Synthesis, cytotoxicity and 99mTc-MIBI tumor cell uptake evaluation of 2-phenylbenzothiazole tagged triazole derivatives

Future Med Chem. 2024;16(19):1999-2012. doi: 10.1080/17568919.2024.2389771. Epub 2024 Sep 4.

Abstract

Aim: The extensive utilization of 2-phenylbenzothiazole due to their wide array of biological activities, particularly in cancer therapy, has caused great attention to explore more potent derivatives.Materials & methods: We report the synthesis of 2-phenylbenzothiazole tagged 1,2,3-triaozle (8) through Cu(I)-catalyzed cycloaddition of alkyne side chain with aryl-substituted azides.Results: The in vitro experiments, using MTT and 99mTc-MIBI cell uptake methods, demonstrated the remarkable anticancer activity of these compounds against A549, SKOV3 and MCF7 cell lines.Conclusion: Compounds 8b, 8f and 8i possessed high cytotoxic activity as compared with doxorubicin. Compound 8g has a similar inhibitory effect on the proliferation of breast cancer cells as doxorubicin. In silico study indicated that compound 8 would be a good lead for the development of new potent anticancer agents.

Keywords: 2-phenylbenzothiazole; 99mTc-MIBI; anticancer; cellular uptake; triazole.

Plain language summary

[Box: see text].

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
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship
  • Technetium Tc 99m Sestamibi / chemistry
  • Thiazoles
  • Triazoles* / chemical synthesis
  • Triazoles* / chemistry
  • Triazoles* / pharmacology

Substances

  • Benzothiazoles
  • Antineoplastic Agents
  • Triazoles
  • 2-phenylbenzothiazole
  • Technetium Tc 99m Sestamibi
  • Thiazoles