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Long-Range Charge Transfer in DNA I pp 1–25Cite as

Effects of Duplex Stability on Charge-Transfer Efficiency within DNA

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 236))

Abstract

In the first part of the chapter, emphasis is placed on the description of the main reactions of radical cations of the four predominant DNA purine and pyrimidine bases and minor 5-methylcytosine in aerated aqueous solutions. Information is also provided on the final one-electron oxidation products of 8-oxo-7,8-dihydroguanine, an ubiquitous decomposition product of DNA with most chemical and physical oxidizing agents, that exhibits a low ionization potential, and is therefore an excellent sink for positive hole migration within double-stranded DNA. In the second part of the review, it is shown that duplex stability plays a major role in the redistribution of positive holes generated by high intensity UV laser pulses on purine and pyrimidine bases towards guanine residues. These results were obtained by measurement of several oxidized nucleosides within DNA using a sensitive and accurate high performance liquid chromatography-tandem mass spectrometry assay.

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Abbreviations

dAdo:

2′-deoxyadenosine

dCyd:

2′-deoxycytidine

dGuo:

2′-deoxyguanosine

5-MedCyd:

5-methyl-2′-deoxycytidine

Thd:

thymidine

FapyAde:

4,6-diamino-5-formamidopyrimidine

FapyGua:

2,6-diamino-4-hydroxy-5-formamidopyrimidine

5-FordUrd:

5-formyl-2′-deoxyuridine

5-HmdUrd:

5-(hydroxymethyl)-2′-deoxyuridine

5-OHdCyd:

5-hydroxy-2′-deoxycytidine

5-OHdUrd:

5-hydroxy-2′-deoxyuridine

8-oxodAdo:

8-oxo-7,8-dihydro-2′-deoxyadenosine

8-oxodGuo:

8-oxo-7,8-dihydro-2′-deoxyguanosine

ThdGly:

5,6-dihydroxy-5,6-dihydrothymidine

Sp:

spiroiminodihydantoin

Gh:

guanidinohydantoin

MQ:

menadione

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Authors and Affiliations

  1. Laboratoire “Lésions des Acides Nucléiques”, SCIB, Département de Recherche Fondamentale sur la Matière Condensée, CEA/Grenoble, 38054, Grenoble Cedex 9, France

    Thierry Douki, Jean-Luc Ravanat & Jean Cadet

  2. Institute of Solid State Physics, Bulgarian Academy of Sciences, 1784, Sofia, Bulgaria

    Dimitar Angelov

  3. Département de Médecine Nucléaire et Radiobiologie, Faculté de médecine, Université de Sherbrooke, Sherbrooke, Québec , J1H 5N4, Canada

    J. Richard Wagner

Authors
  1. Thierry Douki
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  2. Jean-Luc Ravanat
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  3. Dimitar Angelov
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  4. J. Richard Wagner
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  5. Jean Cadet
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Correspondence to Jean Cadet .

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G.B. Schuster

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Douki, T., Ravanat, JL., Angelov, D., Wagner, J.R., Cadet, J. (2004). Effects of Duplex Stability on Charge-Transfer Efficiency within DNA. In: Schuster, G. (eds) Long-Range Charge Transfer in DNA I. Topics in Current Chemistry, vol 236. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b94409

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  • DOI: https://doi.org/10.1007/b94409

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