Synthesis and biological evaluation of 1-phenyl-tetrahydro-β-carboline-based first dual PRMT5/EGFR inhibitors as potential anticancer agents

Eur J Med Chem. 2024 Apr 5:269:116341. doi: 10.1016/j.ejmech.2024.116341. Epub 2024 Mar 18.

Abstract

Protein arginine methyltransferase 5 (PRMT5) and epidermal growth factor receptor (EGFR) are both involved in the regulation of various cancer-related processes, and their dysregulation or overexpression has been observed in many types of tumors. In this study, we designed and synthesized a series of 1-phenyl-tetrahydro-β-carboline (THβC) derivatives as the first class of dual PRMT5/EGFR inhibitors. Among the synthesized compounds, 10p showed the most potent dual PRMT5/EGFR inhibitory activity, with IC50 values of 15.47 ± 1.31 and 19.31 ± 2.14 μM, respectively. Compound 10p also exhibited promising antiproliferative activity against A549, MCF7, HeLa, and MDA-MB-231 cell lines, with IC50 values below 10 μM. Molecular docking studies suggested that 10p could bind to PRMT5 and EGFR through hydrophobic, π-π, and cation-π interactions. Furthermore, 10p displayed favorable pharmacokinetic properties and oral bioavailability (F = 30.6%) in rats, and administrated orally 10p could significantly inhibit the growth of MCF7 orthotopic xenograft tumors. These results indicate that compound 10p is a promising hit compound for the development of novel and effective dual PRMT5/EGFR inhibitors as potential anticancer agents.

Keywords: 1-Phenyl-tetrahydro-β-carboline (THβC) derivative; Antitumor activity; EGFR inhibitor; PRMT5 inhibitor; Pharmacokinetic profiles.

MeSH terms

  • Animals
  • Antineoplastic Agents* / chemistry
  • Carbolines*
  • Cell Line, Tumor
  • Cell Proliferation
  • Drug Screening Assays, Antitumor
  • ErbB Receptors
  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • Protein Kinase Inhibitors / pharmacology
  • Protein-Arginine N-Methyltransferases
  • Rats
  • Structure-Activity Relationship

Substances

  • tryptoline
  • Antineoplastic Agents
  • ErbB Receptors
  • Protein Kinase Inhibitors
  • PRMT5 protein, human
  • Protein-Arginine N-Methyltransferases
  • EGFR protein, human
  • Carbolines