168701-80-2Relevant articles and documents
Role of nitrite on nitration of 2′-deoxyguanosine by nitryl chloride
Chen, Hauh-Jyun Candy,Wang, Tze-Fan,Chen, Yuan-Mao
, p. 275 - 281 (2002)
Nitryl chloride and peroxynitrite are reactive nitrogen species generated by activated phagocytes against invading pathogens during infections and inflammation. In our previous report, formation of 8-nitroxanthine and 8-nitroguanine was observed in reaction of 2′-deoxyguanosine or calf thymus DNA with nitryl chloride generated by mixing hypochlorous acid (HOCl) with nitrite (NO2-). The present study investigates factors controlling the yields of 8-nitroxanthine and 8-nitroguanine formation in nitration of 2′-deoxyguanosine by nitryl chloride. We found that the yields of 8-nitroxanthine and 8-nitroguanine in reaction of 2′- deoxyguanosine with nitryl chloride were highly dependent on the ratio of NO2- versus HOCl concentration. The yields of 8-nitroxanthine and 8-nitroguanine reached a plateau when the ratio of NO 2- versus HOCl concentration was higher than 2. A possible mechanism was postulated to explain this observation. While 8-nitroguanine is not stable in the presence of peroxynitrite, 8-nitroxanthine is sensitive to HOCl. The stability of these two nitrated adducts might be a factor on their final yields in this reaction. Since HOCl is produced by neutrophils at sites of inflammation where the level of NO2- is elevated, it is conceivable that nitryl chloride contributes to DNA base nitration in vivo, forming 8-nitroxanthine and 8-nitroguanine.
Base modification and strand breakage in isolated calf thymus DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3- morpholinosydnonimine
Spencer, Jeremy P. E.,Wong, Jon,Jenner, Andrew,Aruoma, Okezie I.,Cross, Caroll E.,Halliwell, Barry
, p. 1152 - 1158 (1996)
Exposure of isolated calf thymus DNA and human skin epidermal keratinocytes to peroxynitrite or the peroxynitrite generator, 3- morpholinosydnonimine (SIN-1), led to extensive DNA base modification. Large increases in xanthine and hypoxanthine, possible deamination products of guanine and adenine, respectively, and in 8-nitroguanine were observed, but only small changes in some oxidized base products were seen. This pattern of damage suggests that hydroxyl radicals were not major contributors to base modification caused by peroxynitrite, as OH· is known to cause multiple oxidative modifications to all four DNA bases. Instead, it seems that reactive nitrogen species play a much greater role in the mechanism of base damage, producing both nitration and deamination of purine bases when DNA or whole cells are exposed to peroxynitrite. If this pattern of damage is unique to peroxynitrite, it might act as a marker of cellular damage by this species in vivo.
Nitration of 2′-deoxyguanosine by a NO/O2 gas mixture: Identification and characterization of N2-nitro-2′ -deoxyguanosine
Yamada, Masaki,Suzuki, Toshinori,Kanaori, Kenji,Tajima, Kunihiko,Sakamoto, Shunji,Kodaki, Tsutomu,Makino, Keisuke
, p. 3173 - 3176 (2003)
(Matrix presented) A gas mixture of NO and O2 was bubbled into 2′-deoxyguanosine solution at neutral pH and 37°C. A novel nitrated nucleoside was generated in the reaction mixture in addition to 8-nitroguanine, 8-nitroxanthine, 2′-deoxyxanthosine, xanthine, and guanine. The novel nucleoside was identified as N2-nitro-2′-deoxyguanosine by spectrometric data.