De Novo Design of Boron-Based Peptidomimetics as Potent Inhibitors of Human ClpP in the Presence of Human ClpX

J Med Chem. 2019 Jul 11;62(13):6377-6390. doi: 10.1021/acs.jmedchem.9b00878. Epub 2019 Jun 26.

Abstract

Boronic acids have attracted the attention of synthetic and medicinal chemists due to boron's ability to modulate enzyme function. Recently, we demonstrated that boron-containing amphoteric building blocks facilitate the discovery of bioactive aminoboronic acids. Herein, we have augmented this capability with a de novo library design and a virtual screening platform modified for covalent ligands. This technique has allowed us to rapidly design and identify a series of α-aminoboronic acids as the first inhibitors of human ClpXP, which is responsible for the degradation of misfolded proteins.

Publication types

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

MeSH terms

  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Boronic Acids / metabolism
  • Drug Design
  • Endopeptidase Clp / antagonists & inhibitors*
  • Endopeptidase Clp / metabolism
  • Enzyme Assays
  • Humans
  • Peptide Library
  • Peptidomimetics / chemical synthesis
  • Peptidomimetics / chemistry*
  • Peptidomimetics / metabolism
  • Protein Binding
  • Staphylococcus aureus / enzymology
  • Stereoisomerism

Substances

  • Boronic Acids
  • Peptide Library
  • Peptidomimetics
  • ClpP protein, human
  • Endopeptidase Clp
  • CLPX protein, human