Structure, photophysics, electrochemistry, DFT calculation, and in-vitro antioxidant activity of coumarin Schiff base complexes of Group 6 metal carbonyls

Datta, P. K.; Mukhopadhyay, Achintya; Manna, Prasenjit; Tiekink, Edward R. T.; Sil, Parames C.; Sinha, Chittaranjan

doi:10.1016/j.jinorgbio.2010.04.013

Cited by 44 publications

(6 citation statements)

References 66 publications

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“…40 It is earlier reported in literature that complexes possessing O and N donor bidentate ligands have better reactivity for dioxygen. 66 Therefore, scavenging effects on superoxide anion radical were carried out in terms of IC 50 (Table 5). The obtained data suggested that The photocleavage assay also revealed that [(L 1 ) 2 Cu] complex exhibited appreciable photocleavage activity, which makes it a potential photoactivated chemotherapeutic agent.…”

Section: Scavenging Activity By Dpphmentioning

confidence: 99%

Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment

et al. 2020

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Four mononuclear bioefficient imine-based coordination complexes, [(L 1 ) 2 Cu], [(L 1 ) 2 Zn], [(L 2 )Cu(H 2 O)], and [(L 2 )Zn(H 2 O)], were synthesized using ligands [L 1 = 2-(((3-hydroxynaphthalen-2-yl)methylene)amino)-2-methylpropane-1,3-diol and L 2 = 4-(1-((1,3-dihydroxy-2-methylpropan-2-yl)imino)ethyl)benzene-1,3-diol]. The formation of the complexes was ascertained by elemental analysis, Fourier transform infrared, 1H NMR, 13C NMR, electrospray ionization–mass spectroscopy, electron paramagnetic resonance, and thermogravimetric analysis. The comparative binding propensity profiles of the above-synthesized complexes with the DNA/human serum albumin (HSA) were investigated via UV absorption, fluorescence, and Förster resonance energy-transfer studies. On the basis of extended conjugation and planarity, L 1 complexes exhibited superior bioactivity with greater calculated DNA binding constant values, (K b) 2.9444 × 103 [(L 1 ) 2 Cu] and 2.2693 × 103 [(L 1 ) 2 Zn], as compared to L 2 complexes, 1.793 × 103 [(L 2 )Cu(H 2 O)] and 9.801 × 102 [(L 2 )Zn(H 2 O)]. The competitive displacement assay of complexes was performed by means of fluorogenic dyes (EtBr and Hoechst), which corroborates the occurrence of minor groove binding because of the enhanced displacement activity with Hoechst 33258. The minor groove binding of the [(L 1 ) 2 Cu] complex is further confirmed by the molecular docking study. Moreover, the HSA study demonstrated effective static quenching of complexes with substantial K sv values. The [(L 1 ) 2 Cu] complex was found to have pronounced cleavage efficiency as evaluated from sodium dodecyl sulfate polyacrylamide gel electrophoresis electrophoresis. Furthermore, in vitro antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals further proclaimed the remarkable bioefficiency of compounds, which make them promising as active chemotherapeutic agents.

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Section: Scavenging Activity By Dpphmentioning

confidence: 99%

Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment

et al. 2020

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“…[9][10][11][12] Coumarins are widely studied naturally occurring compounds, which are well known for their pharmacological and biological responses like antimicrobial, anticoagulant, antitumor, anti-HIV, chemotherapeutics, and bio-analytical reagents. [13][14][15][16] Certain coumarin derivatives viz. clorobiocin and novobiocin are commercialized as prescription drugs.…”

