CN107325273B - Polymer and its preparation method and application in acid-sensitive amphiphilic nanomicelle - Google Patents
Polymer and its preparation method and application in acid-sensitive amphiphilic nanomicelle Download PDFInfo
- Publication number
- CN107325273B CN107325273B CN201710482160.8A CN201710482160A CN107325273B CN 107325273 B CN107325273 B CN 107325273B CN 201710482160 A CN201710482160 A CN 201710482160A CN 107325273 B CN107325273 B CN 107325273B
- Authority
- CN
- China
- Prior art keywords
- parts
- toluene
- polymer
- preparation
- completely
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 23
- 239000002253 acid Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 45
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 18
- ZSKAJFSSXURRGL-PKNBQFBNSA-N (2e)-1,1-dimethoxy-3,7-dimethylocta-2,6-diene Chemical compound COC(OC)\C=C(/C)CCC=C(C)C ZSKAJFSSXURRGL-PKNBQFBNSA-N 0.000 claims abstract description 11
- 239000000693 micelle Substances 0.000 claims abstract description 11
- 239000001695 (2E)-1,1-dimethoxy-3,7-dimethylocta-2,6-diene Substances 0.000 claims abstract description 10
- 239000000376 reactant Substances 0.000 claims abstract description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 238000001338 self-assembly Methods 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- KEAYESYHFKHZAL-OUBTZVSYSA-N sodium-24 Chemical group [24Na] KEAYESYHFKHZAL-OUBTZVSYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000003937 drug carrier Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 2
- 206010057249 Phagocytosis Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 2
- 230000008782 phagocytosis Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- 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
- C08G2230/00—Compositions for preparing biodegradable polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Crystallography & Structural Chemistry (AREA)
- Composite Materials (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Medicinal Preparation (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Abstract
本发明公开一种高分子聚合物及其制备方法和在酸敏感型两亲性纳米胶束的应用，该高分子聚合物以柠檬醛二甲缩醛、聚乙二醇单甲醚为反应物，以对甲苯磺酸为催化剂，甲苯为溶液，并在115‑130℃下蒸馏反应而成。本发明的优点是：利用化合物的两亲性可在水中较为方便的自组装成粒径较小的纳米胶束，并在酸条件下发生降解，可作为抗癌药物的载体。
The invention discloses a polymer, its preparation method and its application in acid-sensitive amphiphilic nano micelles. The polymer uses citral dimethyl acetal and polyethylene glycol monomethyl ether as reactants , using p-toluenesulfonic acid as a catalyst, toluene as a solution, and reacting by distillation at 115-130°C. The invention has the advantages that the amphiphilicity of the compound can be conveniently self-assembled into nanometer micelles with smaller particle diameters in water, and degrades under acid conditions, and can be used as a carrier of anticancer drugs.
Description
技术领域technical field
本发明属于高分子材料领域，具体是指一种高分子聚合物及其制备方法和在酸敏感型两亲性纳米胶束的应用。The invention belongs to the field of polymer materials, and specifically refers to a polymer, a preparation method thereof and an application in acid-sensitive amphiphilic nano micelles.
背景技术Background technique
癌症乃全球重大公共医疗卫生问题之一，2015年，仅中国因癌死亡人数即达到280多万(约平均7500人/天)，但目前临床抗癌药物在实际应用中尚存在毒性强、水溶性差、半衰期短、体内易降解、无特定靶向等系列制约因素，因此，急待新型药物载体的研发制备。Cancer is one of the major public health problems in the world. In 2015, the number of cancer deaths in China alone reached more than 2.8 million (about 7,500 people per day on average). However, the current clinical anticancer drugs still have strong toxicity, water-soluble There are a series of restrictive factors such as poor drug resistance, short half-life, easy degradation in vivo, and no specific targeting. Therefore, the research and development of new drug carriers is urgently needed.
