Design and Optimization of Selectivity-Tunable Toll-like Receptor 7/8 Agonists as Novel Antibody-Drug Conjugate Payloads

J Med Chem. 2024 Sep 12;67(17):15756-15779. doi: 10.1021/acs.jmedchem.4c01384. Epub 2024 Aug 22.

Abstract

Toll-like receptors 7 and 8 are involved in modulating the adaptive and innate immune responses, and their activation has shown promise as a therapeutic strategy in the field of immuno-oncology. While systemic exposure to TLR7/8 agonists can result in poor tolerance, combination therapies and targeted delivery through antibody-drug conjugates (ADCs) can help mitigate adverse effects. Described herein is the identification of a novel and potent series of pyrazolopyrimidine-based TLR7/8 agonists with tunable receptor selectivity. Representative agonists from this series were successfully able to induce the production of various proinflammatory cytokines and chemokines from human peripheral blood mononuclear cells. Anti-HER2-25 and anti-HER2-26 ADCs made from this class of payloads demonstrated mechanism-based activation of TLR7/8 in a THP1/N87 coculture system.

MeSH terms

  • Cytokines / metabolism
  • Drug Design*
  • Humans
  • Immunoconjugates* / chemistry
  • Immunoconjugates* / pharmacology
  • Leukocytes, Mononuclear / drug effects
  • Leukocytes, Mononuclear / immunology
  • Leukocytes, Mononuclear / metabolism
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology
  • Receptor, ErbB-2 / antagonists & inhibitors
  • Receptor, ErbB-2 / metabolism
  • Structure-Activity Relationship
  • Toll-Like Receptor 7* / agonists
  • Toll-Like Receptor 8* / agonists
  • Toll-Like Receptor 8* / metabolism

Substances

  • Toll-Like Receptor 7
  • Toll-Like Receptor 8
  • Immunoconjugates
  • TLR7 protein, human
  • TLR8 protein, human
  • Pyrimidines
  • Cytokines
  • Receptor, ErbB-2
  • Pyrazoles