ABSTRACT
A series of adenine-copper complexes (1-6) with various ligands (Cl(-), SCN(-), BF(4)(-) and acac [acetylacetonate ion]) have been synthesized and characterized by elemental analysis, infrared spectroscopy and thermal analysis. Among the six complexes only complex (1), Cu(2)(adenine)(4)Cl(4).2EtOH (abbreviated as Cu-Ad), demonstrated some toxic effect on different cell lines. In vitro investigations of the biological effect of Cu-Ad complex have shown that it: (1) binds genomic DNA; (2) decreases significantly, the viability of cells in culture in a concentration (15-125 microM)-dependant manner; an estimated IC(50) of: 45 microM with HepG2; 73 microM with C2C12; 103 microM with NIH3T3; and 108 microM with MCF7. Cu-Ad had no effect on A549 cells; (3) inhibits Taq polymerase-catalyzed reaction; (4) inhibits the binding of the transcription factor GATA-5 to labeled DNA probes; (5) inhibits mitochondrial NADH-UQ-reductase with an estimated IC(50) of 2.8 nmol, but had no effect on succinate dehydrogenase activity; (6) increases reactive oxygen species (60%) at 45 microM Cu-Ad; and (7) decreases ATP (80%) at 50 microM Cu-Ad. The new compound Cu(2)(adenine)(4)Cl(4).2EtOH (Cu-Ad), belongs to a class of copper-adenylate complexes that target many biochemical sites and with potential anti-cancer activity.
Subject(s)
Adenine/analogs & derivatives , Antineoplastic Agents/chemical synthesis , Copper/pharmacology , Organometallic Compounds/chemical synthesis , Organometallic Compounds/pharmacology , Adenine/chemistry , Adenine/pharmacology , Adenosine Triphosphate/antagonists & inhibitors , Adenosine Triphosphate/metabolism , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Calorimetry, Differential Scanning , Cell Line, Tumor , Cell Survival/drug effects , Copper/chemistry , Electron Transport Complex I/antagonists & inhibitors , Electron Transport Complex I/metabolism , Electrophoretic Mobility Shift Assay , GATA5 Transcription Factor/antagonists & inhibitors , GATA5 Transcription Factor/metabolism , Humans , Inhibitory Concentration 50 , Organometallic Compounds/chemistry , Reactive Oxygen Species/metabolism , Spectrophotometry, Ultraviolet , Spectroscopy, Fourier Transform Infrared , Succinate Dehydrogenase/antagonists & inhibitors , Succinate Dehydrogenase/metabolism , Taq Polymerase/antagonists & inhibitors , Taq Polymerase/metabolism , ThermogravimetryABSTRACT
Copper and cobalt complexes with 4-chloro-3-nitrobenzoate (ClNBz) and the nitrogen ligands 1,3-diaminopropane (1,3-DAP) or o-phenylenediamine (o-PDA), were prepared and characterized. The complexes [Cu(ClNBz)2(1,3-DAP)] (1), [Cu(ClNBz)(o-PDA)]Cl (2), [Co(ClNBz)2(1,3-DAP)] (3) and [Co(ClNBz)2(o-PDA)2] (4) were characterized by FTIR, UV-Visible absorption, elemental analysis and thermal analysis. Complex [Cu(ClNBz)(o-PDA)]Cl (2) shows high antibacterial activity as indicated by its ability to inhibit the growth of Staphylococcus aureus, Enterococcus faecalis.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Chlorobenzoates/chemistry , Cobalt/chemistry , Copper/chemistry , Nitrogen/chemistry , Bacteria/drug effects , Ligands , Microbial Sensitivity Tests , Molecular Conformation , Nitrogen/metabolismABSTRACT
Sixteen Schiff bases obtained from the condensation of benzaldehyde or salicylaldehyde with various amines (aniline, 4-carboxyaniline, phenylhydrazine, 2,4-dinitrophenylhydrazine, ethylenediamine, hydrazine, o-phenylenediamine and 2,6-pyridinediamine) are studied with UV-vis spectroscopy to observe the effect of solvents, substituents and other structural factors on the spectra. The bands involving different electronic transitions are interpreted. Computerized analysis and multiple regression techniques were applied to calculate the regression and correlation coefficients based on the equation that relates peak position lambda(max) to the solvent parameters that depend on the H-bonding ability, refractive index and dielectric constant of solvents.
