Imidazole-2-carboxaldehyde Chitosan Thiosemicarbazones and their Copper(II) Complexes: Synthesis, Characterization and Antitumorigenic Activity against Madin-Darby Canine Kidney Cell Line

Hari Sharan Adhikari,Rameshwar Adhikari,Paras Nath Yadav,Aditya Garai,Chetana Khanal

doi:10.14233/ajchem.2021.23078

Abstract

Chitosan oligosaccharide and high molecular weight crab shell chitosan were functionalized as imidazole-2-carboxaldehyde chitosan thiosemicarbazones and their copper(II) complexes were synthesized. The synthesized compounds were characterized by FT-IR, 13C NMR, EPR spectroscopy, powder X-ray diffraction (PXRD) analysis, elemental analysis and magnetic susceptibility measurements. The low molecular weight chitosan thiosemicarbazones showed higher in vitro inhibitory activity as studied by MTT assay against the tumorigenic epithelial Madin-Darby Canine Kidney (MDCK) cell line than the corresponding high molecular weight chitosan derivative. The antitumorigenic enhancement upon the complex formation was revealed by the better inhibitory activity of copper(II) chitosan thiosemicarbazone chelates.

Highlights

Chitin is a natural polymer of D-glucosamine units connected by β-(1-4)-linkages and chitosan is a polymer of N-acetyl D-glucosamine units obtained by a prolonged deacetylation of chitin (Fig. 1) with alkali [1]
Chitosan has been reported as an anticancer agent with minimal toxicity on noncancer cells [8] and its activity against the proliferation of tumour cell lines has been found to increase with decrease in molecular weight (Mw) and increase in degree of deacetylation (DDA) [9]
On the basis of these literature reports, present current work was focused on the synthesis of imidazole-2carboxaldehyde based novel chitosan thiosemicarbazones and their copper(II) complexes and the assessment of their antiproliferative activity against the tumorigenic epithelial MadinDarby Canine Kidney (MDCK) cell line in vitro

Summary

Introduction

Chitin is a natural polymer of D-glucosamine units connected by β-(1-4)-linkages and chitosan is a polymer of N-acetyl D-glucosamine units obtained by a prolonged deacetylation of chitin (Fig. 1) with alkali [1]. Anticancer activity of imidazole-derived thiosemicarbazones was enhanced upon their copper(II) complex formation [22]. On the basis of these literature reports, present current work was focused on the synthesis of imidazole-2carboxaldehyde based novel chitosan thiosemicarbazones and their copper(II) complexes and the assessment of their antiproliferative activity against the tumorigenic epithelial MadinDarby Canine Kidney (MDCK) cell line in vitro.

Results

Conclusion