+ Translate
+ Most Popular
The pigeon tick (Argas reflexus): its biology, ecology, and epidemiological aspects
Prevalence of hemoglobin abnormalities in Kebili (Tunisian South)
Lipogranuloma: a preventable complication of dacryocystorhinostomy
Value of basal plasma cortisol assays in the assessment of pituitary-adrenal insufficiency
Bees from the Belgian Congo. The acraensis group of Anthophora
Placing gingival retraction cord
Total serum IgE, allergy skin testing, and the radioallergosorbent test for the diagnosis of allergy in asthmatic children
Acariens plumicoles Analgesoidea parasites des oiseaux du Maroc
Injuries of terminal phalanges of the fingers in children
Biology of flowering and nectar production in pear (Pyrus communis)
Das Reliktvorkommen der Aspisviper (Vipera aspis L.) im Schwarzwald
Hydrological modelling of drained blanket peatland
Pathologic morphology and clinical significance of the anomalous origin of the left circumflex coronary artery from the right coronary artery. General review and autopsy analysis of 30 cases
Cyto genetic analyses of lymphocyte cultures after exposure to calcium cyclamate
Axelrodia riesei, a new characoid fish from Upper Rio Meta in Colombia With remarks concerning the genus Axelrodia and description of a similar, sympatric, Hyphessobrycon-species
Favorable evolution of a case of tuberculosis of pancreas under antibiotic action
RIFM fragrance ingredient safety assessment, Valencene, CAS Registry Number 4630-07-3
Parenteral microemulsions: an overview
Temperate pasture: management for grazing and conservation
Evaluation of a new coprocessed compound based on lactose and maize starch for tablet formulation
Thermal expansion and cracking of three confined water-saturated igneous rocks to 800C
Revision of the genera of the tribe Stigmoderini (Coleoptera: Buprestidae) a discussion of phylogenetic relationships
Anal tuberculosis. Report of a case
Gastric tuberculosis in the past and present
Adaptive responses of the cardiovascular system to prolonged spaceflight conditions: assessment with Holter monitoring

Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(II), copper(II), zinc(II) and cadmium(II). Antiproliferative and superoxide dismutase activity

Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(II), copper(II), zinc(II) and cadmium(II). Antiproliferative and superoxide dismutase activity

Journal of Inorganic Biochemistry 105(9): 1187-1195

ISSN/ISBN: 0162-0134

PMID: 21718655

DOI: 10.1016/j.jinorgbio.2011.05.025

Some new complexes of meclofenamic acid (N-(2,6-dichloro-m-tolyl)anthranilic acid), Hmeclo (1), with potentially interesting biological activities are described. Complexes [Mn(meclo)(2)] (2), [Cu(meclo)(2)(H(2)O)(2)] (3), [Zn(meclo)(2)(H(2)O)(2)] (4) and [Cd(meclo)(2)(H(2)O)(2)] (5) were prepared and structurally characterized by means of vibrational, electronic and (1)H and (13)C NMR spectroscopies. The crystal structure of complexes [Cu(4)(meclo)(6)(OH)(2)(DMSO)(2)]2DMSO (3a) and [Cd(meclo)(2)(DMSO)(3)] (5a) have been determined by X-ray crystallography. Complex (3a) is a centrosymmetric tetramer built up around the planar cyclic Cu(2)(OH)(2) unit. Complex 5a is mononuclear seven-coordinated complex with the meclofenamato ligand behaving as a bidentate deprotonated chelating ligand. Intra and intermolecular hydrogen bonds stabilize these two structures, while the crystal packing is determined by π-π and C-H--π interactions. Meclofenamic acid and its metal complexes have been evaluated for antiproliferative activity in vitro against the cells of three human cancer cell lines, MCF-7 (breast cancer cell line), T24 (bladder cancer cell line), and A-549 (non-small cell lung carcinoma), and a mouse fibroblast L-929 cell line. Complex 5 exhibits the highest selectivity against MCF-7 and 4 shows the highest selectivity against T-24. Complexes 2-5 were found to be more potent cytotoxic agents against T-24 and complex 5 against MCF-7 cancer cell lines than the prevalent benchmark metallodrug, cis-platin. The superoxide dismutase activity was measured by the Fridovich test which showed that complex [Cu(meclo)(2)(H(2)O)(2)] is a good superoxide scavenger.

