Design, Synthesis, and Evaluation of Novel 1,2,3-Triazole-Tethered Glycolipids as Vaccine Adjuvants

Debabrata Bhunia, Preethi M.C. Pallavi, Srinivasa Reddy Bonam, Sandeep A. Reddy, Yogesh Verma, M. Sampath Kumar Halmuthur

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


A Cu-mediated azide-alkyne click chemistry protocol was employed for the synthesis of a focused library of novel 1,2,3-triazolyl conjugates bearing various carbohydrate-steroid/triterpenoid entities. The immunogenicity of these compounds was examined initially by ex vivo assays. The lead compound 15g was further subjected to in vivo evaluation in BALB/c mice immunized with ovalbumin. These in vivo biological studies revealed an increase in B cell-mediated proliferation, higher expression levels of IL-2, TNF-α, IL-12, and IFN-γ indicating Th1 activation, together with an enhanced OVA-specific antibody (IgG) response compared to alum, affirming adjuvanticity of these glycolipids. The primary indications of response skewed toward Th1 immunity induced by the new triazoyl analogs indicate the potential of these molecules for possible application as adjuvants. A focused library of 1,2,3-triazole-tethered glycolipid conjugates are synthesized and their immunogenicity is examined against ovalbumin in BALB/c mice. Increased B cell-mediated proliferation and antibody titers compared to alum confirm a stronger immune response. The production of IL-2, TNF-α, IL-12, and IFN-γ indicates improved Th1 polarization, demonstrating the potential of the new triazoyl analogs for possible application as adjuvants.

Original languageEnglish (US)
Pages (from-to)689-703
Number of pages15
JournalArchiv der Pharmazie
Issue number10
StatePublished - Oct 1 2015
Externally publishedYes


  • 1,2,3-Triazoles
  • Adjuvant
  • Click chemistry
  • Glycolipids
  • Th1 immunity

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery


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