Complexes derived from the copper(II)/succinamic acid/N,N′,N″-chelate tertiary reaction systems: Synthesis, structural and spectroscopic studies

Lazarou, Katerina N.; Chadjistamatis, Iordanis; Terzis, Aris; Perlepes, Spyros P.; Raptopoulou, Catherine P.

doi:10.1016/j.poly.2010.03.003

Cited by 18 publications

(11 citation statements)

References 46 publications

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“…with that of Cu(CF 3 SO 3 ) 2 salt, the band at 1289 cm À1 can be attributed to the m as (SAO) of the CF 3 SO 3 À counter-anion, while those at 1240 and 1229 cm À1 are due to the same vibrations of the monodentately coordinated triflate [44][45][46]. Contrary to this, in the IR spectrum of 3a/b, only one very strong band at 1384 cm À1 due to the m as (NO 3 ) is observed, indicating that the nitrate solely acts as counter-ion [42,43], while in that of 4, the band due to the m as (SO 3 ) is split into two bands (1289 and 1252 cm À1 ) as a consequence of its participation in the hydrogen bonding interactions [47]. The protonation of the N7 nitrogen atom in 1,7-phen in compounds 3a/b and 4 is also evident from 1 H NMR spectra; a broad singlet at 3.80 and 4.12 ppm, respectively, was noted.…”

Section: Spectroscopic Characterizationmentioning

confidence: 91%

Different coordination abilities of 1,7- and 4,7-phenanthroline in the reactions with copper(II) salts: Structural characterization and biological evaluation of the reaction products

et al. 2019

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The reactions between equimolar amounts of CuX 2 (X = NO 3 À and CF 3 SO 3 À ) and two aromatic nitrogencontaining heterocycles differing in the position of nitrogen atoms, 1,7-and 4,7-phenanthroline (1,7and 4,7-phen), were performed in ethanol/methanol at room temperature. When CuX 2 salts were mixed with 4,7-phen, two copper(II) complexes, [Cu(NO 3 ) 2 (4,7-Hphen) 2 ](NO 3 ) 2 (1) and [Cu(CF 3 SO 3 )(4,7phen) 2 (H 2 O) 2 ]CF 3 SO 3 (2), were formed. On the other hand, in the reaction of CuX 2 salts with 1,7-phen, only 1,7-HphenNO 3 (3a/b) and 1,7-HphenCF 3 SO 3 (4) were obtained as the final products. The obtained products 1-4 were characterized by spectroscopic and X-ray diffraction techniques. In the copper(II) complexes 1 and 2, the coordination geometry around the Cu(II) ion is distorted octahedral and square pyramidal, respectively. The antimicrobial potential of the copper(II) complexes 1 and 2 and corresponding compounds used for their synthesis were assessed against four different bacterial species and Candida albicans, displaying moderate growth inhibiting activity. The cytotoxic properties of the investigated complexes were also evaluated against the normal human lung fibroblast cell line (MRC-5) indicating moderate, yet more pronounced cytotoxicity than antimicrobial properties. ⇑ Corresponding author. Fax: +381 34 335 040.

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Section: Spectroscopic Characterizationmentioning

confidence: 91%

Different coordination abilities of 1,7- and 4,7-phenanthroline in the reactions with copper(II) salts: Structural characterization and biological evaluation of the reaction products

et al. 2019

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“…us, the bands at 1279, 1251, and 1024 cm −1 (2) and 1280, 1251, and 1025 cm −1 (3) are attributed to the asymmetric and symmetric stretching modes of the -SO 3 group [33]. e splitting of the band due to the asymmetric stretching vibration of -SO 3 group can be the consequence of its participation in hydrogen bonding interactions leading to its "pseudomonodentate" spectroscopic behavior [35]. Besides that, the two bands at 1223 and 1160 cm −1 (2) and 1222 and 1156 cm −1 (3) can be attributed to the symmetric and asymmetric stretching modes of -CF 3 group of the triflate, respectively [34].…”

Section: Spectral Characterizationmentioning

confidence: 99%

Antimicrobial Activity and DNA/BSA Binding Affinity of Polynuclear Silver(I) Complexes with 1,2-Bis(4-pyridyl)ethane/ethene as Bridging Ligands

