Chemical Name: 3-(4-Morpholinyl)sydnonimine, hydrochloride
Appearance: White or slightly yellowish needles or crystalline powderStorage Condition: -20ºC
MW: 206.63, C6H11ClN4O2
Shipping Condition: protect from light and moisture with blue ice or dry ice
Product DescriptionSIN-1, a metabolite of the vasodilator molsidomine, is utilized to separately estimate the effectiveness of NO and peroxynitrite with other NO donors. SIN-1 spontaneously decomposes in the presence of molecular oxygen to generate NO and superoxide. Both products bind very rapidly to form peroxynitrite (rate constant k: 3.7x10-7 M-1s-1). Therefore, SIN-1 is a useful compound that generates peroxynitrite in an efficient manner. Peroxynitrite is a very strong oxidant that generates hydroxyl and nitrosyldioxyl radicals under physiological conditions. Peroxynitrite also decomposes to generate nitrate ion quickly in acidic conditions and slowly in basic conditions. Those species have a different bioactivity from NO.
Reaction of NO release and peroxynitrite production
1. M. Feelisch, et al., On the Mechanism of NO Release from Sydnonimines. J Cardiovasc Pharmacol. 1989;14:S13-S22.
2. M. Feelisch, The Biochemical Pathways of Nitric Oxide Formation from Nitrovasodilators: Appropriate Choice of Exogenous NO Donors and Aspects of Preparation and Handling of Aqueous NO Solutions. J Cardiovasc Pharmacol. 1991;17:S25-S33.
3. N. Hogg, et al., Production of Hydroxyl Radicals from the Simultaneous Generation of Superoxide and Nitric Oxide. Biochem J. 1992;281:419-424.
4. M. E. Murphy, et al., Nitric Oxide Hyperpolarizes Rabbit Mesenteric Arteries via ATP-sensitive Potassium Channels. J Physiol. 1995;486:47-58.
5. H. Kankaanranta, et al., 3-Morpholino-sydnonimine-induced Suppression of Human Neutrophil Degranulation in Not Mediated by Cyclic GMP, Nitric Oxide or Peroxynitrite: Inhibition of the Increase in Intracellular Free Calcium Concentration by N-Morpholinoiminoacetoni. Mol Pharmacol. 1997;51:882-888.
6. S. Yamamoto, et al., Subarachnoid Hemorrhage Impairs Cerebral Blood Flow Response to Nitric Oxide but Not to Cyclic GMP in Large Cerebral Arteries. Brain Res. 1997;757:1-9.
7. S. Pfeiffer, et al., Interference of carboxy-PTIO with Nitric-oxide and Peroxynitrite-mediated Reactions. Free Radic Biol Med. 1997;22:787-794.
8. M. B. Herrero, et al., Tyrosine Nitration in Human Spermatozoa: A Physiological Function of Peroxynitrite, the Reaction Product of Nitric Oxide and Superoxide. Mol Hum Reprod. 2001;7:913-921.
9. P. D. Lu, et al., Cytoprotection by Pre-emptive Conditional Phosphorylation of Translation Initiation Factor 2. EMBO J. 2004;23:169-179.