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L-NAME (hydrochloride)

Cayman Chemical Item Number 80210

L-N^G-Nitroarginine methyl ester (CAS 51298-62-5)

L-NAME (hydrochloride) (CAS 51298-62-5)

See more	Nitric Oxide (101)

Description

L-NAME requires hydrolysis of the methyl ester by cellular esterases to become a fully functional inhibitor (L-NNA).¹ L-NNA exhibits some selectivity for inhibition of neuronal and endothelial isoforms. It exhibits K_i values of 15 nM, 39 nM, and 4.4 µM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively.^2,3,4 The reported K_i value for the inhibition of iNOS ranges from 4-65 µM.^3,5 L-NAME inhibits cGMP formation in endothelial cells with an IC₅₀ of 3.1 µM (in the presence of 30 µM arginine) and reverses the vasodilation effects of acetylcholine in rat aorta rings with an EC₅₀ of 0.54 µM.^6,7

1 Griffith, O.W., and Kilbourn, R.G. Nitric oxide synthase inhibitors: Amino acids. Methods Enzymol 268 375-392 (1996).

2 Buckner, C.K., Saban, R., Castleman, W.L., et al. Analysis of leukotriene receptor antagonists on isolated human intralobar airways. Ann N Y Acad Sci 524 181-186 (1988).

3 Furfine, E.S., Harmon, M.F., Paith, J.E., et al. Selective inhibition of constitutive nitric oxide synthase by L-N^G-nitroarginine. Biochemistry 32 8512-8517 (1993).

4 Garvey, E.P., Tuttle, J.V., Covington, K., et al. Purification and characterization of the constitutive nitric oxide synthase from human placenta. Arch Biochem Biophys 311 235-241 (1994).

5 Abu-Soud, H.M., Feldman, P.L., Clark, P., et al. Electron transfer in the nitric-oxide synthases. Characterization of L-arginine analogs that block heme iron reduction. J Biol Chem 269 32318-32326 (1994).

6 Rees, D.D., Palmer, R.M.J., Schulz, R., et al. Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo. Br J Pharmacol 101 746-752 (1990).

7 Moore, P.K., al-Swayeth, O.A., Chong, N.W.S., et al. L-N^G-Nitro arginine (L-NOARG), a novel, L-arginine-reversible inhibitor of endothelium-dependent vasodilatation in vitro. Br J Pharmacol 99 408-412 (1990).

Synonyms	L-NG-Nitroarginine methyl ester
Formal Name	N5-[imino(nitroamino)methyl]-L-ornithine, methyl ester, monohydrochloride
CAS Number	51298-62-5
Molecular Formula	C₇H₁₅N₅O₄ · HCl
Formula Weight	269.7
Formulation	A crystalline solid
Purity	≥99%
Stability	1 year
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard [H]N(/C(N([H])CCC[C@H](N)C(OC)=O)=N/[H])[N+]([O-])=O.Cl

Background Reading

Moore, P.K., al-Swayeth, O.A., Chong, N.W.S., et al. L-N^G-Nitro arginine (L-NOARG), a novel, L-arginine-reversible inhibitor of endothelium-dependent vasodilatation in vitro. Br J Pharmacol 99 408-412 (1990).

Furfine, E.S., Harmon, M.F., Paith, J.E., et al. Selective inhibition of constitutive nitric oxide synthase by L-N^G-nitroarginine. Biochemistry 32 8512-8517 (1993).

Abu-Soud, H.M., Feldman, P.L., Clark, P., et al. Electron transfer in the nitric-oxide synthases. Characterization of L-arginine analogs that block heme iron reduction. J Biol Chem 269 32318-32326 (1994).

Buckner, C.K., Saban, R., Castleman, W.L., et al. Analysis of leukotriene receptor antagonists on isolated human intralobar airways. Ann N Y Acad Sci 524 181-186 (1988).

Rees, D.D., Palmer, R.M.J., Schulz, R., et al. Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo. Br J Pharmacol 101 746-752 (1990).

Griffith, O.W., and Kilbourn, R.G. Nitric oxide synthase inhibitors: Amino acids. Methods Enzymol 268 375-392 (1996).

Garvey, E.P., Tuttle, J.V., Covington, K., et al. Purification and characterization of the constitutive nitric oxide synthase from human placenta. Arch Biochem Biophys 311 235-241 (1994).

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L-NAME (hydrochloride) is available in the following screening library:

Bio-active Lipid I Screening Library (96-Well)

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