02 Oxidative Stress

SIN-1

SIN-1

NO Detection Reagent

  • Product code
    S264  SIN-1
  • CAS No.
    16142-27-1
  • Chemical name
    3-(4-Morpholinyl)sydnonimine, hydrochloride
  • MW
    C6H11ClN4O2=206.63
Unit size Price Item Code
25 mg $173.00 S264-10

 

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25 mg
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Description

SIN-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: 3.7×10-7 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

References

Open References

1) M. Feelisch, J. Ostrowski and E. Noack, "On the Mechanism of NO Release from Sydnonimines", J. Cardiovasc. Pharmacol.198914, S13. 
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.199117, S25. 
3) N. Hogg, V. M. Darley-Usmar, M. T. Wilson and S. Moncada, "Production of Hydroxyl Radicals from the Simultaneous Generation of Superoxide and Nitric Oxide", Biochem. J.1992281, 419. 
4) M. E. Murphy and J. E. Brayden, "Nitric Oxide Hyperpolarizes Rabbit Mesenteric Arteries via ATP-sensitive Potassium Channels", J. Physiol.1995486(1), 47. 
5) 青柳一正, "腎疾患", 臨床検査, 199640(2), 188. 
6) 川西正祐, 井上純子, "活性酸素とNOによるDNA損傷", 生化学, 199769(8), 1014. 
7) H. Kankaanranta, R. G. Knowles, P. Vuorinen, O. Kosonen, P. Holm and E. Moilanen, "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.199751(5), 882. 
8) S. Yamamoto, S. Nishizawa, T. Yokoyama, H. Ryu and K. Uemura, "Subarachnoid Hemorrhage Impairs Cerebral Blood Flow Response to Nitric Oxide but Not to Cyclic GMP in Large Cerebral Arteries", Brain Res.1997757, 1. 
9) S. Pfeiffer, E. Leopold, B. Hemmens, K. Schmidt, E. R. Werner and B. Mayer, "Interference of carboxy-PTIO with Nitric-oxide and Peroxynitrite-mediated Reactions", Free Radic. Biol. Med.199722, 787. 
10) M. B. Herrero, E. de Lamirande and C. Gagnon, "Tyrosine Nitration in Human Spermatozoa: A Physiological Function of Peroxynitrite, the Reaction Product of Nitric Oxide and Superoxide", Mol. Hum. Reprod., 20017, 913. 
11) P. D. Lu, C. Jousse, S. J. Marciniak, Y. Zhang, I. Novoa, D. Scheuner, R. J. Kaufman, D. Ron and H. P. Harding, "Cytoprotection by Pre-emptive Conditional Phosphorylation of Translation Initiation Factor 2", EMBO J.200423, 169.

Handling and storage condition

Specification
Appearance: White to slightly yellowish white needles or crystalline powder
m.p.: 180 - 190oC (dec.)
Thin Layer Chromatogram: To pass test
Handling and storage condition
-20°C,Protect from light
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