MEG is a selective iNOS inhibitor and scavenger of peroxynitrite. The EC50 values for inhibition of iNOS (LPS-treated rat lung), eNOS (bovine endothelial), and nNOS (rat brain) are 11.5, 110, and 60 µM, respectively.1 MEG reacts with peroxynitrite with a second order rate constant of 1,900 M−1s−1 at 37°C.2 MEG has potent anti-inflammatory activity, which may be due to the combined effect of MEG acting as an inhibitor of iNOS and as a scavenger of peroxynitrite.3
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 Pharmacol117619-632(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 Chem2729030-9036(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 Med24450-459(1998).
Formal Name
(2-mercaptoethyl)-guanidine sulfate
CAS Number
3979-00-8
Molecular Formula
[C3H9N3S]2 · H2SO4
Formula Weight
336.4
Formulation
A crystalline solid
Purity
>98%
Stability
1 year
Storage
4°C
Shipping
Wet ice
in continental US; may vary elsewhere
SMILES
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NC(=N)NCCS
Background Reading
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 Chem2729030-9036(1997).
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 Med24450-459(1998).
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 Pharmacol117619-632(1996).
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