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Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation.

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Niles JC, Wishnok JS, Tannenbaum SR.  2006.  Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation. Nitric Oxide. 14(2):109-21. Google Scholar PubMed

Spiroiminodihydantoin and guanidinohydantoin are the dominant products of 8-oxoguanosine oxidation at low fluxes of peroxynitrite: mechanistic studies with 18O.

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Niles JC, Wishnok JS, Tannenbaum SR.  2004.  Spiroiminodihydantoin and guanidinohydantoin are the dominant products of 8-oxoguanosine oxidation at low fluxes of peroxynitrite: mechanistic studies with 18O. Chem Res Toxicol. 17(11):1510-9. Google Scholar PubMed

Mass spectrometric identification of 4-hydroxy-2,5-dioxo-imidazolidine-4-carboxylic acid during oxidation of 8-oxoguanosine by peroxynitrite and KHSO5/CoCl2.

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Niles JC, Wishnok JS, Tannenbaum SR.  2004.  Mass spectrometric identification of 4-hydroxy-2,5-dioxo-imidazolidine-4-carboxylic acid during oxidation of 8-oxoguanosine by peroxynitrite and KHSO5/CoCl2. Chem Res Toxicol. 17(11):1501-9. Google Scholar PubMed

Peroxynitrite reacts with 8-nitropurines to yield 8-oxopurines.

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Lee JM, Niles JC, Wishnok JS, Tannenbaum SR.  2002.  Peroxynitrite reacts with 8-nitropurines to yield 8-oxopurines. Chem Res Toxicol. 15(1):7-14. Google Scholar PubMed

Spiroiminodihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue.

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Niles JC, Wishnok JS, Tannenbaum SR.  2001.  Spiroiminodihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue. Org Lett. 3(7):963-6. Google Scholar PubMed

A novel nitration product formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-nitro-N’-[1-(2,3,5-tri-O-acetyl-beta-D-erythro-pentofuranosyl)- 2, 4-dioxoimidazolidin-5-ylidene]guanidine.

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Niles JC, Wishnok JS, Tannenbaum SR.  2000.  A novel nitration product formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-nitro-N’-[1-(2,3,5-tri-O-acetyl-beta-D-erythro-pentofuranosyl)- 2, 4-dioxoimidazolidin-5-ylidene]guanidine. Chem Res Toxicol. 13(5):390-6. Google Scholar PubMed

DNA damage in deoxynucleosides and oligonucleotides treated with peroxynitrite.

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Burney S, Niles JC, Dedon PC, Tannenbaum SR.  1999.  DNA damage in deoxynucleosides and oligonucleotides treated with peroxynitrite. Chem Res Toxicol. 12(6):513-20. Google Scholar PubMed

Peroxynitrite-induced reactions of synthetic oligonucleotides containing 8-oxoguanine.

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Tretyakova NY, Niles JC, Burney S, Wishnok JS, Tannenbaum SR.  1999.  Peroxynitrite-induced reactions of synthetic oligonucleotides containing 8-oxoguanine. Chem Res Toxicol. 12(5):459-66. Google Scholar PubMed

The chemistry of DNA damage from nitric oxide and peroxynitrite.

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Burney S, Caulfield JL, Niles JC, Wishnok JS, Tannenbaum SR.  1999.  The chemistry of DNA damage from nitric oxide and peroxynitrite. Mutat Res. 424(1-2):37-49. Google Scholar PubMed