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

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.

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.

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.

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.

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.

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.

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.

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.

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