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Amphiphilic block polymer having folate-targeted pH-reduction dual-response and antineoplastic activity and preparation as well as application thereof

An anti-tumor activity, dual response technology, applied in the field of biomedical applications and polymer chemistry, can solve problems such as cell damage, and achieve the effect of promoting inhibition, reducing damage, and good biocompatibility

Inactive Publication Date: 2016-03-09
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, radiotherapy and chemotherapy are extremely important non-surgical treatments, but while radiotherapy and chemotherapy kill tumor cells, they also cause serious damage to normal cells in the body.

Method used

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  • Amphiphilic block polymer having folate-targeted pH-reduction dual-response and antineoplastic activity and preparation as well as application thereof
  • Amphiphilic block polymer having folate-targeted pH-reduction dual-response and antineoplastic activity and preparation as well as application thereof
  • Amphiphilic block polymer having folate-targeted pH-reduction dual-response and antineoplastic activity and preparation as well as application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] (1) compound Preparation: Weigh 3.08g of bis(2-hydroxyethyl) disulfide and dissolve it in 30mL of dichloromethane, add 4g of triethylamine as an acid-binding agent and stir for 20 minutes, slowly drop 1.08 g of methacryloyl chloride was added, and the stirring reaction was continued for 24 hours. After the reaction was complete, the reaction solution was washed three times with 100 mmol / l pH of phosphate buffer and distilled water of 8.0, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was rotary evaporated, and the crude product was purified by silica gel chromatography to obtain a white 1.62 g solid. is the compound , and the yield was 73%.

[0075] 1 HNMR (400MHz, CDCl 3 ,δ,ppm):6.13(s,1H,CH H =C(CH 3 )CO-),5.59(s,1H,C H H=C(CH 3 )CO-),4.41(t,J=6.6Hz,2H,-COOC H 2 CH 2 SSCH 2 CH 2 OH),3.87(t,J=6.5Hz,2H,-COOCH 2 CH2 SSCH 2 C H 2 OH),2.96(t,J=6.7Hz,2H,-COOCH 2 C H 2 SSCH 2 CH 2 OH),2.87(t,J=5.8Hz,2H,-COOCH 2 CH 2...

Embodiment 2

[0091] (1) compound , , , , , and compound The preparation: with embodiment 1.

[0092] (2) Target compound Preparation: take 0.11g compound (Mn=1.18×10 4 g / mol), 24mg of folic acid monomer and 26mg of AIBN were dissolved in 3ml of DMSO in a Schlenk flask, filled with nitrogen in an ice bath for 30 minutes, then put the Schlenk flask into a constant temperature oil bath, and reacted at 60°C for 24 hours. The reaction solution was precipitated with ether to obtain 0.104g light yellow powder compound , and the yield was 58%. Mn:1.42×10 4 .

[0093] 1 HNMR (400MHz, DMSO-d6, δ, ppm): 8.65 (–C H –of FA heterocyclic), 8.12-7.95 (4H, m, phenyl group of acid labile PEG-macroRAFT), 7.66 (–CH 2 NHC 6 H 2 h 2 CONHCH(COOH)CH 2 CH 2 CO–ofFA), 6.65 (–CH 2 NHC 6 h 2 H 2 CONHCH(COOH)CH 2 CH 2 CO–ofFA), 4.46 (–C H 2 NHC 6 h 4 CONHCH(COOH)CH 2 CH 2 CO–ofFA), 4.41 (2H,t,-COOCH 2 CH 2SSCH 2 C H 2 COOC 6 h 2 (OCH 3 ) 3 of MAOHD-TMOBA), 4.33 (–CH...

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Abstract

The invention provides an amphiphilic block copolymer having folate-targeted pH-reduction dual-response and antineoplastic activity and preparation as well as application thereof; through RAFT polymerization, a functionalized disulfide monomer, methoxy polyethylene glycol responding by acid stimulation and functionalized folic acid form a macromolecular block copolymer, i.e. a disulfide monomer-acidity PEG-folic acid copolymer, being good in biocompatibility. The copolymer has pH and reduction dual stimulus-response, and is provided with a folic acid active targeting polymer drug carrying micelle, and can effectively release adriamycin amycin at a target site. The micelle with intelligent responsibility has low cytotoxicity, is biodegradable, has a proper drug carrying level, and can promote a great quantity of drugs to be more quickly accumulated at a tumor tissue part, thus effects in acidic cytoplasm and between cytoplasm and cell nuclei with high reducibility are achieved, and therefore the amphiphilic block copolymer as a drug carrier has a good application prospect in preparing antineoplastic drugs.

Description

technical field [0001] The invention belongs to the field of macromolecular chemistry, and relates to an amphiphilic block polymer (methacryloyl dithioethanol-trimethoxybenzoic acid)-hydrazone, which has anti-tumor activity with dual response to folic acid targeting pH and reduction Bond-polyethylene glycol-polyfolate; the invention also relates to the preparation of the amphiphilic block copolymer and its application as a drug carrier in the preparation of antitumor drugs, belonging to the field of polymer chemistry and biomedical application technology. Background technique [0002] Cancer has become one of the major threats to human health, and it is on the rise. The main methods of treating cancer today include radiotherapy, chemotherapy, surgical therapy and gene therapy. Among them, radiotherapy and chemotherapy are extremely important non-surgical treatments, but while killing tumor cells, radiotherapy and chemotherapy also cause serious damage to normal cells in the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/32A61K9/107A61K31/704A61P35/02A61P35/00C08F293/00
CPCA61K9/1075A61K31/704A61K47/32C08F293/005
Inventor 袁建超宋开润骆雯博张丹华马敏苑莹芝
Owner NORTHWEST NORMAL UNIVERSITY
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