Design, Synthesis, and Immunological Evaluation of Benzyloxyalkyl-Substituted 1,2,3-Triazolyl α-GalCer Analogues

Yogesh Kumar Verma, Bonam Srinivasa Reddy, Mithun S. Pawar, Debabrata Bhunia, Halmuthur M. Sampath Kumar

Research output: Contribution to journalArticlepeer-review

28 Scopus citations


Replacement of the amide moiety in the structure of α-GalCer with a 1,2,3-triazole linker is known to elicit a response skewed toward Th2 immunity, and glycolipids containing an aromatic ring in the terminus of their acyl or phytosphingosine structural component exhibit an enhanced Th1 immune response. In the current study, synthesis and immunological screening of a focused library of benzyloxyalkyl-substituted 1,2,3-triazolyl α-GalCer analogues are reported. The novel α-GalCer analogues activate invariant natural killer T (iNKT) cells via CD1d mediated presentation, which was confirmed by in vitro tests performed on iNKT hybridomas incubated with CD1d proteins. When tested on isolated murine splenocytes, the T1204B and T1206B compounds stimulated higher levels of both IFN-γ and IL-4 cytokine expression in vitro compared to that of α-GalCer.

Original languageEnglish (US)
Pages (from-to)172-176
Number of pages5
JournalACS Medicinal Chemistry Letters
Issue number2
StatePublished - Feb 11 2016
Externally publishedYes


  • IFN-γ
  • IL-4
  • Th1/Th2
  • benzyloxyalkyl α-GalCer
  • iNKT hybridoma
  • kinetic release

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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