Nitrosation of N-Methyl Derivatives of Uric Acid and Their Transnitrosation Ability to N-Acetylcysteine

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2010
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Suzuki, Toshinori
Yamamoto, Hiroshi
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When 1,3-dimethyluric acid was treated with a nitric oxide donor, diethylamine NONOate, in an aerobic neutral solution and the reaction was analyzed by HPLC, 1,3-dimethyluric acid was consumed to yield a nitrosated derivative, which decomposed with a half-life of 17.9 min at pH 7.4 and 37 °C. When 1,3,7-trimethyluric acid was treated with diethylamine NONOate, no consumption of 1,3,7-trimethyluric acid was observed. However, in the reaction of N-acetylcysteine with diethylamine NONOate, the yield of N-acetyl-S-nitrosocysteine increased by the addition of 1,3,7-trimethyluric acid as well as 1,3-dimethyluric acid. For 1,3,7,9-tetramethyluric acid, no consumption in the reaction with diethylamine NONOate and no effect on the S-nitrosation were observed. These results suggest that 1,3-dimethyluric and 1,3,7-trimethyluric acids are both nitrosated by diethylamine NONOate on the nitrogen atom of their oxoimidazole ring, although the half-life of the nitrosated 1,3,7-trimethyluric acid is too short to detect by HPLC. Consequently, these two acids can act as vehicles of nitric oxide.

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540 Chemie
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1,3-dimethyluric acid, 1,3,7-trimethyluric acid, N-acetylcysteine, nitrosation, nitric oxide
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ISO 690SUZUKI, Toshinori, Hiroshi YAMAMOTO, Wolfgang PFLEIDERER, 2010. Nitrosation of N-Methyl Derivatives of Uric Acid and Their Transnitrosation Ability to N-Acetylcysteine. In: Chemical and Pharmaceutical Bulletin. Pharmaceutical Society of Japan. 2010, 58(9), pp. 1271-1275. ISSN 0009-2363. eISSN 1347-5223. Available under: doi: 10.1248/cpb.58.1271
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@article{Suzuki2010Nitro-51825,
  year={2010},
  doi={10.1248/cpb.58.1271},
  title={Nitrosation of N-Methyl Derivatives of Uric Acid and Their Transnitrosation Ability to N-Acetylcysteine},
  number={9},
  volume={58},
  issn={0009-2363},
  journal={Chemical and Pharmaceutical Bulletin},
  pages={1271--1275},
  author={Suzuki, Toshinori and Yamamoto, Hiroshi and Pfleiderer, Wolfgang}
}
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