Synthesis, characterization, and anticancer activity of chitosan functionalized isatin based thiosemicarbazones, and their copper(II) complexes

Abstract

The one-pot synthetic method of condensation of isatin and 5-chloroisatin on to amino group at C2 position of the pyranose ring chitosan in chitosan thiosemicarbazide was employed to get these chitosan thiosemicarbazones (TSCs). The partial incorporation of thiosemicarbazone moiety in chitosan was shown by FT-IR and ¹³C NMR spectroscopic studies, powder X ray diffraction, and CHNS microanalysis. The NOS tridentate coordination behavior of TSCs with copper(II) chloride to give the square planar complexes was established by FT-IR spectroscopic data, magnetic susceptibility measurement, and EPR spectral analysis. The thermal stability of these biomaterial chitosan derivatives till the commencement of chain disruption at 200C was shown by thermal studies. As revealed by colorimetric MTT assays, the in vitro anticancer activity enhancement accorded with the functionalization of chitosan as isatin based chitosan TSCs, and NOS tridentate coordination of TSCs plus a monodentate coordination of chloride ion with copper(II) ion. Only a marginal activity difference of these compounds was observed against the tumorigenic MDCK and MCF-7 cancer cell lines, irrespective of unit molecular weight (M_w) and degree of deacetylation (DDA) of ring chitosan. The 5-chloroisatin chitosan TSCs showed better activity than isatin chitosan TSCs against both the cell lines.

Keywords: 5-Chloroisatin; Anticancer activity; Characterization; Chitosan; Copper(II) chitosan thiosemicarbazones; Isatin; ONS Tridentate chitosan thiosemicarbazones.