CN105412924B - Nano-particle of the photodynamic therapy containing sugar and preparation method thereof with blood stability and targeting - Google Patents
Nano-particle of the photodynamic therapy containing sugar and preparation method thereof with blood stability and targeting Download PDFInfo
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- CN105412924B CN105412924B CN201410418189.6A CN201410418189A CN105412924B CN 105412924 B CN105412924 B CN 105412924B CN 201410418189 A CN201410418189 A CN 201410418189A CN 105412924 B CN105412924 B CN 105412924B
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Abstract
The invention discloses a kind of with blood stability and targeting containing sugared photodynamic therapy nano-particle with and preparation method thereof.The nano-particle wraps up photosensitizer small molecule by DMA and DMAEMA synthetic copolymers, and one layer of sugar-containing polymer composition of outer layer covers, which is 180nm~300nm.Preparation method is that self assembly package photosensitizer molecule forms nano-particle to DMA in water with DMAEMA copolymers, the nano-particle is mixed with the glycopolymers solution that end group is carboxyl, so that glycopolymers is gathered in nanoparticle surface by electrostatic interaction and is formed containing sugared photodynamic therapy nano-particle.This method have it is easy to operate, a variety of photodynamic agents can be wrapped up.The polymer of use shows electropositive, can be combined with a variety of electronegative carbohydrate polymers, while nanoparticle surface assembles sugar-containing polymer, has blood stability and targeting and biocompatibility.
Description
Technical field
The present invention relates to a kind of nano-particles of polymer wrapped photosensitizer, and in particular to one kind have blood stability and
Nano-particle of the photodynamic therapy containing sugar of targeting and preparation method thereof.
Background technology
Photosensitizer (photosensitizer, PS) is a kind of substance for having and absorbing, transmitting, convert light energy, this kind of object
If matter is enriched to the cell surface to be acted on or intracellular, light power can be generated under specific wavelength light source excitation
Effect is to kill cell.Based on the understanding to photosensitizer, people have invented a kind of brand-new therapy for tumour, i.e.,
Photodynamic therapy (photodynamic therapy, PDI).The basic principle of the treatment technology is sensitiser absorption photon energy
Amount, by ground state transition to excitation state, physics de excitation process generates fluorescence, medical diagnosis on disease can be carried out by spectrofluorimetry；
Its chemical de excitation process can generate some active oxygen species (ROS), wherein most importantly singlet oxygen.Active oxygen species can be with
Cell membrane and intracellular a variety of interaction of biomacromolecules may result in cell when active oxygen species reach certain value
Damage is dead, to generate therapeutic effect.Small molecule photosensitizer is due to water-soluble general poor, without targeting, limitation
Its application.
Glycan molecule have good hydrophily, bio-identification and biological degradability, this make containing sugar polymer biology,
Medicine etc. tool has been widely used.One significant difference of cancer cell and normal cell is exactly that endocellular sugar metabolism is vigorous,
Usually there are some on the cell membrane of cancer cell can occur the albumen of specific effect, such as glucose transporter with sugar
(Glucose Transporters, GLUT) is the hypotype being almost present in all cancerous cell lines, and is had found in many people
There is overexpression in class tumour.Based on the understanding to cancer cell this respect, prepares and cancer is carried out containing sugared light power nano-particle
Targeted therapy has broad application prospects.
Invention content
Purpose of the present invention is to：A kind of nano-particle of the photodynamic therapy containing sugar with blood stability and targeting is provided
And preparation method thereof, the method for utilizing active free radical polymerization, preparation structure regular controllable DOPA amine polymer and end group
Sugar-containing polymer with carboxyl, with DOPA amine polymer, photosensitizer package is wherein formed nanoparticle by self assembly in water
Son makes sugar be gathered in nanoparticle surface with electrostatic effect, and synthetic method economy convenient for extensive synthesis, and is prepared into
There is the sugar package nano-particle arrived good blood stability, strong fluorescence to have good killing effect to cancer cell.
The technical scheme is that：
A kind of nano-particle of the photodynamic therapy containing sugar with blood stability and targeting, which is characterized in that described
Nano-particle wraps up photosensitizer small molecule by DMA and DMAEMA synthetic copolymers, and one layer of sugar-containing polymer of outer layer covers forms,
Wherein DMA is N-3,4- dihydroxy benzenes ethyl methacrylamides, DMAEMA N, N- dimethylaminoethyl methacrylates, institute
It is 180nm~300nm to state nano-particle average grain diameter.
