Novel Menadione Hybrids: Synthesis, anticancer activity and cell based studies

Abstract

A series of novel menadione based triazole hybrids were designed and synthesized by employing copper catalyzed azide-alkyne cycloaddition (CuAAC). All the synthesized hybrids were characterized by their spectral data (¹H NMR, ¹³C NMR, IR and HRMS). The synthesized compounds were evaluated for their anticancer activity against five selected cancer cell lines including lung (A549), prostate (DU-145), cervical (Hela), breast (MCF-7) and mouse melanoma (B-16) by using MTT assay. The screening results showed that majority of the synthesized compounds displayed significant anticancer activity. Among the tested compounds, the triazoles 5 and 6 exhibited potent activity against all cell lines. In particular, compound 6 showed higher potency than the standard tamoxifen and parent menadione against MCF-7 cell line. Flow cytometric analysis revealed that compound 6 arrested cell cycle at G0/G1 phase and induced apoptotic cell death which was further confirmed by Hoechst staining, measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay. Thus, compound 6 can be considered as lead molecule for further development as potent anticancer therapeutic agent.

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Menadione based triazole hybrids were synthesized by employing copper catalyzed azide-alkyne cycloaddition (CuAAC). The synthesized compounds were evaluated for their anticancer activity against five selected cancer cell lines. Compound 6 showed higher potency than the standard tamoxifen and parent menadione against MCF-7 cell line, arrested cell cycle at G0/G1 phase and induced apoptotic cell death.

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