Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (II)

Jianguo Cui, Lei Fan, Yanmin Huang, Yi Xin, Aimin Zhou

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Hydroximinosteroids isolated from marine sponges display a variety of biological functions including cytotoxicity and anti-virus. In this study, we synthesized a series of hydroximinosteroid derivatives with a different functional group on the ring A or B and various side chains at position 17, and analyzed the cytotoxicity of these compounds against sk-Hep-1, H-292, PC-3 and Hey-1B cancer cells. Our results revealed that although a cholesterol-type side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship between the chemical structure and biological function.

Original languageEnglish (US)
Pages (from-to)989-995
Number of pages7
JournalSteroids
Volume74
Issue number12
DOIs
StatePublished - Nov 4 2009

Keywords

  • Antiproliferative activity
  • Cytotoxicity
  • Steroidal oximes
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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