Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH

Geetha Velmourougane, Ravinder Raju, Gabriel Bricard, Jin S. Im, Gurdyal S. Besra, Steven A. Porcelli, Amy R. Howell

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

An α-galactosyl ceramide (α-GalCer) 2 was synthesized and evaluated for its ability to stimulate iNKT-cell proliferation and elicit T-helper cytokines, IL-4 and IFNγ. Compound 2 combines the acyl chain of the potent, Th2 biasing α-GalCer 1 with a sphingoid base of the same length as that found in OCH, which also exhibits Th2 skewing, Such complementation may enhance cytokine bias, which is thought to be important for therapeutic applications of iNKT cell stimulation. Two related α-GalCers, 3 and 4, with saturated acyl chains were prepared for comparison.

Original languageEnglish (US)
Pages (from-to)3386-3388
Number of pages3
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number13
DOIs
StatePublished - Jul 1 2009

Fingerprint

Natural Killer T-Cells
Galactosylceramides
Cytokines
Cell proliferation
Interleukin-4
Cell Proliferation
tetracosanoic acid 1-galactopyranosyloxy-3,4-dihydroxydec-2-yl amide
Therapeutics

Keywords

  • Alpha-galactosyl ceramides
  • CD1d
  • Glycolipids
  • iNKT cell stimulation

ASJC Scopus subject areas

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

Cite this

Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH. / Velmourougane, Geetha; Raju, Ravinder; Bricard, Gabriel; Im, Jin S.; Besra, Gurdyal S.; Porcelli, Steven A.; Howell, Amy R.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 19, No. 13, 01.07.2009, p. 3386-3388.

Research output: Contribution to journalArticle

Velmourougane, Geetha ; Raju, Ravinder ; Bricard, Gabriel ; Im, Jin S. ; Besra, Gurdyal S. ; Porcelli, Steven A. ; Howell, Amy R. / Synthesis and evaluation of an acyl-chain unsaturated analog of the Th2 biasing, immunostimulatory glycolipid, OCH. In: Bioorganic and Medicinal Chemistry Letters. 2009 ; Vol. 19, No. 13. pp. 3386-3388.
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