Binuclear copper(II) complexes of tolfenamic: synthesis, crystal structure, spectroscopy and superoxide dismutase activity

Kovala‐Demertzi, Dimitra; Galani, Angeliki; Demertzis, Mavroudis A.; Skoulika, Stavroula; Kotoglou, Chronis

doi:10.1016/j.jinorgbio.2003.11.004

Cited by 89 publications

(31 citation statements)

References 23 publications

(43 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Two binuclear copper(II) tolfenamates of formula [Cu 2 (tolf 2 ) 4 L 2 ], where L is H 2 O or dmf have been reported by Kovala-Demertzi and co-authors [9,27]. Crystal structure of [Cu 2 (tolf 2 ) 4 (dmf) 2 ] showed that the tolfenamate ligands are bidentate and act as syn-syn bridging ligands between the centrosymmetric copper atoms.…”

Section: Introductionmentioning

confidence: 94%

“…Several copper(II) fenamates have been crystallographically characterized [6,7]. X-ray analysis of some copper(II) fenamates (ArCO 2 -) of general formula [Cu 2 (ArCO 2 ) 4 L 2 ], where L is H 2 O, dmf, dmso or caffeine showed, that the copper(II) atoms are bridged in pairs by four fenamate groups to form binuclear molecules [8][9][10][11][12][13][14][15][16][17]. On the other hand, X-ray analysis of some copper(II) fenamates of general formula [Cu(ArCO 2 ) 2 L 2 (H 2 O) n ], where n = 0-2 and L = N,N-dietylnicotinamide, 2-pyridylmethanol, pyridine or imidazole revealed the presence of monomeric complexes with tetragonal-pyramidal or tetragonal-bipyramidal environment about the copper atom [18][19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Structural and spectroscopic characterization of copper(II) tolfenamate complexes

Švorec

Lörinc

Moncóľ

et al. 2009

Transition Met Chem

View full text Add to dashboard Cite

The synthesis and characterization of four new solid complexes, Cu(tolf) 2 L 2 (tolf = tolfenamate, L = 2-pyridylmethanol (2-pyme), 3-pyridylmethanol (3-pyme), nicotinamide (na)) and Cu(tolf) 2 (dena) 2 (H 2 O) 2 (dena = N,N-diethylnicotinamide) is reported. The composition and stereochemistry as well as the mode for ligand coordination have been determined by elemental analysis, IR, electronic and EPR spectra. The carboxyl group of the tolfenamate anion coordinates to the Cu(II) atom as an unidentate or as a chelating ligand. The EPR spectra of the powdered solids are consistent with spin S = . The crystal structure of Cu(tolf) 2 (dena) 2 (H 2 O) 2 has been determined at 293 K. The Cu(II) atom has a tetragonal-bipyramidal arrangement (CuO 4 N 2 ). The spectroscopic data indicate that each copper(II) atom in Cu(tolf) 2 L 2 has a tetragonal-bipyramidal environment built up by bidentate unsymmetrically coordinate tolfenamates and unidentate N-donor atom ligands.

show abstract

Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Structural and spectroscopic characterization of copper(II) tolfenamate complexes

Švorec

Lörinc

Moncóľ

et al. 2009

Transition Met Chem

View full text Add to dashboard Cite

show abstract

“…The four carboxylate groups from four ligands are in a bidentate bridging mode. The square-pyramidal geometry with a DMF O-atom or H 2 O occupying both apical positions as was established by single-crystal X-ray study [9] [14]. The solution spectral data indicate that the Mn, Co, and Ni complexes are all solvated with two solvent molecules coordinating in a pseudo-octahedral arrangement (Reaction 6).…”

mentioning

confidence: 92%

“…The superoxide dismutase activity was measured, and IC 50 value was determined by the Fridovich test. According to the usual criteria, the Cu complex of tolfenamic is considered as potent SOD mimic [9]. A review of the synthesis and crystal structures of a number of anti-inflammatory compounds as ligands in organotin complexes, and a review of Cu complexes with NSAIDs have recently been published [10] O], and the complexes were tested for their antioxidant and anti-inflammatory activities in the carrageenin-induced rat paw edema assay.…”

mentioning

confidence: 99%

Anti‐Inflammatory, Antiproliferative, and Radical‐Scavenging Activities of Tolfenamic Acid and Its Metal Complexes

Kovala‐Demertzi

Hadjipavlou‐Litina

Primikiri

et al. 2009

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

Some new complexes of tolfenamic acid (=2-[(2-methyl-3-chlorophenyl)amino]benzoic acid; Htolf) with potentially interesting biological activities are described. The complexes [Mn(tolf)(2)(H(2)O)(2)], [Co(tolf)(2)(H(2)O)(2)], [Ni(tolf(2)(H(2)O)(2)], [Cu(tolf)(2)(H(2)O)](2), and [Zn(tolf)(2)(H(2)O)] were prepared by the reaction of tolfenamic acid, a potent anti-inflammatory drug, with metal salts. The radical-scavenging activities of the complexes were evaluated using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical-scavenging assay. Their ability to inhibit soybean lipoxygenase, beta-glucuronidase, and trypsin-induced proteolysis was studied. Their inhibitory effects on rat paw edema induced by carrageenin was studied and compared with those of tolfenamic acid. The complex [Zn(tolf)(2)(H(2)O)] exhibited the strongest in vivo inhibitory effect at 0.1 mm/kg Body Weight (BW; 93.0+/-0.9%), superior than the inhibition induced by tolfenamic acid at the same molar dose (76.0+/-0.9%). Tolfenamic 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. The complexes [Mn(tolf)(2)(H(2)O)(2)] and [Cu(tolf)(2)(H(2)O)](2) have shown selectivity against T24 cell line. The IC(50) values of these two complexes against T24 cancer cell lines are in a micromolar range similar or better to that of the antitumor drug cisplatin.

show abstract

“…Superoxide dismutase activity was measured as described by reported method [27]. The assay is based on the reduction of nitroblue tetrazolium (NBT) by superoxide ions generated by the xanthine-xanthine oxidase (X-XO) system.…”

Section: Superoxide Scavenging Assaymentioning

confidence: 99%

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: A structure–activity relationship study

Prashanth

Madaiah

Revanasiddappa

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

View full text Add to dashboard Cite

Binuclear copper(II) complexes of tolfenamic: synthesis, crystal structure, spectroscopy and superoxide dismutase activity

Cited by 89 publications

References 23 publications

Structural and spectroscopic characterization of copper(II) tolfenamate complexes

Structural and spectroscopic characterization of copper(II) tolfenamate complexes

Anti‐Inflammatory, Antiproliferative, and Radical‐Scavenging Activities of Tolfenamic Acid and Its Metal Complexes

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: A structure–activity relationship study

Contact Info

Product

Resources

About