Further, it is preferred that the photosensitizer be phthalocyanine Zn, phthalocyanine Si, porphyrin and be based on phthalocyanine Zn, phthalocyanine Si or porphin
One kind in the derivative of quinoline.
Simultaneously the present invention also provides the preparation method of above-mentioned nano-particle, this method comprises the following steps：
(1) DMA and DMAEMA copolymers are prepared, the copolymer and a certain amount of photosensitizer are substantially dissolved in solvent,
It takes the mixed liquor to be slowly dropped in a small amount of water, is thoroughly mixed, obtain blue clear solution, blue clear solution is shifted
Into bag filter, it is protected from light dialysis 2-4 days, changes water 6-12 times, obtains DMA and DMAEMA copolymer the self assembly package of blue-tinted transparent
The nano-particle solution of photosensitizer small molecule；
(2) synthesis end group is the glycopolymers of carboxyl, which is added receiving for step 1) synthesis by a certain percentage
It in rice corpuscles solution, is thoroughly mixed, so that glycopolymers is gathered in nanoparticle surface to get containing sugared light by electrostatic interaction
Photodynamic therapy nano-particle, the glycopolymers structural formula is as follows,
Wherein, n value ranges are 10-150, wherein R, and R' is phenyl ring, the structures such as cyano, or the alkyl of not more than 10 C.
Further, the step of DMA and DMAEMA copolymers are prepared described in step (1) is as follows：It is poly- using SET-RAFT
Conjunction method weighs a certain amount of DMA and DMAEMA, and wherein DMA and DMAEMA molar ratios are 1:1~6, a certain amount of initiation is added
Agent, chain-transferring agent, catalyst and ligand, are dissolved in solvent, 3h~8h are reacted under conditions of 20~40 DEG C of anaerobics, in ether
Coagulation obtains dark green solid, filters, is drying to obtain；
Further, the step of glycopolymers that end group is carboxyl are synthesized described in step (2) is as follows：It weighs thin with targeting
The good organic monomer of born of the same parents' compatibility, chain-transferring agent and initiator, are dissolved in solvent, react 20 under conditions of 60~80 DEG C of anaerobics
~for 24 hours, it is cooling after coagulation in methyl alcohol, obtain red precipitate, filter, be dissolved in water, be transferred in bag filter, dialysis 2~3
It, changes water 6~10 times, and freeze-drying obtains red solid, and red solid, which is dissolved in water, obtains the glycopolymers solution that end group is carboxyl.
Further, it is preferred that in the step of the preparation DMA and DMAEMA copolymers, the initiator is that 2- bromos are different
Ethyl butyrate (EBIB), the chain-transferring agent are thioesters RAFT agent, and the catalyst is copper powder, and the ligand is
Pentamethyl-diethylenetriamine (PMEDTA), wherein initiator, chain-transferring agent, catalyst, ligand molar ratio are 1:3:1:2~10；
Further, it is preferred that it is described synthesis end group be carboxyl glycopolymers the step of in, the initiator be AIBN,
BPO or ACPA, the chain-transferring agent are the RAFT agent containing carboxyl end groups, and the organic monomer is selected from galactolipin, Portugal
A kind of in grape sugar or mannose, Chain transfer agent, initiator molar ratio are 8~2:1.
Further, it is preferred that chain-transferring agent is α-two sulphur described in the step of the preparation DMA and DMAEMA copolymers
For naphthoic acid isobutyronitrile ester.
Further, it is preferred that chain-transferring agent is 4- described in the step of synthesis end group is the glycopolymers of carboxyl
Cyano -4- (phenyl formyl sulfenyl) valeric acid, the organic monomer are 2- (methacryl amido) glucopyranose.
Further, solvent described in the step of preparation DMA and DMAEMA copolymers is DMSO.
Further, in the step of synthesis end group is the glycopolymers of carboxyl, the initiator and chain-transferring agent are
When oil-soluble, the solvent is DMF, DMAc or DMSO, and when the initiator and chain-transferring agent are water-soluble, the solvent is
Water.
