Stereochemical analysis and cytotoxicity of kulokekahilide-2 and its analogues

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

    Research output: Contribution to journalArticle

    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

    Fingerprint

    Cytotoxicity
    Depsipeptides
    Conformations
    Chemical bonds
    Cell growth
    Dimethyl Sulfoxide
    Amides
    Esters
    Cells
    Growth
    Pharmaceutical Preparations
    kulokekahilide-2
    Neoplasms

    Keywords

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

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Stereochemical analysis and cytotoxicity of kulokekahilide-2 and its analogues. / Umehara, Masahiro; Negishi, Takayuki; Maehara, Yukie; Nakao, Youichi; Kimura, Junji.

    In: Tetrahedron, Vol. 69, No. 14, 08.04.2013, p. 3045-3053.

    Research output: Contribution to journalArticle

    Umehara, Masahiro ; Negishi, Takayuki ; Maehara, Yukie ; Nakao, Youichi ; Kimura, Junji. / Stereochemical analysis and cytotoxicity of kulokekahilide-2 and its analogues. In: Tetrahedron. 2013 ; Vol. 69, No. 14. pp. 3045-3053.
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