Synthesis, characterization and biological studies of copper(II) complexes with 2-aminobenzimidazole derivatives

Joseph, J.; Suman, A.; Nagashri, K.; Joseyphus, R. Selwin; Balakrishnan, Nisha

doi:10.1016/j.molstruc.2017.02.021

Cited by 19 publications

(3 citation statements)

References 29 publications

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“…There are few reports of the molar conductivity values of mixed copper(II) compound in water [ 54 ] or DMF [ 55 , 56 , 57 ]. On the other hand, there are conductivity reports for some copper(II) coordination compounds wherein non-ionic complexes were obtained and electrical conductivity data in DMSO were reported, with values between 6 and 11 μS, which indicates that these are non-electrolyte species [ 58 ]. Therefore, our compounds show a small dissociation of an NO 3 counterion.…”

Section: Resultsmentioning

confidence: 99%

Casiopeinas of Third Generations: Synthesis, Characterization, Cytotoxic Activity and Structure–Activity Relationships of Mixed Chelate Compounds with Bioactive Secondary Ligands

et al. 2022

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Casiopeinas are a family of copper(II) coordination compounds that have shown an important antineoplastic effect and low toxicity in normal cells. These compounds induce death cells by apoptosis through a catalytic redox process with endogenous reducing agents. Further studies included a structural variation, improving the activity and selectivity in cancer cells or other targets. In the present work we report the third generation, which contains a bioactive monocharged secondary ligand, as well as the design, synthesis, characterization and antiproliferative activity, of sixteen new copper(II) coordination compounds with curcumin or dimethoxycurcumin as secondary ligands. All compounds were characterized by elemental analysis, FTIR, UV-Vis, magnetic susceptibility, mass spectra with MALDI-flight time, cyclic voltammetry, electron paramagnetic resonance (EPR) spectroscopy and X-ray diffraction. Crystallization of two complexes was achieved in dimethylsulfoxide (DMSO) with polar solvent, and crystal data demonstrated that a square-based or square-base pyramid geometry are possible. A 1:1:1 stoichiometry (diimine: copper: curcuminoid) ratio and the possibility of a nitrate ion as a counterion were supported. 1H, 13C NMR spectra were used for the ligands. A sulforhodamine B assay was used to evaluate the cytotoxicity effect against two human cancer cell lines, SKLU-1 and HeLa. Electronic descriptors and redox potential were obtained by DFT calculations. Structure–activity relationships are strongly determined by the redox potential (E1/2) of copper(II) and molar volume (V) of the complexes. These compounds can be used as a template to open a wide field of research both experimentally and theoretically.

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Section: Resultsmentioning

confidence: 99%

Casiopeinas of Third Generations: Synthesis, Characterization, Cytotoxic Activity and Structure–Activity Relationships of Mixed Chelate Compounds with Bioactive Secondary Ligands

et al. 2022

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“…The plates were allowed to stand for an hour in order to facilitate the diffusion of the drug solution. Then the plates were incubated at 37 °C, 48 h for fungi and the diameter of the inhibition zones were read …”

Section: Experimental Procedures For Biological Studiesmentioning

confidence: 99%

Preparation, characterizations and biological evaluations of new copper(II) complexes containing ONO pincer type ligands

Elamathi

Butcher

Prabhakaran

2018

Applied Organom Chemis

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A new heterocyclic Schiff bases, 6‐methyl/8methyl‐2‐oxo‐1,2‐dihydroquinoline‐3‐carboxaldehyde semicarbazones (H2‐6MOQsc‐H) (H2L1) and (H2‐8MOQsc‐H) (H2L2) and their corresponding copper(II) complexes [CuCl2(H2‐6MOQsc‐H)].3H2O (1), [CuCl2(H2‐8MOQsc‐H)].3H2O (2), [CuNO3(H2‐6MOQsc‐H)(H2O)].NO3 (3) and [CuNO3(H2‐8MOQsc‐H)(H2O)].NO3 (4) have been synthesized and characterized by various physicochemical techniques. The single crystal X‐ray diffraction and spectral data revealed that all of the complexes (1‐4), the ligands coordinated to the Cu(II) ion in a neutral manner via ONO donor atoms and all the complexes exhibited distorted squarepyramidal geometry. The consequence of electronegativity and ring size of nitrogen heterocyclic moiety of ONO donor type of copper(II) chelates on nucleic acid interaction and albumin binding was investigated by in vitro experiments. The interaction of compounds with calf‐thymus DNA (CT‐DNA) has been explored by absorption and emission titration, which exposed those ligands/complexes, could bind with CT‐DNA through electrostatic interaction. The results of gel electrophoresis proved the ability of complexes (1‐4) to cleave the pBR322 plasmid DNA. The interaction of serum albumin (BSA) was investigated by UV‐Vis, fluorescence, synchronous and three dimensional fluorescence spectra. In addition, radical scavenging activity, antifungal activity and cytotoxicity of the newly synthesized compounds were also evaluated. From the results of in vitro studies, it is seen that complex 3 has more potential as compared with other complexes and ligands.

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“…Other interesting applications of benzimidazoles include their used as ionic liquids [7] and N-heterocyclic carbine precursors [8,9]. Guanidine-containing organic compounds such as 2aminobenzimidazole [10,11] present a wide spectrum of applications in the field of pharmaceutical and biological drug design, being the activity against multidrug resistant bacteria the most notable example (Scheme 1) [12][13][14][15]. More recently, chiral 2aminobenzimidazoles have been successfully used as bifunctional Brønsted base/hydrogen bonding organocatalysts [16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Design and preparation of [4,4′-bipyridine]-1,1′-diium trinitromethanide (BPDTNM) as a novel nanosized ionic liquid catalyst: application to the synthesis of 1-(benzoimidazolylamino)methyl-2-naphthols

et al. 2017

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Synthesis, characterization and biological studies of copper(II) complexes with 2-aminobenzimidazole derivatives

Cited by 19 publications

References 29 publications

Casiopeinas of Third Generations: Synthesis, Characterization, Cytotoxic Activity and Structure–Activity Relationships of Mixed Chelate Compounds with Bioactive Secondary Ligands

Casiopeinas of Third Generations: Synthesis, Characterization, Cytotoxic Activity and Structure–Activity Relationships of Mixed Chelate Compounds with Bioactive Secondary Ligands

Preparation, characterizations and biological evaluations of new copper(II) complexes containing ONO pincer type ligands

Design and preparation of [4,4′-bipyridine]-1,1′-diium trinitromethanide (BPDTNM) as a novel nanosized ionic liquid catalyst: application to the synthesis of 1-(benzoimidazolylamino)methyl-2-naphthols

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