Document Detail

Effects of uric acid on nitrosation of N-acetylcysteine by diethylamine NONOate and N-acetyl-N-nitrosotryptophan.
MedLine Citation:
PMID:  19571422     Owner:  NLM     Status:  MEDLINE    
Uric acid of human plasma concentration accelerated nitrosation of N-acetylcysteine by diethylamine NONOate at neutral pH, but diminished that of N-acetyltryptophan. Uric acid also accelerated nitrosation of N-acetylcysteine by N-acetyl-N-nitrosotryptophan, having a nitroso group on the nitrogen atom of the indole ring. N-Acetyl-S-nitrosocysteine was stable even in the presence of uric acid and N-acetyltryptophan at neutral pH, while decomposition of N-acetyl-N-nitrosotryptophan was accelerated by uric acid and N-acetylcysteine. The results indicate that uric acid receives a nitroso group from diethylamine NONOate or N-acetyl-N-nitrosotryptophan, and passes it to the thiol group of N-acetylcysteine resulting in N-acetyl-S-nitrosocysteine. This implies that uric acid may act as an effective transporter of nitric oxide to thiols resulting in accumulation of nitrosothiols in humans.
Toshinori Suzuki; Atsushi Naka; Haruka Kimura
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  57     ISSN:  0009-2363     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2009 Jul 
Date Detail:
Created Date:  2009-07-02     Completed Date:  2009-08-10     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  736-9     Citation Subset:  IM    
School of Pharmacy, Shujitsu University.
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MeSH Terms
Acetylcysteine / chemistry*
Azo Compounds / chemistry*
Diethylamines / chemistry*
Nitrosamines / chemistry*
Tryptophan / analogs & derivatives*,  chemistry
Uric Acid / chemistry*
Reg. No./Substance:
0/Azo Compounds; 0/Diethylamines; 0/N-acetyl-N-nitrosotryptophan; 0/Nitrosamines; 0/diethylamine diazeniumdiolate; 616-91-1/Acetylcysteine; 69-93-2/Uric Acid; 73-22-3/Tryptophan

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