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Preparation method of oxidation-reduction double-response type macromolecular camptothecin prodrug

A camptothecin and polymer technology, applied in the field of medicinal chemistry, can solve the problems of uncontrollable release, poor selectivity of anti-tumor drugs, low drug loading rate, etc., and achieve the effect of high micellar stability

Inactive Publication Date: 2019-02-22
SOUTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of this, one of the objectives of the present invention is to provide a redox double responsive polymer camptothecin prodrug preparation method and Its application in the field of cancer treatment

Method used

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  • Preparation method of oxidation-reduction double-response type macromolecular camptothecin prodrug
  • Preparation method of oxidation-reduction double-response type macromolecular camptothecin prodrug
  • Preparation method of oxidation-reduction double-response type macromolecular camptothecin prodrug

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Experimental program
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Embodiment 1

[0028] Example 1 Redox double responsive polymer camptothecin prodrug

[0029] A redox double responsive polymer camptothecin prodrug CP GR The overall synthesis schematic of figure 1 As shown, it mainly includes the following steps:

[0030] (1) CPT GSH Preparation of monomers, at 25°C, 2-10Pa under argon atmosphere ① Dissolve BHD (4.8 g, 40.5 mmoL) in 50 mL of anhydrous THF, and add TEA (3.3 mL, 23.7 mmoL); methacryloyl chloride (2.2mL, 22.7 mmoL) was dispersed in 15 mL of anhydrous THF and slowly added dropwise to the above reaction system under ice-bath conditions, kept in ice-bath for 1h and then slowly rose to room temperature, the reaction was Under dark conditions at 25°C for 12 hours, the intermediate MABHD containing disulfide bonds was obtained by column purification; ② CPT (2.78 g, 8 mmoL) and DMAP (3.12 g, 22.6 mmoL) were dissolved in 120 mL of anhydrous DCM; BTC (1 g, 3.37 mmoL) was dissolved in 20 mL of anhydrous DCM and added dropwise to the above solution,...

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Abstract

The invention discloses a preparation method of an oxidation-reduction double-response type macromolecular camptothecin prodrug. Beta-cyclodextrin-CD is used as a carrier to stimulate splitting decomposition of disulfide bonds and oxalate bonds in prodrug molecules respectively through high-concentration glutathione and hydrogen peroxide in tumor microenvironment and to release an anti-cancer drugcamptothecin CPT. The preparation method comprises the following steps of 1 preparation of camptothecin monomers CPTGSH and CPTROS containing functional bonds, 2 preparation of a drug initiator beta-CD-Br, 3 preparation of CD-b-P (CPTGSH-co-CPTROS-co-OEGMA named as CPGR. The obtained monomolecular micelles formed by the dual-response prodrug have the advantages of high drug loading capacity (40%or above by weight), high micelle stability, sensitive stimulus response, superior biocompatibility, low toxic side effects and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of a redox double-responsive polymer camptothecin prodrug and its application in the field of cancer treatment. Background technique [0002] Cyclodextrin (Cyclodextrin, referred to as CD, a polysaccharide, molecular formula (C6H10O5) n) is the general name of a series of cyclic oligosaccharides produced by amylose in Bacillus, usually containing 6-12 D-glucopyranose unit. Cyclodextrin is a cyclic macromolecular polysaccharide formed by the polymerization of several glucose molecules, which can effectively increase the solubility of some poorly water-soluble drugs in water, and is a good drug carrier. Camptothecin (CPT for short, molecular formula: C 20 h 16 N 2 O 4 , CAS No.: 7689-03-4, relative molecular weight: 348.43) is a cytotoxic quinoline alkaloid that can selectively inhibit topoisomerase Ⅰ (Topo Ⅰ), bind to the complex formed by T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/61A61K31/4745A61K9/107A61P35/00C08B37/16
CPCA61K9/1075A61K31/4745A61K47/61A61P35/00C08B37/0012
Inventor 许志刚杨娇徐大为白霜
Owner SOUTHWEST UNIV
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