ml.
3) synthesizing end group is the glycopolymers of carboxyl: take organic monomer 2-(methacryl amido) mannopyranose 0.5g (2mmol) and RAFT agent 4-cyano group-4-(phenyl formyl sulfenyl) valeric acid 11mg (0.04mmol) and initiator B PO1.2 (0.005mmol), be dissolved in DMF, 24h is reacted under the condition of 70 DEG C of anaerobics, after cooling in methanol coagulation, obtain red precipitate, sucking filtration, be dissolved in water, transfer in bag filter, dialyse 2 days, change water 8 times, lyophilizing obtains red solid.Take above-mentioned red solid 0.003mmol to be dissolved in 10ml water and to obtain the glycopolymers solution that end group is carboxyl.
4) prepare sugary photodynamic therapy nanoparticle: get above-mentioned steps 3) the glycopolymers solution 2ml for preparing joins above-mentioned steps 2) in synthesis 1ml nano-particle solution in, fully be uniformly mixed, obtain sugary photodynamic therapy nanoparticle.
Certain above-described embodiment is just exemplifying of illustrating that technical conceive of the present invention and feature do and non exhaustive, its object is to person skilled in the art can be understood content of the present invention and implement according to this, can not limit the scope of the invention with this.All modifications done according to the spirit of main technical schemes of the present invention, all should be encompassed within protection scope of the present invention.
Claims (9)
1. one kind has the sugary photodynamic therapy nanoparticle of blood stability and targeting, it is characterized in that, described nanoparticle wraps up photosensitizer micromolecule by DMA and DMAEMA synthetic copolymer, its outer layer covers one deck sugar-containing polymer forms, wherein DMA is N-3,4-dihydroxy benzenes ethyl methacrylamide, and DMAEMA is N, N-dimethylamino methyl ethyl acrylate, described nanoparticle mean diameter is 180nm ~ 300nm.
2. the sugary photodynamic therapy nanoparticle with blood stability and targeting according to claim 1, it is characterized in that, described photosensitizer micromolecule is phthalocyanine Zn, phthalocyanine Si, porphyrin and based on phthalocyanine Zn, the one in the derivant of phthalocyanine Si or porphyrin.
3. have a preparation method for the sugary photodynamic therapy nanoparticle of blood stability and targeting as claimed in claim 1, it is characterized in that, the method comprises the steps:
(1) DMA and DMAEMA copolymer is prepared, this copolymer and a certain amount of photosensitizer are fully dissolved in a solvent, getting this mixed liquor is slowly added drop-wise in a small amount of water, fully be uniformly mixed, obtain blue settled solution, blue settled solution is transferred in bag filter, lucifuge dialysis 2-4 days, change water 6-12 time, obtain the micromolecular nano-particle solution of DMA and DMAEMA copolymer self assembly parcel photosensitizer of blue-tinted transparent;
(2) synthesizing end group is the glycopolymers of carboxyl, this glycopolymers is added step 1 by a certain percentage) in the nano-particle solution of synthesizing, fully be uniformly mixed, glycopolymers is made to be gathered in nanoparticle surface by electrostatic interaction, obtain sugary photodynamic therapy nanoparticle, described glycopolymers structural formula is as follows
Wherein, n span is 10-150, R, R' is phenyl ring, the alkyl of cyano group or no more than 10 C.
4. preparation method according to claim 3, is characterized in that:
The step preparing DMA and DMAEMA copolymer described in step (1) is as follows: adopt SET-RAFT polymerization, take a certain amount of DMA and DMAEMA, wherein DMA and DMAEMA mol ratio is 1:1 ~ 6, adds a certain amount of initiator, chain-transferring agent, catalyst and part, be dissolved in solvent, under the condition of 20 ~ 40 DEG C of anaerobics, react 3h ~ 8h, coagulation in ether, obtain dark green solid, sucking filtration, be drying to obtain;
Synthesizing end group described in step (2) is that the step of the glycopolymers of carboxyl is as follows: take and have the good organic monomer of targeted cells affinity, chain-transferring agent and initiator, be dissolved in solvent, 20 ~ 24h is reacted under the condition of 60 ~ 80 DEG C of anaerobics, after cooling in methanol coagulation, obtain red precipitate, sucking filtration, be dissolved in water, transfer in bag filter, dialyse 2 ~ 3 days, change water 6 ~ 10 times, lyophilizing obtains red solid, obtains water-soluble for red solid the glycopolymers solution that end group is carboxyl.
5. preparation method according to claim 4, is characterized in that,
In the step of described preparation DMA and DMAEMA copolymer, described initiator is 2-isobutyl ethyl bromide, described chain-transferring agent is sulfo-esters RAFT agent, described catalyst is copper powder, described part is pentamethyl-diethylenetriamine, and wherein initiator, chain-transferring agent, catalyst, part mol ratio are 1:3:1:2 ~ 10;
Described synthesis end group is in the step of the glycopolymers of carboxyl, described initiator is AIBN, BPO or ACPA, described chain-transferring agent is the RAFT agent containing carboxyl end groups, described organic monomer is selected from galactose, glucose or mannose a kind of, and its Chain transfer agent, initiator mol ratio are 8 ~ 2:1.
6. preparation method according to claim 4, is characterized in that, described in the step of described preparation DMA and DMAEMA copolymer, chain-transferring agent is α-dithio naphthoic acid isopropyl cyanide ester; Chain-transferring agent described in the step of the glycopolymers that described synthesis end group is carboxyl is 4-cyano group-4-(phenyl formyl sulfenyl) valeric acid, and described organic monomer is 2-(methacryl amido) Glucopyranose..
7. preparation method according to claim 4, is characterized in that, described in the step of described preparation DMA and DMAEMA copolymer, solvent is DMSO; When described in the step of the glycopolymers that described synthesis end group is carboxyl, initiator and chain-transferring agent are oil-soluble, described solvent is DMF, DMAc or DMSO, and when described initiator and chain-transferring agent are water solublity, described solvent is water.
8. preparation method according to claim 3, is characterized in that, described in step (1), photosensitizer is phthalocyanine Zn, phthalocyanine Si, porphyrin and based on phthalocyanine Zn, the one in phthalocyanine Si or derivatives of porphyrin; Described copolymer and photosensitizer mol ratio are 1:1 ~ 20; Described solvent is DMF, DMAC or THF; In described mixed liquor, copolymer concentration is 0.5 ~ 1mg/ml; Described mixed liquor and a small amount of water volume ratio are 1:3 ~ 8; Copolymer mol ratio in glycopolymers described in step (2) and nano-particle solution is 120 ~ 40:1.
9. preparation method according to claim 3, is characterized in that, described in step (1), photosensitizer is phthalocyanine Zn.
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