Design and Discovery of Novel Quinoxaline Derivatives as Dual DNA Intercalators and Topoisomerase II Inhibitors

Anticancer Agents Med Chem. 2018;18(2):195-209. doi: 10.2174/1871520617666170710182405.

Abstract

Backgroun/Methods: In attempt to develop new potent anti-tumor agents, a series of quinoxaline derivatives was designed and synthesized. The novel compounds were tested in vitro for their anti-proliferative activities against HePG-2, MCF-7 and HCT-116 cell lines. Additionally, DNA binding affinities as well as DNA-top II inhibitory activities of the synthesized compounds were investigated as potential mechanism for anticancer activity. Compounds 13, 15, 16 and 19 exhibited good cytotoxicity activities against the three cell lines (IC50 ranging from 7.6 to 32.4 µM) comparable to that of doxorubicin (IC50 = 9.8 µM).

Results: Interestingly, the results of DNA binding and DNA-top II inhibition assays were in agreement with those of the cytotoxicity tests, where the most potent anticancer compounds showed good DNA binding affinities (IC50 ranging from 25.1 to 32.4 µM) and DNA-top II inhibitory activities (IC50 ranging from 6.4 to 15.3 µM) comparable to those of doxorubicin (IC50 = 28.1 and 3.8 μM, respectively). Furthermore, molecular docking studies were carried out for the new compounds in order to investigate their binding pattern with the prospective target, DNA-top II complex (PDB-code: 3qx3).

Keywords: Anti-cancer; DNA intercalators; docking; quinoxaline; topoisomerase II..

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • DNA / drug effects*
  • DNA Topoisomerases, Type II / metabolism*
  • Dose-Response Relationship, Drug
  • Doxorubicin / chemistry
  • Doxorubicin / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Intercalating Agents / chemical synthesis
  • Intercalating Agents / chemistry
  • Intercalating Agents / pharmacology*
  • Models, Molecular
  • Molecular Structure
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry
  • Quinoxalines / pharmacology*
  • Structure-Activity Relationship
  • Topoisomerase II Inhibitors / chemical synthesis
  • Topoisomerase II Inhibitors / chemistry
  • Topoisomerase II Inhibitors / pharmacology*

Substances

  • Antineoplastic Agents
  • Intercalating Agents
  • Quinoxalines
  • Topoisomerase II Inhibitors
  • Doxorubicin
  • DNA
  • DNA Topoisomerases, Type II