Design, Synthesis, and Biological Evaluation of New Benzimidazole-1,2,4-Triazole Derivatives as Potential Anticancer Agents

Chem Biol Drug Des. 2024 Dec;104(6):e70033. doi: 10.1111/cbdd.70033.

Abstract

New series of benzimidazole-1,2,4-triazole derivatives were designed, synthesized, and characterized using 1H-NMR, 13C-NMR, and HRMS. These compounds were evaluated for anticancer activity toward HTB-9 bladder and HT-29 colorectal cancer cell lines. Compounds 7h and 7ı were found to be the most active against HTB-9 cell line, with IC50 6.27 and 6.44 μM, respectively, comparable to positive control cisplatin (IC50 = 11.40 μM). Additionally, in HT-29 cell line, compounds 7a and 7ı exhibited the lowest IC50 values (20.37 and 22.71 μM, respectively), which was higher than those of cisplatin (19.79 μM). All active compounds induced apoptosis and caspase 3/7 activity and reduced the migration ability in both cell lines. Particularly, HT-29 cells treated with compound 7ı exerted a higher apoptotic index than cisplatin-treated cells. Furthermore, compounds 7h and 7ı led to G1 cell cycle arrest of HTB-9, and compounds 7a and 7ı against HT-29 induced S and G1 cell cycle arrest, respectively. In conclusion, the antiproliferative effect of active compounds is associated with the induction of apoptosis through caspase 3/7 activation and cell cycle arrest at different phases in HTB-9 and HT-29 cell lines.

Keywords: 1,2,4‐triazole; anticancer activity; apoptosis; benzimidazole; caspase 3/7 activation.

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Apoptosis* / drug effects
  • Benzimidazoles* / chemical synthesis
  • Benzimidazoles* / chemistry
  • Benzimidazoles* / pharmacology
  • Caspase 3 / metabolism
  • Caspase 7* / metabolism
  • Cell Line, Tumor
  • Cell Movement / drug effects
  • Cell Proliferation / drug effects
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Structure-Activity Relationship
  • Triazoles* / chemical synthesis
  • Triazoles* / chemistry
  • Triazoles* / pharmacology

Substances

  • Antineoplastic Agents
  • Triazoles
  • Benzimidazoles
  • Caspase 7
  • Caspase 3
  • 1,2,4-triazole