Chemistry of a Marine Depsipeptide, Hapalosin, and Its Reversing Activity against the P-Glycoprotein-mediated Multidrug Resistance.

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  • Nishiyama Shigeru
    Department of Chemistry, Faculty of Science and Technology, Keio University

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  • 多剤耐性癌克服活性を有するデプシペプチド海洋天然物ハパロシンの化学と生物活性
  • タザイ タイセイガン コクフク カッセイ オ ユウスル デプシペプチド カイヨウ テンネンブツ ハパロシン ノ カガク ト セイブツ カッセイ

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Abstract

Hapalosin isolated from Hapalosisiphon welwitschii W. & G. S. West, is a cyclic depsipeptide carrying the reversing activity against multidrug-resistance (MDR) of cancer cells acquired during chemotherapy. The 12-membered-ring structure that consists of 2-hydroxy-3-methylbutanoic acid, 3-hydroxy-2-methyldecanoic acid, and 3-hydroxy-4-(methylamino)-5-phenylpentanoic acid, adopts a 3:1 mixture of conformers related to the amide residue. From biological and stereochemical points of view, many research groups have challenged this intriguing target. This review discloses chemical investigations of hapalosin and related derivatives, as well as their biological activities.

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