Design of Trehalose-Based Amide/Sulfonamide C-type Lectin Receptor Signaling Compounds

ChemMedChem. 2021 Apr 20;16(8):1246-1251. doi: 10.1002/cmdc.202000775. Epub 2021 Feb 9.

Abstract

Mincle agonists have been shown to induce inflammatory cytokine production, such as tumor necrosis factor-alpha (TNF) and promote the development of a Th1/Th17 immune response that might be crucial to development of effective vaccination against pathogens such as Mycobacterium tuberculosis. As an expansion of our previous work, a library of 6,6'-amide and sulfonamide α,α-d-trehalose compounds with various substituents on the aromatic ring was synthesized efficiently in good to excellent yields. These compounds were evaluated for their ability to activate the human C-type lectin receptor Mincle by the induction of cytokines from human peripheral blood mononuclear cells. A preliminary structure-activity relationship (SAR) of these novel trehalose diamides and sulfonamides revealed that aryl amide-linked trehalose compounds demonstrated improved activity and relatively high potency cytokine production compared to the Mincle ligand trehalose dibehenate adjuvant (TDB) and the natural ligand trehalose dimycolate (TDM) inducing dose-dependent and human-Mincle-specific stimulation in a HEK reporter cell line.

Keywords: Mincle; TH-17; adjuvants; trehalose tuberculosis; vaccines.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis
  • Adjuvants, Immunologic / pharmacology*
  • HEK293 Cells
  • Humans
  • Interleukin-1beta / metabolism
  • Interleukin-6 / metabolism
  • Lectins, C-Type / agonists*
  • Receptors, Immunologic / agonists*
  • Small Molecule Libraries / chemical synthesis
  • Small Molecule Libraries / pharmacology
  • Sulfonamides / chemical synthesis
  • Sulfonamides / pharmacology*
  • Trehalose / analogs & derivatives*
  • Trehalose / pharmacology*
  • Tumor Necrosis Factor-alpha / metabolism

Substances

  • Adjuvants, Immunologic
  • CLEC4D protein, human
  • IL1B protein, human
  • IL6 protein, human
  • Interleukin-1beta
  • Interleukin-6
  • Lectins, C-Type
  • Receptors, Immunologic
  • Small Molecule Libraries
  • Sulfonamides
  • Tumor Necrosis Factor-alpha
  • Trehalose