Methylene blue plus light mediates 8-hydroxy 2'-deoxyguanosine formation in DNA preferentially over strand breakage

Schneider, Jens; Price, S. J. W.; Maidt, Lindsay; Gutteridge, John M.C.; Floyd, Robert A.

doi:10.1093/nar/18.3.631

Cited by 215 publications

(119 citation statements)

References 17 publications

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“…The same mutational pattern (G to T transversions, 63.0 % of 65 base substitutions) was obtained after transfection of 1 O 2 -treated M13lacZ bacteriophage DNA in Escherichia coli (49). Also, 8-oxo-dGuo is a frequent lesion detected in DNA exposed to 1 O 2 (39,(50)(51)(52). These findings suggest that 1 O 2 causes 8-oxo-dGuo formation and this accounts for the G to T transversions.…”

Section: Discussionsupporting

confidence: 65%

Formation of 8-Oxo-7,8-dihydro-2‘-deoxyguanosine (8-Oxo-dGuo) by PAH o-Quinones: Involvement of Reactive Oxygen Species and Copper(II)/Copper(I) Redox Cycling

Park

Gopishetty

Szewczuk

et al. 2005

Chem. Res. Toxicol.

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Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants and procarcinogens that require activation by host metabolism. Metabolic activation of PAHs by AldoKeto-Reductases (AKRs) leads to formation of reactive and redox active o-quinones, which may cause oxidatively generated DNA damage. Spectrophotometric assays showed that NADPH caused PAH o-quinones to enter futile redox-cycles, which result in the depletion of excess cofactor. Copper (II) amplified NADPH-dependent redox-cycling of the o-quinones. Concurrent with NADPH oxidation, molecular oxygen was consumed, indicating the production of ROS. To determine whether PAH o-quinones can cause 8-oxo-dGuo formation in salmon testis DNA, three pre-requisite experimental conditions were satisfied. Quantitative complete enzymatic hydrolysis of DNA was achieved, adventitious oxidation of dGuo was eliminated by the use of chelex and desferal, and basal levels of less than 2.0 8-oxo-dGuo/10 5 dGuo were obtained. The HPLC-ECD analytical method was validated by spiking the DNA with standard 8-oxo-dGuo and demonstrating quantitative recovery. HPLC-ECD analysis revealed that in the presence of NADPH and Cu(II), submicromolar concentrations of PAH o-quinones generated > 60.0 8-oxo-dGuo adducts/10 5 dGuo. The rank order of 8-oxo-dGuo generated in isolated DNA was NP-1,2-dione > BA-3,4-dione > 7,12-DMBA-3,4-dione > BP-7,8-dione. The formation of 8-oxo-dGuo by PAH o-quinones was concentrationdependent. It was completely or partially inhibited when catalase, tiron or a Cu(I) specific chelator, bathocuproine were added, indicating the requirement for H 2 O 2 , O 2 − and Cu(I), respectively. Methional which is a copper-hydroperoxo complex (Cu(I)OOH) scavenger also suppressed 8-oxodGuo formation. By contrast, mannitol, sodium benzoate and sodium formate, which act as hydroxyl radical scavengers, did not block its formation. Sodium azide which can act as both a hydroxyl radical and 1 O 2 scavenger abolished the formation of 8-oxo-dGuo. These data showed that the production of 8-oxo-dGuo was dependent on Cu(II) /Cu(I) catalyzed redox cycling of PAH o-quinones to

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Section: Discussionsupporting

confidence: 65%

Formation of 8-Oxo-7,8-dihydro-2‘-deoxyguanosine (8-Oxo-dGuo) by PAH o-Quinones: Involvement of Reactive Oxygen Species and Copper(II)/Copper(I) Redox Cycling

Park

Gopishetty

Szewczuk

et al. 2005

Chem. Res. Toxicol.

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“…3) as the trap on this basis. This modified base is often detected as a byproduct of oxidative damage (14,20,23,31,(33)(34)(35)(36). Although structural information is not available for PNA-containing duplexes, Williams and coworkers (37) recently determined the structure of a DNA duplex having an 8-OxoG substitution by x-ray crystallography and found that the oxidized base caused little perturbation.…”

Section: Resultsmentioning

confidence: 99%

Peptide nucleic acid–DNA duplexes: Long range hole migration from an internally linked anthraquinone

Armitage

Ly²,

Koch³

et al. 1997

Proc. Natl. Acad. Sci. U.S.A.

