Skip Navigation

This Article
Right arrow Full Text Freely available
Right arrow Print PDF (497K) Freely available
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in ISI Web of Science
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Add to My Personal Archive
Right arrow Download to citation manager
Right arrow Search for citing articles in:
ISI Web of Science (20)
Right arrowRequest Permissions
Right arrow Commercial Re-use Guidelines
for Open Access NAR Content
Google Scholar
Right arrow Articles by Liu, Z.
Right arrow Articles by Wang, Y.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Liu, Z.
Right arrow Articles by Wang, Y.
Social Bookmarking
Add to CiteULike   Add to Connotea   Add to Del.icio.us  
What's this?

Nucleic Acids Research, 2003, Vol. 31, No. 18 5413-5424
© 2003 Oxford University Press

Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone

Zhenjiu Liu, Yuan Gao and Yinsheng Wang*

Department of Chemistry-027, University of California at Riverside, Riverside, CA 92521-0403, USA

*To whom correspondence should be addressed. Tel: +1 909 787 2700; Fax: +1 909 787 4713; Email: yinsheng.wang{at}ucr.edu

We report the isolation and characterization for the first time of a cross-link lesion between two adjacent cytosines from the 2-methyl-1,4-naphthoquinone (menadione)-sensitized 365-nm irradiation of d(CpC). Electrospray ionization mass spectrometry (ESI-MS), tandem MS and 1H NMR results indicate that the cross-link occurs between the C5 carbon atom of one cytosine and the N4 nitrogen atom of the other cytosine. Furthermore, we synthesized d(CpC) with a 15N being incorporated on the amino group of either of the two cytosines. We then irradiated the two 15N-labeled dinucleoside monophosphates, isolated the cross-link products and characterized them by MS and multi-stage tandem MS. The latter results established unambiguously that the N4 nitrogen atom of the 3'-nucleobase is involved in the covalent bond formation between the two cytosines. This, in combination with two-dimensional nuclear Overhauser effect spectroscopy (NOESY) results, demonstrates that the cross-link arises from the formation of a covalent bond between the C5 carbon atom of the 5' cytosine and the N4 nitrogen atom of the 3' cytosine. We also show that the solution pH has a significant effect on the formation of the cross-link lesion, which supports that the deprotonation at the exocyclic amino group of cytosine cation radical is essential for the formation of the cross-link lesion.


Add to CiteULike CiteULike   Add to Connotea Connotea   Add to Del.icio.us Del.icio.us    What's this?


This article has been cited by other articles:


Home page
 Nucleic Acids ResHome page
Y. Zeng and Y. Wang
Sequence-dependent formation of intrastrand crosslink products from the UVB irradiation of duplex DNA containing a 5-bromo-2'-deoxyuridine or 5-bromo-2'-deoxycytidine
Nucleic Acids Res., December 2, 2006; 34(22): 6521 - 6529.
[Abstract] [Full Text] [PDF]

Home page
 Nucleic Acids ResHome page
Q. Zhang and Y. Wang
Generation of 5-(2'-deoxycytidyl)methyl radical and the formation of intrastrand cross-link lesions in oligodeoxyribonucleotides
Nucleic Acids Res., March 14, 2005; 33(5): 1593 - 1603.
[Abstract] [Full Text] [PDF]

Home page
 Nucleic Acids ResHome page
F. Bergeron, D. Houde, D. J. Hunting, and J. R. Wagner
Electron transfer in DNA duplexes containing 2-methyl-1,4-naphthoquinone
Nucleic Acids Res., December 7, 2004; 32(21): 6154 - 6163.
[Abstract] [Full Text] [PDF]


Disclaimer: Please note that abstracts for content published before 1996 were created through digital scanning and may therefore not exactly replicate the text of the original print issues. All efforts have been made to ensure accuracy, but the Publisher will not be held responsible for any remaining inaccuracies. If you require any further clarification, please contact our Customer Services Department.