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Nucleic Acids Research 2004 32(21):6154-6163; doi:10.1093/nar/gkh950
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Published online 7 December 2004

Nucleic Acids Research, Vol. 32 No. 21 © Oxford University Press 2004; all rights reserved

Electron transfer in DNA duplexes containing 2-methyl-1,4-naphthoquinone

François Bergeron1, Daniel Houde1, Darel J. Hunting1 and J. Richard Wagner1,2,*

1 Group in the Radiation Sciences, University of Sherbrooke, Sherbrooke (Quebec), Canada J1H 5N4 and 2 The Research Center of Aging, Sherbrooke University Geriatrics Institute, 1036 Rue Belvedere Sud, Sherbrooke (Quebec), Canada J1H 4C4

* To whom correspondence should be addressed at Research Center of Aging, Sherbrooke University Geriatrics Institute, 1036 Rue Belvedere Sud, Sherbrooke (Quebec), Canada J1H 4C4. Tel: +1 819 821 7011, Ext 2286; Fax: +1 819 829 7141; Email: Richard.Wagner{at}Usherbrooke.ca

Received August 27, 2004; Revised October 13, 2004; Accepted November 1, 2004

2-Methyl-1,4-naphthoquinone (menadione, MQ) was linked to synthetic oligonucleotides and exposed to near-UV light to generate base radical cations in DNA. This model system of electron transfer induced alkali-labile breaks at GG doublets, similar to anthraquinone and metallointercalators systems. In sharp contrast to other systems, the photolysis of MQ–DNA duplexes gave interstrand cross-links and alkali-labile breaks at bases on the complementary strand opposite the MQ moiety. For sequences with an internal MQ, the formation of cross-links with A and C opposite the MQ moiety was 2- to 3-fold greater than that with G and T. The yield of cross-links was more than 10-fold greater than that of breaks opposite MQ, which in turn was more than 2-fold greater than breaks at GG doublets. The yield of damage at GG doublets greatly increased for a sequence with a terminal MQ. The distribution of base damage was measured by enzymatic digestion and HPLC analysis (dAdo > dThd > dGuo > dCyd). The formation of novel products in MQ–DNA duplexes was attributed to the ability of excited MQ to generate the radical cations of all four DNA bases; thus, this photochemical reaction provides an ideal model system to study the effects of ionizing radiation and one-electron oxidants.


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