Enhancing excess electron transport in DNA

Fakhari, Fazel; Chen, Yun-Yun K.; Rokita, Steven E.

doi:10.1039/c3cc43887b

Cited by 5 publications

(3 citation statements)

References 43 publications

(21 reference statements)

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“…Migration of a charge away from its site of entry in DNA is thus infrequent relative to its primary injection unless a system is designed to enhance separation of the initial charges. [39][40][41][42] Materials and methods…”

Section: Resultsmentioning

confidence: 99%

Electron transport in DNA initiated by diaminonaphthalene donors alternatively bound by non-covalent and covalent association

Campbell

Rokita

2014

Org. Biomol. Chem.

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Covalent conjugation is typically used to fix a potential charge donor to a chosen site for studying either hole or excess electron transport in duplex DNA. A model system based on oligonucleotides containing an abasic site and (Br)dU was previously developed to provide a rapid method of screening new donors without the need of synthetic chemistry. While this strategy is effective for discovering important lead compounds, it is not appropriate for establishing extensive correlations between molecular structure and donor efficiency as demonstrated with a series of closely related electron donors based on diaminonaphthalene. The non-covalent system accurately identified the ability of the donors to reduce a distal (Br)dU in DNA, but their varying efficiencies were not recapitulated when attached covalently to an equivalent sequence of DNA. Reduction within the covalent system was not sensitive to the strong donor potentials as consistent with charge recombination dominating the net migration of charge.

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Section: Resultsmentioning

confidence: 99%

Electron transport in DNA initiated by diaminonaphthalene donors alternatively bound by non-covalent and covalent association

Campbell

Rokita

2014

Org. Biomol. Chem.

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“…On the other hand, reductive or excess electron hopping over thymines can be fast (10 10 s −1 ) 7. Hence, current research efforts are focused on how electron‐transfer hopping over long ranges8 can be improved while keeping the spontaneous self‐assembly as the most attractive feature of such DNA architectures 9–12. It has been evidenced that organic aromatic compounds such as ethynyl pyrenes10 and phenanthrenes11 are able to enhance the excess electron‐transfer efficiency.…”

Section: Methodsmentioning

confidence: 99%

“…Hence, a selective excitation of Ap–dU to induce electron hopping can be achieved by using LEDs at 385 nm. In analogy to the hole‐hopping experiments over guanines3 and electron‐hopping experiments using 5‐bromo‐2′‐deoxyuridine (Br‐dU) as acceptor,4, 5, 9–11 which both yield strand cleavage products, the irradiation experiments with DNA1–DNA3 were analyzed by gel electrophoresis. The corresponding gel images (Figure 2) revealed a light‐dependent strand cleavage product that occurs on the 5′‐side of the Hq modification.…”

Section: Methodsmentioning

confidence: 99%

Acceleration of Long‐Range Photoinduced Electron Transfer through DNA by Hydroxyquinolines as Artificial Base Pairs

Bätzner¹,

Liang²,

Schweigert³

et al. 2015

ChemPhysChem

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The C-nucleoside based on the hydroxyquinoline ligand (Hq) is complementary to itself and forms stable Hq-Hq pairs in double-stranded DNA. These artificial Hq-Hq pairs may serve as artificial electron carriers for long-range photoinduced electron transfer in DNA, as elucidated by a combination of gel electrophoretic analysis of irradiated samples and time-resolved transient absorption spectroscopy. For this study, the Hq-Hq pair was combined with a DNA-based donor-acceptor system consisting of 6-N,N-dimethylaminopyrene conjugated to 2'-deoxyuridine as photoinducible electron donor, and methyl viologen attached to the 2'-position of uridine as electron acceptor. The Hq radical anion was identified in the time-resolved measurements and strand cleavage products support its role as an intermediate charge carrier. Hence, the Hq-Hq pair significantly enhances the electron hopping capability of DNA compared to natural DNA bases over long distances while keeping the self-assembly properties as the most attractive feature of DNA as a supramolecular architecture.

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Controlling Electron Rebound within Four‐Base π‐Stacks in Z‐DNA by Changing the Sugar Moiety from Deoxy‐ to Ribonucleotide

Sannohe

Kizaki

Kanesato

et al. 2013

Chemistry A European J

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Charge transfer through DNA is of great interest because of the potential of DNA to be a building block for nanoelectronic sensors and devices. The photochemical reaction of 5-halouracil has been used for probing charge-transfer processes along DNA. We previously reported on unique charge transfer following photochemical reaction of 5-bromouracil within four-base π-stacks in Z-DNA. In this study, we incorporated a guanosine instead of a deoxyguanosine into Z-DNA, and found that electron transfer occurs in a different mechanism through four-base π-stacks.

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Enhancing excess electron transport in DNA

Abstract: The efficiency of excess electron transport in duplex DNA can be enhanced by limiting the pathways available for migration and using a donor of moderate strength that suppresses radical recombination through selective electron transfer to distal pyrimidines rather than proximal purines.

Cited by 5 publications

References 43 publications

Electron transport in DNA initiated by diaminonaphthalene donors alternatively bound by non-covalent and covalent association

Electron transport in DNA initiated by diaminonaphthalene donors alternatively bound by non-covalent and covalent association

Acceleration of Long‐Range Photoinduced Electron Transfer through DNA by Hydroxyquinolines as Artificial Base Pairs

Controlling Electron Rebound within Four‐Base π‐Stacks in Z‐DNA by Changing the Sugar Moiety from Deoxy‐ to Ribonucleotide

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