Anti-inflammatory hybrids of secondary amines and amide-sulfamide derivatives

Eur J Med Chem. 2018 Apr 25:150:195-205. doi: 10.1016/j.ejmech.2018.02.085. Epub 2018 Mar 2.

Abstract

The CXCR4/CXCL12 chemokine axis can chemotactically accumulate inflammatory cells to local tissues and regulate the release of inflammatory factors. Developing novel CXCR4 modulators may provide a desirable strategy to control the development of inflammation. A series of novel hybrids were designed by integrating the key pharmacophores of three CXCR4 modulators. The majority of compounds displayed potent CXCR4 binding affinity. Compound 7a exhibited 1000-fold greater affinity than AMD3100 and significantly inhibited invasion of CXCR4-positive tumor cells. Additionally, compound 7a blocked mice ear inflammation by 67% and suppressed the accumulation of inflammatory cells in an in vivo mouse ear edema evaluation. Western blot analyses revealed that 7a inhibited the CXCR4/CXCL12-mediated phosphorylation of Akt and p44 in a dose-dependent manner. Moreover, compound 7a had no observable cytotoxicity and displayed a favorable plasma stability in our preliminary pharmacokinetic study. These results confirmed that this is a feasible method to develop CXCR4 modulators for the regulation and reduction of inflammation.

Keywords: Amide-sulfamide; CXCR4; Hybrids; Inflammation; Inflammatory cell accumulation.

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology*
  • Amines / chemistry
  • Amines / pharmacology*
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation
  • Cell Survival
  • Chemokine CXCL12 / antagonists & inhibitors*
  • Chemokine CXCL12 / metabolism
  • Dose-Response Relationship, Drug
  • Ear
  • Edema / drug therapy
  • Edema / metabolism
  • Edema / pathology
  • Humans
  • Inflammation / drug therapy*
  • Inflammation / metabolism
  • Inflammation / pathology
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Receptors, CXCR4 / antagonists & inhibitors*
  • Receptors, CXCR4 / metabolism
  • Structure-Activity Relationship

Substances

  • Amides
  • Amines
  • Anti-Inflammatory Agents, Non-Steroidal
  • CXCL12 protein, human
  • CXCR4 protein, human
  • Chemokine CXCL12
  • Receptors, CXCR4