Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000)

Masao Shiozaki, Takuya Tashiro, Hiroyuki Koshino, Ryusuke Nakagawa, Sayo Inoue, Tomokuni Shigeura, Hiroshi Watarai, Masaru Taniguchi, Kenji Mori

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

These three ester analogues showed activity for IFNγ, and IL-4 production of iNKT cells. α-Galactosylceramide (αGalCer, KRN7000) has been identified as a modulator of immunological processes through its capacity to bind iNKT cells mediated by CD1d molecules. Some analogues in while the amide group in αGalCer is replaced with ester or ether groups were synthesized from d-arabinitol or l-ribose to evaluate their ability to activate iNKT cells. Ester analogues 30a, 31a, and 61 showed activity for IFNγ and IL-4 production of iNKT cells, while ether (31b) and 4-methoxy ester (76) analogues of α-galactosylceramide were not active for iNKT cells.

Original languageEnglish
Pages (from-to)1663-1684
Number of pages22
JournalCarbohydrate Research
Volume345
Issue number12
DOIs
Publication statusPublished - 2010 Aug 16

Keywords

  • Ester analogues of α-galactosylceramide
  • Glycolipid
  • Glycosylation
  • KRN7000
  • iNKT cells

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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  • Cite this

    Shiozaki, M., Tashiro, T., Koshino, H., Nakagawa, R., Inoue, S., Shigeura, T., Watarai, H., Taniguchi, M., & Mori, K. (2010). Synthesis and biological activity of ester and ether analogues of α-galactosylceramide (KRN7000). Carbohydrate Research, 345(12), 1663-1684. https://doi.org/10.1016/j.carres.2010.05.003