Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens

Shinichi Nishimura, Shigeki Matsunaga, Satoru Yoshida, Yoichi Nakao, Hiroshi Hirota, Nobuhiro Fusetani

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Structure-activity relationship of 13-deoxytedanolide showed that the southern and northern hemispheres play independent roles to exhibit potent biological activity. To obtain information of structure-activity relationships (SARs) of 13-deoxytedanolide, its chemical transformation has been carried out, targeting on such functional groups as an epoxide, hydroxyls, ketones, and olefins. A total of 10 derivatives have been prepared and their cytotoxicity against P388 murine leukemia cells and inhibitory activity of polypeptide elongation in yeast cell lysate provided some important SARs; the southern hemisphere comprises the pharmacophore, while the epoxide-bearing side chain is essential for the activity.

Original languageEnglish
Pages (from-to)455-462
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number2
DOIs
Publication statusPublished - 2005 Jan 17
Externally publishedYes

Keywords

  • 13-Deoxytedanolide
  • Antitumor
  • Cytotoxicity
  • Marine sponge-derived macrolide
  • Protein synthesis inhibition
  • SAR

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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