Further, photosensitizer described in step (1) is phthalocyanine Zn, phthalocyanine Si or porphyrin and is based on and is based on phthalocyanine
One kind in the derivative of Zn, phthalocyanine Si or porphyrin.；
Further, copolymer and photosensitizer molar ratio are 1 in step (1):1~20；
Further, solvent described in step (1) is DMF, DMAC or THF；
Further, 0.5~1mg/ml that copolymer concentration is in mixed liquor described in step (1)；
Further, mixed liquor described in step (1) and a small amount of water volume ratio are 1:3~8；
Further, glycopolymers described in step (2) and the copolymer molar ratio in mixed solution are 120~40:1.
Further, it is preferred that photosensitizer described in step (1) is phthalocyanine Zn.
It is an advantage of the invention that：
1) use polymer water in self assembly wrap up light power reagent, have it is easy to operate, a variety of photodynamics can be wrapped up
Reagent.The polymer of use shows electropositive, can be combined with a variety of electronegative polymer.
2) nanoparticle surface assembles sugar-containing polymer, has blood stability and targeting, biocompatibility.
Description of the drawings
The invention will be further described with reference to the accompanying drawings and embodiments：
Fig. 1 is the SEM figures that DMA wraps up phthalocyanine Zn nano-particles with DMAEMA copolymers in embodiment 1；
Fig. 2 is the SEM figures containing sugared photodynamic therapy nano-particle in embodiment 1；
Fig. 3 is that DMA wraps up phthalocyanine Zn nano-particles DLS figures with DMAEMA copolymers in embodiment 1；
Fig. 4 is in embodiment 1 containing sugared photodynamic therapy nano-particle DLS figures；
Fig. 5 is copolymer and phthalocyanine Zn mixed liquors and phthalocyanine the Zn figure compared with singlet oxygen in DMF phases in embodiment 1；
Fig. 6 is in embodiment 1 containing sugared photodynamic therapy nano-particle water phase singlet oxygen test chart；
Fig. 7 be embodiment 1 in containing sugared photodynamic therapy nano-particle containing the stability in BSA, serum solution with
And with characteristic PROTEIN C on A action diagrams.
Specific implementation mode
Embodiment 1：Prepare the nano-particle of the photodynamic therapy containing sugar with blood stability and targeting
Its step are as follows：
1) synthesis DMA and DMAEMA copolymers:Weigh the DMA and 1.0g (0.0064mol) of 0.3g (0.0013) mol
DMAEMA is added in ampere bottle, and 1.6 μ l (0.013mmol) EBIB, 10.8mg (0.039mmol) chain-transferring agent α-two sulphur are added
It for naphthoic acid isobutyronitrile ester and 2.5mg (0.013mmol) Cu powder, is dissolved in 2ml DMSO, leads to 15minAr and exclude air, be added
8.3 μ l (0.039mmol) PMEDTA, tube sealing react 7h under conditions of 20 DEG C of anaerobics, are diluted after reaction with 5mlTHF,
Cross Al2O3Chromatographic column removes unreacted Cu powder and Cu2+, the coagulation in ether obtains dark green solid, filters, is drying to obtain
Copolymer.Above-mentioned obtained polymer molecular weight is 12300, and molecular weight distribution is 1.32 or so.
2) copolymer package photosensitizer nano-particle is prepared：Take above-mentioned preparation 10mg (0.000813mmol) copolymers and
2.0mg (0.0035mmol) phthalocyanines Zn is substantially dissolved in 10ml solvent DMFs, and mixed liquor 1ml is taken to be slowly dropped to 6ml water
In, it is thoroughly mixed, obtains blue clear solution, blue clear solution is transferred in bag filter, be protected from light dialysis 2 days, change
Water 6 times obtains the nano-particle solution of DMA and DMAEMA copolymer self assembly package photosensitizer molecule of blue-tinted transparent about
15ml。
Fig. 1 is above-mentioned nano-particle SEM photograph, and Fig. 3 is that the DLS of above-mentioned nano-particle schemes, and can be seen that institute from two figures
Show the nano particle diameter of polymer self assembles formation in 150nm or so.
3) synthesis end group is the glycopolymers of carboxyl：Weigh organic monomer 2- (methacryl amido) glucopyranose
0.5g (2mmol), RAFT agent 4- cyano -4- (phenyl formyl sulfenyl) valeric acid 11mg (0.04mmol), initiator
AIBN 1.6mg (0.01mmol) are added in 5ml amperes of bottles, and 2ml DMAc are added and fully dissolve, under conditions of 70 DEG C of anaerobics
Reaction for 24 hours, it is cooling after coagulation in methyl alcohol, obtain red precipitate, filter, be dissolved in water, be transferred in bag filter, dialyse 3 days,
Change water 10 times, freeze-drying obtains red solid, and obtained polymer molecular weight is about 6730, and molecular weight distribution is 1.2 or so.It weighs
It states red solid 0.003mmol and is dissolved in the glycopolymers solution that 10ml water obtains end group as carboxyl.
