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

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3066-3079
Number of pages14
JournalBioorganic and Medicinal Chemistry
Volume21
Issue number11
DOIs
Publication statusPublished - 2013 Jun 1

Keywords

  • CD1d
  • Cytokine
  • KRN7000
  • Natural killer T cell
  • α-Galactosyl ceramide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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