d-Glycero-β-d-Manno-Heptose 1-Phosphate and d-Glycero-β-d-Manno-Heptose 1,7-Biphosphate Are Both Innate Immune Agonists

J Immunol. 2018 Oct 15;201(8):2385-2391. doi: 10.4049/jimmunol.1801012. Epub 2018 Sep 17.

Abstract

d-Glycero-β-d-manno-heptose 1,7-biphosphate (β-HBP) is a novel microbial-associated molecular pattern that triggers inflammation and thus has the potential to act as an immune modulator in many therapeutic contexts. To better understand the structure-activity relationship of this molecule, we chemically synthesized analogs of β-HBP and tested their ability to induce canonical TIFA-dependent inflammation in human embryonic kidney cells (HEK 293T) and colonic epithelial cells (HCT 116). Of the analogs tested, only d-glycero-β-d-manno-heptose 1-phosphate (β-HMP) induced TIFA-dependent NF-κB activation and cytokine production in a manner similar to β-HBP. This finding expands the spectrum of metabolites from the Gram-negative ADP-heptose biosynthesis pathway that can function as innate immune agonists and provides a more readily available agonist of the TIFA-dependent inflammatory pathway that can be easily produced by synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adaptor Proteins, Signal Transducing / metabolism
  • Gram-Negative Bacteria / physiology*
  • HEK293 Cells
  • Heptoses / chemical synthesis
  • Heptoses / immunology*
  • Humans
  • Immunity, Innate*
  • Immunization
  • Immunologic Factors / chemical synthesis
  • Immunologic Factors / immunology*
  • Inflammation / chemically induced
  • Inflammation / immunology*
  • Mannose / chemical synthesis
  • Mannose / immunology*
  • Pathogen-Associated Molecular Pattern Molecules / immunology*
  • Phosphates / chemical synthesis
  • Phosphates / immunology*
  • Pyrans / chemical synthesis
  • Pyrans / immunology*
  • Signal Transduction
  • Structure-Activity Relationship
  • Substrate Specificity

Substances

  • Adaptor Proteins, Signal Transducing
  • Heptoses
  • Immunologic Factors
  • Pathogen-Associated Molecular Pattern Molecules
  • Phosphates
  • Pyrans
  • TIFA protein, human
  • d-glycero-beta-d-manno-heptose 1,7-biphosphate
  • d-glycero-beta-d-manno-heptose 1-phosphate
  • glycero-manno-heptose
  • Mannose

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