4) it prepares containing sugared photodynamic therapy nano-particle：Taking above-mentioned steps 3) the glycopolymers solution 1ml for preparing is added
To above-mentioned steps 2) in synthesize 1ml nano-particle solutions in, be thoroughly mixed to get containing sugared photodynamic therapy nanoparticle
Son.
Fig. 2 is the SEM photograph containing sugared photodynamic therapy nano-particle of above-mentioned preparation, and Fig. 4 schemes for its DLS, from two figures
In as can be seen that step 1) prepare nano-particle solution mixed with sugar juice after, DLS measures nano particle diameter and becomes larger.By
What it is in DLS surveys is hydration radius, bigger than the nano-particle radius that SEM is surveyed.
Fig. 5 be concurrent mixture with phthalocyanine Zn the figure compared with phthalocyanine Zn singlet oxygens in DMF phases, wherein 1,3- diphenyl benzo
Furans is agent for capturing, and concurrent mixture and phthalocyanine Zn mixed liquor yields are lower, illustrates that phthalocyanine Zn is wrapped up by concurrent mixture to make single line
State oxygen yield reduces.Fig. 6 is sugar package nano-particle water phase singlet oxygen test chart, and spermine is agent for capturing, is illustrated in water phase
Nano-particle still has good singlet oxygen yield.
Fig. 7 be sugar package nano-particle containing in BSA, serum solution stability and with characteristic PROTEIN C on A make
With figure, illustrate that prepared nano-particle has specific recognition capability.
Embodiment 2：Prepare the nano-particle of the photodynamic therapy containing sugar with blood stability and targeting
Its step are as follows：
1) synthesis DMA and DMAEMA copolymers:Weigh the DMA and 0.86g (0.0055mol) of 0.5g (0.0022mol)
DMAEMA is added in ampere bottle, and 1.6 μ l (0.013mmol) EBIB, 10.8mg (0.039mmol) chain-transferring agent α-two sulphur are added
It for naphthoic acid isobutyronitrile ester and 2.5mg (0.013mmol) Cu powder, is dissolved in 2ml DMSO, leads to 15minAr and exclude air, be added
24.9 μ l (0.117mmol) PMEDTA, tube sealing react 6h under conditions of 20 DEG C of anaerobics, are diluted after reaction with 5mlTHF,
Cross Al2O3Chromatographic column removes unreacted Cu powder and Cu2+, the coagulation in ether obtains dark green solid, filters, is drying to obtain
Copolymer.
2) copolymer package photosensitizer nano-particle is prepared：Take above-mentioned preparation 10mg (0.000813mmol) copolymers and
1.0mg (0.0018mmol) phthalocyanines Si is substantially dissolved in 10ml solvents THF, and mixed liquor 1ml is taken to be slowly dropped to 5ml water
In, it is thoroughly mixed, obtains blue clear solution, blue clear solution is transferred in bag filter, be protected from light dialysis 3 days, change
Water 8 times obtains the nano-particle solution of DMA and DMAEMA copolymer self assembly package photosensitizer molecule of blue-tinted transparent about
15ml。
3) synthesis end group is the glycopolymers of carboxyl：Weigh organic monomer 2- (methacryl amido) glucopyranose
0.5g (2mmol) and RAFT agent 4- cyano -4- (phenyl formyl sulfenyl) valeric acid 5mg (0.018mmol) and initiation
Agent ACPA0.8mg (0.0029mmol), is dissolved in DMF, is reacted under conditions of 70 DEG C of anaerobics for 24 hours, gathers in methyl alcohol after cooling
It is heavy, red precipitate is obtained, is filtered, is dissolved in water, is transferred in bag filter, dialyses 2 days, changes water 8 times, freeze-drying obtains red solid
Body.It weighs above-mentioned red solid 0.003mmol and is dissolved in the glycopolymers solution that 10ml water obtains end group as carboxyl.
4) it prepares containing sugared photodynamic therapy nano-particle：Take above-mentioned steps 3) prepare glycopolymers solution 1.5ml add
Enter to above-mentioned steps 2) in synthesize 1ml nano-particle solutions in, be thoroughly mixed to get containing sugared photodynamic therapy nanometer
Particle.
