Synthesis, spectroscopic, and biological studies on copper(II) complexes containing equatorial–apical chloride bridges: crystal structure of [Cu2(μ-Cl)2(O-2-butoxyethylpyridine-2-carboximidate)2Cl2]

Devi, Rachna; Devi, S. Pramodini; Singh, Raj K.; Singh, Ritu; Swu, Toka; Devi, W. Radhapiyari; Singh, Chingakham Brajakishor

doi:10.1080/00958972.2014.902449

Cited by 22 publications

(8 citation statements)

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“…From the [DNA]/(ε a − ε f ) versus [DNA] plot (inset in figure 4), the K b value for 1 was estimated to be 6.16 × 10 4 M −1 (R = 0.9989 for six points), lower than that of a classical intercalator, such as EB-DNA [41], but higher than those of some bi- [42][43][44] and tetracopper(II) complexes [45], and has the same level as those of well-established intercalation agents [46], indicating that 1 strongly binds to HS-DNA, and this may be related to structural characteristics. Comparing the K b value of 1 (K b , 6.16 × 10 4 M −1 ) with those of our previously reported analogous polymeric copper(II) complexes {[Cu 2 (dmaepox)(dabt)](pic)·H 2 O} n (K b , 1.25 × 10 4 M −1 ) and {[Cu 2 (dmapob)(dabt)](NO 3 )·0.6H 2 O} n (K b , 1.04 × 10 4 M −1 ) [20], the K b value of 1 is higher than those of the previously reported polymeric copper(II) complexes, indicating that 1 strongly binds to HS-DNA by intercalation.…”

Section: Dna Interaction Studiesmentioning

confidence: 99%

Synthesis and structure of a 1-D copper(II) coordination polymer bridged both by oxamido and carboxylate: in vitro anticancer activity and reactivity toward DNA and protein BSA

Zheng

et al. 2015

Journal of Coordination Chemistry

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2015) Synthesis and structure of a 1-D copper(II) coordination polymer bridged both by oxamido and carboxylate: in vitro anticancer activity and reactivity toward DNA and protein BSA, Journal of Coordination Chemistry, 68:5, 928-948, A new 1-D copper(II) coordination polymer was synthesized and structurally characterized. In vitro anticancer activity and reactivity toward DNA and protein of the copper(II) polymer was studied.A 1-D copper(II) coordination polymer formulated as {[Cu 2 (bdpox)(dabt)](NO 3 )·H 2 O} n , where H 3 bdpox and dabt denote N-benzoate-N′-[3-(diethylamino)propyl]oxamide and 2,2′-diamino-4,4′-bithiazole, respectively, was synthesized and characterized by elemental analyses, molar conductance *Corresponding authors.Downloaded by [University of Saskatchewan Library] at 07:16 17 March 2015 measurement, IR and electronic spectra studies, and single-crystal X-ray diffraction. The crystal structure analysis reveals that copper(II) ions are bridged by both cis-oxamido and carboxylato groups to form a 1-D coordination polymer with corresponding Cu···Cu separations of 5.2420(10) and 5.1551(8) Å. The endo-and exo-copper(II) ions of the cis-oxamido-bridge are located in distorted square-planar and square-pyramidal geometries, respectively. There is a 2-D hydrogen bonding network in the crystal. The in vitro anticancer activities suggest that the copper(II) complex is active against selected tumor cell lines. The reactivities toward herring sperm DNA and bovine serum albumin (BSA) reveal that the copper(II) complex can interact with DNA by intercalation and effectively quench the intrinsic fluorescence of BSA via a static mechanism. The influence of hydrophobicity of the substituents in bridging ligands on DNA and protein binding properties and the in vitro anticancer activities of such copper(II) polymers is discussed.

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Section: Dna Interaction Studiesmentioning

confidence: 99%

Synthesis and structure of a 1-D copper(II) coordination polymer bridged both by oxamido and carboxylate: in vitro anticancer activity and reactivity toward DNA and protein BSA

Zheng

et al. 2015

Journal of Coordination Chemistry

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“…Complex-8 also showed an infrared stretching assigned to metal-oxygen bonds in the region of 511 cm -1 that correlates to coordinated water molecules (Arjmand, Sayeed, & Muddassir, 2011;Mohamed et al, 2016;Nakamoto, 1997). Two bands in complex-7, which have proximate energy and intensity, correlate to the bridging vibrational mode for the chlorine atoms relative to the metal (Berlini et al, 2009;Devi et al, 2014;Indoria et al, 2015;Nakamoto, 1997). In complex-8, four absorptions of low to medium intensity, in the range 268 to 341 cm -1 , are also associated to bridge and terminal vibrational modes for the metal-chlorine bonds (Devi et al, 2014;Nakamoto, 1997).…”

