RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 with a sulfonamide linkage: Their synthesis and bioactivity for mouse natural killer T cells to produce Th2-biased cytokines

Takuya Tashiro, Naomi Hongo, Ryusuke Nakagawa, Ken ichiro Seino, Hiroshi Watarai, Yasuyuki Ishii, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

RCAI-17, 22, 24-26, 29, 31, 34-36, 38-40, and 88, the analogs of KRN7000 (1) with a sulfonamide linkage instead of an amide bond, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells. RCAI-17, 22, 24-26, 29, 31, 34-36, and 88 are the aromatic sulfonamide analogs, while RCAI-39 and 40 are the aliphatic ones. RCAI-38 is a C-galactoside analog of RCAI-26, which is the p-toluenesulfonamide analog of KRN7000. According to their bioassay, these sulfonamide analogs were shown to be the stimulants of mouse NKT cells to induce the production of Th2-biased cytokines in vitro, while RCAI-38 did not induce any cytokine production.

Original languageEnglish
Pages (from-to)8896-8906
Number of pages11
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number19
DOIs
Publication statusPublished - 2008 Oct 1

Keywords

  • Cytokines
  • NKT cell
  • OCH
  • Sulfonamide
  • α-Galactosylceramides

ASJC Scopus subject areas

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

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