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Synthesis of diglycosylceramides and evaluation of their iNKT cell stimulatory properties

Academic Article
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Overview

authors

  • Liu, Y.
  • Deng, S.
  • Bai, L.
  • Freigang, S.
  • Mattner, J.
  • Teyton, Luc
  • Bendelac, A.
  • Savage, P. B.

publication date

  • May 2008

journal

  • Bioorganic & Medicinal Chemistry Letters  Journal

abstract

  • Stimulation of iNKT cells is highly dependent on the structures of the glycolipids presented by CD1d. Furthermore, antigen processing and CD1d loading in lysosomes play central roles in controlling the stimulatory properties of glycolipid antigens. Previously, we determined that substitution at C6'' on alpha-galactosylceramides did not significantly impact stimulatory properties; however, it was not known if substitution at this position influenced lysosomal processing of oligoglycosylceramides. We have prepared a series of mono- and di-galactosylceramides to observe the impact of C6'' substitution on glycosidase truncation of these glycolipids. We found that substitution did not significantly impact glycosidase activity or loading into CD1d.

subject areas

  • Adjuvants, Immunologic
  • Animals
  • Antigen Presentation
  • Antigens, CD1
  • Antigens, CD1d
  • Cells, Cultured
  • Dendritic Cells
  • Galactosylceramides
  • Glycoside Hydrolases
  • Hybridomas
  • Killer Cells, Natural
  • Lysosomes
  • Mice
  • Molecular Structure
  • Structure-Activity Relationship
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Research

keywords

  • IL-2 release
  • NKT cells
  • glycosphingolipid synthesis
  • glycosylation
  • stimulatory activity
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Identity

PubMed Central ID

  • PMC2846726

International Standard Serial Number (ISSN)

  • 0960-894X

Digital Object Identifier (DOI)

  • 10.1016/j.bmcl.2007.12.067

PubMed ID

  • 18206371
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Additional Document Info

start page

  • 3052

end page

  • 3055

volume

  • 18

issue

  • 10

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