Identification of Benzothiazoles Bearing 1,3,4-Thiadiazole as Antiproliferative Hybrids Targeting VEGFR-2 and BRAF Kinase: Design, Synthesis, BIO Evaluation and In Silico Study

Molecules. 2024 Jul 4;29(13):3186. doi: 10.3390/molecules29133186.

Abstract

Cancer remains a leading cause of death worldwide, often resulting from uncontrolled growth in various organs. Protein kinase inhibitors represent an important class of targeted cancer therapies. Recently, the kinases BRAF and VEGFR-2 have shown synergistic effects on tumor progression. Seeking to develop dual BRAF/VEGFR-2 inhibitors, we synthesized 18 amino-benzothiazole derivatives with structural similarities to reported dual inhibitors. Four compounds-4a, 4f, 4l, and 4r-demonstrated remarkable cytotoxicity, with IC50 values ranging from 3.58 to 15.36 μM, against three cancer cell lines. Furthermore, these compounds showed IC50 values of 38.77-66.22 μM in the case of a normal cell line, which was significantly safer than the reference, sorafenib. Subsequent investigation revealed that compound 4f exhibited the capacity to inhibit the BRAF and VEGFR-2 enzymes, with IC50 values similar to sorafenib (0.071 and 0.194 μM, respectively). Moreover, compound 4f caused G2-M- and S-phase cycle arrest. Molecular modeling demonstrated binding patterns compatible with inhibition for both targets, where 4f exerted the critical interactions in the BRAF site and interacted in the VEGFR-2 site in a manner akin to sorafenib, demonstrating affinity similar to dabrafenib.

Keywords: BRAF inhibition; VEGFR-2 inhibition; antitumor activity; apoptosis; benzothiazoles; cell cycle analysis; molecular docking.

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Benzothiazoles* / chemical synthesis
  • Benzothiazoles* / chemistry
  • Benzothiazoles* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Computer Simulation
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Docking Simulation*
  • Molecular Structure
  • Protein Kinase Inhibitors* / chemical synthesis
  • Protein Kinase Inhibitors* / chemistry
  • Protein Kinase Inhibitors* / pharmacology
  • Proto-Oncogene Proteins B-raf* / antagonists & inhibitors
  • Proto-Oncogene Proteins B-raf* / metabolism
  • Sorafenib / chemistry
  • Sorafenib / pharmacology
  • Structure-Activity Relationship
  • Thiadiazoles* / chemical synthesis
  • Thiadiazoles* / chemistry
  • Thiadiazoles* / pharmacology
  • Vascular Endothelial Growth Factor Receptor-2* / antagonists & inhibitors
  • Vascular Endothelial Growth Factor Receptor-2* / metabolism

Substances

  • Vascular Endothelial Growth Factor Receptor-2
  • Proto-Oncogene Proteins B-raf
  • Protein Kinase Inhibitors
  • Benzothiazoles
  • Thiadiazoles
  • Antineoplastic Agents
  • 1,3,4-thiadiazole
  • BRAF protein, human
  • KDR protein, human
  • Sorafenib