Synthesis and Biological Evaluation of New 1,2,3-Triazole Derivatives of the Chrysin Flavonoid as Anticancer Agents

Anticancer Agents Med Chem. 2022;22(1):160-168. doi: 10.2174/1871520621666210315090527.

Abstract

Background and objective: Chrysin and its derivatives proved to possess potential anti-tumour activity.

Materials and methods: A new series of chrysin analogs containing 1,2,3-triazoles with different substituent groups (5a-5l) was designed, synthesized, and evaluated as potential anticancer agents. The synthesized compounds were characterized using FT-IR, 1H NMR 13C NMR spectroscopy and mass spectrometry.

Results: The anticancer activities of the synthesized compounds were studied in four cancer cell lines viz. PC3, PC3-PSMA, MCF-7 and UM-UC-3 using doxorubicin as standard. Among all the tested compounds, 5c was found as most active with IC50 value of 10.8 ± 0.04 μM in PC3 cells and 20.53 ± 0.21 μMin MCF-7 cells, respectively. Flow cytometry analyses indicated that synthesized compounds 5a, 5c, and 5h arrested MCF-7 cells at the G2/M phase in a dose-dependent manner.

Conclusion: Chyrsin derivatives could be novel anticancer agents.

Keywords: Chrysin; QSAR; anticancer activity; cell cycle analysis; drug design; triazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Flavonoids / chemistry
  • Flavonoids / pharmacology*
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Triazoles / chemical synthesis
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Antineoplastic Agents
  • Flavonoids
  • Triazoles
  • chrysin