Section: Infrared Spectroscopymentioning

confidence: 99%

Synthesis, characterization and antimicrobial effect of Cu(ii) and Zn(ii) compounds derived from 1,2,4-triazoles

et al. 2022

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Compounds of Cu(II) and Zn(II) with 3-R-1H-1,2,4-triazole-5-amine {R = methyl (mta), phenyl (pta)} were prepared and characterized by infrared spectroscopy (IR), multinuclear NMR (1H, 13C), electronic spectroscopy (UV-VIS), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), microanalyses and melting point. Dimeric, monomeric, and polymeric materials were synthesized in this work. The Zn(II)-1,2,4-triazole derivatives have the metal ion at the center of two geometric arrangements, being a tetrahedron for the complex-7 and 9, and an octahedron for the complex-8. The only polymeric material, complex-7, was characterized by the DSC analytical data. The Decomposition reaction of complex-8 in chloroform produced the complex-9, a aminoguanidine derivative, and the Zn(II)-benzoate compound. The IR and UV-VIS of Cu(II)-mta derivatives revealed two possible geometric patterns for the metallic ion; a distorted bipyramidal trigonal geometry for compounds 10 and 11 in solution, and in the solid state, the same geometry for complex-10, but for complex-11, the IR data suggest a distorted octahedral geometry. The biological assay of the 1,2,4-triazole compounds and their metal derivatives against Gram-positive and Gram-negative bacteria shown the compounds of Zn(II) as the only active materials with values of MIC within the range of 133.5 µM (83.3 µg / mL) to 360.7 µM (166.6 µg / mL).

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“…The modified part of the ligand in the complexes can be considered as an ester including the alkoxy group and the imine group. As a rule, an ester is characterized by two bands of asymmetric C-O stretching in the 1300-1000 cm −1 region [47], which in the metal complexes is shifted to higher frequency region [24,30,44]. In all spectra of the complexes 1-4, a strong band at ca.…”

Section: Ir Analysismentioning

confidence: 99%

“…Two triphenylphosphine groups completed the coordination sphere of the metal [20]. In some Cu(II) complexes based on cyanopyridine ligands, similar alcoholysis of cyano groups takes place [20][21][22][23][24][25][26]. The methyl group at the nitrogen atom prevents deprotonation of the imidazole ring in 4,5-dicyano-1-methylimidazole, which is thus less acidic than 4,5-dicyanoimidazole [27].…”

Section: Introductionmentioning

confidence: 99%

“…There are still no known organometallic complexes derived from 4,5-dicyano-1-methylimidazole, where the ligand coordinates to the metal ion in bidentate fashion through the N atoms of the heterocycle and of carboximidate, obtained from CN activation. However, based on reported carboximidate metal complexes derived from cyanopyridine [20][21][22][23][24][25][26] and 4,5-dicyanoimidazol [20], it is logical to assume that such complexes also can be synthesized based on this ligand. Therefore, in the present study, the reactions of 4,5-dicyano-1-methylimidazole with CuCl 2 and CuBr 2 were compared in different alcoholic media.…”

Section: Introductionmentioning

confidence: 99%

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Activation of the Cyano Group at Imidazole via Copper Stimulated Alcoholysis

et al. 2019

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Reactions of 4,5-dicyano-1-methylimidazole with CuX2 (X = Cl, Br) in alcohol solvents (ethanol and methanol) resulted in the formation of Cu(II) carboximidate complexes [CuCl2(5- cyano-4-C(OEt)N-1-methylimidazole)(EtOH)] (1), [Cu2(µ-Cl)2Cl2(5-cyano-4-C(OMe)N-1-methylimidazole)2] (2), [Cu2(µ-Br)2Br2(5-cyano-4-C(OMe)N-1-methylimidazole)2] (3), and [Cu2(µ-Br)2Br2(5-cyano-4-C(OEt)N-1-methylimidazole)2] (4). The structures were determined by the X-ray crystallographic method, and further spectroscopic and computational methods were employed to explain the structural features. The solvent contributed to the alcoholysis reaction of the cyano group, as the result of which the ligand coordinated to the metal center in bidentate mode forming a five-membered chelating ring. In 1, the solvent also acts as an additional ligand, which coordinates to the metal center of a monomeric complex. In compounds 2–4, two halogen ligands link the metal atoms forming dihalo-bridged copper dimers. The infrared absorption characteristics were verified by simulation of the infrared spectra at the density functional theory level. In addition, the electronic absorption characteristics were explained by simulation of the UV–Vis spectra using the TD-DFT method. Molecular modelling at the DFT level was performed to study the effects of halogen type and steric hindrance of the alkoxy groups in forming the copper(II) complexes.

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Synthesis, spectroscopic, and biological studies on copper(II) complexes containing equatorial–apical chloride bridges: crystal structure of [Cu₂(μ-Cl)₂(O-2-butoxyethylpyridine-2-carboximidate)₂Cl₂]

Cited by 22 publications

References 69 publications

Synthesis and structure of a 1-D copper(II) coordination polymer bridged both by oxamido and carboxylate: in vitro anticancer activity and reactivity toward DNA and protein BSA

Synthesis and structure of a 1-D copper(II) coordination polymer bridged both by oxamido and carboxylate: in vitro anticancer activity and reactivity toward DNA and protein BSA

Synthesis, characterization and antimicrobial effect of Cu(ii) and Zn(ii) compounds derived from 1,2,4-triazoles

Activation of the Cyano Group at Imidazole via Copper Stimulated Alcoholysis

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