Radical-induced DNA damage by cytotoxic square-planar copper(II) complexes incorporating o-phthalate and 1,10-phenanthroline or 2,2′-dipyridyl

Kellett, Andrew; Howe, Orla; O’Connor, Mark J.; McCann, Malachy; Creaven, Bernadette S.; McClean, Siobhán; Kia, Agnieszka Foltyn-Arfa; Casey, Alan; Devereux, Michael

doi:10.1016/j.freeradbiomed.2012.05.034

Cited by 71 publications

(63 citation statements)

References 82 publications

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“…The following metal chelates were prepared using previously published methods: [Cu(ph)(phen)(H 2 O) 2 ] ( 1 ) (phH 2 = phthalic acid) (Kellett et al, 2012); [Cu(ph)(phen) 2 ].3H 2 O.2EtOH ( 2 ) (Kellett et al, 2011); [Cu(isoph)(phen) 2 ].6H 2 O.EtOH ( 3 ) (isophH 2 = isophthalic acid) (Kellett et al, 2011); [{Cu(phen) 2 } 2 (terph)](terph).13.5H 2 O.2EtOH ( 4 ) (terphH 2 = terephthalic acid) (Kellett et al, 2011); [Cu 2 (oda)(phen) 4 ](ClO 4 ) 2 .2.76H 2 O.EtOH ( 5 ) (odaH 2 = octanedioic acid) (Devereux et al, 1999); [Cu(phendione) 3 ](ClO 4 ) 2 .4H 2 O ( 6 ) (phendione = 1,10-phenanthroline-5,6-dione) (McCann et al, 2004); [Mn(ph)(phen)(H 2 O) 2 ] ( 8 ) (Devereux et al, 2000); [Mn(ph)(phen) 2 (H 2 O)].4H 2 O ( 9 ) (Devereux et al, 1999); [Mn 2 (isoph) 2 (phen) 3 ].4H 2 O ( 10 ) (Devereux et al, 2000); {[Mn(phen) 2 (H 2 O) 2 ]} 2 (isoph) 2 (phen).12H 2 O ( 11 ) (Devereux et al, 2000); [Mn(tereph)(phen) 2 ].5H 2 O ( 12 ) (Leon, 2000); [Mn 2 (oda)(phen) 4 (H 2 O) 2 ][Mn 2 (oda)(phen) 4 (oda) 2 ].4H 2 O ( 13 ) (Casey et al, 1994); {[Mn(3,6,9-tdda)(phen) 2 ].3H 2 O.EtOH} n ( 14 ) (3,6,9-tddaH 2 = 3,6,9-trioxaundecanedioic acid) (McCann et al, 1997); [Ag(phendione) 2 ]ClO 4 ( 15 ) (McCann et al, 2004); [Ag(phen) 2 ]ClO 4 ( 17 ) (McCann et al, 2004) and [Ag 2 (phen) 3 (udda)].3H 2 O ( 18 ) (uddaH 2 = undecanedioic acid) (Thornton et al, 2016). The novel complexes, {[Cu(3,6,9-tdda)(phen) 2 ].3H 2 O.EtOH} n ( 7 ) and [Ag 2 (3,6,9-tdda)(phen) 4 ].EtOH ( 16 ), were synthesized using the two-step procedures outlined below.…”

Section: Methodsmentioning

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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Section: Methodsmentioning

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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“…It is worthy of note that no external reducing agent was added. This does not necessarily suggest a hydrolytic cleavage mechanism, as several self-activating oxidative Cu metallonucleases have been described [39][40][41][42][43][44][45]. In fact, Cu complexes that actually cleave DNA by a hydrolytic mechanism are less numerous [46][47][48].…”

Section: Dna Cleavage and Phosphate Diester Hydrolysismentioning

confidence: 99%

DNA damage and induction of apoptosis in pancreatic cancer cells by a new dinuclear bis(triazacyclonane) copper complex

