Stereochemical analysis and cytotoxicity of kulokekahilide-2 and its analogues

Masahiro Umehara, Takayuki Negishi, Yukie Maehara, Yoichi Nakao, Junji Kimura

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

We report the conformational analysis of kulokekahilide-2, a cytotoxic cyclic depsipeptide, and its analogues. We also evaluated their cytotoxicity against human cancer cells. Although both the cis and trans conformations are possible for the amide bond between MePhe and MeGly, only one conformation was observed in DMSO. We also reveal that the configuration at C-43 in kulokekahilide-2 controls intramolecular ester exchange between the 26- and 24-membered cyclic depsipeptides. Kulokekahilide-2 and its analogues were evaluated for their cell-growth inhibition profile and using COMPARE analysis, which suggested a mechanism of action different from that of standard anticancer drugs.

Original languageEnglish
Pages (from-to)3045-3053
Number of pages9
JournalTetrahedron
Volume69
Issue number14
DOIs
Publication statusPublished - 2013 Apr 8

Keywords

  • Cytotoxic evaluation
  • Intramolecular ester exchange
  • Kulokekahilide-2
  • Stereochemical analysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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