近年，胶束药物载体研究快速崛起，其结构可控、载药量及负载率高，能够增强药效、降低毒性、提高血药浓度、控制药物缓释、促进疏水药物的增溶与携氧、保护药物逃脱免疫系统吞噬、诱导药物对肿瘤细胞的靶向性及病源刺激响应特性。特别是自组装纳米双亲聚合物胶束药物载体，其亲水外壳能够避免网状内皮系统(RES)识别与吞噬，延长药物体内循环时间；疏水内核可作为疏水药物储存器，具有较强药物负载能力；同时，纳米胶束是唯一能够克服多药耐药的药物载体，并可通过各异的修饰方法实现靶向给药。因此，寻找具有高生物相容性的两亲性纳米胶束成为研究热点之一。In recent years, research on micellar drug carriers has risen rapidly. Its structure is controllable, and its drug loading capacity and loading rate are high. , Protecting drugs from phagocytosis by the immune system, inducing the targeting of drugs to tumor cells and the response characteristics of pathogenic stimuli. In particular, the self-assembled nano-amphiphilic polymer micelle drug carrier, its hydrophilic shell can avoid the recognition and phagocytosis of the reticuloendothelial system (RES), prolonging the circulation time of the drug in vivo; the hydrophobic core can be used as a hydrophobic drug storage, with a strong drug load At the same time, nanomicelle is the only drug carrier that can overcome multidrug resistance, and can achieve targeted drug delivery through various modification methods. Therefore, finding amphiphilic nanomicelles with high biocompatibility has become one of the research hotspots.
发明内容Contents of the invention
本发明的目的是为了克服现有技术存在的缺点和不足，而提供一种高分子聚合物，该聚合物是一种全新结构的聚合物，且能用于制备酸敏感型两亲性纳米胶束，该纳米胶束能作为药物载体。The purpose of the present invention is to provide a high molecular polymer in order to overcome the shortcomings and deficiencies of the prior art, which is a polymer with a new structure, and can be used to prepare acid-sensitive amphiphilic nano glue The nanomicelle can be used as a drug carrier.
本发明的第二个目的是提供一种所述高分子聚合物的制备方法。The second object of the present invention is to provide a method for preparing the high molecular polymer.
本发明的另一个目的是提供一种基于所述高分子聚合物制备酸敏感型两亲性纳米胶束的制备方法。Another object of the present invention is to provide a method for preparing acid-sensitive amphiphilic nanomicelles based on the polymer.
为实现本发明的第一个发明目的，其技术方案是其分子结构式为For realizing first object of the invention of the present invention, its technical scheme is that its molecular structural formula is
其中n为聚合度，其数值是3-700。Where n is the degree of polymerization, and its value is 3-700.
为实现本发明的第二个发明目的，其技术方案是该高分子聚合物以柠檬醛二甲缩醛、聚乙二醇单甲醚为反应物，以对甲苯磺酸为催化剂，甲苯为溶液，并在115-130℃下蒸馏聚合反应而成，其反应方程式为：In order to realize the second object of the invention of the present invention, its technical scheme is that this macromolecular polymer is reactant with citral dimethyl acetal, polyethylene glycol monomethyl ether, is catalyst with p-toluenesulfonic acid, and toluene is solution , and distilled and polymerized at 115-130°C, the reaction equation is:
其中n为聚合度，其数值是3-700。Where n is the degree of polymerization, and its value is 3-700.
进一步设置是包括以下步骤：Further settings include the following steps:
(1)将0.8-1份柠檬醛二甲缩醛与10-13份甲苯在15-30℃下，以200-600r/min速度搅拌，使反应物完全溶解；(1) Stir 0.8-1 part of citral dimethyl acetal and 10-13 parts of toluene at 15-30°C at a speed of 200-600r/min to completely dissolve the reactants;
(2)将2-404份聚乙二醇单甲醚与10-13份甲苯混合与恒压滴液漏斗中，使其完全溶解；(2) Mix 2-404 parts of polyethylene glycol monomethyl ether with 10-13 parts of toluene in a constant pressure dropping funnel to dissolve completely;
(3)将步骤(2)中所得三乙二醇单甲醚与甲苯的混合溶液缓慢滴入步骤(1)所得溶液中；(3) Slowly drop the mixed solution of triethylene glycol monomethyl ether and toluene obtained in step (2) into the solution obtained in step (1);
(4)待步骤(3)中滴加结束后，添加0.0038-0.0048份对甲苯磺酸，搅拌至为完全溶解；(4) After the dropwise addition in step (3), add 0.0038-0.0048 parts of p-toluenesulfonic acid and stir until completely dissolved;
(5)待步骤(4)中完全溶解后，以1500-1800r/min速度搅拌，逐步升温到115-130℃，蒸馏至溶剂完全蒸出；(5) After completely dissolving in step (4), stir at a speed of 1500-1800r/min, gradually heat up to 115-130°C, and distill until the solvent is completely evaporated;
(6)待步骤(5)反应完全，所得溶液溶于10-14份二氯甲烷中，分别用1-3份饱和碳酸氢钠和24-31份水洗涤，收集有机溶液；(6) After step (5) is completely reacted, the obtained solution is dissolved in 10-14 parts of dichloromethane, washed with 1-3 parts of saturated sodium bicarbonate and 24-31 parts of water respectively, and the organic solution is collected;
(7)在35℃、0.09Mpa下干燥5-10min，获得所述高分子聚合物。(7) drying at 35° C. and 0.09 MPa for 5-10 minutes to obtain the high molecular polymer.
