L-Arginine, methyl ester

L-NAME (N-nitro-L-arginine methyl ester), like L-NMMA, is a structural analogue of L-arginine and competes with L-arginine for NO-synthase, which uses L-arginine as a substrate for the formation of NO. L-NMMA and L-NAME are very effective NO-synthesis inhibitors, both in vitro and in vivo. 

C7H(iN204 616-79-5) see Afloqualone nitro-L-arginine methyl ester hydrochloride (C7H ftCIN,04 51298-62-5) see Angiotensinamide... 

N-Nitro-L-arginine methyl ester (L-NAME) is an inhibitor of NOS L-NAME reportedly reduces the volume of cortical and striatal infarct after middle cerebral artery occlusion in the rat. This protection can be reversed by co-injection of L-arginine. L-NAME also reduced the excitotoxic damage induced by NMDA injection. Finally, the authors showed that L-NAME reduced glutamate efflux produced by ischaemic injury in rats. The authors concluded that NOS induced by NMDA receptor overstimulation is a key event in the neuronal injury cascade (Buisson eta/., 1993). 

NO is a gaseous neurotransmitter implicated in signaling in the central and peripheral nervous system as well as in the immune system and the vasculature. NO is formed from L-arginine by nitric oxide synthase (NOS). There are three isoforms of NOS. All isoforms require NADPH as a cofactor, use L-arginine as a substrate, and are inhibited by Nw-nitro-L-arginine methyl ester (L-NAME). The three isoforms are separate gene products. One isoform of NOS is a cytosolic, calcium/calmodulin-independent, inducible enzyme (iNOS). It is found in macrophages, neutrophils, vascular smooth muscle, and endothelia. The iNOS... 

Abbreviations BSO, D.L-buthionine-. i -sulfoxime L , lipid alkyl radicals LH, lipid LO, Upid alkoxyl radicals LOO, Upid peroxyl radicals L-NAME, yV -nitro-L-arginine-methyl ester MBl, methylene bridge index (mean number of h -aUytic methylene positions per fatty add) NO, nitric oxide NOS, nitric oxide synthase NO, nitrite N02, nitrogen dioxide NO2CI, nitryl chloride O2 , superoxide OH, hydroxyl radical OL, epoxyaUyhc radical OLOO, epoxyperoxyl radical 0=NOO , peroxynitrite SNAP, S-nitroso-iV-acetyl-D.L-penicillamine SOD, superoxide dismutase contd. onp. 98, Subcellular Biochemistry, Volume 36 Phospholipid Metabolism in Apoptosis. 

Vffl-Nitro-L-arginine methyl ester (l-NAME) Competitive inhibitor, binds arginine-binding site in NOS Nonselective NOS inhibitor... 

It is well known that synthetic arginine esters, such as NQ -tosyl-L-arginine methyl ester (TAME), are hydrolyzed by thrombin and inhibit the clotting activity of thrombin. Since the binding specificities of arginine derivatives would be determined by the structure of both sides of arginine, i.e., amino as well as carboxyhc sides, a series of studies were undertaken by Okamoto et al. [104-106] to obtain potent and specific inhibitors of thrombin by modifications of the Na-substituent and methyl ester positions of TAME. 

Trichlorophenoxyacetic acid Triallyl cyanurate Trimethylacetamidomethyl A-Methylanilinium trifluoroacetate A-a-p-Tosyl-L-arginine methyl ester hydrochloride tetrakis(acetoxymercuri)methane... 

S. Gumuslu, M. Serteser, T. Ozben, S. Balkan, and E. Balkan, Inhibitory Role of N -nitro-L-Arginine Methyl Ester (L-NAME), a Potent Nitric Oxide Synthase Inhibitor on Brain Malondialdehyde and Conjugated Diene Levels During Focal Cerebral Ischemia in Rats. Clinica ChimicaActa 267(2) (1997) 213-223. 

Vargas F, Osuna A, Fernandez-Rivas A Vascular reactivity and flow-pressure curve in isolated kidneys from rats with N-nitro-L-arginine methyl ester-induced hypertension. J Hypertens 14 373-9,1996... 

An alternative method for preparing derivatives of bromoacetate involves using bromoacetyl bromide or bromoacetyl chloride. The synthesis of the N-bromoacetyl derivative of L-arginine methyl ester with bromoacetyl bromide was carried out by Liu (1967). The product N-bromoacetyl-L-arginine methyl ester was a successful affinity label for streptococcal proteinase. L-Arginine methyl ester dihydrochloride (780 mg 3 mmoles) was dissolved in 6 ml of ice-cold 1 N NaHCOj. Over a period of 20 min, freshly distilled bromoacetylbromide, 3... 

L-NAME (L-A/ -nitro-L-arginine methyl ester Af -nitro-t-arglnine methyl ester nitroarginine methyl ester) is a NITRIC OXIDE SYNTHASE INHIBITOR, extensively used as a pharmacological tool. l>NI 7-nitroindazole. 

---