Copper(II)-sulfonamide Schiff base complexes: Structure, biological activity and theoretical interpretation. (1st September 2018)

• Record Type: Journal Article
• Authors: Mondal, Sudipa; Mondal, Tapan Kumar; Rajesh, Y.; Mandal, Mahitosh; Sinha, Chittaranjan
• Is Part Of: Polyhedron. Volume 151(2018)
• Page Start: 344
• Page End: 354
• Publication Date: 2018-09-01
• Subjects: ADMET adsorption, distribution, metabolism, excretion, toxicity in pharmacokinetics -- B3LYP becke, three parameters, Lee-Yang-Parr -- DFT density functional theory -- DHPS dihydropteroate synthase -- PDB protein data bank -- SMX Sulfamethoxazole -- STZ Sulfathiazole -- TD-DFT time dependent density functional theory; Sulfonamide Schiff bases -- Cu(II) complex -- X-ray structure -- Anticancer activity -- DFT computation; Chemistry, Inorganic -- Periodicals; Chimie inorganique -- Périodiques; Organometaalverbindingen; Anorganische chemie; 546.05
• DOI: 10.1016/j.poly.2018.05.037
• Languages: English
• ISSNs: 0277-5387

Abstract

Graphical abstract: Cu(II) complexes of sulfonamide Schiff bases (1, 2 ) show better drug potency and anticancer activity against MDA-MB 231 cell lines of IC50 for 1, 75 µg/ml and that of 2, 50 µg/ml. DNA interaction determines the binding constants 1.515 × 10 5 M −1 (1 ) and 1.164 × 10 5 M −1 (2 ). Docking with DNA structure (PDB id 3V9D ) has also pointed out for a strong groove binding. The structures are determined by spectroscopic data and also by single crystal X-ray diffraction measurements. Abstract: [(SMX-NC-C6 H2 ( o, p -Cl2 )-O)]2 Cu (1 ) and [(STZ-NC-C6 H2 ( o, p -Cl2 )-O)]2 Cu (2 ) (SMX: Sulfamethoxazole; STZ: Sulfathiazole) have been characterized by spectroscopic data and the structural confirmation of 2 has been carried out by single crystal X-ray diffraction studies. The structure shows distorted square pyramid geometry and ligand serves as N, O chelator and OH2 occupies the axial position. Packing shows hydrogen bonded 1D chain and π—π interaction generates 2D supramolecular structure. Anticancer activity of the complexes against human breast cancer cell (MDA-MB 231) lines shows considerably low IC50, 82 μM (1 ) and 53 μM (2 ). DNA interaction of the complexes, 1 and 2, determines the binding constants 1.515 × 10 5 M −1 (1 ) and 1.164 × 10 5 M −1 (2 ). Docking studies have been performed with the DNA structure (PDB id 1ZEW ) to establish drug activity by groove binding.