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

Abstract

The new macrocyclic complex 2-amino-2-deoxy-N-[2-(1,3,5,8,11-pentaazacyclotridecan-3-yl)ethyl]-beta-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 H2O 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 Kb of 2.4x10(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 IC50 value in the micromolar range for SYSY, similar to the standard drug 5-fluorouracil.

Synthesis and Characterization of an Aminated D-Glucose and its Stability of Cu²⁺Complex

“…A moderate peak at 1629~1608 cm -1 was assigned to a δ(N-H) vibration of the glycosidic ligand in the IR spectrum of aminated glucose compared to the sharp bands at 1631 cm -1 attributed to a δ(HOH) vibration of crystal water in that of D-glucose [9]. Additionally, the signals at 1385 and 1269 cm -1 in the IR spectrum of aminated glucose were ascribed to ν(C-N) and τ(C-H) vibrations [10]. These IR spectra, thus, revealed the presence of the amino-sugar ligand.…”

Design, synthesis, characterization and DNA-binding studies of a triphenyltin(iv) complex of N-glycoside (GATPT), a sugar based apoptosis inducer: in vitro and in vivo assessment of induction of apoptosis by GATPT

“…DNA binding experiments that include absorption titrations, luminescence, circular dichoric experiments and viscosity measurements conformed to the standard methods and practices previously adopted by our laboratory. [23][24][25][26] 2.4.1. Absorption spectral experiments.…”

Systematic coordination chemistry and cytotoxicity of copper(II) complexes with methyl substituted 4-nitropyridine N-oxides

“…In recent years copper(II) complexes with both organic drugs [2,[5][6][7][8][9][10][11][12] and other biological and non-natural ligands [4][5][6][7][8] were found to exhibit comparable to cisplatin cytotoxicity. These species, usually of the mixed ligand type, should exhibit a different pattern of antitumor activity and perhaps more favorable toxicological profiles [2].…”