Đurić

Vojnović

Andrejević

et al. 2020

Bioinorganic Chemistry and Applications

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1,2-Bis(4-pyridyl)ethane (bpa) and 1,2-bis(4-pyridyl)ethene (bpe) were used for the synthesis of polynuclear silver(I) complexes, {[Ag(bpa)]NO 3 } n (1), {[Ag(bpa) 2 ]CF 3 SO 3 . H 2 O} n (2) and {[Ag(bpe)]CF 3 SO 3 } n (3). In complexes 1-3, the corresponding nitrogencontaining heterocycle acts as a bridging ligand between two Ag(I) ions. In vitro antimicrobial activity of these complexes, along with the ligands used for their synthesis, was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi. e silver(I) complexes 1-3 showed selectivity towards Candida spp. and Gram-negative Escherichia coli in comparison to the other investigated bacterial strains, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MICs) between 2.5 and 25 μg/mL and the growth of E. coli, with MIC value being 12.5 μg/mL. Importantly, complex 2 significantly reduced C. albicans filamentation, an essential process for its pathogenesis. Antiproliferative effect on the normal human lung fibroblast cell line MRC-5 was also evaluated with the aim of determining the therapeutic potential of the complexes 1-3. e interactions of these complexes with calf thymus DNA (ctDNA) and bovine serum albumin (BSA) were studied to evaluate their binding activities towards these biomolecules for possible insights on their mode of action.

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“…This is in accordance with the crystal structures of 3 and 4 determined by X-ray diffraction analysis (vide infra). Complex 2 exhibits a very strong band with two sub-maxima at 1108 and 1064 cm À1 and a strong one at 622 cm À1 which can be attributed to the n(ClO) and d(OClO) modes, respectively, of the uncoordinated perchlorate [31].…”

Section: Spectroscopic Characterizationmentioning

confidence: 99%

“…The presence of the two bands attributed to the asymmetric stretching vibration of ClO 4 À ion can be the consequence of its participation in hydrogen bonding interactions, leading to its "pseudomonodentate" spectroscopic behavior [31,32]. As far as complex 5 is concerned, the presence of a strong band at 656 cm À1 in its IR spectra, indicates no coordination of SbF 6 À to the Ag(I) center [36].…”

Section: Spectroscopic Characterizationmentioning

confidence: 99%

Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth

Savić

Vojnović

Glišić

et al. 2018

European Journal of Medicinal Chemistry

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Mononuclear silver(I) complexes with 1,7-phenanthroline (1,7-phen), [Ag(NO-O,O') (1,7-phen-N7)] (1) and [Ag(1,7-phen-N7)]X, X = ClO (2), CFSO (3), BF (4) and SbF (5) were synthesized and structurally characterized by NMR (H and C), IR and UV-Vis spectroscopy and ESI mass spectrometry. The crystal structures of 1, 3 and 4 were determined by single-crystal X-ray diffraction analysis. In all these complexes, 1,7-phen coordinates to the Ag(I) ion in a monodentate fashion via the less sterically hindered N7 nitrogen atom. The investigation of the solution stability of 1-5 in DMSO revealed that they are sufficiently stable in this solvent at room temperature. Complexes 1-5 showed selectivity towards Candida spp. in comparison to bacteria, effectively inhibiting the growth of four different Candida species with minimal inhibitory concentrations (MIC) between 1.2 and 11.3 μM. Based on the lowest MIC values and the lowest cytotoxicity against healthy human fibroblasts with selectivity index of more than 30, the antifungal potential was examined in detail for the complex 1. It had the ability to attenuate C. albicans virulence and to reduce epithelial cell damage in the cell infection model. Induction of reactive oxygen species (ROS) response has been detected in C. albicans, with fungal DNA being one of the possible target biomolecules. The toxicity profile of 1 in the zebrafish model (Danio rerio) revealed improved safety and activity in comparison to that of clinically utilized silver(I) sulfadiazine.

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Complexes derived from the copper(II)/succinamic acid/N,N′,N″-chelate tertiary reaction systems: Synthesis, structural and spectroscopic studies

Cited by 18 publications

References 46 publications

Different coordination abilities of 1,7- and 4,7-phenanthroline in the reactions with copper(II) salts: Structural characterization and biological evaluation of the reaction products

Different coordination abilities of 1,7- and 4,7-phenanthroline in the reactions with copper(II) salts: Structural characterization and biological evaluation of the reaction products

Antimicrobial Activity and DNA/BSA Binding Affinity of Polynuclear Silver(I) Complexes with 1,2-Bis(4-pyridyl)ethane/ethene as Bridging Ligands

Mononuclear silver(I) complexes with 1,7-phenanthroline as potent inhibitors of Candida growth

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