RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines

Takuya Tashiro, Ryusuke Nakagawa, Takatsugu Hirokawa, Sayo Inoue, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Cyclitol [RCAI-37 (1), 59 (5), 92 (7), and 102 (2)] and carbasugar analogs [RCAI-56 (3), 60 (4), and 101 (6)] of KRN7000 were synthesized through coupling reactions of the corresponding cyclitol or carbasugar derivatives with a cyclic sulfamidate (9) as the key step. Bioassay showed RCAI-56 (3, carbagalactose analog of KRN7000), 59 (5, 1-deoxy-neo-inositol analog), and 92 (7, 1-O-methylated 5) to be remarkably potent stimulants of mouse lymphocytes to produce Th1-biased cytokines, such as interferon-γ, in vivo. RCAI-60 (4, carbafucose analog) and RCAI-101 (6, 6-O-methylated 3) showed strong bioactivity, on the other hands, RCAI-37 (1, myo-inositol analog) and 102 (2, neo-inositol analog) induced little cytokine production.

Original languageEnglish
Pages (from-to)6360-6373
Number of pages14
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number17
DOIs
Publication statusPublished - 2009 Sep 1

Keywords

  • Carbasugar
  • Cyclitol
  • KRN7000
  • NKT cell
  • α-GalCer

ASJC Scopus subject areas

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

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