ABSTRACT
To further explore the structural features and potential antibacterial and antitumor activities of polynuclear CuII coordination compounds with nalidixic acid (nx) derivatives, new complexes bearing nx hydrazones with N-pyridinyl moieties substituted at positions 2 and 3 (h2py and h3py) were synthesized. Complexes [Cu3(C18H16N5O2)2(C18H17N5O2)2(H2O)]4BF4âH2O (1), and [Cu3(C18H16N5O2)2(C18H17N5O2)2(H2O)3]4BF4â3H2O (%) (2) were synthesized using h2py and h3py with Cu(BF4)2ânH2O as precursor, whereas the [Cu(C18H17N5O2)Cl2]â0.5H2O complex (3) was synthesized with h2py and CuCl2â2H2O. Crystallographic studies of complex 1, showed that coordination of hydrazones to CuII occurs by tridentate modes of type κ3(O,N,N') as well as bidentate modes of type κ2(O',Nâ³). Complexes 1, 2 and 3 had their antiproliferative activities evaluated in vitro against a panel of tumor cells by the determination of GI50 values. Complexes 1 and 2 were more active than complex 3, suggesting an effect of the complex charge on their activities. The interactions of such complexes towards bovine serum albumin (BSA) and DNA plasmid (pGEX-4 T1) were investigated using fluorescence spectroscopy and gel electrophoresis. All complexes were shown to interact with the DNA model as metallonucleases, but no interaction with BSA was observed. DNA molecular docking of complex 1 encompassing both its trinuclear (TN) form and a possible mononuclear (MN) derivative suggests that naphthyridyl ring performs π-stacking interactions with DNA. The TN species were also shown to be possible minor groove binders.
Subject(s)
Antineoplastic Agents , Coordination Complexes , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Copper/chemistry , Crystallography, X-Ray , DNA/chemistry , Hydrazones/pharmacology , Molecular Docking Simulation , Nalidixic Acid , Pyridines/chemistry , Pyridines/pharmacology , Serum Albumin, Bovine/chemistryABSTRACT
For the new organic salt 1H-imidazol-3-ium 1,4-dioxo-1,4-dihydronaphthalen-2-olate, C3H5N2(+)·C10H5O3(-), ab initio calculations of the gas-phase structures of the lawsonate and imidazolium ions were performed to help in the interpretation of the structural features observed. Three different types of hydrogen bond are responsible for the three-dimensional packing of the salt.
