RCAI-8, 9, 18, 19, and 49-52, conformationally restricted analogues of KRN7000 with an azetidine or a pyrrolidine ring: Their synthesis and bioactivity for mouse natural killer T cells to produce cytokines

Ken ichi Fuhshuku, Naomi Hongo, Takuya Tashiro, Yui Masuda, Ryusuke Nakagawa, Ken ichiro Seino, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)

Abstract

Conformationally restricted analogues of KRN7000, an α-d-galactosyl ceramide, were synthesized to examine their bioactivity for mouse natural killer (NK) T cells to produce cytokines. RCAI-8, 9, 51, and 52 are the analogues with a pyrrolidine ring, and RCAI-18, 19, 49, and 50 are those with an azetidine ring. RCAI-18 was shown to be a potent inducer of cytokine production by mouse NKT cells, while RCAI-51 was a moderately active inducer.

Original languageEnglish
Pages (from-to)950-964
Number of pages15
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number2
DOIs
Publication statusPublished - 2008 Jan 15

Keywords

  • Azetidines
  • Glycosphingolipids
  • KRN7000
  • NKT cell
  • Pyrrolidines
  • α-Galactosyl ceramides

ASJC Scopus subject areas

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

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