New copper(<scp>ii</scp>) complexes of the anti-inflammatory drug mefenamic acid: a concerted study including synthesis, physicochemical characterization and their biological evaluation

Sharma, Raj Pal; Kumar, Santosh; Venugopalan, Paloth; Ferretti, Valeria; Tarushi, Alketa; Psomas, George; Witwicki, Maciej

doi:10.1039/c6ra14706b

Cited by 53 publications

(21 citation statements)

References 81 publications

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“…In the case of 4 , the calculated G value is 2.74, strongly implying that the observed EPR features arise from the coupling of g ‐tensors from differently oriented Cu II coordination polyhedra in the solid state rather than from a d z ² contribution to the copper(II) ground state. [20a] Hence, the ground state of Cu II in 4 is expected to be dominated by the d x ²– y ² molecular orbital and this is further supported by DFT calculations.…”

Section: Resultsmentioning

confidence: 66%

“…The X‐band EPR spectrum of the polycrystalline compound [Cu 2 Cl 4 (L)] · 2CH 3 CN with substituted 1,3,5‐triazine‐2,4,6‐triamine ligand L with g 1 = 2.05, g 2 = 2.11, and g 3 = 2.24 was interpreted by the authors in terms of a rhombic symmetry. [20b] However, the G value calculated by us from these experimental data is equal to 3.06 indicating that the effective g values are not molecular. Our inspection of the crystal structure reveals that while the two Cu II centers with the same CuN 3 Cl 2 donor set in the molecule of [Cu 2 Cl 4 (L)] · 2CH 3 CN are symmetry‐related, their local molecular axes are profoundly misaligned.…”

Section: Resultsmentioning

confidence: 83%

“…In the crystal structure of [Cu(mpppa)Cl 2 ] {mpppa = N ‐methyl‐ N ‐[(6‐pivaloylamido‐2‐pyridyl)methyl]‐ N ‐(2‐pyridylethyl)amine}, the complex molecules with a CuN 3 Cl 2 chromophore are arranged in a 1D helical chain through intermolecular C–H ··· Cl hydrogen‐bonding interactions in the way similar to 4 . [20c] Three distinct g values: g 1 = 2.185, g 2 = 2.140, and g 3 = 2.068 observed in its powder EPR spectrum were also interpreted as arising from a rhombic pattern. The calculated G value of 1.80 does not support this assignment.…”

Section: Resultsmentioning

confidence: 99%

“…The polycrystalline Cu II complex of the asymmetric Schiff base ligand derived from 2‐(2‐aminoethyl)pyridine and 3,5‐di‐ tert ‐butyl‐4‐hydroxybenzaldehyde with a CuN 2 O 3 donor set showed three signals in the Q‐band EPR spectrum with observed g values of 2.180, 2.115, and 2.059. [20d] The spectrum was considered a result of cooperative effects because of the magnetic exchange between the nonequivalent paramagnetic centers with the observed values of g components caused by coupling of the g matrixes. The calculated G value of 2.10 is in accord with the conclusion made by the authors.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, and Magnetic Properties of a Series of Copper(II) Chloride Complexes of Pyridyliminebenzoic Acids

et al. 2018

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A series of Cu II halide complexes, Cu(HL1)Cl 2 ·CH 3 OH (1), [Cu(L1)Cl] 2 ·H 2 O (2), [Cu(HL2)Cl 2 ] 2 ·2DMF (3), [Cu(HL2) 2 Cl] n Cl n · 2nH 2 O (4), and [Cu(L3)Cl] n (5), containing pyridyliminebenzoic acids HL1, HL2, and HL3 derived from o-, m-, and p-aminobenzoic acids, respectively, have been obtained as single crystals and characterized by elemental analysis, IR, EPR spectroscopy, magnetic measurements, and single-crystal X-ray diffraction techniques. The results obtained show the formation of molecular (1), dimeric (2, 3), and polymeric structures (4, 5) based on chloride (1-4) and carboxylate bridges (5) with copper(II) ions in the square pyramidal geometry of varying degrees of distortion. In the case of 2 and 5 the ligand deprotonation was completely achieved even in the absence of a base. The closest Cu···Cu separations are found in the crystal lattices of the polymer 5 (3.33 Å) and dimers 2 (3.35 Å) and 3 (3.38 Å).[a]We have been exploring the chemistry of the Schiff base ligands that originate from the condensation of 2-PCA and aminobenzoic acids towards 3d metals (Cr, Mn, Co, Ni, Zn) with the aim of producing new complexes with diverse potential advantages. [9] We have now extended our investigations to copper and describe herein the formation and crystal structures of five new copper(II) complexes, Cu(HL1)Cl 2 ·CH 3 OH (1), [Cu(L1)Cl] 2 ·H 2 O (2), [Cu(HL2)Cl 2 ] 2 ·2DMF (3), [Cu(HL2) 2 Cl] n Cl n · 2nH 2 O (4), and [Cu(L3)Cl] n (5), containing pyridyliminebenzoic acids HL1, HL2, and HL3 derived from o-, m-and p-aminobenzoic acids, respectively (Scheme 1, DMF = N,N-dimethylformamide). The position of the carboxylate group in the structural isomers HL1-HL3 influences the amount of chloride ligands in the coordination environments around the copper atoms in 1-5 what imposes the particular bridging pattern between the metal centers. Magnetic susceptibility measurements revealed antiferromagnetic (1-3, 5) and ferromagnetic coupling (4) between the Cu atoms. The data obtained were compared to the exchange parameters of other Cu II dimers and polymers with chloro bridges to assess their consistency with known magnetostructural J-correlations. Moreover, theoretical methods were employed to provide a detailed analysis of the electronic structures of the complexes and independent evaluation of the magnetic coupling constants. Scheme 1. Formation of Schiff base ligands HL1, HL2, and HL3 and respective copper(II) complexes 1-5. Figure 5. Fragment of the crystal structure of 5 with principal labeling and displacement ellipsoids for non-H atoms drawn at the 50 % probability level (left). One-dimensional double-stranded polymer formed by Cu-O coordination bonding in complex 5 projected oblique to the b axis (right).

