Cleavage of DNA by coordination complexes. Superoxide formation in the oxidation of 1,10-phenanthroline-cuprous complexes by oxygen - relevance to DNA-cleavage reaction

Graham, Daniel R.; Marshall, Laura E.; Reich, Karl; Sigman, David S.

doi:10.1021/ja00536a063

Cited by 115 publications

(37 citation statements)

References 3 publications

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“…[54] Thus, reduction of the copper to cuprous state leads to the generation of superoxide anion. The O 2 -then dismutates to H 2 O 2 and dioxygen and the hydrogen peroxide reacts with another equivalent of copper(I) to produce hydroxyl radical-like species, which may be bound to the metal.…”

Section: Mechanistic Studiesmentioning

confidence: 99%

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

et al. 2007

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The reaction of 2,4,6‐tri(pyridyl)‐1,3,5‐triazine (ptz) and copper(II) salts in dmf/water (1:1) results in the hydrolysis of ptz and formation of the anions bis(2‐pyridylcarbonyl)amide (ptO2–) and bis(2‐pyridylamine)amide (ptN2–), which are found in the complexes [Cu(ptN2)(OAc)]·3H2O (1), [Cu(ptO2)(OAc)(H2O)]·H2O (2), [Cu(ptN2)(for)]·3H2O (3) (for = formate), [Cu(ptO2)(for)(H2O)] (4), [Cu(ptO2)(benz)]·H2O (5) (benz = benzoate), and [Cu(ptO2)F(H2O)]2·3H2O (6). This report includes the chemical and spectroscopic characterization of all these complexes along with the crystal structures of 4–6. The coordination spheres of CuII in 4 and 5 are best described as distorted tetragonal square pyramidal for the former and distorted square planar for the latter. The crystal structure of 6 shows the presence of two discrete monomeric [Cu(ptO2)F(H2O)] entities in the crystallographic asymmetric unit in which both copper(II) ions have a distorted square‐pyramidal coordination geometry. The binding of the complexes to DNA has been investigated with the aid of viscosity and thermal denaturation studies, both of which indicate that the interaction is probably due to the outer‐sphere mechanism. The ability of the compounds to cleave DNA has also been tested. Efficient oxidative cleavage was observed in the presence of a mild reducing agent (ascorbate) and dioxygen. Mechanistic studies with reactive oxygen species (ROS) scavengers confirm that hydrogen peroxide, the hydroxyl radical, singlet oxygen‐like species, and the superoxide anion are necessary diffusible intermediates in the scission process. A mechanism involving either the Fenton or theHaber–Weiss reaction plus the formation of copper oxene species is proposed for the DNA cleavage mediated by these compounds.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Mechanistic Studiesmentioning

confidence: 99%

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

et al. 2007

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“…In the case of the bis(1,10-phenanthroline), a freely diffusible hydroxyl radical or non-diffusible copper-oxo species is assumed to be the active species [5,[66][67][68].…”

Section: Redox Studiesmentioning

confidence: 99%

Copper(II) complexes of 1,10-phenanthroline-derived ligands: Studies on DNA binding properties and nuclease activity

Hirohama¹,

Kuranuki²,

Ebina³

et al. 2005

Journal of Inorganic Biochemistry

191

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“…10) (22,23). Indeed, several recent studies have inquired into the reaction of copper-phenanthroline, oxygen, a reducing agent, and DNA to degrade double-stranded DNA into acid-soluble fragments (24)(25)(26). As with other copper complexes discussed above, the phenanthroline-Cu complex cycles between Cu(II) and Cu(I) to catalyze the reduction of oxygen to reactive radical species by the reducing agent.…”

Section: Esr Investigations Of Tetradentate Cupric Complexesmentioning

confidence: 99%

ESR of Copper and Iron Complexes with Antitumor and Cytotoxic Properties

Antholine¹,

Kalyanaraman²,

Petering³

1985

Environmental Health Perspectives

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The relatively few iron and copper metal complexes which have been examined in cells and tissues for their redox properties, radical generation properties, and antitumor activity are discussed for studies which utilized electron spin resonance spectroscopy (ESR). A common property of a number of metal complexes, which include bleomycin, adriamycin, and thiosemicarbazones described in this review, is that they are readily reduced by thiol compounds and oxidized by oxygen or reduced species of oxygen to produce radicals. Structural features ofthese reactions are identified by ESR spectroscopy in model systems and-often in cells. Furthermore, ESR spectroscopy has been most useful to probe the environment of the complexes in cells and to measure the rate of reduction of their oxidized forms. As a result of these studies, it is anticipated that more attention will be given to the exploration of redox-active metal complexes as drugs.

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Cleavage of DNA by coordination complexes. Superoxide formation in the oxidation of 1,10-phenanthroline-cuprous complexes by oxygen - relevance to DNA-cleavage reaction

Cited by 115 publications

References 3 publications

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

Copper(II) complexes of 1,10-phenanthroline-derived ligands: Studies on DNA binding properties and nuclease activity

ESR of Copper and Iron Complexes with Antitumor and Cytotoxic Properties

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