Montagner

Gandin

Marzano

et al. 2015

Journal of Inorganic Biochemistry

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The dinuclear copper(II) complex [Cu 2 {bcmp(-H)}(μ-OH)](NO 3 ) 2 ·H 2 O (1, bcmp = 2,6-bis(1,4,7-triazacyclonon-1-ylmethyl)-4-methylphenol) has been synthesized and characterized by electrospray ionization mass spectrometry, potentiometric titration and cyclovoltammetry. The X-ray structure of the analogous perchlorate salt [Cu 2 {bcmp(-H)}(μ-OH)](ClO 4 ) 2 ·2.5H 2 O (2) was determined. Cytotoxicity studies showed very promising activity of 1 against various pancreatic tumor cell lines with IC 50 values comparable or even lower than those of cisplatin. The Cu complex displayed low toxicity against a human non-tumor cell line (HEK 293) demonstrating selectivity for cancer cells. 1 converts supercoiled pUC19 plasmid DNA into the nicked form at micromolar concentrations in the absence of added reductants. A detailed kinetic study on the hydrolysis of the DNA model bis(2,4-dinitrophenyl) phosphate (BDNPP) has been performed. 1 hydrolyses BDNPP with a second order rate constant of 0.047 M s −1 at pH 8 and 40°C. Finally, single cell electrophoresis (comet assay) and fluorescence microscopy analysis showed that 1 interacts with cellular DNA and induces apoptotic cell death of Capan-1 pancreatic cancer cells. Western blotting analysis indicated that the Cu complex activates the p53 dependent pathway of apoptosis.

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“…The hydroxyl radicals participate in the oxidation of the deoxyribose moiety, followed by hydrolytic cleavage of a sugar phosphate backbone 51,52 . In the presence of the biological reductant (ascorbic acid) and the oxidant (H 2 O 2 ), artificial metallonucleases relaxes the super coiled form of the DNA to the circular form and linear form [51][52][53] .…”

Section: Dna Bindingmentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Activity of New Complexes of Some Lanthanide Ions with 15-Crown-5 and 18-Crown-6

Al-Amery¹,

Al-Abdaly²,

Albayaty³

2015

Orient. J. Chem

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Complexes of some lanthanide picrates (Ln 3+ = Pr 3+, Nd 3+ and Dy 3+ ) with 15-crown-5 and 18-crown-6 were synthesized and characterized by elemental analysis, ICP-AES, FTIR, 1 H-NMR, 13C-NMR and UV-Visible spectrophotometric methods, thermal analysis (TGA & DTG), magnetic susceptibility , molar conductance and melting points. Also an in-vitro study on pathogenic gram positive (Staphylococcus aureus) and pathogenic gram negative bacteria (Escherichia coli, Salmonella and pseudomonas aeruginosa) was performed and the results were compared to those of a broad spectrum antibiotic (Chloramphinicol). 3+ and Dy 3+ were coordinated with two 15-crown-5 ligands and one picrate anion through its phenolic oxygen and the oxygen of it's ortho nitro group, except for Pr 3+ which was coordinated with only one 15-crown-5 ligand leaving three picrate anions as counter ions. In 18-crown-6 complexes both Pr 3+ and Nd 3+ were coordinated with one 18-crown-6 ligand leaving all the three picrate anions as counter ions outside the coordination sphere, except for the Dy 3+ complex which was coordinated with one 18-crown-6 ligand and one picrate anion.

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Radical-induced DNA damage by cytotoxic square-planar copper(II) complexes incorporating o-phthalate and 1,10-phenanthroline or 2,2′-dipyridyl

Cited by 71 publications

References 82 publications

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

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

DNA damage and induction of apoptosis in pancreatic cancer cells by a new dinuclear bis(triazacyclonane) copper complex

Synthesis, Characterization and Antibacterial Activity of New Complexes of Some Lanthanide Ions with 15-Crown-5 and 18-Crown-6

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