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 journalArticle

44 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
Externally publishedYes

Fingerprint

Natural Killer T-Cells
T-cells
Bioactivity
Galactosylceramides
Cytokines
azetidine
KRN 7000
pyrrolidine

Keywords

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

ASJC Scopus subject areas

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

Cite this

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

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 2, 15.01.2008, p. 950-964.

Research output: Contribution to journalArticle

Fuhshuku, Ken ichi ; Hongo, Naomi ; Tashiro, Takuya ; Masuda, Yui ; Nakagawa, Ryusuke ; Seino, Ken ichiro ; Taniguchi, Masaru ; Mori, Kenji. / 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. In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 2. pp. 950-964.
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AU - Fuhshuku, Ken ichi

AU - Hongo, Naomi

AU - Tashiro, Takuya

AU - Masuda, Yui

AU - Nakagawa, Ryusuke

AU - Seino, Ken ichiro

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