Embodiment 3：Prepare the nano-particle of the photodynamic therapy containing sugar with blood stability and targeting
Its step are as follows：
1) synthesis DMA and DMAEMA copolymers:Weigh the DMA and 0.60g (0.0038mol) of 0.88g (0.0038mol)
DMAEMA is added in ampere bottle, and 1.6 μ l (0.013mmol) EBIB, 10.8mg (0.039mmol) chain-transferring agent α-two sulphur are added
It for naphthoic acid isobutyronitrile ester and 2.5mg (0.013mmol) Cu powder, is dissolved in 2ml DMSO, leads to 15minAr and exclude air, be added
8.3 μ l (0.039mmol) PMEDTA, tube sealing react 6h under conditions of 20 DEG C of anaerobics, are diluted after reaction with 5mlTHF,
Cross Al2O3Chromatographic column removes unreacted Cu powder and Cu2+, the coagulation in ether obtains dark green solid, filters, is drying to obtain
Copolymer.
2) copolymer package photosensitizer nano-particle is prepared：Take above-mentioned preparation 10mg (0.000813mmol) copolymers and
9.1mg (0.0162mmol) protoporphyrin is substantially dissolved in 10ml solvents DMAc, and mixed liquor 1ml is taken to be slowly dropped to 5ml water
In, it is thoroughly mixed, obtains blue clear solution, blue clear solution is transferred in bag filter, be protected from light dialysis 2 days, change
Water 6 times obtains the nano-particle solution of DMA and DMAEMA copolymer self assembly package photosensitizer molecule of blue-tinted transparent about
15ml。
3) synthesis end group is the glycopolymers of carboxyl：Weigh organic monomer 2- (methacryl amido) mannopyranose
0.5g (2mmol) and RAFT agent 4- cyano -4- (phenyl formyl sulfenyl) valeric acid 11mg (0.04mmol) and initiation
Agent BPO1.2 (0.005mmol), is dissolved in DMF, is reacted under conditions of 70 DEG C of anaerobics for 24 hours, it is cooling after coagulation in methyl alcohol, obtain
It to red precipitate, filters, is dissolved in water, is transferred in bag filter, dialyse 2 days, change water 8 times, freeze-drying obtains red solid.It weighs
Above-mentioned red solid 0.003mmol is dissolved in 10ml water and obtains the glycopolymers solution that end group is carboxyl.
4) it prepares containing sugared photodynamic therapy nano-particle：Taking above-mentioned steps 3) the glycopolymers solution 2ml for preparing is added
To above-mentioned steps 2) in synthesize 1ml nano-particle solutions in, be thoroughly mixed to get containing sugared photodynamic therapy nanoparticle
Son.
It is enumerated and non exhaustive, mesh made by the technical concepts and features of certain above-described embodiment only to illustrate the invention
Be allow person skilled in the art to can understand the content of the present invention and implement it accordingly, can not be limited with this present invention
Protection domain.The modification that all Spirit Essences according to main technical schemes of the present invention are done should all cover the protection in the present invention
Within the scope of.
Claims (6)
1. a kind of nano-particle of the photodynamic therapy containing sugar with blood stability and targeting, which is characterized in that described to receive
Rice corpuscles wraps up photosensitizer small molecule by DMA and DMAEMA synthetic copolymers, and one layer of sugar-containing polymer of outer layer covers forms,
Middle sugar-containing polymer structural formula is as follows：
Wherein, n value ranges are 10-150, and R, R' are the alkyl of phenyl ring, cyano or not more than 10 C, and DMA is N-3,4-
Dihydroxy benzenes ethyl methacrylamide, DMAEMA N, N- dimethylaminoethyl methacrylates, the nano-particle are average
Grain size is 180nm~300nm.
2. the photodynamic therapy containing the sugar nano-particle according to claim 1 with blood stability and targeting,
It is characterized in that, the photosensitizer small molecule is phthalocyanine Zn, phthalocyanine Si, porphyrin and is based on phthalocyanine Zn, and phthalocyanine Si or porphyrin spread out
One kind in biology.
