Peroxynitrite and NO+ donors form colored nitrite adducts with sinapinic acid: potential applications

Nitric Oxide : Biology and Chemistry
Shirin AkhterBulent Mutus

Abstract

Sinapinic acid (3,5-dimethoxy-4-hydroxycinnamic acid, SA) reacted with peroxynitrous acid at neutral pH with a second-order rate constant of 812 M(-1)s(-1), to yield a red product (lambda(max), 532 nm). The identical colored product could be formed with acidified decomposed peroxynitrous acid solutions or nitrite at slower rates (0.1M HCl, 8.32 M(-1)s(-1); 10% acetic acid, 0.0004 M(-1)s(-1)). The red compound is thought to be O-nitrososinapinic acid (3,5-dimethoxy-4-nitrosooxycinnamic acid) which can be formed by reaction with either peroxynitrous acid or nitrous acid. The extinction coefficient of O-nitrososinapinic acid (ONSA) was estimated to be 8419 M(-1)cm(-1) at 510 nm in 10% acetic acid and 90% acetonitrile. ONSA was also formed via NO(+) transfer from S-nitrosoglutathione (GSNO). ONSA in turn can S-nitrosate low molecular weight thiols and protein thiols. SA was also shown to act as a peroxynitrite sink as it effectively prevented the oxidation of dihydrorhodamine under physiological conditions. The fact that O-nitrososinapinic acid is stable and can be used to S-nitrosate thiol containing amino acids, peptides, and proteins makes it a potentially useful reagent in the study of S-nitrosothiol biochemistry and physiology...Continue Reading

References

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Citations

May 19, 2005·Analytical and Bioanalytical Chemistry·Sarah A SheeleyJonathan V Sweedler
Aug 26, 2011·Chemico-biological Interactions·L Pari, A Mohamed Jalaludeen
Oct 20, 2009·Biochimica Et Biophysica Acta·Vasantha Madhuri KallakuntaBulent Mutus
Jun 16, 2007·Life Sciences·Byung Hoon YoonJong Hoon Ryu
Oct 4, 2007·Journal of Pineal Research·Anna KopczakMichael Kirsch
Apr 14, 2016·Oxidative Medicine and Cellular Longevity·Chunye Chen

Related Concepts

3-morpholinosydnonimine N-ethylcarbamide
Sinapinic acid
Dihydrorhodamine 6G
Coumaric Acids
Molsidomin von ct
Nitrites
Nitrous Acid
Rhodamine
Nitric Oxide Donors
S-Nitrosoglutathione

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