Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Brief Communication
  • Published:

Paradoxical hotspots for guanine oxidation by a chemical mediator of inflammation

Nature Chemical Biology volume 2, pages 365–366 (2006)Cite this article

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.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

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.

Similar content being viewed by others

References

  1. Hall, D.B., Holmlin, R.E. & Barton, J.K. Nature 382, 731–735 (1996).

    Article  CAS  Google Scholar 

  2. Ly, D., Kan, Y., Armitage, B. & Schuster, G.B. J. Am. Chem. Soc. 118, 8747–8748 (1996).

    Article  CAS  Google Scholar 

  3. Saito, I. et al. J. Am. Chem. Soc. 120, 12686–12687 (1998).

    Article  CAS  Google Scholar 

  4. Dedon, P.C. & Tannenbaum, S.R. Arch. Biochem. Biophys. 423, 12–22 (2004).

    Article  CAS  Google Scholar 

  5. Shafirovich, V., Dourandin, A., Huang, W. & Geacintov, N.E. J. Biol. Chem. 276, 24621–24626 (2001).

    Article  CAS  Google Scholar 

  6. Tretyakova, N.Y. et al. Mutat. Res. 447, 287–303 (2000).

    Article  CAS  Google Scholar 

  7. Cloutier, J.F. et al. J. Mol. Biol. 313, 539–557 (2001).

    Article  CAS  Google Scholar 

  8. Joffe, A., Geacintov, N.E. & Shafirovich, V. Chem. Res. Toxicol. 16, 1528–1538 (2003).

    Article  CAS  Google Scholar 

  9. Ravanat, J.L., Saint-Pierre, C. & Cadet, J. J. Am. Chem. Soc. 125, 2030–2031 (2003).

    Article  CAS  Google Scholar 

  10. Dong, M. et al. Mutat. Res. 594, 120–134 (2006).

    Article  CAS  Google Scholar 

  11. Spassky, A. & Angelov, D. Biochemistry 36, 6571–6576 (1997).

    Article  CAS  Google Scholar 

  12. Misiaszek, R., Crean, C., Geacintov, N.E. & Shafirovich, V. J. Am. Chem. Soc. 127, 2191–2200 (2005).

    Article  CAS  Google Scholar 

  13. Douki, T. & Cadet, J. Free Rad. Res. 24, 369–380 (1996).

    Article  CAS  Google Scholar 

  14. Rodriguez, H. et al. Biochemistry 38, 16578–16588 (1999).

    Article  CAS  Google Scholar 

Download references

Acknowledgements

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

Author information

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
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jean-Francois Cloutier
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vladimir Shafirovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nicholas E Geacintov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Peter C Dedon
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Peter C Dedon.

Ethics declarations

Competing interests

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)

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

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

This article is cited by

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing