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AdipoGen Life Sciences
Phosphoramidon . disodium salt
120
CHF
CHF 120.00
In stock
AG-CP3-7008-M0055 mgCHF 120.00
AG-CP3-7008-M02525 mgCHF 480.00
| Product Details | |
|---|---|
| Synonyms | N-[N-[[(6-Deoxy-α-L-mannopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]-L-tryptophan disodium salt; NSC 694280 |
| Product Type | Chemical |
| Properties | |
| Formula |
C23H32N3O10P . 2Na |
| MW | 541.5 . 46.0 |
| CAS | 164204-38-0 |
| Source/Host Chemicals | Synthetic. Originally isolated from Streptomyces tanashiensis. |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | White solid. |
| Solubility | Soluble in water (25mg/ml) or DMSO (10mg/ml). |
| InChi Key | OQKHVXFOYFBMDJ-FXPXQDEJSA-L4 |
| Smiles | C[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](OP(N[C@H](CC(C)C)C(N[C@@H](CC2=CNC3=C2C=CC=C3)C([O-])=O)=O)([O-])=O)O1.[Na+].[Na+] |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light and moisture. |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Phosphoramidon is a potent, reversible and competitive inhibitor of multiple soluble and membrane-bound zinc metalloproteases, particularly gluzincins, such as neutral endopeptidase NEP (Neprilysin; CD10; EC 3.4.24.11) (Ki = 2nM), NEP2 (Neprilysin-2) (Ki ~ 2nM), or endothelin-converting enzyme (ECE) (IC50 = 0.68μM). It inhibits the thermostable neutral metalloproteinase enzyme thermolysin and the integral membrane protein zinc metalloprotease ZMPSTE24. It has little or no effect on a variety of other proteases, including trypsin, papain, chymotrypsin, pepsin and angiotensin-converting enzyme.
- Shows anti-inflammatory, anti-neurodegenerative and cardioprotective properties. Blocks through NEP degradation of amyloid β peptides and increases Aβ levels in rodents, indicating that abnormal amyloid processing in Alzheimer's disease may be carried out by a metalloendopeptidase. Plays also a role in the regulation of neuropeptide signaling and in the metabolism of bioactive peptides, such as bradykinin, neurotensin and enkephalin, via plasma membranes. Blocks the formation of endothelin-1, a proinflammatory mediator implicated in the pathogenesis of a variety of lung diseases.
Product References
- Letter: A thermolysin inhibitor produced by Actinomycetes: phospholamidon: H. Suda, et al.; J. Antibiot. (Tokyo) 26, 621 (1973)
- Phosphoramidon, a metalloproteinase inhibitor, suppresses the hypertensive effect of big endothelin-1: Y. Matsumura, et al.; Eur. J. Pharmacol. 185, 103 (1990)
- Neutral endopeptidase-24.11 inhibitors: from analgesics to antihypertensives?: B.P. Roques & A. Beaumont; Trends Pharmacol. Sci. 11, 245 (1990)
- Regional differences in endothelin converting enzyme activity in rat brain: inhibition by phosphoramidon and EDTA: T.D. Warner; Br. J. Pharmacol. 106, 948 (1992)
- Molecular pharmacology of endothelin converting enzymes: A.J. Turner & L.J. Murphy; Biochem. Pharmacol. 51, 91 (1996)
- Neutral endopeptidase and angiotensin-converting enzyme inhibitors increase nitric oxide production in isolated canine coronary microvessels by a kinin-dependent mechanism: X. Zhang, et al.; J. Cardiovasc. Pharmacol. 31, 623 (1998)
- Soluble human endothelin-converting enzyme-1: expression, purification, and demonstration of pronounced pH sensitivity: K. Ahn, et al.; Arch. Biochem. Biophys. 359, 258 (1998)
- Neurotensin is metabolized by endogenous proteases in prostate cancer cell lines: T.W. Moody, et al.; Peptides 19, 253 (1998)
- Cell-specific activity of neprilysin 2 isoforms and enzymic specificity compared with neprilysin: C. Rose, et al.; Biochem. J. 363, 697 (2002)
- Cardioprotective effects of phosphoramidon on myocardial structure and function in murine Chagas' disease: L.A. Jelicks, et al.; Int. J. Parasitol. 32, 1497 (2002)
- Human neprilysin-2 (NEP2) and NEP display distinct subcellular localisations and substrate preferences: A.R. Whyteside & A.J. Turner; FEBS Lett. 582, 2382 (2008)
- Phosphoramidon, an endothelin-converting enzyme inhibitor, attenuates lipopolysaccharide-induced acute lung injury: T.M. Bhavsar, et al.; Exp. Lung Res. 34, 141 (2008)
- Amyloid-beta and Alzheimer’s disease: the role of neprilysin-2 in amyloid-beta clearance: R.A. Marr & D.M. Hafez; Front. Aging Neurosci. 6, 187 (2014)
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