RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

Takuya Tashiro, Ryusuke Nakagawa, Tomokuni Shigeura, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

研究成果: Article査読

17 被引用数 (Scopus)

抄録

We synthesized ten new analogs of 6′-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by α-selective galactosylation of ceramide 9 with the 6-modified d-galactopyranosyl fluorides (8a-8f) or l-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6′-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-γ even at a low concentration in mice in vivo.

本文言語English
ページ(範囲)3066-3079
ページ数14
ジャーナルBioorganic and Medicinal Chemistry
21
11
DOI
出版ステータスPublished - 2013 6月 1
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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