进一步设置是所述柠檬醛二甲缩醛、对甲苯磺酸、甲苯的质量份数比为：0.8:0.0038:20。The further setting is that the mass-number ratio of the citral dimethyl acetal, p-toluenesulfonic acid, and toluene is: 0.8:0.0038:20.
进一步设置是所述柠檬醛二甲缩醛、对甲苯磺酸、甲苯的质量份数比为：1:0.0048:26。The further setting is that the mass-number ratio of the citral dimethyl acetal, p-toluenesulfonic acid, and toluene is 1:0.0048:26.
本发明还提供一种基于所述高分子聚合物制备敏感型两亲性纳米胶束的制备方法，采用自组装的方法将所述高分子聚合物制成酸敏感两亲性纳米胶束。The present invention also provides a preparation method for preparing sensitive amphiphilic nano-micelles based on the high-molecular polymer. The high-molecular polymer is prepared into acid-sensitive amphiphilic nano-micelles by a self-assembly method.
本发明的优点是：The advantages of the present invention are:
1、原料柠檬醛二甲缩醛可作为香精和药物，有很好的生物相容性；1. The raw material citral dimethyl acetal can be used as flavor and medicine, and has good biocompatibility;
2、反应物具有优良的酸降解性，可作为药物载体，在人体能很好应用。2. The reactant has excellent acid degradability, can be used as a drug carrier, and can be well applied in the human body.
下面结合具体实施方式对本发明做进一步介绍。The present invention will be further introduced below in combination with specific embodiments.
附图说明Description of drawings
图1本发明实施例1的反应方程式；The reaction equation of Fig. 1 embodiment of the present invention 1;
图2本发明实施例1产物的DLS粒径图；The DLS particle size figure of Fig. 2 embodiment 1 product of the present invention;
图3本发明实施例1产物的红外光谱图。Fig. 3 is the infrared spectrogram of the product of Example 1 of the present invention.
具体实施方式Detailed ways
下面通过实施例对本发明进行具体的描述，只用于对本发明进行进一步说明，不能理解为对本发明保护范围的限定，该领域的技术工程师可根据上述发明的内容对本发明作出一些非本质的改进和调整。The present invention is specifically described below by the embodiment, only for further illustrating the present invention, can not be interpreted as the limitation of protection scope of the present invention, the technical engineer of this field can make some non-essential improvements and improvements to the present invention according to the content of the above-mentioned invention Adjustment.
如图1至图3所示，本发明实施例1中，包括以下步骤：As shown in Figures 1 to 3, in Embodiment 1 of the present invention, the following steps are included:
(1)将0.99g(0.005mol)柠檬醛二甲缩醛(CAS号7549-37-3)与15ml甲苯在15-30℃下，以200-600r/min速度搅拌，使反应物完全溶解；(1) Stir 0.99g (0.005mol) of citral dimethyl acetal (CAS No. 7549-37-3) and 15ml of toluene at 15-30°C at a speed of 200-600r/min to completely dissolve the reactants;
(2)将2.13g(0.013mol)三乙二醇单甲醚(CAS号112-35-6)与15ml甲苯混合与恒压滴液漏斗中，使其完全溶解；(2) Mix 2.13g (0.013mol) of triethylene glycol monomethyl ether (CAS No. 112-35-6) with 15ml of toluene and place it in a constant pressure dropping funnel to dissolve it completely;
(3)将步骤(2)中所得三乙二醇单甲醚与甲苯的混合溶液缓慢滴入步骤(1)所得溶液中；(3) Slowly drop the mixed solution of triethylene glycol monomethyl ether and toluene obtained in step (2) into the solution obtained in step (1);
(4)待步骤(3)中滴加结束后，添加4.75mg对甲苯磺酸，搅拌至为完全溶解；(4) After the dropwise addition in step (3) is completed, add 4.75 mg p-toluenesulfonic acid and stir until completely dissolved;
(5)待步骤(4)中完全溶解后，以1500-1800r/min速度搅拌，逐步升温到115-130℃，蒸馏至溶剂完全蒸出；(5) After completely dissolving in step (4), stir at a speed of 1500-1800r/min, gradually heat up to 115-130°C, and distill until the solvent is completely evaporated;
(6)待步骤(5)反应完全，所得溶液溶于10ml二氯甲烷中，分别用30ml饱和碳酸氢钠和30ml水洗涤，收集有机溶液；(6) until the reaction of step (5) is complete, the resulting solution is dissolved in 10ml of dichloromethane, washed with 30ml of saturated sodium bicarbonate and 30ml of water respectively, and the organic solution is collected;
(7)在35℃、0.09Mpa下干燥5-10min，获得产物；(7) Dry at 35°C and 0.09Mpa for 5-10min to obtain the product;
(8)称取10mg两亲性聚合物，溶解在1ml的DMF溶剂中；(8) Weigh 10 mg of amphiphilic polymer and dissolve it in 1 ml of DMF solvent;
