Synthesis of amide analogs of arenastatin A

Nobutoshi Murakami, Weiqi Wang, Naoki Ohyabu, Takeshi Ito, Satoru Tamura, Shunji Aoki, Motomasa Kobayashi, Isao Kitagawa

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

In order to probe the metabolism of arenastatin A, a potent cytotoxic depsipeptide from the marine sponge Dysidea arenaria, we synthesized three analogs in which the ester linkages were replaced by amide bonds. Triamide analog-II and tetraamide analog, both of which contained a 15,20-amide linkage, showed stability in serum. However, arenastatin A and triamide analog-I, which both contained a 15,20-ester moiety, were readily metabolized in serum. Among the three amide analogs, only triamide analog-II exhibited potent cytotoxic activity against KB cells.

Original languageEnglish
Pages (from-to)9121-9128
Number of pages8
JournalTetrahedron
Volume56
Issue number46
DOIs
Publication statusPublished - 2000 Nov 10

Keywords

  • Cytotoxin
  • Depsipeptide
  • Marine metabolite
  • Marine sponge

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Murakami, N., Wang, W., Ohyabu, N., Ito, T., Tamura, S., Aoki, S., Kobayashi, M., & Kitagawa, I. (2000). Synthesis of amide analogs of arenastatin A. Tetrahedron, 56(46), 9121-9128. https://doi.org/10.1016/S0040-4020(00)00766-3