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

Shinichi Nishimura, Shigeki Matsunaga, Satoru Yoshida, Youichi 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

Fingerprint

Epoxy Compounds
Macrolides
Porifera
Structure-Activity Relationship
Bearings (structural)
Alkenes
Cytotoxicity
Bioactivity
Ketones
Hydroxyl Radical
Leukemia P388
Yeast
Functional groups
Elongation
Cells
Derivatives
Peptides
Yeasts
13-deoxytedanolide

Keywords

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

ASJC Scopus subject areas

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

Cite this

Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens. / Nishimura, Shinichi; Matsunaga, Shigeki; Yoshida, Satoru; Nakao, Youichi; Hirota, Hiroshi; Fusetani, Nobuhiro.

In: Bioorganic and Medicinal Chemistry, Vol. 13, No. 2, 17.01.2005, p. 455-462.

Research output: Contribution to journalArticle

Nishimura, Shinichi ; Matsunaga, Shigeki ; Yoshida, Satoru ; Nakao, Youichi ; Hirota, Hiroshi ; Fusetani, Nobuhiro. / Structure-activity relationship study on 13-deoxytedanolide, a highly antitumor macrolide from the marine sponge Mycale adhaerens. In: Bioorganic and Medicinal Chemistry. 2005 ; Vol. 13, No. 2. pp. 455-462.
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