The eosinophil peroxidase-hydrogen peroxide-bromide system of human eosinophils generates 5-bromouracil, a mutagenic thymine analogue

Biochemistry
J P HendersonJ W Heinecke

Abstract

Eosinophils use eosinophil peroxidase, hydrogen peroxide (H(2)O(2)), and bromide ion (Br(-)) to generate hypobromous acid (HOBr), a brominating intermediate. This potent oxidant may play a role in host defenses against invading parasites and eosinophil-mediated tissue damage. In this study, we explore the possibility that HOBr generated by eosinophil peroxidase might oxidize nucleic acids. When we exposed uracil, uridine, or deoxyuridine to reagent HOBr, each reaction mixture yielded a single major oxidation product that comigrated on reversed-phase HPLC with the corresponding authentic brominated pyrimidine. The eosinophil peroxidase-H(2)O(2)-Br(-) system also converted uracil into a single major oxidation product, and the yield was near-quantitative. Mass spectrometry, HPLC, UV--visible spectroscopy, and NMR spectroscopy identified the product as 5-bromouracil. Eosinophil peroxidase required H(2)O(2) and Br(-) to produce 5-bromouracil, implicating HOBr as an intermediate in the reaction. Primary and secondary bromamines also brominated uracil, suggesting that long-lived bromamines also might be physiologically relevant brominating intermediates. Human eosinophils used the eosinophil peroxidase-H(2)O(2)-Br(-) system to oxidize...Continue Reading

References

Nov 1, 1989·The Journal of Clinical Investigation·J H JacksonM Dizdaroglu
Apr 1, 1987·Journal of Leukocyte Biology·D C PetrecciaR A Clark
Oct 1, 1970·British Journal of Urology·H Talib
Aug 1, 1983·The Journal of Clinical Investigation·E L ThomasM M Jefferson
Nov 14, 1997·The Biochemical Journal·C J van DalenA J Kettle
Jul 21, 2000·Alimentary Pharmacology & Therapeutics·K W Heaton

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Citations

Jul 6, 2004·Archives of Biochemistry and Biophysics·Emily HoTammy M Bray
Nov 26, 2003·Mutation Research·Svein Bjelland, Erling Seeberg
May 10, 2003·Chemosphere·Gordon W Gribble
Sep 11, 2002·Breast Cancer Research and Treatment·Michael SamoszuStanley L Hazen
Jan 19, 2010·The Journal of Biological Chemistry·Takashi AsahiToshihiko Osawa
Jul 3, 2007·The Journal of Biological Chemistry·Michael T MorganAlexander C Drohat
Mar 12, 2008·Antioxidants & Redox Signaling·Michael J DaviesMartin D Rees
Jan 5, 2011·PloS One·Gilles MoulayAntoine Kichler
Feb 8, 2011·Journal of Clinical Biochemistry and Nutrition·Michael J Davies
Oct 30, 2009·Biochemistry·Jacob A TheruvathuLawrence C Sowers
Jan 26, 2010·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·M Alcolea PalafoxV K Rastogi
Dec 8, 2015·Free Radical Biology & Medicine·Ali R ManiKevin P Moore
Oct 24, 2009·Archives of Biochemistry and Biophysics·Christine SuquetJames K Hurst
May 12, 2009·Bioorganic & Medicinal Chemistry Letters·Toshinori SuzukiMichiyo Inukai
Mar 25, 2008·Bioorganic & Medicinal Chemistry·Toshinori SuzukiMichiyo Inukai
Feb 9, 2012·International Forum of Allergy & Rhinology·Kristin A SeiberlingLawrence C Sowers
Nov 22, 2005·Archives of Biochemistry and Biophysics·Jianguo Wang, Arne Slungaard
Aug 30, 2005·Archives of Biochemistry and Biophysics·Revathy Senthilmohan, Anthony J Kettle
May 30, 2013·Bioorganic & Medicinal Chemistry Letters·Toshinori SuzukiMichiyo Inukai
May 21, 2013·Bioorganic & Medicinal Chemistry·Toshinori SuzukiMichiyo Inukai
Mar 19, 2014·Free Radical Biology & Medicine·Benjamin S RaynerClare L Hawkins
Feb 6, 2020·Bioinformatics·Rostislav K SkitchenkoAlbert Guskov
Apr 23, 2003·The Journal of Biological Chemistry·Jeffrey P HendersonJay W Heinecke
Sep 10, 2017·Journal of Computer-aided Molecular Design·Farzaneh SarramiAmir Karton
Jul 15, 2020·Cellular and Molecular Life Sciences : CMLS·Agnes Ulfig, Lars I Leichert
Mar 16, 2021·Frontiers in Medicine·Filippo FagniGiacomo Emmi
Sep 22, 2006·The Journal of Physical Chemistry. a·Xingbang HuWanchun Liang
Jul 15, 2006·The Journal of Physical Chemistry. a·Jan Cz DobrowolskiAleksander P Mazurek

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