(9)量取10mg/ml的聚合物DMF溶液20ul于试管中，缓慢加入2ml的超纯水；(9) Measure 20ul of 10mg/ml polymer DMF solution in a test tube, slowly add 2ml of ultrapure water;
(10)通过振荡器振荡制得纳米胶束。(10) Prepare nano micelles by vibrating with an oscillator.
参照图1所示：实施例1的反应方程式。Shown with reference to Fig. 1: the reaction equation of embodiment 1.
参照图2所示：实施例1所得产物自组装后的纳米胶束，其粒径在酸降解的前后的变化。Shown with reference to Fig. 2: the nano-micelle of the product obtained in embodiment 1 self-assembly, its particle size changes before and after acid degradation.
参照图3所示：实施例1所得聚合物的红外光谱图。从红外谱图中可以看出，在2878cm-1处有一宽吸收峰，判定为-OCH3，在1046cm-1有一强吸收峰，判定为C-O-C。Shown with reference to Fig. 3: the infrared spectrogram of embodiment 1 gained polymer. It can be seen from the infrared spectrum that there is a broad absorption peak at 2878cm -1 , judged to be -OCH 3 , and a strong absorption peak at 1046cm -1 , judged to be COC.
图2和图3同时证明了实例1所得为可酸降解的纳米胶束，其结构式为Fig. 2 and Fig. 3 have proved simultaneously that example 1 gained is the nano-micelle that can be degraded by acid, and its structural formula is
以上仅为本发明的一个实施例，但是在本领域的技术人员应当理解，在不脱离本发明精神的情况下，可以对本文的实施例进行改变。当然不能以此来限定本发明之权利范围，因此依本发明权利要求所作的等同变化，仍属本发明所涵盖的范围。The above is only an embodiment of the present invention, but those skilled in the art should understand that the embodiments herein can be changed without departing from the spirit of the present invention. Of course, the scope of rights of the present invention cannot be limited by this, so equivalent changes made according to the claims of the present invention still fall within the scope of the present invention.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710482160.8A CN107325273B (en) | 2017-06-22 | 2017-06-22 | Polymer and its preparation method and application in acid-sensitive amphiphilic nanomicelle |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710482160.8A CN107325273B (en) | 2017-06-22 | 2017-06-22 | Polymer and its preparation method and application in acid-sensitive amphiphilic nanomicelle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107325273A CN107325273A (en) | 2017-11-07 |
| CN107325273B true CN107325273B (en) | 2019-09-20 |
Family
ID=60195312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710482160.8A Expired - Fee Related CN107325273B (en) | 2017-06-22 | 2017-06-22 | Polymer and its preparation method and application in acid-sensitive amphiphilic nanomicelle |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107325273B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232267B (en) * | 2018-10-10 | 2022-12-06 | 温州大学 | Photosensitive amphiphilic compound and preparation method and application thereof |
| CN109438302B (en) * | 2018-12-03 | 2020-08-04 | 温州大学 | Acid/reductive degradation amphiphilic compound and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1268107A (en) * | 1997-06-27 | 2000-09-27 | 普罗格特-甘布尔公司 | Pro-fragrance linear acetals and ketals |
| CN1268127A (en) * | 1997-06-27 | 2000-09-27 | 普罗格特-甘布尔公司 | Pro-fragrance cyclic acetals |
| CN101495149A (en) * | 2005-03-31 | 2009-07-29 | 阿帕医药有限公司 | PEG-polyacetal diblock and triblock copolymers and pharmaceutical compositions |
| CN102227418A (en) * | 2008-12-01 | 2011-10-26 | 弗门尼舍有限公司 | Acetals as Perfuming Ingredients |
-
2017
- 2017-06-22 CN CN201710482160.8A patent/CN107325273B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1268107A (en) * | 1997-06-27 | 2000-09-27 | 普罗格特-甘布尔公司 | Pro-fragrance linear acetals and ketals |
| CN1268127A (en) * | 1997-06-27 | 2000-09-27 | 普罗格特-甘布尔公司 | Pro-fragrance cyclic acetals |
| CN101495149A (en) * | 2005-03-31 | 2009-07-29 | 阿帕医药有限公司 | PEG-polyacetal diblock and triblock copolymers and pharmaceutical compositions |