3. it is a kind of it is as described in claim 1 with blood stability and targeting containing sugared photodynamic therapy nano-particle
Preparation method, which is characterized in that this method comprises the following steps：
(1) DMA and DMAEMA copolymers are prepared, the copolymer and a certain amount of photosensitizer are substantially dissolved in solvent, this is taken
Mixed liquor is slowly dropped in a small amount of water, is thoroughly mixed, and blue clear solution is obtained, and blue clear solution is transferred to
It analyses in bag, is protected from light dialysis 2-4 days, changes water 6-12 times, DMA and DMAEMA copolymer the self assembly package for obtaining blue-tinted transparent are photosensitive
The nano-particle solution of agent small molecule；
(2) synthesis end group is the sugar-containing polymer of carboxyl, which is added receiving for step 1) synthesis by a certain percentage
It in rice corpuscles solution, is thoroughly mixed, so that glycopolymers is gathered in nanoparticle surface to get containing sugared light by electrostatic interaction
Photodynamic therapy nano-particle, the sugar-containing polymer structural formula is as follows,
Wherein, n value ranges are 10-150, and R, R' are the alkyl of phenyl ring, cyano or not more than 10 C.
4. preparation method according to claim 3, it is characterised in that：DMA and DMAEMA is prepared described in step (1) to be copolymerized
The step of object, is as follows：A certain amount of DMA and DMAEMA is weighed, wherein DMA and DMAEMA molar ratios are 1:1~6, it is added a certain amount of
Initiator, chain-transferring agent, catalyst and ligand, are dissolved in solvent, 3h~8h are reacted under conditions of 20~40 DEG C of anaerobics, in second
Coagulation in ether obtains dark green solid, filters, is drying to obtain；Initiator described in the step is 2- isobutyl ethyl bromides, institute
It is the thio naphthoic acid isobutyronitrile esters of α-two to state chain-transferring agent, and the catalyst is copper powder, and the ligand is pentamethyl divinyl three
Amine, wherein initiator, chain-transferring agent, catalyst, ligand molar ratio are 1:3:1:2~10, the solvent is DMSO；
The step of sugar-containing polymer that end group is carboxyl is synthesized described in step (2) is as follows：It weighs with targeting cellular affinity
Good organic monomer, chain-transferring agent and initiator, are dissolved in solvent, react 20 under conditions of 60~80 DEG C of anaerobics~for 24 hours, it is cold
But coagulation in methyl alcohol after, obtains red precipitate, filters, is dissolved in water, is transferred in bag filter, dialyses 2~3 days, change water 6~
10 times, freeze-drying obtains red solid, and red solid, which is dissolved in water, obtains the sugar-containing polymer solution that end group is carboxyl；In the step
The initiator is AIBN, BPO or ACPA, and the chain-transferring agent is 4- cyano -4- (phenyl formyl sulfenyl) valeric acid, described
Organic monomer is 2- (methacryl amido) glucopyranose, and Chain transfer agent, initiator molar ratio are 8~2:1；And
When the initiator and chain-transferring agent are oil-soluble, the solvent is DMF, DMAc or DMSO, the initiator and chain tra nsfer
When agent is water-soluble, the solvent is water.
5. preparation method according to claim 3, which is characterized in that photosensitizer described in step (1) is phthalocyanine Zn, phthalocyanine
Si, porphyrin and it is based on phthalocyanine Zn, one kind in phthalocyanine Si or derivatives of porphyrin；The copolymer is 1 with photosensitizer molar ratio:
1~20；The solvent is DMF, DMAC or THF；Copolymer concentration is 0.5~1mg/ml in the mixed liquor；The mixed liquor
It is 1 with a small amount of water volume ratio:3~8；Sugar-containing polymer described in step (2) and the copolymer molar ratio in nano-particle solution
It is 120~40:1.
6. preparation method according to claim 3, which is characterized in that photosensitizer described in step (1) is phthalocyanine Zn.
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| CN108187068B (en) * | 2018-01-15 | 2019-04-23 | 江南大学 | A kind of preparation and its application of photosensitizer composite Nano multifunctional material |
| CN113444201A (en) * | 2021-06-29 | 2021-09-28 | 苏州大学 | Fluorescent sugar-containing polymer and preparation method thereof |
| CN113786492B (en) * | 2021-08-13 | 2023-03-28 | 四川大学华西医院 | Polymer carrier for photodynamic therapy and preparation method and application thereof |
| CN113797350B (en) * | 2021-08-13 | 2023-05-05 | 四川大学华西医院 | Glycosyl polymer and preparation method and application thereof |
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