Derivatives of Dapsone (dap): Synthesis and Study on In Vitro Anticancer Activity and DNA Laddering Against Hep G2 and C6 Human Cancer Cell Lines

Abstract

AbstractInteresting biological profile of dapsone (dap) has encouraged us to derivatize it further into a novel series of diamines 4,4’‐bis(2‐(alkylamino) acetamido) diphenylsulfone L1‐L3 and their ensuing metallomacrocyclic complexes of the type [M2‐μ2‐bis‐{(κ2S,S‐S2CN(R)CH2CONHC6H4)2SO2}] {R=Cy, M=NiII 1 a, CuII 1 b, ZnII 1 c; R=iPr, M=NiII 2 a, CuII 2 b, ZnII 2 c; R=nBu, M=NiII 3 a, CuII 3 b, ZnII 3 c}. These compounds were characterized by standard spectroscopic methods. A DFT level calculation has been performed on selected compounds. In vitro anticancer activity against Hep G2 (hepatoma) and C6 (Glioblastoma) cell lines suggests specificity of these compounds for cancer cells over normal liver cells. Interestingly, complex 2c holding zinc(II) and N‐iPr substituents shows nearly 3 fold better cytotoxic activity against both Hep G2 (8.47±0.016 μg/mL) and C6 (4.3±0.019 μg/mL) cell lines, compared to the reference drug Cisplatin. The morphological changes and moderate to heavy DNA laddering clearly demonstrate the induction of apoptotic cell death, required for major chemical therapeutic implications.