Development of a Water Soluble Self-assembling Analogue of Vizantin

  • Nakano Mayo
    Faculty of Pharmaceutical Science, Tokushima Bunri University
  • Sakamoto Kyohei
    Faculty of Pharmaceutical Science, Tokushima Bunri University
  • Yamasaki Naoto
    Faculty of Pharmaceutical Science, Tokushima Bunri University Institute of Pharmacognosy, Tokushima Bunri University
  • Asano Yui
    Faculty of Pharmaceutical Science, Tokushima Bunri University
  • Oda Masataka
    Control of Innate Immunity Collaborative Innovation Partnership Department of Research and Development, Lecher Co., Ltd.
  • Takahashi Hironobu
    Faculty of Pharmaceutical Science, Tokushima Bunri University
  • Kawakami Takashige
    Faculty of Pharmaceutical Science, Tokushima Bunri University
  • Inoue Masahisa
    Faculty of Pharmaceutical Science, Tokushima Bunri University
  • Yamamoto Hirofumi
    Faculty of Pharmaceutical Science, Tokushima Bunri University Institute of Pharmacognosy, Tokushima Bunri University

抄録

<p>Vizantin, 6,6′-bis-O-(3-nonyldodecanoyl)-α,α′-trehalose, has been developed as a safe immunostimulator on the basis of a structure–activity relationship study with trehalose 6,6′-dicorynomycolate. Our recent study indicated that vizantin acts as an effective Toll-like receptor-4 (TLR4) partial agonist to reduce the lethality of an immune shock caused by lipopolysaccharide (LPS). However, because vizantin has low solubility in water, the aqueous solution used in in vivo assay systems settles out in tens of minutes. Here, vizantin was chemically modified in an attempt to facilitate the preparation of an aqueous solution of the drug. This paper describes the concise synthesis of a water-soluble vizantin analogue in which all the hydroxyl groups of the sugar unit were replaced by sulfates. The vizantin derivative displayed micelle-forming ability in water and potent TLR-4 partial agonist activity.</p>

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