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1.
J Inorg Biochem ; 103(1): 35-42, 2009 Jan.
Article in English | MEDLINE | ID: mdl-18947878

ABSTRACT

Cobalt, nickel, copper and zinc coordination compounds of two thiosemicarbazones with general composition ML(2) (L: monodeprotonated ligand corresponding to 2-acetyl-gamma-butyrolactone thiosemicarbazone, HL(1), and 2-furancarbaldehyde thiosemicarbazone, HL(2)) and also complexes with general composition MCl(2)(HL(2)) were synthesized (except [NiCl(2)(HL(2))] and [Co(L(2))(2)]). The interaction of CuCl(2) with HL(2) gave [CuCl(HL(2))], a copper(I) complex. The ligands and metal complexes were characterized by IR, (1)H and (13)C NMR spectroscopy, and magnetic susceptibility measurements. The crystal structure of [Ni(L(2))(2)]x 2dmso was determined and a trans-square planar coordination of the two kappa(2)-N,S chelate rings forming polymeric strips through H-bonds with dmso was observed. Actually, in all the reported complexes both ligands behaved as kappa(2)-N,S chelates, except in the case of [Co(L(1))(2)] in which HL(1) is tridentate kappa(3)-N,S,O. The antimicrobial properties of all compounds were studied using a wide spectrum of bacterial and fungal strains. The copper complexes of HL(2) were the most active against all strains, including dermatophytes and phytopathogenic fungi. Most of the studied compounds, especially [Cu(L(1))(2)], presented good activity against Haemophilus influenzae, a very harmful bacterium to humans.


Subject(s)
4-Butyrolactone/pharmacology , Aldehydes/pharmacology , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Furans/pharmacology , Thiosemicarbazones/pharmacology , 4-Butyrolactone/chemical synthesis , 4-Butyrolactone/chemistry , Aldehydes/chemical synthesis , Aldehydes/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Bacteria/drug effects , Cobalt/chemistry , Copper/chemistry , Crystallography, X-Ray , Fungi/drug effects , Furans/chemical synthesis , Furans/chemistry , Nickel/chemistry , Thiosemicarbazones/chemical synthesis , Thiosemicarbazones/chemistry , Zinc/chemistry
2.
J Inorg Biochem ; 101(1): 138-47, 2007 Jan.
Article in English | MEDLINE | ID: mdl-17070919

ABSTRACT

Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of 2-thiophenecarbonyl and isonicotinoyl hydrazones of 3-(N-methyl)isatin (HL(1) and HL(2), respectively) were synthesized and characterized, being the crystal structures of HL(1), HL(2) and [Ni(L(1))(2)].2CHCl(3) elucidated by X-ray diffraction techniques. The in vitro antimicrobial activity of all these compounds was tested against several bacteria and fungi. HL(1)and its complexes exhibited a strong inhibition of the growth of Haemophilus influenzae (MIC 0.15-1.50microg/mL) and good antibacterial properties towards Bacillus subtilis (MIC 3-25microg/mL). The minimal inhibitory concentration (MIC) was defined as the lowest concentration of compound inhibiting the growth of each strain. The antibacterial effectiveness was confirmed against a number of Gram positive bacteria, including methicillin-resistant Staphylococcus aureus. Yeasts and moulds showed a low susceptibility, except the dermatophyte mould Epidermophyton floccosum that is inhibited at concentrations ranging from 6 to 50microg/mL. In general, the antimicrobial activity of the thiophene derivatives was greater than that of the isonicotinic analogues.


Subject(s)
Anti-Bacterial Agents/pharmacology , Hydrazones/pharmacology , Indoles/pharmacology , Thiophenes/pharmacology , Anti-Bacterial Agents/chemistry , Crystallography, X-Ray , Hydrazones/chemistry , Indoles/chemistry , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Thiophenes/chemistry
3.
J Inorg Biochem ; 98(2): 313-21, 2004 Feb.
Article in English | MEDLINE | ID: mdl-14729311

ABSTRACT

Nickel, copper, and zinc complexes of isatin (H(2)L(1)) and N-methylisatin 3-picolinoyl hydrazone (HL(2)), were synthesized and characterized by means of spectroscopic techniques. H(2)L(1) and a nickel complex [Ni(L(2))(2)].2C(6)H(14) were also characterized by X-ray diffractometry. Biological studies, carried out in vitro on human leukemic cell lines TOM 1 and NB4, have shown that both ligands and some copper and nickel complexes are active in inhibiting cell proliferation. Compounds H(2)L(1), Cu(HL(1))(2).2H(2)O, Zn(HL(1))(2).2H(2)O inhibit DNA synthesis and act constantly with time between 0 and 72 h. The cell cycle analysis has highlighted a reduction in the number of cells in phase S of about 40%. The same compounds present only a precocious action on cell line NB4 and therefore their activity is cell target specific.


Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Hydrazones/chemistry , Hydrazones/metabolism , Isatin/chemistry , Isatin/metabolism , Metals, Heavy/chemistry , Animals , Antineoplastic Agents/chemical synthesis , Apoptosis , Cell Cycle , Cell Line, Tumor , Copper/metabolism , Crystallography, X-Ray , Humans , Hydrazones/chemical synthesis , Isatin/analogs & derivatives , Isatin/chemical synthesis , Isatin/pharmacology , Leukemia/therapy , Metals, Heavy/metabolism , Nickel/metabolism , Spectrophotometry, Infrared , Zinc/metabolism
4.
Inorg Chem ; 42(19): 5871-9, 2003 Sep 22.
Article in English | MEDLINE | ID: mdl-12971755

ABSTRACT

Two novel photoactivatable Ca(2+) compounds were synthesized to achieve a fast concentration jump of calcium ions in solution; this is of paramount importance for investigating the physiological cellular response. The light-sensitive ligands 4-(2-nitrophenyl)-3,6-dioxaoctane dioic acid (H2L1) and 4-(4,5-dimethoxy-2-nitrophenyl)-3,6-dioxaoctane dioic acid (H2L2) were generated by multistep syntheses, and the corresponding calcium complexes, Ca1 and Ca2, were isolated and characterized. The solution equilibria of H2L1 and H2L2 with Ca2+ were investigated; for both ligands, the formation of a 1:2 Ca2+/ligand species is detected and the complete characterization is presented. The crystal structures of Ca1 and Ca2 were determined. In Ca1 the solid state assembly is attained by a polymeric association of [(CaL1(H2O))2(mu-OH2)] dimeric units. Each calcium ion coordinates four oxygen atoms of one ligand (two ethereal, one carboxylic, and one bridging carboxylic oxygen atom), one water molecule, one bridging water molecule, and a carboxylate group of the other ligand within the dimer. The octacoordination of the metal is completed by an interaction with the adjacent dimeric unit. The crystal structure of the complex Ca2 does not show a polymeric nature, but it is a centrosymmetric dimer. The coordination number of the metal ion is still 8:4 oxygen atoms of the ligand; 3 water molecules; 1 bridging carboxylate group. A preliminary study of the photochemical features of the complexes Ca1 and Ca2 is reported: photoexcitation by a nanosecond pulsed UV laser induces the cleavage of the ligand. This drastically reduces the affinity of the ligand toward Ca2+, which is then released in solution.

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