MEG (sulfate)A selective NOS2 inhibitor

MEG (sulfate) (CAS 3979-00-8)

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Synonym: (2- mercaptoethyl)-guanidine sulfate; Mercaptoethylguanidine hemisulfate salt
Application: A selective NOS2 inhibitor
CAS Number: 3979-00-8
Molecular Weight: 336.46
Molecular Formula: [C3H9N3S]2•H2SO4
* Refer to Certificate of Analysis for lot specific data (including water content).
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MEG (sulfate) is a selective scavenger of peroxynitrite and a NOS2 (iNOS) inhibitor. The EC50 values for inhibition of NOS2 (LPS-treated rat lung), NOS3 (eNOS) (bovine endothelial), and NOS1 (nNOS) (rat brain) are 11.5, 110, and 60 μM, respectively. MEG reacts with peroxynitrite with a second order rate constant of 1,900 M-1s-1 at 37°C. MEG (sulfate) also has potent anti-inflammatory activity, which may be due to the combined effect of MEG acting as an inhibitor of NOS2 and as a scavenger of peroxynitrite.


References

1 Southan, G.J., Zingarelli, B., O'Connor, M., et al. Spontaneous rearrangement of aminoalkylisothioureas into mercaptoalkylguanidines, a novel class of nitric oxide synthase inhibitors with selectivity towards the inducible isoform. Br J Pharmacol 117 619-632 (1996). 2 Szabó, C., Ferrer-Sueta, G., Zingarelli, B., et al. Mercaptoethylguanidine and guanidine inhibitors of nitric-oxide synthase react with peroxynitrite and protect against peroxynitrite-induced oxidative damage. J Biol Chem 272 9030-9036 (1997). 3 Cuzzocrea, S., Zingarelli, B., Hake, P., et al. Antiinflammatory effects of mercaptoethylguanidine, a combined inhibitor of nitric oxide synthase and peroxynitrite scavenger, in carrageenan-induced models of inflammation. Free Radic Biol Med 24 450-459 (1998).

Physical State :
Solid
Solubility :
Soluble in ethanol, DMSO, DMF, PBS, pH 7.2 (~10 mg/ml), and water (10 mg/ml at 25° C).
Storage :
Store at 4° C
Melting Point :
181.0° C
Boiling Point :
645.7° C at 760 mmHg (Predicted)
IC50 :
iNOS: EC5050 = 11.5 µM (LPS treated rat lung); nNOS: EC5050 = 60 µM (rat brain); eNOS: EC5050 = 110 µM (bovine endothelial)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
16219710
MDL Number :
MFCD03789572
SMILES :
C(CS)N=C(N)N.C(CS)N=C(N)N.OS(=O)(=O)O

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Certificate of Analysis

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