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.
[reaction: see text]. The potent oxidant, peroxynitrite, will oxidize 8-oxo-7,8-dihydroguanosine to give several products. In the presence of a thiol agent, the major final product has been determined to be a spiroiminodihydantoin compound. Additionally, we have found that the spiroiminodihydantoin, and not the previously reported 4-hydroxy-8-oxo-4,8-dihydroguanosine, is the major final product formed during the methylene blue-mediated photooxidation of guanosine.
Division of Bioengineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Room 56-731A, Cambridge, Massachusetts 02139, USA.
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Niles
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Wishnok
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Tannenbaum
D002851:Chromatography, High Pressure Liquid; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008751:Methylene Blue / Q000737:chemistry; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry
D009566:Nitrates; D016877:Oxidants; D013141:Spiro Compounds; D013438:Sulfhydryl Compounds; C408822:spiroiminodihydantoin; D006151:Guanosine; C039642:peroxynitric acid; C046215:8-hydroxyguanosine; D008751:Methylene Blue