CPe-III-S Metabolism in Vitro and in Vivo and Molecular Simulation of Its Metabolites Using a p53-R273H Mutant

J Agric Food Chem. 2016 Sep 28;64(38):7095-103. doi: 10.1021/acs.jafc.6b01996. Epub 2016 Sep 15.

Abstract

It was previously found that CPe-III-S, synthesized according to the chickpea peptide CPe-III (RQSHFANAQP), exhibited an antiproliferative effect. The aim of this study was to investigate the antiproliferative mechanism of CPe-III-S. CPe-III-S was treated by pepsin and trypsin in a simulated gastrointestinal digestion environment as well as in an animal experiment. With HPLC-ESI-MS analysis, three peptide fragments of Ser-His, His-Phe, and Ala-Asn-Ala-Gln were identified. Ser-His was the only common product from both in vitro and in vivo environments. The specific bindings between three peptides and p53-R273H were performed by molecular docking, and the molecular dynamic simulation between Ser-His and p53-R273H revealed the stability of the binding complex. The binding free energy of the complex was -12.56 ± 1.03 kcal/mol with a reliable hydrogen bond between the ligand and Thr284 of p53. Ser-His may restore mutant p53-R273H activity or inhibit its binding with a downstream signal. This metabolite is a potential anticancer factor for suppressing cell proliferation.

Keywords: CPe-III; Ser-His; molecular docking; molecular dynamics simulation; p53 mutation.

MeSH terms

  • Animals
  • Antineoplastic Agents / pharmacology
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dipeptides / pharmacology*
  • Female
  • Humans
  • MCF-7 Cells
  • Mice
  • Mice, Inbred BALB C
  • Molecular Docking Simulation*
  • Molecular Dynamics Simulation*
  • Pepsin A / chemistry
  • Peptide Fragments / pharmacology
  • Protein Conformation
  • Trypsin / chemistry
  • Tumor Suppressor Protein p53 / genetics
  • Tumor Suppressor Protein p53 / metabolism*

Substances

  • Antineoplastic Agents
  • Dipeptides
  • Peptide Fragments
  • Tumor Suppressor Protein p53
  • seryl-histidine
  • histidylphenylalanine
  • Trypsin
  • Pepsin A
  • alanylglutamine