R7385

Phosphoramidon disodium salt

powder, ≥97% (HPLC)

• Synonyme(s) : N-(α-Rhamno­pyranosyl­oxy­hydroxy­phosphinyl)-Leu-Trp disodium salt, N-(α-Rhamno­pyranosyl­phos­phono)-L-leucyl-L-tryptophan disodium salt
• Formule empirique (notation de Hill): C₂₃H₃₂N₃Na₂O₁₀P
• Numéro CAS: 119942-99-3
• Poids moléculaire : 587.47
• Numéro Beilstein : 8105669
• Numéro MDL: MFCD00077870
• Code UNSPSC : 12352202
• ID de substance PubChem : 24278681
• Nomenclature NACRES : NA.77

Propriétés

• product name: Phosphoramidon disodium salt, ≥97% (HPLC)
• Source biologique: Streptomyces sp.
• Pureté: ≥97% (HPLC)
• Forme: powder
• Solubilité: H₂O: 50 mg/mL
• Température de stockage: −20°C
• Chaîne SMILES: [Na+].[Na+].CC(C)C[C@H](NP([O-])(=O)O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C([O-])=O
• InChI: 1S/C23H34N3O10P.2Na/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15;;/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34);;/q;2*+1/p-2/t12-,16-,17-,18-,19+,20+,23-;;/m0../s1
• Clé InChI: OQKHVXFOYFBMDJ-ODIUWQMJSA-L

Description

Description générale

Phosphoramidon [N-(α-rhamnopyranosyl-oxyhydroxyphosphinyl)-Leu-Trp] is a competitive inhibitor of several soluble zinc metalloproteases. Phosphoramidate is produced naturally by Streptomyces tanashiensis.

Application

Phosphoramidon disodium salt has been used:

• as the neprilysin (NEP) inhibitor: in amyloid beta (Aβ) uptake and degradation
• to study its effect on keratinase activity
• to treat primary microglia from wild-type mice

Identification of phosphoramidon as a metallo-endopeptidase inhibitor was used to characterize endothelin converting enzyme as a metallo-endopeptidase. Phosphoramidon increases the production of β-amyloid protein, but not amyloid precursor protein, indicating that abnormal amyloid processing in Alzheimer′s disease may be carried out by a metallo-endopeptidase.

Actions biochimiques/physiologiques

Phosphoramidon can inhibit ZMPSTE24, an integral membrane protein zinc metalloprotease. It is capable of blocking thermolysin.

Phosphoramidon is a potent inhibitor of thermolysin and other metallo-endopeptidases. It trongly inhibits mammalian enkephalinase and it does not inhibit trypsin, papain, chymotrypsin or pepsin. It weakly inhibits collagenase.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)