CN113717354A - Amphiphilic polyester and preparation method and application thereof - Google Patents
Amphiphilic polyester and preparation method and application thereof Download PDFInfo
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- CN113717354A CN113717354A CN202110933279.9A CN202110933279A CN113717354A CN 113717354 A CN113717354 A CN 113717354A CN 202110933279 A CN202110933279 A CN 202110933279A CN 113717354 A CN113717354 A CN 113717354A
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- 229920000728 polyester Polymers 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 33
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000002994 raw material Substances 0.000 claims abstract description 14
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims abstract description 13
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 claims abstract description 12
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001361 adipic acid Substances 0.000 claims abstract description 10
- 235000002906 tartaric acid Nutrition 0.000 claims abstract description 10
- 239000011975 tartaric acid Substances 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 20
- 238000003786 synthesis reaction Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000000502 dialysis Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 12
- 229940079593 drug Drugs 0.000 abstract description 12
- 239000007864 aqueous solution Substances 0.000 abstract description 5
- 239000000693 micelle Substances 0.000 abstract description 4
- 230000002194 synthesizing effect Effects 0.000 abstract description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 16
- 239000000839 emulsion Substances 0.000 description 10
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical compound C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 6
- 238000012377 drug delivery Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229920003232 aliphatic polyester Polymers 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Biological Depolymerization Polymers (AREA)
- Polyamides (AREA)
Abstract
The invention discloses an amphiphilic polyester and a preparation method and application thereof. Tartaric acid, 1, 3-dibromopropane and 1, 6-adipic acid are used as raw materials, dimethyl sulfoxide or N, N-dimethylformamide is used as a raw material, and three-step reaction is carried out under the catalysis of tetramethylguanidine; step one, respectively synthesizing a hydrophobic chain segment A and a hydrophilic chain segment B, wherein the terminal functional groups of the hydrophobic chain segment A and the hydrophilic chain segment B are different; secondly, mixing the hydrophobic chain segment A and the hydrophilic chain segment B, and reacting for 24 hours; the conversion rate of the invention reaches more than 90%. In addition, the finally prepared amphiphilic polyester can be assembled into a nano micelle in an aqueous solution, and can be loaded with drugs, particularly hydrophobic drugs; meanwhile, the polymer has excellent biocompatibility and biodegradability, and the used raw materials are natural and non-toxic. The invention has the advantages that: simple operation, easily obtained raw materials and normal temperature preparation.
Description
Technical Field
The invention relates to the technical field of polymer synthesis, in particular to an amphiphilic polyester and a preparation method and application thereof.
Background
Drug Delivery Systems (DDSs) are of great interest to researchers because they can achieve targeted release of drugs at tumors in time, space, and dosage. Amphiphilic Block Polymer (ABP) is a widely researched drug delivery system, can be self-assembled in an aqueous solution to form a nano micelle with a core-shell structure, and a core can play a role in loading drugs, so that the stability and water solubility of the drugs are improved. At the same time, good biocompatibility and biodegradability are essential as a drug delivery system. The linear aliphatic polyester has good biocompatibility and biodegradability, so that the linear aliphatic polyester is widely applied to the fields of tissue engineering, biomedicine and the like. Therefore, the development of amphiphilic polyester compounds is of great significance.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide an amphiphilic polyester.
In order to achieve the purpose, the invention provides the following technical scheme:
an amphiphilic polyester, which is a mixture of at least one amphiphilic polyester,
the chemical structure is as follows:
wherein the molecular weight of the polymer of the hydrophobic segment is between 1000-12000; the polymer molecular weight of the hydrophilic segment is between 1000-12000.
As a further improvement of the present invention,
the catalyst is prepared by the following reaction of the following components in parts by mole:
1, 6-adipic acid: 100 portions of
1, 3-dibromopropane: 205 to 220 portions
Solvent: 160 to 200 portions of
Catalyst: 420 to 480 portions
Tartaric acid: 80 parts of the raw materials.
