Highly specific oxidative damage of double-strand DNA by copper aminoglycosides

Patwardhan, Anjali; Cowan, J. A.

doi:10.1039/b103789g

Cited by 32 publications

(22 citation statements)

References 15 publications

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“…Oxidative cleavage of DNA by metal complexes can be achieved in the presence of external reagents, while common reductant were ascorbic acid, mercaptopropionic acid (MPA), polyphenol and S(IV) complexes (Patwardhan and Cowan 2001;Jin and Cowan 2005;Lainé et al 2004;Thyagarajan et al 2006;Alipázaga et al 2008). Recent report from our laboratory has shown that 1, 10-phenanthroline/Lthreonine copper (II) complexes with chlorogenic acid as biological reductant can induce DNA oxidative damage (Wang et al 2010).…”

Section: Introductionmentioning

confidence: 98%

Copper (II) complex of 1,10-phenanthroline and l-tyrosine with DNA oxidative cleavage activity in the gallic acid

2011

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Copper (II) complex of formulation [Cu-Phen-Tyr](H(2)O)](ClO(4)) (Phen = 1,10-phenanthroline, L: -Tyr = L: -tyrosine), has been prepared, and their induced DNA oxidative cleavage activity studied. The complex binds to DNA by intercalation, as deduced from the absorption and fluorescence spectral data. Scatchard plots constructed from the absorption titration data gave binding constant 2.44 × 10(4) M(-1) of base pairs. Extensive hypochromism, broadening, and red shifts in the absorption spectra were observed. Upon binding to DNA, the fluorescence from the DNA--ethidium bromide system was efficiently quenched by the copper (II) complex. Stern--Volmer quenching constant 0.61 × 10(3) M(-1) obtained from the linear quenching plots. [Cu-Phen-Tyr] complex efficiently cleave the supercoiled DNA to its nicked circular form with gallic acid as biological reductant at appropriate complex concentration. The gallic acid as reductant could observably improve copper (II) complex to DNA damage. The pseudo-Michaelis-Menten kinetic parameters (k(cat), K(M)) were calculated to be 1.32 h(-1) and 5.46 × 10(-5) M for [Cu-Phen-Tyr] complex. Mechanistic studies reveal the involvement of superoxide anions and hydroxyl radical (HO(·)) as the reactive species under an aerobic medium.

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Section: Introductionmentioning

confidence: 98%

Copper (II) complex of 1,10-phenanthroline and l-tyrosine with DNA oxidative cleavage activity in the gallic acid

2011

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“…[32][33][34][35] In particular, copper complexes afford facile nucleic acid oxidative cleavage in the presence of oxidizing and reducing agents, [36][37][38][39][40][41][42][43] in addition to the hydrolytic mechanism. [23,27,29] Most of these artificial phosphatases and nucleases offer homogeneous catalysis, while only limited applications of heterogeneous catalysts have been reported.…”

Section: Resultsmentioning

confidence: 99%

A Copper‐Metalated, Hybrid Inorganic–Organic Polymer as an Oxidative Nuclease

et al. 2005

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Keywords: Chemical nucleases / Phosphazenes / Pendant polymers / Copper complexes / Phosphate ester hydrolysis / Heterogeneous catalysisThis study describes nucleolytic activity of a copper-metalated, multisite-coordinating, hybrid polymer CPPL-Cu under oxidative conditions. Rapid relaxation of supercoiled plasmid DNA was observed and mechanistic probing by chemical and enzymatic assays revealed involvement of singlet-oxy-

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“…[22] variations in reactivity for copper and nickel peptides could reflect either the large gain in LFSE accompanying the transition from d 9 (Cu 2+ ) to d 8 (Cu 3+ ), relative to the smaller gain in LFSE for the transition from d 8 (Ni 2+ ) to d 7 (Ni 3+ ), or relative changes in coordination geometry, where the geometry for copper in both the d 8 and d 9 configurations is expected to be similar (square planar), while for nickel derivatives a distinct coordination preference would be expected for the d 7 and d 8 configurations. Such differences in activity most likely reflect subtle variations in the orientation of the metal-associated reactive oxygen species relative to the RNA [17,23], and emphasize optimal positioning of the metal-associated reactive oxygen species, relative to scissile bonds, as a major criterion for development of efficient catalytic nucleases or therapeutics.…”

Section: Discussionmentioning

confidence: 98%

“…The structural complexity of RNA, coupled with the functional activity that is often essential for the survival of pathogenic organisms and viruses [10,11], has spurred renewed interest in RNA from both a fundamental perspective and for potential applications in medicine [12,13], genetic regulation [14], and other areas of cellular chemistry [15,16]. Metal-promoted scission of structured RNA targets is a developing area of metallodrug design [17]. Important for the development of such drugs is a detailed understanding of the mechanism for metal-promoted cleavage of RNA, especially when mediated by oxidative damage.…”

Section: Introductionmentioning

confidence: 99%