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Cis-platinum coordination compound and preparation method thereof

A complex, cisplatin technology, applied in the field of cisplatin complex and its preparation, can solve the problems of poor polymer biocompatibility, limited application, inability to degrade, etc., achieve good stability, improve curative effect, and avoid cisplatin sudden release effect

Active Publication Date: 2012-07-25
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the obtained micelles are formed by cross-linking between polyamino acid side chains, and the freeze-dried powder of the complex obtained by this method is sometimes difficult to redissolve
Stenzel et al. used "mercapto-alkynyl" and "mercapto-alkenyl" Click reactions to introduce thioglycolic acid and mercaptosuccinic acid into the polymer side chain to obtain a complex (Biomacromolecules 12(5): 1738-1751). The substance has good solubility, but the polymer used as the carrier has poor biocompatibility and cannot be degraded, which limits its further application.

Method used

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  • Cis-platinum coordination compound and preparation method thereof
  • Cis-platinum coordination compound and preparation method thereof
  • Cis-platinum coordination compound and preparation method thereof

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preparation example Construction

[0055] The invention provides a kind of preparation method of cisplatin complex, comprising the following steps:

[0056] Cisplatin and a block copolymer having a structure of formula (III) or formula (IV) cooperate in an aqueous medium to generate a cisplatin complex;

[0057]

[0058] In formula (III) and formula (IV), R 1 independently selected from hydrogen, alkyl or substituted alkyl;

[0059] R 2 independently selected from -NH- or -R 4 (CH 2 ) r NH-, where, R 4 is -O-, -OCONH-, -OCO-, -NHCOO- or -NHCO-, 1≤r≤8;

[0060] R 3 independently selected from hydrogen or hydrophobic groups;

[0061] m is the degree of polymerization, 40≤m≤250; n is the degree of polymerization, 1≤n≤200; y is the degree of polymerization, 0≤y≤100.

[0062] In the present invention, the block copolymer with the structure of formula (III) or formula (IV) is a carrier for carrying cisplatin, and the Pt in cisplatin and the carboxyl group of the block copolymer form a seven Member ring s...

Embodiment 1

[0083] The block copolymer having the structure of formula (V-a), m=45 and x=10 is denoted as mPEG 45 -b-PPLG 10 .

[0084] Add 0.2003g mPEG to the dry reaction vial 45 -b-PPLG 10 , after stirring and dissolving with 5mL N,N-dimethylformamide, blow nitrogen for 0.5 hours, add 14.0mg benzoin dimethyl ether and 0.6543g mercaptosuccinic acid at room temperature under the condition of nitrogen protection, and react with 365nm ultraviolet light for 2h, The product was obtained; the product was dialyzed for 72 hours, the water was changed 12 times, and freeze-dried to obtain a block copolymer freeze-dried powder having a structure of formula (III-a).

[0085] The nuclear magnetic resonance test was carried out on the block graft copolymer, and the grafting rate was calculated to be 61.8%, and the reaction conversion rate was 30.2%. The block copolymer with the structure of formula (III-a) m=45, n=6, y=4, denoted as mPEG 45 -b-PPLG 10 -g-MSA 12 .

Embodiment 2

[0087] A block copolymer having a knot of formula (V-a), m=113 and x=25, denoted as mPEG 113 -b-PPLG 25 .

[0088] Add 0.2008g mPEG to the dry reaction vial 113 -b-PPLG 25 , after stirring and dissolving with 5mL N,N-dimethylformamide, blow nitrogen gas for 0.5 hours, add 14.0mg benzoin dimethyl ether and 1.3201g mercaptosuccinic acid at room temperature under the condition of nitrogen protection, and react with 365nm ultraviolet light for 2h, The product was obtained; the product was dialyzed for 72 hours, the water was changed 12 times, and freeze-dried to obtain a block copolymer freeze-dried powder having a structure of formula (III-a).

[0089] The nuclear magnetic resonance test was carried out on the block graft copolymer, and the calculated graft rate was 60.0%, and the reaction conversion rate was 16.1%. The block copolymer with the structure of formula (III-a) m=113, n=15, y=10, denoted as mPEG 113 -b-PPLG 25 -g-MSA 30 .

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Abstract

The invention provides a cis-platinum coordination compound which has a formula (I) structure or a formula (II) structure. The preparation method of the cis-platinum coordination compound is as follows: cis-platinum and a block copolymer with a formula (III) or a formula (IV) are subjected to coordination action in a water-based medium so as to generate the cis-platinum coordination compound. The cis-platinum coordination compound has good dissolubility and good biocompatibility and is degradable. In the water-based medium, the cis-platinum is protected by a poly (Gamma-propinyl-L-glutamate-g-dimercaptosuccinic acid) block and a polyethylene glycol block, so that the cis-platinum coordination compound has good stability. In addition, carboxyl contained in the cis-platinum coordination compound has PH-value sensibility, and in a lower PH-value environment, the carboxyl trends to be deprotonated, the releasing of the medicaments is promoted, and the curative effects of the medicaments are improved.

Description

technical field [0001] The invention relates to the field of polymer medicine, in particular to a cisplatin complex and a preparation method thereof. Background technique [0002] Cis-diamine dichloroplatinum, referred to as cisplatin (CDDP), is a metal complex with anticancer activity, which was first discovered in 1965 by B. Rosenborg et al. Cisplatin has the characteristics of broad anticancer spectrum, strong effect, synergistic effect with many antitumor drugs, and no cross-resistance. Therefore, cisplatin is one of the most commonly used drugs in combination chemotherapy. At present, cisplatin has a good effect on the treatment of reproductive system tumors, head and neck cancer, bladder cancer, lung cancer, and malignant lymphoma. Oral administration of cisplatin is ineffective, and the clinical application method is mostly administered by intravenous infusion. After intravenous injection, cisplatin disappears rapidly in the plasma and is rapidly distributed through...

Claims

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Application Information

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IPC IPC(8): C08G69/48A61K47/48A61K33/24A61P35/00
Inventor 汤朝晖李明强宋万通陈学思陈杰庄秀丽
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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