As a further improvement of the present invention,
the catalyst is tetramethylguanidine.
As a further improvement of the present invention,
the solvent is any one of dimethyl sulfoxide and N, N-dimethylformamide.
As another object of the present invention, there is provided a process for producing an amphiphilic polyester,
the method comprises the following steps:
synthesis of hydrophobic segment a: dissolving 100 parts by mole of 1, 6-adipic acid and 120 parts by mole of 105-dibromopropane in 80-100 parts by mole of a solvent, and slowly dropping 200 parts by mole of a catalyst for reaction for 24 hours;
step two: synthesis of a hydrophilic chain segment B: dissolving 100 parts by mole of 1, 3-dibromopropane and 140 parts by mole of tartaric acid in 80-100 parts by mole of a solvent, and slowly dropping 220-280 parts by mole of a catalyst for reaction for 24 hours;
step three: and (3) synthesis of amphiphilic polyester: slowly dripping the solution obtained in the first step into the solution obtained in the second step, reacting for 12 hours, then pouring the reaction liquid into water, dialyzing for 24 hours in a dialysis bag, and freeze-drying.
As a further improvement of the present invention,
the catalyst is tetramethylguanidine.
As a further improvement of the present invention,
the solvent is any one of dimethyl sulfoxide and N, N-dimethylformamide.
As a further improvement of the present invention,
the reaction temperature of the first step, the second step and the third step is room temperature.
The amphiphilic polyester prepared by the invention is used as a drug carrier.
The amphiphilic polyester prepared by the invention mainly comprises two parts, one is a hydrophobic chain segment, the part without hydroxyl is the hydrophobic chain segment, the other is a hydrophilic chain segment, and the part with hydroxyl is the hydrophilic chain segment; therefore, in the preparation process, the hydrophobic chain segment and the hydrophilic chain segment are separately synthesized, and then the two chain segments are polymerized to obtain the final amphiphilic polyester, so that the separate synthesis has the advantages that the hydrophobic chain segment and the hydrophilic chain segment cannot interfere with each other, and the stable amphiphilic polyester is finally obtained.
Wherein the reaction equation of the hydrophobic segment is as follows:
wherein the reaction equation of the hydrophilic segment is:
the reaction equation for mutual polymerization of the hydrophobic segment and the hydrophilic segment is as follows:
tartaric acid, 1, 3-dibromopropane and 1, 6-adipic acid are used as raw materials, dimethyl sulfoxide or N, N-dimethylformamide is used as a raw material, and three-step reaction is carried out under the catalysis of tetramethylguanidine; step one, respectively synthesizing a hydrophobic chain segment A and a hydrophilic chain segment B, wherein the terminal functional groups of the hydrophobic chain segment A and the hydrophilic chain segment B are different; secondly, mixing the hydrophobic chain segment A and the hydrophilic chain segment B, and reacting for 24 hours; the conversion rate of the invention reaches more than 90%. In addition, the finally prepared amphiphilic polyester can be assembled into a nano micelle in an aqueous solution, and can be loaded with drugs, particularly hydrophobic drugs; meanwhile, the polymer has excellent biocompatibility and biodegradability, and the used raw materials are natural and non-toxic. The invention has the advantages that: simple operation, easily obtained raw materials and normal temperature preparation.
Drawings
FIG. 1 is a nuclear magnetic spectrum of a hydrophobic segment polymer A of example 2;
FIG. 2 is a nuclear magnetic spectrum of a hydrophilic segment polymer B of example 2;
FIG. 3 is a nuclear magnetic spectrum of the amphiphilic polymer of example 2;
FIG. 4 shows the fluorescence absorption spectrum of the amphiphilic polymer of example 2 before and after wrapping Nile red;
FIG. 5 is fluorescence absorption spectra of amphiphilic polymer coated nile red of example 2 in PBS solution at pH5.0 for various times;
FIG. 6 is fluorescence absorption spectrum of amphiphilic polymer coated nile red of example 2 in PBS solution at pH7.4 for different time periods;
FIG. 7 is fluorescence absorption spectra of amphiphilic polymer coated nile red of example 2 in PBS solution at pH9.0 for various times;
FIG. 8 is an assembled electron micrograph of the amphiphilic polymer of example 2;
fig. 9 is a DLS plot of the amphiphilic polymer of example 2.
