Novel carboranyl-BODIPY conjugates: design, synthesis and anti-cancer activity

Abstract

A series of four carboranyl-BODIPY conjugates (o-CB-10, m-CB-15, Me-o-CB-28, and Me-o-CB-35) and one phenylene-BODIPY conjugate (PB-20) were synthesized. The carboranyl-BODIPY conjugates incorporate boron clusters, specifically ortho- and meta-carboranes, covalently linked to BODIPY fluorophores while the phenylene-BODIPY conjugate features a phenylene ring covalently linked to BODIPY fluorophore. The newly synthesized conjugates were characterized by ¹H NMR, ¹³C NMR, ¹¹B NMR, ¹⁹F NMR, FT-IR, and high-resolution mass spectral analysis. In vitro cytotoxicity of the synthesized conjugates has been evaluated against the HeLa cervical cancer cell line. The study reveals that o-CB-10 shows a maximum cell death potential at lower concentrations (12.03 μM) and inhibited cell proliferation and migration in cancer (HeLa) cells. Additionally, flow cytometry study reveals that o-CB-10 and Me-o-CB-28 arrest the cell cycle at the S phase. The results indicate that the carboranyl-BODIPY conjugates have the potential to be effective anticancer agents.