Oxidative Nucleobase Modifications Leading to Strand Scission

We have developed a method to deposit Cu metal onto surface-attached DNA, forming nanowirelike structures that are ∼3 nm tall. DNA is first aligned on a silicon surface and then treated with aqueous Cu(NO3)2. After the copper(II) has electrostatically associated with the DNA, it is reduced by ascorbic acid to form a metallic copper sheath around the DNA. The resulting nanostructures have been observed and characterized by atomic force microscopy. A more complete coating can be obtained by repeating the Cu(II) and ascorbic acid treatment. Control experiments involving treatments with aqueous solutions containing either NO3- or the divalent cation Mg2+ show no change in DNA height upon ascorbic acid exposure. These experiments indicate that copper nanowires, which may be valuable as interconnects in nanoscale integrated circuitry, can be readily generated from DNA molecules on surfaces.

DNA-Templated Construction of Copper Nanowires

s hydrogen atom from glutathione with a rate constant of 1.6 × 106 M-1 s-1 to produce the hydroperoxide 41. Therefore, in these model reactions, performed without any metal complex, the strand cleavage mechanism depends on the concentration of the hydrogen donor. At low concentration of glutathione, the “heterolytic cleavage pathway” is favored even under aerobic conditions. The result of this analysis is that for 250 μM O2 and 0.1 mM of glutathione, which are classical concentrations to study DNA cleavage with metal complexes, the pathways involving the C4′peroxide 41 and the heterolytic cleavage forming 56 can be in competition (except if the metal complex favors one pathway). Other data obtained on these models concern the reduction of the C4′-radical 39 by glutathione (a rate constant of 1.9 × 106 M-1 s-1 was determined) to give predominantly the natural 2′-deoxyribonucleotide in the case of duplex Figure 17. “Tetraoxide reaction pathway” of the C4′-radical in the presence of dioxygen. This reaction pathway was established in the case of DNA oxidation by neocarzinostatin or HO• generators and from the analysis of C4′-radical models. The presence of question marks reflects that, for not well understood reasons, different metal complexes do not induce base propenal (45) release, although 3′-phosphoglycolate fragments (37) are clearly observed. It has been proposed that these last systems induce malondialdehyde (48) release instead of base propenal (45). The C4′-radical is shown in red. Figure 18. Tetraoxide cleavage pathways. Activation of DNA C-H Bonds by Metal Complexes Chemical Reviews, 2010, Vol. 110, No. 2 1029

Activation of DNA carbon-hydrogen bonds by metal complexes.

Transition metal salen complexes in bioinorganic and medicinal chemistry

Interactions of copper complexes with nucleic acids

Synthesis, dna binding, and cleaving properties of an ellipticine : salen.copper conjugate

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Synthesis, dna binding, and cleaving properties of an ellipticine : salen.copper conjugate