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Section: Resultsmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis, Characterization, and Magnetic Properties of a Series of Copper(II) Chloride Complexes of Pyridyliminebenzoic Acids

et al. 2018

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“…X-ray crystallography [23, 24, 40-48, 50, 136-138, 140-142, 145, 150, 151, 156-214] IR-spectroscopy [37, 41, 51, 54, 137, 140, 142, 145, 148, 149, 156, 158-161, 166-170, 172-174, 178, 179, 181, 182, 184-186, 188, 189, 191-198, 200, 202, 204, 205, 207-210, 215-233] Circular dichroism spectroscopy [8, 33-35, 39, 40, 142, 141, 143, 145-149, 163, 168, 169, 172, 179, 185, 189, 193, 196, 199, 202, 203, 206, 216, 219, 221, 223, 225, 226, 229, 231-239] EPR-spectroscopy [49,51,54,159,167,181,187,197,200,201,209,215,216,219,222,223,240] NMR-spectroscopy [37, 41, 52, 140, 142, 149, 155, 158, 161, 172, 179, 181, 183, 185, 188, 191, 192, 200, 202, 204, 205, 207, 209, 210, 214, 218-221, 223, 225, 227, 229-232, 236, 238, 241-243] Cyclic voltammetry [42-46, 48, 50, 54, 149, 151, 159, 164, 167, 173, 175, 176, 179, 184, 189, 208, 211-213, 221, 230, 240, 241, 244-247] X-ray crystallography, as a rule, is used for corroboration or specification of the structure of coordinated metal complexes themselves, [24,40,42] in particular, new biologically active compounds or earlier unknown coordination structures. [7,41,43,44,248] X-ray photoelectron spectroscopy for C, N, and O is used to obtain the information of the changes in the energy of atom bonds of these elements in the protein during the formation .…”

Section: Methods Sourcementioning

confidence: 99%

Supramolecular interaction of transition metal complexes with albumins and DNA: Spectroscopic methods of estimation of binding parameters

Galkina

Проскурнин

2018

Applied Organom Chemis

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Binding parameters of metal complexes with albumins and DNA since the middle of 1990s are considered and summarized. The most widespread spectroscopic methods of estimation of binding parameters are discusseddirect fluorescent methods, indirect fluorescent methods (by fluorescence quenching parameters), and ways of estimation of binding constants by other optical spectroscopic methods. The methods and approaches to calculations used for the determination of binding constants are discussed. The data on the already found binding constants and kinetic parameters is systematized.KEYWORDS albumins, DNA, metal complexes, proteins, supramolecular interaction Funding information: Russian Foundation for Basic Research, Grant/Award Number: 16-03-01089_a 16-53-50027_YaF_a Abbreviations and designations used: F 0 , fluorescence intensity in the absence of a quencher; F, fluorescence intensity in the presence of a acid); NTSC, a new thiosemicarbazone; o-cbiaH, 5-(2-carboxybenzyloxy)isophthalic acid; o-van-gln, a Schiff base derived from o-vanillin and glutamine; o-van-L-met, Schiff base derived from o-vanillin and L-methionine; oxo, 5-

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A trinuclear copper (II) complex of naproxen‐appended salicylhydrazide: Synthesis, crystal structure, DNA binding and molecular docking study

Bhattacherjee

Roy

Naskar

et al. 2021

Applied Organom Chemis

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A trinuclear copper complex [Cu 3 (napxshz) 2 (phen) 2 ] has been synthesised using a tribasic naproxen-appended ligand [propanoyl) benzohydrazide] and 1,10-phenanthroline. The complex was characterised by different spectroscopic methods such as Fouriertransform infrared (FT-IR), ultraviolet-visible (UV-Vis) and electrospray ionisation (ESI)-mass spectroscopy. The solid-state structure of the ligand and complex 1 was established by single-crystal X-ray diffraction analysis. The interaction of the complex and the ligand with DNA was investigated by UV-visible spectroscopy and fluorometric titrations. The calculated binding constants (K b ) of the complex and the ligand with ct-DNA show that the complex has a higher binding affinity than the ligand H 3 napxshz. Quantum chemical calculations were performed to understand the structural aspects of the complex and its interactions with DNA. The molecular docking study reveals the interaction between DNA, and the complex is in intercalative mode.

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New copper(ii) complexes of the anti-inflammatory drug mefenamic acid: a concerted study including synthesis, physicochemical characterization and their biological evaluation

Abstract: The interaction of three newly synthesized copper(ii) mefenamate complexes with bovine/human serum albumin was studied by fluorescence emission spectroscopy.

Cited by 53 publications

References 81 publications

Synthesis, Characterization, and Magnetic Properties of a Series of Copper(II) Chloride Complexes of Pyridyliminebenzoic Acids

Synthesis, Characterization, and Magnetic Properties of a Series of Copper(II) Chloride Complexes of Pyridyliminebenzoic Acids

Supramolecular interaction of transition metal complexes with albumins and DNA: Spectroscopic methods of estimation of binding parameters

A trinuclear copper (II) complex of naproxen‐appended salicylhydrazide: Synthesis, crystal structure, DNA binding and molecular docking study

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