Triphenylphosphonium cations of betulinic acid derivatives: synthesis and antitumor activity
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- 作者：Anna Yu. Spivak ; Darya A. Nedopekina ; Rezeda R. Khalitova…
- 关键词：Pentacyclic triterpenoids ; Betulin ; Betulinic acid ; Triphenylphosphonium derivatives ; Anticancer agents
- 刊名：Medicinal Chemistry Research
- 出版年：2017
- 出版时间：March 2017
- 年：2017
- 卷：26
- 期：3
- 页码：518-531
- 全文大小：
- 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
- 出版者：Springer US
- ISSN：1554-8120
- 卷排序：26
文摘
A series of lupane triterpenoid conjugates with the triphenylphosphonium cation, in which the terpenoid molecules are linked to one or two triphenylphosphonium moieties at the С-2, С-28, or С-30 positions by carbon–carbon or ester bonds, have been designed and synthesized as potential anti-cancer agents. The pharmacological results showed that all of the prepared triphenylphosphonium salts displayed considerable antitumor activities against the tested cancer murine tumor (Ehrlich ascites carcinoma, (Р-815), and human tumor (MCF-7) (IC50 < 2 μg/mL)) cell lines. The presence of the triphenylphosphonium cation in the triterpenoid conjugates markedly enhanced the cytotoxic action as compared to the parent compound (betulinic acid) (IC50 24.7 μg/mL for Ehrlich cells and 18.7 μg/mL for Р-815 cells), while the correlation between the cytotoxic activity and the chemical structure of phosphonium salts was not observed.