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The discovery that peptide nucleic acids (PNA) mimic DNA and RNA by forming complementary duplex structures following Watson-Crick base pairing rules opens fields in biochemistry, diagnostics, and medicine for exploration. Progress requires the development of modified PNA duplexes having unique and well defined properties. We find that anthraquinone groups bound to internal positions of a PNA oligomer intercalate in the PNA-DNA hybrid. Their irradiation with near-UV light leads to electron transfer and oxidative damage at remote GG doublets on the complementary DNA strand. This behavior mimics that observed in related DNA duplexes and provides the first evidence for long range electron (hole) transport in PNA-DNA hybrid. Analysis of the mechanism for electron transport supports hole hopping.Peptide nucleic acid (PNA) oligomers are DNA͞RNA analogs (see Fig. 1) in which the natural sugar-phosphate backbone is replaced by a synthetic peptide backbone (1). PNA oligomers that contain purine and pyrimidine nucleobases hybridize with complementary DNA and RNA strands to form right-handed, double-helical complexes according to the Watson-Crick rules of hydrogen bond-mediated base pair formation (2). Although much has been learned about the structural (3) and thermodynamic (4) factors involved in hybridization, little is known about the chemical reactivity of PNA͞DNA hybrids. It is crucial to understand how PNA͞DNA hybrids mimic the reactions and functions of duplex DNA. Of immediate importance for their application as clinical diagnostic agents is investigation of the conductivity of DNA and its PNA analogs (5, 6).DNA must balance the dual requirements of chemical stability and ease of transcription and replication (7). It is clear that DNA is far from inert toward a variety of different reactive species, particularly oxidizing agents. Oxidative damage to DNA produced by normal metabolism, deep-UV laser irradiation (8), gamma rays (9), or pulse radiolysis (10) accumulates at guanine residues, an effect attributed to one-dimensional migration of a radical cation (''hole'') along the DNA helix (11). Both the low oxidation potential and reactivity of the guanine radical cation contribute to the effectiveness of guanine as a trap for the migrating hole. Because guanine lesions may be the major cause of mutations (12), intense attention is focused on understanding the conductivity properties of DNA to elucidate the mechanisms by which migration of oxidative damage occurs (13). In this regard, the recent reports by Barton and coworkers are particularly important (14, 15). They describe a system consisting of a rhodium complex that is covalently linked to one end of a DNA duplex. Irradiation caused damage to the DNA more than 30 Å from where the complex was presumed to intercalate. This observation opens up exciting opportunities to study the factors that control hole migration in nucleic acids.Photosensitizers often react with nucleic acids by single electron transfer to oxidize a base. Recent findings reveal that the...

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“…[20][21][22][23][24] As with the hydroxyl radical, the mechanism for this attack is explained by two equally plausible theories. In both cases, the creation of 8-oxoguanine proceeds to form an intermediate product:…”

Section: -Hydroxy-2'-deoxyguanosinementioning

confidence: 99%

Analytics of oxidative stress markers in the early diagnosis of oxygen DNA damage

Dąbrowska¹,

Wiczkowski²

2017

Adv Clin Exp Med

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Under homeostatic conditions, an equilibrium state between amounts of free radicals formed and their scavenging is observed. Free radicals are destructive only when present in excess. Pathological changes within cells and tissues can result from a persistent excess of free radicals. Living organisms are increasingly exposed to oxidative stress, resulting in oxidative DNA modifications. One such modification is 8-hydroxy-2'-deoxyguanosine (8-OHdG). It is considered a biomarker of oxidative stress and oxidative DNA damage. It has been found both in physiological fluids and in cells. This paper presents methods found in the literature for determining 8-OHdG expression in various kinds of biological material -blood, urine or liver homogenates. Methods for determining the biomarker expression have been grouped into direct and indirect methods, and the various levels of 8-hydroxy-2'-deoxyguanosine that can be determined by the different techniques are presented. The basic pros and cons of the various techniques are also discussed.

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Methylene blue plus light mediates 8-hydroxy 2'-deoxyguanosine formation in DNA preferentially over strand breakage

Cited by 215 publications

References 17 publications

Formation of 8-Oxo-7,8-dihydro-2‘-deoxyguanosine (8-Oxo-dGuo) by PAH o-Quinones: Involvement of Reactive Oxygen Species and Copper(II)/Copper(I) Redox Cycling

Formation of 8-Oxo-7,8-dihydro-2‘-deoxyguanosine (8-Oxo-dGuo) by PAH o-Quinones: Involvement of Reactive Oxygen Species and Copper(II)/Copper(I) Redox Cycling

Peptide nucleic acid–DNA duplexes: Long range hole migration from an internally linked anthraquinone

Analytics of oxidative stress markers in the early diagnosis of oxygen DNA damage

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