Please choose payment method:

(PDF emailed within 0-6 h: $19.90)

Accession: 056085549

Download citation: RISBibTeXText

Related references

Organotin meclofenamic complexes: Synthesis, crystal structures and antiproliferative activity of the first complexes of meclofenamic acid - novel anti-tuberculosis agents. Journal of Inorganic Biochemistry 103(5): 738-744, 2009

Differential regulation of copper-zinc superoxide dismutase and manganese superoxide dismutase in the rat corpus luteum: induction of manganese superoxide dismutase messenger ribonucleic acid by inflammatory cytokines. Biology of Reproduction 59(1): 208-215, 1998

Metal complexes of anti-inflammatory drugs. Part V. Meclofenamic acid complexes of manganese(II), iron(III), cobalt(II), nickel(II), copper(II) and zinc(II). Inorganica Chimica Acta 152(3): 171-175, 1988

Binuclear copper(II) complexes of tolfenamic: synthesis, crystal structure, spectroscopy and superoxide dismutase activity. Journal of Inorganic Biochemistry 98(2): 358-364, 2004

Anti-oxidant, in vitro, in vivo anti-inflammatory activity and antiproliferative activity of mefenamic acid and its metal complexes with manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II). Journal of Enzyme Inhibition and Medicinal Chemistry 24(3): 742-752, 2009

Hormonal regulation of copper-zinc superoxide dismutase and manganese superoxide dismutase messenger ribonucleic acid in the rat corpus luteum: induction by prolactin and placental lactogens. Biology of Reproduction 59(3): 599-605, 1998

Time- and dose-dependent differential regulation of copper-zinc superoxide dismutase and manganese superoxide dismutase enzymatic activity and mRNA level by vitamin E in rat blood cells. Redox Report: Communications in Free Radical Research 17(3): 101-107, 2012

Synthesis of dinuclear metal complexes of a macrocyclic ligand with multi-ligating pendant-arms. Crystal structures of its manganese(II) and cadmium(II) complexes. Inorganica Chimica Acta 305(1): 83-90, 2000

Alteration of endogenous glutathione peroxidase, manganese superoxide dismutase, and glutathione transferase activity in cells transfected with a copper-zinc superoxide dismutase expression vector. Explanation for variations in paraquat resistance. Journal of Biological Chemistry 265(19): 10872-10875, 1990

Cloning and sequencing of a rat copper zinc superoxide dismutase complementary dna correlation between copper zinc superoxide dismutase messenger rna level and enzyme activity in rat and mouse tissues. European Journal of Biochemistry 166(1): 181-188, 1987

Zinc(II) complexes derived from pyridine-2-carbaldehyde thiosemicarbazone and (1E)-1-pyridin-2-ylethan-1-one thiosemicarbazone. Synthesis, crystal structures and antiproliferative activity of zinc(II) complexes. Journal of Inorganic Biochemistry 100(9): 1558-1567, 2006

Synthesis, structural and spectroscopic characterization and biomimetic properties of new copper, manganese, zinc complexes: identification of possible superoxide-dismutase mimics bearing hydroxyl radical generating/scavenging abilities. Journal of Inorganic Biochemistry 104(8): 820-830, 2010

The amino-acid sequence of copper/zinc superoxide dismutase from swordfish liver. Comparison of copper/zinc superoxide dismutase sequences. European Journal of Biochemistry 145(3): 477-484, 1984

Intracellular ii associated superoxide scavenging activity protects copper zinc manganese superoxide dismutase deficient saccharomyces cerevisiae against dioxygen stress. Journal of Biological Chemistry 264(21): 12172-12178, 1989

Synthesis, Superoxide Dismutase Mimetic and Anticancer Activities of Metal Complexes of 2,2-Dimethylpentanedioic Acid(2dmepdaH(2)) and 3,3-Dimethylpentanedioic acid(3dmepdaH(2)): X-Ray Crystal Structures of [Cu(3dmepda)(bipy)](2). 6H(2)O and [Cu(2dmepda)(bipy)(EtOH)](2). 4EtOH (bipy = 2,2'Bipyridine). Bioinorganic Chemistry and Applications 2006: 80283, 2006