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
Externally publishedYes

Fingerprint

Carbasugars
Cyclitols
Lymphocytes
Inositol
Bioactivity
Cytokines
Bioassay
Biological Assay
Interferons
Derivatives
KRN 7000

Keywords

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

ASJC Scopus subject areas

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

Cite this

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

In: Bioorganic and Medicinal Chemistry, Vol. 17, No. 17, 01.09.2009, p. 6360-6373.

Research output: Contribution to journalArticle

Tashiro, Takuya ; Nakagawa, Ryusuke ; Hirokawa, Takatsugu ; Inoue, Sayo ; Watarai, Hiroshi ; Taniguchi, Masaru ; Mori, Kenji. / 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. In: Bioorganic and Medicinal Chemistry. 2009 ; Vol. 17, No. 17. pp. 6360-6373.
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