Aryl Trehalose Derivatives as Vaccine Adjuvants for Mycobacterium tuberculosis

J Med Chem. 2020 Jan 9;63(1):309-320. doi: 10.1021/acs.jmedchem.9b01598. Epub 2019 Dec 20.

Abstract

Mycobacterium tuberculosis (Mtb) continues to be a major health threat worldwide, and the development of Mtb vaccines could play a pivotal role in the prevention and control of this devastating epidemic. Th17-mediated immunity has been implicated in disease protection correlates of immune protection against Mtb. Currently, there are no approved adjuvants capable of driving a Th17 response in a vaccine setting. Recent clinical trial results using trehalose dibehenate have demonstrated a formulation-dependant proof of concept adjuvant system CAF01 capable of inducing long-lived protection. We have discovered a new class of Th17-inducing vaccine adjuvants based on the natural product Brartemicin. We synthesized and evaluated the capacity of a library of aryl trehalose derivatives to drive immunostimulatory reresponses and evaluated the structure-activity relationships in terms of the ability to engage the Mincle receptor and induce production of innate cytokines from human and murine cells. We elaborated on the structure-activity relationship of the new scaffold and demonstrated the ability of the lead entity to induce a pro-Th17 cytokine profile from primary human peripheral blood mononuclear cells and demonstrated efficacy in generating antibodies in combination with tuberculosis antigen M72 in a mouse model.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis
  • Adjuvants, Immunologic / metabolism
  • Adjuvants, Immunologic / therapeutic use*
  • Animals
  • Binding Sites
  • Cattle
  • Cell Line
  • Female
  • Humans
  • Lectins, C-Type / agonists
  • Lectins, C-Type / metabolism
  • Mice, Inbred BALB C
  • Molecular Docking Simulation
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Receptors, Immunologic / agonists
  • Receptors, Immunologic / metabolism
  • Structure-Activity Relationship
  • Trehalose / analogs & derivatives*
  • Trehalose / chemical synthesis
  • Trehalose / metabolism
  • Trehalose / therapeutic use
  • Tuberculosis / therapy
  • Tuberculosis Vaccines / therapeutic use

Substances

  • Adjuvants, Immunologic
  • CLEC4D protein, human
  • Lectins, C-Type
  • Receptors, Immunologic
  • Tuberculosis Vaccines
  • brartemicin
  • Trehalose