Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity

Creaven, Bernadette S.; Devereux, Michael; Karcz, Dariusz; Kellett, Andrew; McCann, Malachy; Noble, Andy; Walsh, Maureen

doi:10.1016/j.jinorgbio.2009.05.017

Cited by 101 publications

(45 citation statements)

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“…It is worth to mention that the IR spectrum of the ligand displays another band at 1723 cm −1 , which can be attributed to the presence of the lactone group in the coumarin ring [28, 29]. The band observed at 1272 cm −1 is assigned to ν (C–O–C) of the coumarin ring [30], while the band at 1253 cm −1 is ascribed to the phenolic C–O stretching vibrations [31], and another one in the region from 1567 to 1483 cm −1 is assigned to the combination of ν (C=C) of the aromatic ring system [32]. The broad band in the region of 3142–3180 cm −1 in the free ligand is assigned to the stretching vibration of the amide group (NH).…”

Section: Resultsmentioning

confidence: 99%

Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine

2017

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A hydrazone Schiff base ligand was synthesized by the condensation of 3-formyl-4-hydroxycoumarin and oxalyldihydrazide in the molar ratio 2:1. The Schiff base ligand acts as a mono-, bi-, tri- or even tetradentate ligand with metal cations in the molar ratios 1:1 or 2:1 (M:L) to yield either mono- or binuclear complexes as keto or enol isomers, where M = Co(II), Ni(II), Cu(II), VO(IV), and Fe(III). The ligand and its metal complexes were characterized by elemental analyses, IR, 1H NMR, mass, and UV–Vis spectroscopy. Furthermore, the magnetic moments were calculated from the measured electric conductivities of the complexes. According to the received data, the dihydrazone ligand contains one or two units of ONO domains and can bind to the metal ions via the azomethine nitrogen, the carbonyl oxygen atoms, and/or the phenolic oxygen atoms. Electronic spectra and the magnetic moments of all complexes show that the complexes’ geometries are either octahedral, tetrahedral, square planar, or square pyramidal. Cyclic voltammograms of the mononuclear Co(II) and Ni(II) complexes show quasi-reversible peaks. Tests against two pathogenic bacteria as Gram-positive and Gram-negative bacteria for both, the Schiff base ligand and its metal complexes were carried out. In addition, also one kind of fungi was tested. The synthesized complexes demonstrate mild antibacterial and antifungal activities against these organisms.Graphical abstract Electronic supplementary materialThe online version of this article (doi:10.1007/s00706-017-2075-9) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine

2017

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“…Inorganic medicinal chemistry, an interdisciplinary research field, is advancing our knowledge of metal toxicity and facilitating the design of metal-containing compounds as effective and targeted antimicrobials, offering a realistic alternative to organic antibiotics (Lemire et al, 2013). We have previously demonstrated that Cu(II), Mn(II), and Ag(I) chelates containing phen-type ligands exhibit antifungal activity against clinical isolates of C. albicans (Devereux et al, 2000; Geraghty et al, 2000; Coyle et al, 2003; McCann et al, 2004; Creaven et al, 2009). Therefore, we were prompted to assess the antifungal chemotherapeutic potential of this class of metal chelate against the highly resistant C. haemulonii species complex.…”

Section: Discussionmentioning

confidence: 99%

Antifungal Potential of Copper(II), Manganese(II) and Silver(I) 1,10-Phenanthroline Chelates Against Multidrug-Resistant Fungal Species Forming the Candida haemulonii Complex: Impact on the Planktonic and Biofilm Lifestyles

et al. 2017

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Candida haemulonii, Candida haemulonii var. vulnera and Candida duobushaemulonii, which form the C. haemulonii complex, are emerging etiologic agents of fungal infections known to be resistant to the most commonly used antifungals. The well-established anti-Candida potential of metal complexes containing 1,10-phenanthroline (phen) ligands encouraged us to evaluate different copper(II), manganese(II), and silver(I) phen chelates for their ability to inhibit planktonic growth and biofilm of C. haemulonii species complex. Two novel coordination complexes, {[Cu(3,6,9-tdda)(phen)2].3H2O.EtOH}n and [Ag2(3,6,9-tdda)(phen)4].EtOH (3,6,9-tddaH2 = 3,6,9-trioxaundecanedioic acid), were synthesized in a similar fashion to the other, previously documented, sixteen copper(II), manganese(II), and silver(I) chelates employed herein. Three isolates of each C. haemulonii species complex were used and the effect of the metal chelates on viability was determined utilizing the CLSI standard protocol and on biofilm-growing cells using the XTT assay. Cytotoxicity of the chelates was evaluated by the MTT assay, employing lung epithelial cells. The majority of the metal chelates were capable of interfering with the viability of planktonic-growing cells of all the fungal isolates. The silver complexes were the most effective drugs (overall geometric mean of the minimum inhibitory concentration (GM-MIC) ranged from 0.26 to 2.16 μM), followed by the manganese (overall GM-MIC ranged from 0.87 to 10.71 μM) and copper (overall GM-MIC ranged from 3.37 to >72 μM) chelates. The manganese chelates (CC50 values ranged from 234.51 to >512 μM) were the least toxic to the mammalian cells, followed by the silver (CC50 values ranged from 2.07 to 13.63 μM) and copper (CC50 values ranged from 0.53 to 3.86 μM) compounds. When tested against mature biofilms, the chelates were less active, with MICs ranging from 2- to 33-fold higher levels when compared to the planktonic MIC counterparts. Importantly, manganese(II), copper(II), and silver(I) phen chelates are relatively cheap and easy to synthesize and they offer significant antifungal chemotherapeutic potential for the treatment of highly resistant pathogens.

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“…On the other hand, the band observed at 1272 cm -1 is assigned to ν(C-O-C) of coumarine ring [24] while the band at 1264-1267 cm -1 is ascribed to ν(C-O) stretching vibrations and around the region from 1567 to 1483 cm -1 is assigned to the combination of ν(C=C) of the aromatic ring [25].…”

Section: Schiff Base Hl Ligandmentioning

confidence: 99%

Synthesis, spectroscopic studies and inhibitory activity against bactria and fungi of acyclic and macrocyclic transition metal complexes containing a triamine coumarine Schiff base ligand

Mahmoud

Linert

2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity

Cited by 101 publications

References 71 publications

Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine

Syntheses, characterization, and biological activity of novel mono- and binuclear transition metal complexes with a hydrazone Schiff base derived from a coumarin derivative and oxalyldihydrazine

Antifungal Potential of Copper(II), Manganese(II) and Silver(I) 1,10-Phenanthroline Chelates Against Multidrug-Resistant Fungal Species Forming the Candida haemulonii Complex: Impact on the Planktonic and Biofilm Lifestyles

Synthesis, spectroscopic studies and inhibitory activity against bactria and fungi of acyclic and macrocyclic transition metal complexes containing a triamine coumarine Schiff base ligand

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