Detailed Description
The invention will be further described in detail with reference to the following examples, which are given in the accompanying drawings.
Example 1
Synthesizing an amphiphilic polymer;
the method comprises the following steps: synthesis of hydrophobic segment a: 0.68g of 1, 6-adipic acid and 1.01gde1, 3-dibromopropane are dissolved in 6ml of dimethyl sulfoxide, and then 1.08g of tetramethylguanidine is slowly dropped to react for 24 hours;
step two: synthesis of a hydrophilic chain segment B: 1.94g of 1, 3-dibromopropane and 1.50g of tartaric acid are dissolved in 10ml of dimethyl sulfoxide, and then 2.30g of tetramethylguanidine is slowly dropped to react for 24 hours;
step three: and (3) synthesis of amphiphilic polyester: slowly dripping the solution obtained in the step one into the solution obtained in the step two, reacting for 12 hours, pouring the reaction liquid into water, dialyzing for 24 hours in a dialysis bag, and then freeze-drying.
Example 2
Synthesis of amphiphilic polymer:
the method comprises the following steps: synthesis of hydrophobic segment a: 0.69g of 1, 6-adipic acid and 1.01g of 1, 3-dibromopropane are dissolved in 6ml of dimethyl sulfoxide, and then 1.10g of tetramethylguanidine is slowly dropped to react for 24 hours;
step two: synthesis of a hydrophilic chain segment B: 1.94g of 1, 3-dibromopropane and 1.50g of tartaric acid are dissolved in 10ml of dimethyl sulfoxide, and then 2.30g of tetramethylguanidine is slowly dropped to react for 24 hours;
step three: and (3) synthesis of amphiphilic polyester: slowly dripping the solution obtained in the step one into the solution obtained in the step two, reacting for 12 hours, pouring the reaction liquid into water, dialyzing for 24 hours in a dialysis bag, and then freeze-drying.
Example 3
Synthesis of amphiphilic polymers
The method comprises the following steps: synthesis of hydrophobic segment a: 0.70g of 1, 6-adipic acid and 1.01g of 1, 3-dibromopropane are dissolved in 6ml of dimethyl sulfoxide, and then 1.11g of tetramethylguanidine is slowly dropped to react for 24 hours;
step two: synthesis of a hydrophilic chain segment B: 1.94g of 1, 3-dibromopropane and 1.50g of tartaric acid are dissolved in 10ml of dimethyl sulfoxide, and then 2.30g of tetramethylguanidine is slowly dropped to react for 24 hours;
step three: and (3) synthesis of amphiphilic polyester: slowly dripping the solution obtained in the step one into the solution obtained in the step two, reacting for 12 hours, pouring the reaction liquid into water, dialyzing for 24 hours in a dialysis bag, and then freeze-drying.
And (3) detection:
1. the hydrophobic segment a, the hydrophilic segment B, and the final product obtained in example 2 were subjected to nuclear magnetic detection, and fig. 1, fig. 2, and fig. 3 were obtained, respectively.
