Oxidative Strand Scission of Nucleic Acids:  Routes Initiated by Hydrogen Abstraction from the Sugar Moiety

Pogozelski, Wendy; Tullius, Thomas D.

doi:10.1021/cr960437i

Cited by 998 publications

(875 citation statements)

References 144 publications

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“…[68][69][70][71] Indeed, the cleavage with artificial metallo-nucleases is following either an oxidative or a hydrolytic mechanism. 67,[72][73][74] The former is observed with redox-active metal complexes while the latter one is based on the Lewis-acidity of metal ions. At this point, we emphasise that we will cover only work in which PNAs are covalently linked to a metal complex and act as a recognition fragment for a complementary DNA or RNA sequence.…”

Section: Metal-containing Pnas As Artificial Nucleasesmentioning

confidence: 99%

Metal-containing peptide nucleic acid conjugates

2011

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Peptide Nucleic Acids (PNAs) are non-natural DNA/RNA analogues with favourable physicochemical properties and promising applications. Discovered nearly 20 years ago, PNAs have recently re-gained quite a lot of attention. In this Perspective article, we discuss the latest advances on the preparation and utilisation of PNA monomers and oligomers containing metal complexes. These metalconjugates have found applications in various research fields such as in the sequence-specific detection of nucleic acids, in the hydrolysis of nucleic acids and peptides, as radioactive probes or as modulators of PNA˙DNA hybrid stability, and last but not least as probes for molecular and cell biology.

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Section: Metal-containing Pnas As Artificial Nucleasesmentioning

confidence: 99%

Metal-containing peptide nucleic acid conjugates

2011

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“…The results achieved from the experiments in the presence of various radical scavengers, and from the religation experiments show that a non-hydrolytic pathway not related to OH*, superoxide or singlet dioxygen is involved. [39] To further investigate in detail the nature of the cleaving properties of 1 and 5, pUC19 plasmid DNA treated with either complex 1 or 5 was relegated and was used for celltransformation tests. As shown in Figure 12, the religation of PstI-linearised pUC19 DNA (notated as LC) is achieved with an efficiency of about 94 %.…”

Section: Dna Cleavage Studiesmentioning

confidence: 99%

Unique Ligand‐Based Oxidative DNA Cleavage by Zinc(II) Complexes of Hpyramol and Hpyrimol

Maheswari

Barends

Özalp-Yaman

et al. 2007

Chemistry A European J

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The zinc(II) complexes reported here have been synthesised from the ligand 4‐methyl‐2‐N‐(2‐pyridylmethyl)aminophenol (Hpyramol) with chloride or acetate counterions. All the five complexes have been structurally characterised, and the crystal structures reveal that the ligand Hpyramol gradually undergoes an oxidative dehydrogenation to form the ligand 4‐methyl‐2‐N‐(2‐pyridylmethylene)aminophenol (Hpyrimol), upon coordination to ZnII. All the five complexes cleave the ϕX174 phage DNA oxidatively and the complexes with fully dehydrogenated pyrimol ligands were found to be more efficient than the complexes with non‐dehydrogenated Hpyramol ligands. The DNA cleavage is suggested to be ligand‐based, whereas the pure ligands alone do not cleave DNA. The DNA cleavage is strongly suggested to be oxidative, possibly due to the involvement of a non‐diffusible phenoxyl radical mechanism. The enzymatic religation experiments and DNA cleavage in the presence of different radical scavengers further support the oxidative DNA cleavage by the zinc(II) complexes.

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“…The dicopper(I) complex [Cu I 2 (N4)(MeCN) 2 ](ClO 4 ) 2 9 was prepared in a solution of MeOH (~1 mM, 15 mL) under anaerobic conditions in a glovebox and handled on the benchtop using standard Schlenk techniques. The solution was cooled to −78° C with an acetone/dry ice bath and dry O 2 gas was bubbled through the solutions for a few minutes allowing full formation of the peroxo-dicopper(II) complex [Cu II 2 (N4)(O 2 )](ClO 4 ) 2 .…”

Section: Exogenous Substrate Oxidationmentioning

confidence: 99%

“…3-mercaptopropanoic acid (MPA)) and dioxygen. 7 Results to date suggest that DNA is oxidized by an intermediate Cu 2 -O 2 species, but no definitive evidence of this has been gathered. The role of such an intermediate became even more intriguing after an alternative but related binuclear copper complex Cu II 2 (PD′-O)(H 2 O) 2 ](ClO 4 ) 3 ·2H 2 O (PD′-O is a phenolate containing binucleating ligand) was found to promote guanine oxidation rather than strand scission.…”

Section: Introductionmentioning

confidence: 99%

Selective DNA Strand Scission with Binuclear Copper Complexes: Implications for an Active Cu₂−O₂ Species

et al. 2006

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A homologous series of binuclear copper(II) complexes [Cu II 2 (Nn)(Y) 2 ] 2+ (1-3) (n = 3-5 and Y = (ClO 4 ) − or (NO 3 ) − ) were studied to investigate the intermediate(s) responsible for selective DNA strand scission in the presence of MPA/O 2 (MPA = 3-mercaptopropanoic acid). While the N3 complex does not react, the N4 and N5 analogues show comparable activity with strand scission occurring at a single-strand/double-strand junction. Identical reactivity is also observed in the alternate presence

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Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety

Cited by 998 publications

References 144 publications

Metal-containing peptide nucleic acid conjugates

Metal-containing peptide nucleic acid conjugates

Unique Ligand‐Based Oxidative DNA Cleavage by Zinc(II) Complexes of Hpyramol and Hpyrimol

Selective DNA Strand Scission with Binuclear Copper Complexes: Implications for an Active Cu₂−O₂ Species

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Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety

Cited by 998 publications

References 144 publications

Metal-containing peptide nucleic acid conjugates

Metal-containing peptide nucleic acid conjugates

Unique Ligand‐Based Oxidative DNA Cleavage by Zinc(II) Complexes of Hpyramol and Hpyrimol

Selective DNA Strand Scission with Binuclear Copper Complexes: Implications for an Active Cu2−O2 Species

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Selective DNA Strand Scission with Binuclear Copper Complexes: Implications for an Active Cu₂−O₂ Species