Pyrimido[4,5-b]indole derivatives bearing 1,2,4-oxadiazole moiety as MDM2 inhibitor candidates in cancer treatment

Future Med Chem. 2023 Mar;15(6):517-532. doi: 10.4155/fmc-2023-0012. Epub 2023 Apr 25.

Abstract

Aim: In this study, novel hybrid structures of pyrimido-indole-oxadiazole were developed as MDM2 inhibitors for restoring the regular function of the p53. Materials & methods: A multistep chemical pathway was used to synthesize the derivatives. Nutlin-3a was used as a standard lead in molecular docking and molecular dynamics simulations. Finally, cytotoxicity was evaluated against MCF-7 cancer cells versus Doxorubicin. Results: The most promising candidate was 12c, which had an NO2 group in the para position of the oxadiazole ring (IC50: 1.1 μM). A satisfactory result was obtained with the combined application of 12c and Doxorubicin (IC50 decreased to 0.63 μM), which could be potentially attributed to MDM2 inhibition. Conclusion: These hybrid structures can be further investigated as potential MDM2 inhibitors.

Keywords: MD simulation; MDM2 inhibitor; cytotoxicity; oxadiazole; pyrimidoindole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents* / pharmacology
  • Doxorubicin
  • Humans
  • Indoles / chemistry
  • Indoles / pharmacology
  • Molecular Docking Simulation
  • Neoplasms*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology
  • Proto-Oncogene Proteins c-mdm2 / metabolism
  • Tumor Suppressor Protein p53 / metabolism

Substances

  • Antineoplastic Agents
  • Doxorubicin
  • MDM2 protein, human
  • Proto-Oncogene Proteins c-mdm2
  • Tumor Suppressor Protein p53
  • Indoles
  • Oxadiazoles