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Role of Nitrite on Nitration of 2′‐Deoxyguanosine by Nitryl Chloride
Author(s) -
Chen HauhJyun Candy,
Wang TzeFan,
Chen YuanMao
Publication year - 2002
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200200043
Subject(s) - chemistry , deoxyguanosine , peroxynitrite , hypochlorous acid , nitrite , nitration , chloride , reactive nitrogen species , medicinal chemistry , organic chemistry , biochemistry , oxidative stress , nitrate , superoxide , enzyme
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 (NC 2 − ). The present study investigates factors control ling 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 NO 2 − versus HOCl concentration. The yields of 8‐nitroxanthine and 8‐nitroguanine reached a plateau when the ratio of NC 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 ad ducts 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 NC 2 − is elevated, it is conceivable that nitryl chloride contributes to DNA base nitration in vivo , forming 8‐nitroxanthine and 8‐nitroguanine.