2. Wrapped nile red experiment:
(1) accurately weighing 200mg of the amphiphilic polymer synthesized in the example 2, and dissolving the amphiphilic polymer in 2ml of dimethyl sulfoxide to form a solution A;
(2) accurately weighing 200mg of the amphiphilic polymer synthesized in the embodiment 2 and 40mg of nile red, and dissolving the amphiphilic polymer and the nile red in 2ml of dimethyl sulfoxide to form a solution B;
(3) dripping the solution A and the solution B into 100ml of vigorously stirred pure water respectively, stirring for 3 hours, and then pouring into dialysis bags respectively for dialysis for 24 hours to obtain emulsion C and emulsion D respectively;
(4) respectively taking 4ml of emulsion C and emulsion D, and carrying out fluorescence absorption test to obtain the front and back fluorescence absorption spectra of the amphiphilic polymer coated Nile red (figure 4);
(5) adding 1ml of emulsion D into 4ml of buffer solution with pH value of 5.0, pH value of 7.4 and pH value of 9.0 to obtain emulsion E, emulsion F and emulsion G, and performing fluorescence absorption test at different time to obtain fluorescence absorption spectra of the amphiphilic polymer in buffer solutions with different pH values at different time (corresponding to FIG. 5, FIG. 6 and FIG. 7 respectively).
3. The polymer obtained in example 2 was examined by a scanning electron microscope, and fig. 8 was obtained.
4. The polymer obtained in example 2 was analyzed for particle size by a nanosize particle size analyzer (DLS) and a ZETA potential analyzer (DLS), and fig. 9 was obtained.
The amphiphilic polyester prepared by the invention mainly comprises two parts, one is a hydrophobic chain segment, and the other is a hydrophilic chain segment; therefore, in the preparation process, the hydrophobic chain segment and the hydrophilic chain segment are separately synthesized, and then the two chain segments are polymerized to obtain the final amphiphilic polyester, so that the separate synthesis has the advantages that the hydrophobic chain segment and the hydrophilic chain segment cannot interfere with each other, and the stable amphiphilic polyester is finally obtained.
Wherein the reaction equation of the hydrophobic segment is as follows:
wherein the reaction equation of the hydrophilic segment is:
the reaction equation for mutual polymerization of the hydrophobic segment and the hydrophilic segment is as follows:
as can be seen from fig. 1 to 3, the polymers contemplated in examples 1 to 3 were all synthesized.
And as can be seen from fig. 4, emulsion C does not contain nile red and does not fluoresce when directly exposed to an aqueous solution, and thus does not fluoresce in the fluorescence absorption spectrum, whereas emulsion D does fluoresce in the fluorescence absorption spectrum, thus illustrating that the polymer prepared in example 2 can carry hydrophobic drugs.
Fig. 5 to 7 show the release of the drug at different pH values, and the drug is released continuously with time, so that the fluorescence decreases.
FIG. 8 illustrates that the amphiphilic polymer can be assembled into nano-sized particles, and the morphology of the particles is reflected by an electron microscope and is spherical
The DLS diagram of fig. 9 reflects the size and size distribution of the assembled nanoparticles, and the particle sizes are mainly distributed around 100nm, so it is said that the particles with a size of 100nm can be enriched in solid tumors, thereby achieving the purpose of targeted delivery.
Tartaric acid, 1, 3-dibromopropane and 1, 6-adipic acid are used as raw materials, dimethyl sulfoxide or N, N-dimethylformamide is used as a raw material, and three-step reaction is carried out under the catalysis of tetramethylguanidine; step one, respectively synthesizing a hydrophobic chain segment A and a hydrophilic chain segment B, wherein the terminal functional groups of the hydrophobic chain segment A and the hydrophilic chain segment B are different; secondly, mixing the hydrophobic chain segment A and the hydrophilic chain segment B, and reacting for 24 hours; the conversion rate of the invention reaches more than 90%. In addition, the finally prepared amphiphilic polyester can be assembled into a nano micelle in an aqueous solution, and can be loaded with drugs, particularly hydrophobic drugs; meanwhile, the polymer has excellent biocompatibility and biodegradability, and the used raw materials are natural and non-toxic. The invention has the advantages that: simple operation, easily obtained raw materials and normal temperature preparation.
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and embellishments within the scope of the invention may occur to those skilled in the art without departing from the principle of the invention, and are considered to be within the scope of the invention.
