nor-NOHA

Cayman Chemical Item Number 10006861

Nω-hydroxy-nor-Arginine (CAS 189302-40-7)

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Description

L-Arginine serves as a common substrate for both nitric oxide synthase (NOS) and arginase in the cell. NOS catalyzes the oxidation of arginine to citrulline and NO with Nω-hydroxy-L-arginine (NOHA) formed as an intermediate. Arginase, on the other hand, catalyzes the hydrolysis of arginine into urea and L-ornithine. nor-NOHA is a potent, reversible inhibitor of rat liver arginase with a Ki value of 0.5 µM, which is 20-fold lower than the Ki of 10 µM observed for NOHA.1 It is about 40-fold more potent than NOHA as an inhibitor of arginase from mouse macrophages, exhibiting an IC50 of 10-12 µM.2 nor-NOHA is not a substrate for any of the 3 NOS isoforms and does not inhibit nNOS or iNOS.3,4

1. Custot, J., Moali, C., Brollo, M., et al. A new a-amino acid Nw-hydroxy-nor-L-arginine: A highly-affinity inhibitor of arginase well adapted to bind to its manganese cluster. J Am Chem Soc 119 4086-4087 (1997).

2. Tenu, J., Lepoivre, M., Moali, C., et al. Effects of the new arginase inhibitor Nw-hydroxy-nor-L-arginine on NO synthase activity in murine macrophages. Nitric Oxide 3(6) 427-438 (1999).

3. Dijols, S., Perollier, C., Lefevre-Groboillot, D., et al. Oxidation of Nw-hydroxyarginine analogues by NO-synthase: The simple, non amino acid N-butyl N'-hydroxyguanidine is almost as efficient an NO precursor as Nw-hydroxyarginine. J Med Chem 44(20) 3199-3202 (2001).

4. missing reference text

Synonyms
  • Nω-hydroxy-nor-Arginine
Formal Name 2S-​amino-​4-​[[(hydroxyamino)iminomethyl]amino]-​butanoic acid,​ dihydrochloride,​ hydrate
CAS Number 189302-40-7
Molecular Formula C5H12N4O3
Formula Weight 176.2
Formulation A lyophilized powder
Purity ≥97%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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N/C(N([H]​)​CC[C@H]​(N)​C(O)​=O)​=N\O
InCHI Code
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​1S/C5H12N4O3/c6-3(4(10)​11)​1-2-8-5(7)​9-12/h3,12H,1-2,6H2,(H,10,11)​(H3,7,8,9)​
InCHI Key
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KOBHCUDVWOTEKO-UHFFFAOYSA-N

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nor-NOHA is available in the following screening library:

Size Price Quantity Subtotal
1 mg $17.00 $0.00
5 mg $77.00 $0.00
10 mg $136.00 $0.00
50 mg $595.00 $0.00
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