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Paradoxical hotspots for guanine oxidation by a chemical mediator of inflammation

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A Corrigendum to this article was published on 01 March 2007

Abstract

Guanine in DNA is a major oxidation target owing to its low ionization potential (IP), and there is often an inverse correlation between damage frequency and sequence-dependent variation in guanine IP. We report that the biological oxidant nitrosoperoxycarbonate (ONOOCO2–) paradoxically selects guanines with the highest IP in GC-containing contexts. Along with sequence-dependent variation in damage chemistry, this behavior points to factors other than charge migration as determinants of genomic DNA oxidation.

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Figure 1: Sequence-selective guanine oxidation in duplex DNA by ONOOCO2– and riboflavin-mediated photooxidation3.
Figure 2: Sequence selectivity of ONOOCO2–-induced guanine oxidation chemistry.

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Acknowledgements

This research was supported by the National Cancer Institute (CA110261 and CA026731) and the National Institute of Environmental Health Sciences (ES002109).

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Authors and Affiliations

  1. Biological Engineering Division, Massachusetts Institute of Technology, Cambridge, 02139, Massachusetts, USA

    Yelena Margolin, Jean-Francois Cloutier & Peter C Dedon

  2. Chemistry Department and Radiation and Solid State Laboratory, New York University, New York, 10003, New York, USA

    Vladimir Shafirovich & Nicholas E Geacintov

  3. Faculté de Pharmacie, Université Laval, Québec, G1K 7P4, Québec, Canada

    Jean-Francois Cloutier

Authors
  1. Yelena Margolin
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  2. Jean-Francois Cloutier
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  3. Vladimir Shafirovich
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  4. Nicholas E Geacintov
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  5. Peter C Dedon
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Corresponding author

Correspondence to Peter C Dedon.

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The authors declare no competing financial interests.

Supplementary information

Supplementary Fig. 1

Illustrative sequencing gel (PDF 33 kb)

Supplementary Fig. 2

Comparison of Fpg- and piperidine-induced DNA cleavage (PDF 94 kb)

Supplementary Fig. 3

Damage in single-stranded oligos (PDF 73 kb)

Supplementary Fig. 4

Illustrative LMPCR gel (PDF 229 kb)

Supplementary Methods (PDF 23 kb)

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Margolin, Y., Cloutier, JF., Shafirovich, V. et al. Paradoxical hotspots for guanine oxidation by a chemical mediator of inflammation. Nat Chem Biol 2, 365–366 (2006). https://doi.org/10.1038/nchembio796

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  • DOI: https://doi.org/10.1038/nchembio796

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