1. Academic Validation
  2. Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer

Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer

  • J Med Chem. 2007 Feb 8;50(3):585-9. doi: 10.1021/jm061243q.
Taeho Lee 1 Minjae Cho Sung-Youl Ko Hyun-Jun Youn Dong Jae Baek Won-Jea Cho Chang-Yuil Kang Sanghee Kim
Affiliations

Affiliation

  • 1 College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
Abstract

alpha-GalCer is the first defined and most potent agonistic antigen of the T cell receptor of natural killer T cells. We have prepared a series of 1,2,3-triazole-containing alpha-GalCer analogues in which the lipid chain lengths have been incrementally varied. We found that this isosteric replacement of alpha-GalCer's amide moiety with triazole increases the IL-4 versus IFN-gamma bias of released cytokines. The stimulatory effect was influenced by the length of the attached chain. In particular, the long-chained triazole analogues have a comparable stimulatory effect on cytokine production as alpha-GalCer and exhibit a stronger Th2 cytokine response.

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