Harnessing potential COX-2 engagement for boosting anticancer activity of substituted 2-mercapto-4(3H)-quinazolinones with promising EGFR/VEGFR-2 inhibitory activities

Bioorg Chem. 2024 Dec:153:107951. doi: 10.1016/j.bioorg.2024.107951. Epub 2024 Nov 12.

Abstract

We designed and synthesized new quinazolinone-tethered phenyl thiourea/thiadiazole derivatives 4-26. Based on their structural characteristics, these compounds were proposed to have a multi-target mode of action for their anticancer activities. Using the MTT assay method, antiproliferative effects were assessed against three human cancer cell lines (HEPG-2, MCF-7, and HCT-116). In vitro assessment for enzymatic inhibitory activity of the most active compounds 4, 9 and 20 was done for EGFR, VEGFR-2 and COX-2 as potential targets. The screened compounds showed low micromolar IC50 inhibitory effects against the three targets. Compound 9 demonstrated similar EGFR/VEGFR-2 inhibitory effect to the control drugs and potential inhibitory activity for COX-2 enzyme. In MCF-7 cells, the most active analog 9 caused 41.02% total apoptosis, and arrested the cell cycle at the G2/M phase. Taken as a whole, the findings of this study provide significant new understandings into the relationship between COX inhibition and cancer therapy. Furthermore, the outcomes showcased the encouraging efficacy of these compounds with a multi-target mechanism, making them excellent choices for additional research and development into possible anticancer drug.

Keywords: 2-mercapto-4(3H)-quinazolinones; Anticancer activity; Apoptosis; COX-2 inhibitory activity; Cell cycle; EFGR inhibitory activity; Molecular modeling; Quinazolin-4(3H)-one; Thiourea; VEGFR-2 inhibitory activity.

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Apoptosis* / drug effects
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Cyclooxygenase 2 Inhibitors / chemical synthesis
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / pharmacology
  • Cyclooxygenase 2* / metabolism
  • Dose-Response Relationship, Drug*
  • Drug Screening Assays, Antitumor*
  • ErbB Receptors* / antagonists & inhibitors
  • ErbB Receptors* / metabolism
  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • Quinazolinones* / chemical synthesis
  • Quinazolinones* / chemistry
  • Quinazolinones* / pharmacology
  • Structure-Activity Relationship
  • Vascular Endothelial Growth Factor Receptor-2* / antagonists & inhibitors
  • Vascular Endothelial Growth Factor Receptor-2* / metabolism

Substances

  • ErbB Receptors
  • Antineoplastic Agents
  • Cyclooxygenase 2
  • Vascular Endothelial Growth Factor Receptor-2
  • EGFR protein, human
  • Quinazolinones
  • Cyclooxygenase 2 Inhibitors
  • KDR protein, human