| CN102227418A (en) * | 2008-12-01 | 2011-10-26 | 弗门尼舍有限公司 | Acetals as Perfuming Ingredients |
Non-Patent Citations (1)
| Title |
|---|
| Universal concept for the implementation of a single cleavable unit at tunable position in functional poly(ethylene glycol)s;Carsten dingels et al;《Biomacromolecules》;20121220;第14卷;第453页scheme3 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107325273A (en) | 2017-11-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106727314B (en) | Preparation and characterization of a hyaluronic acid-based photosensitizer/antitumor drug self-assembled nano-drug delivery system | |
| Danafar | Study of the composition of polycaprolactone/poly (ethylene glycol)/polycaprolactone copolymer and drug-to-polymer ratio on drug loading efficiency of curcumin to nanoparticles | |
| CN103720675B (en) | A kind of have the curcumin prodrug micelle of isotope of redox-sensitive, micelle monomer and preparation method thereof | |
| WO2015120692A1 (en) | Docetaxel nano-polymeric micelle lyophilised formulation and preparation method for same | |
| CN104945538A (en) | Hyaluronic acid vitamin E derivative and preparation and application | |
| Kang et al. | Modulation of cyclic topology toward enhanced drug delivery, from linear and tadpole-like to dumbbell-shaped copolymers | |
| CN105194670A (en) | Cationic polymer-loaded paclitaxel/indocyanine green co-delivery micelle and preparation method thereof | |
| CN107325273B (en) | Polymer and its preparation method and application in acid-sensitive amphiphilic nanomicelle | |
| CN109306058A (en) | A kind of pluronic copolymer co-modified with folic acid and triphenylphosphine and its preparation method and use | |
| CN103893769B (en) | Polyethylene lactide-containing targeting polymer drug carrier and preparation method thereof | |
| CN105837836A (en) | Acid-sensitive amphipathic stearic acid amidated glucan polymer nano-micelle and preparation method thereof | |
| CN111012918B (en) | Cholesterol biguanide conjugate with anti-tumor and carrier effects and application of salt thereof in microparticle administration preparation | |
| CN105963262B (en) | A kind of preparation method of amphipathic pectin-dihydroartemisinine nanoparticle | |
| Guo et al. | Well-defined podophyllotoxin polyprodrug brushes: preparation via RAFT polymerization and evaluation as drug carriers | |
| CN104622813B (en) | A kind of nanoparticle formed based on host-guest interaction and its preparation method and purposes | |
| CN106883394B (en) | FA-F127-PCL folate-targeted copolymers and the preparation method and application thereof | |
| CN107998405B (en) | Preparation method and application of NO-donor polymeric micelle composition containing poorly soluble drugs | |
| CN103059297B (en) | Multifunctional degradable polyasparaginate modified polymer and preparation method thereof | |
| CN106905532A (en) | The polymer micelle of side chain with PAMAM and preparation method thereof | |
| CN104399085A (en) | Folic acid modified heparin-vitamin E succinate polymer and synthesis method thereof | |
| CN116440283A (en) | A dual-targeting/drug-loaded tumor reduction-sensitive nanocarrier and its application | |
| CN105879051A (en) | Preparation and application of self-assembled nano-drug of core-shell structure | |
| Zhuang et al. | Redox-sensitive polymeric micelles based on tetraphenylethylene-conjugated copolymer for aggregation-induced emission active imaging and drug delivery | |
| CN110330639B (en) | Polymerizable acid-sensitive amphiphilic compound | |
| CN102552930B (en) | Water-soluble paclitaxel derivative with cell targeting effect and preparation thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20190920 |