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3-Morpholinosydnonimine

BML-CN245

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Releases NO and superoxide anion under physiological conditions

SIN-1 is a metabolite of molsidomine which decomposes spontaneously in solution in the presence of oxygen, releasing NO and superoxide anion under physiological conditions. Since NO and superoxide react to form peroxynitrite, SIN-1 may actually produce peroxynitrite under physiological conditions. It is a potent vasodilator and inhibitor of platelet aggregation and produces significant protective effects in myocardial ischemia-reperfusion. The effects of SIN-1 are markedly attenuated by nitroglycerin-induced tolerance. Inhibits cysteine proteases.

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Product Details

Alternative Name	SIN-1, Linsidomine
Appearance	White to off-white solid.
CAS	33876-97-0
Couple Target	Protease
Couple Type	Inhibitor
Formula	C₆H₁₀N₄O₂ . HCl
Identity	Determined by NMR.
MW	206.6
MeltingPoint	186-187°C
Purity	≥98% (HPLC)
Solubility	Soluble in water (25mg/ml), 100% ethanol or DMSO (>5mg/ml).

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended.
Handling	Use freshly prepared solutions.
Long Term Storage	-20°C
Shipping	Ambient Temperature

Regulatory Status	RUO – Research Use Only

(2-Aminobenzothiazole)-Methyl-1,1-Bisphosphonic Acids: Targeting Matrix Metalloproteinase 13 Inhibition to the Bone: A. Laghezza, et al.; Pharmaceuticals (Basel) 14, 85 (2021), Abstract
Tissue-specific contributions of Tmem79 to atopic dermatitis and mast cell-mediated histaminergic itch: J.J. Emrick, et al.; PNAS 115, 12091 (2018), Application(s): Neuronal cell culture, Abstract — Full Text
Modification of HSP proteins and Ca2+ are responsible for the NO-derived peroxynitrite mediated neurological damage in PC12 cell: J. Wen, et al.; Int. J. Clin. Exp. Pathol. 8, 4492 (2015), Abstract — Full Text
EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines: S.I. Dikalov, et al.; Free Rad. Res. 45, 417 (2011), Abstract
Interactions of peroxynitrite with uric acid in the presence of ascorbate and thiols: implications for uncoupling endothelial nitric oxide synthase: N. Kuzkaya et al.; Biochem. Pharmacol. 70, 343 (2005), Abstract
New glycosidase activated nitric oxide donors: glycose and 3-morphorlinosydnonimine conjugates: T.B. Cai et al.; J. Org. Chem. 70, 3518 (2005), Abstract
In vitro cytotoxicity of glyco-S-nitrosothiols. a novel class of nitric oxide donors: H. Babich & H.L. Zuckerbaun; Toxicol. In Vitro 15, 181 (2001), Abstract
An activity in rat tissues that modifies nitrotyrosine-containing proteins: Y. Kamisaki et al.; PNAS 95, 11584 (1998), Abstract
Nitric oxide regulates cardiac Ca2+ current. Involvement of cGMP-inhibited and cGMP-stimulated phosphodiesterases through guanylyl cyclase activation: P.F. Mery et al.; J. Biol. Chem. 268, 26286 (1993), Abstract
Neuronal growth cone collapse and inhibition of protein fatty acylation by nitric oxide: D.T. Hess et al.; Nature 366, 562 (1993), Abstract

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3-Morpholinosydnonimine

BML-CN245

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