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Synthesis and Characterization of a New Macrocyclic Copper(II) Complex with an N ‐Glycosidic Pendant Arm: in vitro Cytotoxicity and Binding Studies with Calf‐Thymus DNA
Author(s) -
Mathur Suvigya,
Tabassum Sartaj
Publication year - 2006
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200690034
Subject(s) - chemistry , circular dichroism , binding constant , stereochemistry , copper , titration , molar conductivity , cytotoxicity , dna , cyclic voltammetry , in vitro , glycosidic bond , crystallography , nuclear chemistry , metal , binding site , enzyme , inorganic chemistry , organic chemistry , biochemistry , electrochemistry , electrode
The new macrocyclic complex 2‐amino‐2‐deoxy‐ N ‐[2‐(1,3,5,8,11‐pentaazacyclotridecan‐3‐yl)ethyl]‐ β ‐ D ‐glucopyranosylamine copper(II) dichloride ( 1a ) was prepared and thoroughly characterized by various techniques. Molar‐conductance measurements showed that 1a (and its Ni analogue 1b ) are ionic in nature. On the basis of spectroscopic data, both complexes were assigned a square‐planar geometry, and found to be highly stabile and hydrolytically robust in H 2 O over a wide range of pH, as confirmed by cyclic voltammetry (CV). The Cu II complex 1a was found to bind to CT‐DNA, with a binding constant K b of 2.4×10 3 M −1 , as derived by UV/VIS titration, and confirmed by CV, circular dichroism (CD), and viscosity measurements. DNA binding seems to occur mostly via H‐bonding. In an in vitro antitumor MTT assay, 1a exhibited significant anticancer activity against the SY5Y and PC‐12 cell lines, with an estimated IC 50 value in the micromolar range for SYSY, similar to the standard drug 5‐fluorouracil.