2. Academic Validation
  3. Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin

Design, Synthesis, and Cancer Cell Growth Inhibitory Activity of Triphenylphosphonium Derivatives of the Triterpenoid Betulin

  • J Nat Prod. 2017 Aug 25;80(8):2232-2239. doi: 10.1021/acs.jnatprod.7b00105.
Olga V Tsepaeva 1,  Andrey V Nemtarev 1 2,  Timur I Abdullin 2,  Leysan R Grigor'eva 2,  Elena V Kuznetsova 2,  Rezeda A Akhmadishina 2,  Liliya E Ziganshina 2,  Hanh H Cong 2,  Vladimir F Mironov 1 2
Affiliations

Affiliations

  • 1 A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences , Arbuzov Street 8, 420088, Kazan, Russian Federation.
  • 2 Kazan (Volga Region) Federal University , Kremlevskaya Street 18, 420008, Kazan, Russian Federation.
PMID: 28782948 DOI: 10.1021/acs.jnatprod.7b00105
Abstract

A series of new triphenylphosphonium (TPP) derivatives of the triterpenoid betulin (1, 3-lup-20(29)-ene-3β,28-diol) have been synthesized and evaluated for cytotoxic effects against human breast Cancer (MCF-7), prostate adenocarcinoma (PC-3), vinblastine-resistant human breast Cancer (MCF-7/Vinb), and human skin fibroblast (HSF) cells. The TPP moiety was applied as a carrier group through the acyl linker at the 28- or 3- and 28-positions of betulin to promote cellular and mitochondrial accumulation of the resultant compounds. A structure-activity relationship study has revealed the essential role of the TPP group in the biological properties of the betulin derivatives produced. The present results showed that a conjugate of betulin with TPP (3) enhanced antiproliferative activity toward vinblastine-resistant MCF-7 cells, with an IC50 value as low as 0.045 μM.

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