PhosphoramidonAn inhibitor of NEP 24.11 and NEP2

Phosphoramidon (CAS 119942-99-3)

Phosphoramidon | CAS 119942-99-3 is rated 5.0 out of 5 by 1.
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Synonym: Phosphoramidon sodium salt;N-(α-Rhamnopyranosyloxyhydroxyphosphinyl)-Leu-Trp disodium salt;N-(α-Rhamnopyranosylphosphono)-L-leucyl-L-tryptophan disodium salt
Application: An inhibitor of NEP 24.11 and NEP2
CAS Number: 119942-99-3
Purity: ≥97%
Molecular Weight: 587.47
Molecular Formula: C23H32N3O10P•2Na
* Refer to Certificate of Analysis for lot specific data (including water content).
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Phosphoramidon is an inhibitor of CD10 (neutral endopeptidase 24.11, NEP), metalloproteases (MMPs), and Neprilysin-2 (NEP2), which belong to a group of type II integral membrane glycoproteins. In addtion, the NEP enzyme has been shown to play a role in the regulation of neuropeptide signaling and in the metabolism of bioactive peptides via plasma membranes. NEP2 is a homologue of NEP with a high degree of sequence identity, however, research shows that they have different physiological actions. Studies show that phosphoramidon and thiorphan (sc-201287), another NEP inhibitor, can increase nitrile production. Additionally, LNCaP cell studies show that phosphoramidon can inhibit the metabolism of neurotensin (NT). Phosphoramidon is an inhibitor of endothelial converting enzyme (ECE).


References

1. Hiranuma, T., et al. 1997. J. Pharmacol. Exp. Ther. 281: 769-774. PMID: 9152384
2. Zhang, X., et al. 1998. J. Cardiovasc. Pharmacol. 31: 623-629. PMID: 9554814
3. Moody, T.W., et al. 1998. Peptides. 19: 253-258. PMID: 9493857
4. Rose, C., et al. 2002. Biochem. J. 363: 697-705. PMID: 11964170
5. Whyteside, A.R., et al. 2008. FEBS Lett. 582: 2382-2386. PMID: 18539150

Physical State :
Solid
Solubility :
Soluble in water (1 mM), DMSO, and methanol. Insoluble in benzene, hexane, and chloroform.
Storage :
Store at -20° C
IC50 :
endothelin-converting enzyme (EC50E): IC50 = 0.68 µM
Ki Data :
neutral endopeptidase 24.11 (NEP, neprilysin; EC 3.4.24.11): Ki= 2 nM; neprilysin 2: Ki= ~2 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
16219931
MDL Number :
MFCD00077870
EC Number :
252-996-3
Beilstein Registry :
8105669
SMILES :
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)[O-])[O-])O)O)O.[Na+].[Na+]

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Certificate of Analysis

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Phosphoramidon  Product Citations

See how others have used Phosphoramidon. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 24247244  McDonald, AJ. et al. 2014. J. Biol. Chem. 289: 803-13.

PMID: # 24343520  Bolos, M. et al. 2014. Cell. Mol. Life Sci. 71: 2947-55.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Rose et al Rose et al. (PubMed ID 11964170) used phosphoramidon to inhibit NEP and NEP2 to analyze cell-specific activity of NEP2 isoforms. -SCBT Publication Review
Date published: 2015-07-01
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