Potential anti-cancer performance of chitosan-based β-ketosulfone derivatives

Abstract

Abstract A series of chitosan-based β-ketosulfone derivatives (CsB-β-KS) were synthesized, characterized, and evaluated as anti-cancer agents against three types of cancer cell lines, including the colon carcinoma (HCT), liver hepatocellular carcinoma (HEPG2), and breast carcinoma (MCF-7) cell lines. Before product formation, the β-ketosulfone derivatives, 1-(4-halophenyl)-2-(phenylsulfonyl)ethanone, were synthesized by the reaction of phenacyl halide with sodium benzene sulfinate. The (CsB-β-KS)a-e derivatives were synthesized by chemical modification of chitosan (Cs) with freshly prepared p-halo-β-ketosulfone derivatives in a mildly acidic aqueous solution. Various loading percentages, 5%, 10%, 15%, and 20%, of the p-halo-β-ketosulfone derivative (by weight) with respect to the Cs weight were evaluated. The chemical structures were confirmed by variable elemental and spectral analyses, including FT-IR, 1H-NMR, 13C-NMR, and mass spectroscopes. The (CsB-β-KS)a-e derivatives were also characterized by various techniques, such as FT-IR, 1H-NMR, XRD, FE-SEM, and thermal analyses. FT-IR spectroscopy and XRD confirmed the formation of these products. Moreover, the XRD results proved the strong interactions between the organic substituent and the Cs host molecule. All (CsB-β-KS)a-e derivatives showed similar thermal stabilities in three degradation steps. Among these derivatives, (CsB-β-KS)a3 showed the highest thermal stability. The synthesized compounds showed significant biological screening against Gram-positive and Gram-negative bacteria and fungi. Among the tested products, (CsB-β-KS)a3 displayed high efficiencies toward the three types of cancer cell lines under investigation with low concentrations. The ranking of the anti-cancer activity was (CsB-β-KS)a3 > (CsB-β-KS)d3 > (CsB-β-KS)d2.