Section: Introductionmentioning

confidence: 99%

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

et al. 2021

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Four copper(II) complexes 1-4 of 3-acetylchromene-2-one and substituted 3-acetylchromene-2-one derived Schiff bases were synthesized and structurally characterized using analytical and spectral techniques. The molecular structure of complex 1 has been confirmed by single crystal X-ray diffraction studies, which revealed that ligand 3-acetylchromene-2-one-4 N-semicarbazone is coordinated to the metal as ONO pincer type ligand. Two nitrate molecules are coordinated to the copper ion through oxygen atoms, of which one nitrate molecule was found to coordinate via two oxygen atoms, thereby achieving six-coordination. Preliminary biological studies like DNA and protein binding analyses indicated the binding of the ligands and complexes to CT-DNA (Calf Thymus DNA) and BSA (Bovine Serum Albumin). We investigated the effects of complexes 1-4 against amyloid-β (Aβ) toxicity using transgenic Caenorhabditis elegans strains expressing muscle-and neuronal-specific human Aβ 1-42 . The results showed that the complexes 2-4 remarkably reduced the Aβ-induced paralysis phenotype, Aβ plaque deposition, and other Alzheimer's disease-associated functional deficits in C. elegans by their potent antioxidant and antiaggregative properties. Complexes 2-4 delayed Alzheimer's disease pathologies, providing a basis for further investigating these effects on higher models.

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“…Another example involves quinoline with 4(N,N)-dimethylthiosemicarbazone which produced a novel water-soluble sulphur-bridged binuclear copper(II) complex (Senthil Raja et al 2011). Coumarin derivatives, such as 3-acetylcoumarin opted for in this work, are attractive because of their wide variety of antioxidant, antibacterial, antifungal and cytotoxic activities (Datta et al 2011;Bagihalli et al 2008;Phaniband et al 2011;Kulkarni et al 2009;Creaven et al 2009). Moreover, previously reported coumarin Schiff bases and their metal complexes were shown to exhibit outstanding luminescence (Datta et al 2011) which may be advantageous for application of related compounds as probes.…”

Section: Introductionmentioning

confidence: 99%

“…Coumarin derivatives, such as 3-acetylcoumarin opted for in this work, are attractive because of their wide variety of antioxidant, antibacterial, antifungal and cytotoxic activities (Datta et al 2011;Bagihalli et al 2008;Phaniband et al 2011;Kulkarni et al 2009;Creaven et al 2009). Moreover, previously reported coumarin Schiff bases and their metal complexes were shown to exhibit outstanding luminescence (Datta et al 2011) which may be advantageous for application of related compounds as probes. Other studies revealed that the coumarin derivatives interact strongly with DNA and can cause DNA cleavage (Phaniband et al 2011;Kulkarni et al 2009).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin

et al. 2015

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Cu(II), Zn(II) and Re(I) complexes have been synthesized with the Schiff base, N'-[1-(2-oxo-2H-chromen-3-yl)-ethylidene]-hydrazinecarbodithioic acid benzyl ester (SBCM-H) which was prepared by condensation of S-benzyldithiocarbazate and 3-acetylcoumarin. The metal complexes were characterized on the basis of various physico-chemical and spectroscopic techniques including elemental analysis and electrochemical studies, and FT-IR, UV-Vis, NMR, EPR and mass spectroscopy. The Schiff base was found to behave as a bidentate ligand coordinating with Cu(II) and Zn(II) in the thiolate form with 1:2 metal to ligand stoichiometry. Crystals suitable for X-ray diffractometry (XRD) were obtained from the reaction of ReCl(CO)5 with SBCM-H forming a centrosymmetric dimeric complex Re2L2(CO)6 linked by Re-S-Re bridges, where S is the thiolate sulfur of the N,S-bidentate ligand. This Re(I) complex is the first metal carbonyl complex with a bidentate dithiocarbazate ligand to have been characterized by XRD. Cytotoxicity assays revealed enhancement of the bioactivity of SBCM-H upon complexation. Both Cu(II) and Re(I) complexes are found to be active against human breast adenocarcinoma cancer cell lines MDA-MB-231 and MCF-7. TOC diagram.

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Structure, photophysics, electrochemistry, DFT calculation, and in-vitro antioxidant activity of coumarin Schiff base complexes of Group 6 metal carbonyls

Cited by 44 publications

References 66 publications

Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment

Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

Synthesis, characterization and biological activity of Cu(II), Zn(II) and Re(I) complexes derived from S-benzyldithiocarbazate and 3-acetylcoumarin

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