Claims (9)
1. An amphiphilic polyester characterized by:
the chemical structure is as follows:
wherein the molecular weight of the polymer of the hydrophobic segment is between 1000-12000; the polymer molecular weight of the hydrophilic segment is between 1000-12000.
2. An amphiphilic polyester according to claim 1, wherein:
the catalyst is prepared by the following reaction of the following components in parts by mole:
1, 6-adipic acid: 100 portions of
1, 3-dibromopropane: 205 to 220 portions
Solvent: 160 to 200 portions of
Catalyst: 420 to 480 portions
Tartaric acid: 80 parts of the raw materials.
3. An amphiphilic polyester according to claim 2, wherein:
the catalyst is tetramethylguanidine.
4. An amphiphilic polyester according to claim 2, wherein:
the solvent is any one of dimethyl sulfoxide and N, N-dimethylformamide.
5. The process for the preparation of an amphiphilic polyester according to claim 1, characterized in that:
the method comprises the following steps:
synthesis of hydrophobic segment a: dissolving 100 parts by mole of 1, 6-adipic acid and 120 parts by mole of 105-dibromopropane in 80-100 parts by mole of a solvent, and slowly dropping 200 parts by mole of a catalyst for reaction for 24 hours;
step two: synthesis of a hydrophilic chain segment B: dissolving 100 parts by mole of 1, 3-dibromopropane and 140 parts by mole of tartaric acid in 80-100 parts by mole of a solvent, and slowly dropping 220-280 parts by mole of a catalyst for reaction for 24 hours;
step three: and (3) synthesis of amphiphilic polyester: slowly dripping the solution obtained in the first step into the solution obtained in the second step, reacting for 12 hours, then pouring the reaction liquid into water, dialyzing for 24 hours in a dialysis bag, and freeze-drying.
6. The process for the preparation of an amphiphilic polyester according to claim 5, characterized in that:
the catalyst is tetramethylguanidine.
7. The process for the preparation of an amphiphilic polyester according to claim 5, characterized in that:
the solvent is any one of dimethyl sulfoxide and N, N-dimethylformamide.
8. The process for the preparation of an amphiphilic polyester according to claim 5, characterized in that:
the reaction temperature of the first step, the second step and the third step is room temperature.
9. Use of an amphiphilic polyester according to any one of claims 1 to 4, characterized in that:
can be used as drug carrier.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1436802A (en) * | 2003-01-24 | 2003-08-20 | 中国科学院上海有机化学研究所 | Aliphatic polyester with hydrophilic functional lateral group and its prepn and use |
| CN103242519A (en) * | 2013-04-27 | 2013-08-14 | 深圳先进技术研究院 | Amphiphilic polymer as well as preparation method and application thereof |
| CN106496571A (en) * | 2016-10-17 | 2017-03-15 | 江苏师范大学 | Reduction response Amphipathilic block polymer and nano-micelle and application |
| CN109010840A (en) * | 2018-09-29 | 2018-12-18 | 清华大学 | A kind of preparation method of amphipathic biodegradable carrier micelle |
-
2021
- 2021-08-13 CN CN202110933279.9A patent/CN113717354A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1436802A (en) * | 2003-01-24 | 2003-08-20 | 中国科学院上海有机化学研究所 | Aliphatic polyester with hydrophilic functional lateral group and its prepn and use |
| CN103242519A (en) * | 2013-04-27 | 2013-08-14 | 深圳先进技术研究院 | Amphiphilic polymer as well as preparation method and application thereof |
| CN106496571A (en) * | 2016-10-17 | 2017-03-15 | 江苏师范大学 | Reduction response Amphipathilic block polymer and nano-micelle and application |
| CN109010840A (en) * | 2018-09-29 | 2018-12-18 | 清华大学 | A kind of preparation method of amphipathic biodegradable carrier micelle |
Non-Patent Citations (1)
| Title |
|---|
| 李秋云等: "折叠链聚酯脲的合成与表征及其自组装行为研究", 《高分子学报》 * |
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