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Anti-cancer medicinal aspirin platinum complex and preparation method thereof

An aspirin and complex technology, which is applied in the field of anticancer medicinal aspirin tetravalent platinum complex and its preparation, can solve the problems of unsatisfactory antitumor effect, increased fat solubility, large toxic and side effects, etc., and achieves superiority Antitumor activity, inhibition of replication, effects of minor toxic side effects

Inactive Publication Date: 2013-02-27
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although cisplatin has achieved remarkable success in the treatment of tumors, the two major factors of toxic side effects and drug resistance limit its clinical use; ) pointed out that the side effects of cisplatin include nephrotoxicity, neurotoxicity, ototoxicity, hair loss, nausea and vomiting, among which the cumulative neurotoxicity is difficult to overcome for all current platinum drugs; Cisplatin is congenitally resistant, and other patients gradually develop resistance during the use of cisplatin
Although the new generation of divalent platinum has been synthesized and used to reduce some toxic and side effects, there are still a lot of toxic and side effects, and the problem of drug resistance still exists
Tetravalent platinum has been widely concerned because of its small toxic side effects on the body and increased fat solubility. Isoproplatin and cis-dichloro-trans-diacetyl-ammonia-methylamine platinum (IV) (JM216) have It is used in clinical research as an oral platinum anticancer drug, and other tetravalent platinums, such as the tetravalent platinums mentioned in Japanese patent applications JP-A61-33192, JP-A-61-7283 and JP-A-1-294684 Although valent platinum has excellent water solubility and low nephrotoxicity, according to Chinese Patent Application Publication No. CN1193627A, its antitumor effect is not very satisfactory, so it is necessary to find new tetravalent platinum anticancer drugs

Method used

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  • Anti-cancer medicinal aspirin platinum complex and preparation method thereof
  • Anti-cancer medicinal aspirin platinum complex and preparation method thereof
  • Anti-cancer medicinal aspirin platinum complex and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: c,c,t-[Pt(NH 3 ) 2 Cl 2 (OH)(Aspirin)] preparation

[0019] Dissolve 1 mmol of cisplatin in 5 mL of water, add 10 mmol of hydrogen peroxide, stir the reaction at 50°C for 1.5 h, then stir the reaction at room temperature for 12 h, remove the solvent by rotary evaporation to obtain a solid, wash the solid three times with cold water, and then wash it with ether Washed 3 times and dried in vacuum to obtain the cisplatin oxidation product; it was characterized by electrospray mass spectrometry, the data was MW=332.80, and it could be confirmed that the obtained product was c,c,t-[Pt(NH 3 ) 2 Cl 2 (OH) 2 ];

[0020] Take 1 mmol of this substance, dissolve it in 10 mL of dimethyl sulfoxide, add 1 mmol of o-acetylsalicylic anhydride, stir and react at 30°C for 12 hours, freeze-dry to remove the solvent to obtain a solid, add 10-100 mL of acetone to the solid, and centrifuge The resulting precipitate was washed three times with acetone, then three times with ...

Embodiment 2

[0022] Embodiment 2: Preparation of Oxaliplatin (IV)-aspirin compound

[0023] Dissolve 1mmol potassium hexachloroplatinate in 10mL water, add 0.5mmol hydrazine hydrochloride, stir and react at 55°C for at least 3h, then react at 85°C for 6min, place the reaction solution in an ice water bath for 30min, and then perform centrifugation. Take out the supernatant, and remove the solvent by rotary evaporating the supernatant to obtain potassium tetrachloroplatinate;

[0024] Dissolve 1mmol potassium tetrachloroplatinate in 5mL water, add 1mmol trans-1,2-cyclohexanediamine, stir at room temperature for 24h, centrifuge to obtain a solid, dissolve the solid in 5mL water, and then add 2mmol nitric acid Silver, stirred at room temperature for 24 hours, centrifuged, took out the supernatant, then added excess KI, reacted for 12 hours, then centrifuged to take out the supernatant, added equimolar oxalic acid, stirred for 24 hours, centrifuged to separate the solid; First wash 3 times wi...

Embodiment 3

[0028] Example 3: c,c,t-[Pt(NH 3 ) 2 Cl 2 (Aspirin) 2 ] preparation

[0029] Dissolve 1 mmol of cisplatin in 5 mL of water, add 10 mmol of hydrogen peroxide, stir the reaction at 50°C for 1.5 h, then stir the reaction at room temperature for 12 h, remove the solvent by rotary evaporation to obtain a solid, wash the solid three times with cold water, and then wash with ether Washed 3 times and dried in vacuum to obtain the cisplatin oxidation product, which was characterized by electrospray mass spectrometry, the data was MW=332.80, and it could be confirmed that the obtained product was c,c,t-[Pt(NH 3 ) 2 Cl 2 (OH) 2 ];

[0030] Take 1 mmol of this substance, dissolve it in 10 mL of dimethyl sulfoxide, add 5 mmol of o-acetylsalicylic anhydride, stir and react at 70 ° C for 12 h, freeze-dry to remove the solvent, add 10-100 mL of acetone to the obtained solid, and centrifuge to separate the precipitate. The precipitate was washed 3 times with acetone, then 3 times with ...

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Abstract

The invention discloses an anti-cancer medicinal aspirin platinum complex and a preparation method thereof. The method comprises the following steps of coordinating amine or heterocyclic amine on a platinum atom through a coordinated N atom and the coordination function of the platinum, introducing halogen or hydroxyl, carboxylate radical or substituted carboxylate radical through the coordination function, and oxidizing the platinum atom into tetravalent platinum, connecting aspirin molecular axially to form tetravalent platinum complex with one aspirin molecular single substitute or two aspirin molecular double substitutes axially. As the tetravalent state of the platinum is relatively inert, the toxic side effect on organs is small, and moreover, the uptake route of drug is changed, the anticancer activity of the drug is improved, the anti-tumor activity which is same to or even more excellent than that of cis-platinum is realized, and the killing function to the drug resistant cells is good. The preparation method provided by the invention is simple in structure, low in cost and suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of platinum complexes for anticancer drugs, in particular to aspirin tetravalent platinum complexes for anticancer drugs and a preparation method thereof. Background technique [0002] Cancer threatens human health and life. According to data released by the International Union Against Cancer in 2010 at the 21st World Anti-Cancer Congress, in 2008, 12.7 million people worldwide suffered from cancer, and the death toll was as high as 7.6 million, accounting for 13% of the world's death toll that year. Worldwide, cancer kills more people than AIDS, malaria and combined diseases combined. In China, the mortality rate of cancer has increased by 80% in the past 30 years, and 1.8 million people die from it every year. Cisplatin was found to have anticancer activity in 1967, was used clinically in 1969, and was approved for use by the US Food and Drug Administration in 1978. Although cisplatin has achieved remar...

Claims

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Application Information

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IPC IPC(8): C07F15/00A61P35/00
Inventor 刘扬中师红东闵元增程芹芹
Owner UNIV OF SCI & TECH OF CHINA
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