Discovery of novel aminopiperidinyl amide CXCR4 modulators through virtual screening and rational drug design

Eur J Med Chem. 2020 Sep 1:201:112479. doi: 10.1016/j.ejmech.2020.112479. Epub 2020 Jun 6.

Abstract

The C-X-C chemokine receptor type 4 (CXCR4) is a potential therapeutic target for HIV infection, metastatic cancer, and inflammatory autoimmune diseases. In this study, we screened the ZINC chemical database for novel CXCR4 modulators through a series of in silico guided processes. After evaluating the screened compounds for their binding affinities to CXCR4 and inhibitory activities against the chemoattractant CXCL12, we identified a hit compound (ZINC 72372983) showing 100 nM affinity and 69% chemotaxis inhibition at the same concentration (100 nM). To increase the potency of our hit compound, we explored the protein-ligand interactions at an atomic level using molecular dynamics simulation which enabled us to design and synthesize a novel compound (Z7R) with nanomolar affinity (IC50 = 1.25 nM) and improved chemotaxis inhibition (78.5%). Z7R displays promising anti-inflammatory activity (50%) in a mouse edema model by blocking CXCR4-expressed leukocytes, being supported by our immunohistochemistry study.

Keywords: C-X-C chemokine receptor type 4 (CXCR4); Chemokine modulator; Ligand shape similarity; Molecular docking; Molecular dynamics; Structure-based drug design.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemical synthesis
  • Anti-Inflammatory Agents / metabolism
  • Anti-Inflammatory Agents / therapeutic use*
  • Cell Line, Tumor
  • Drug Design
  • Humans
  • Inflammation / drug therapy*
  • Mice
  • Molecular Docking Simulation
  • Molecular Dynamics Simulation
  • Molecular Structure
  • Piperidines / chemical synthesis
  • Piperidines / metabolism
  • Piperidines / therapeutic use*
  • Protein Binding
  • Receptors, CXCR4 / metabolism*
  • Structure-Activity Relationship

Substances

  • Anti-Inflammatory Agents
  • CXCR4 protein, human
  • Piperidines
  • Receptors, CXCR4