598510

DL-Thiorphan

A thiol containing amido-acid that selectively binds to the active site zinc of metalloproteinases and blocks their activity (IC₅₀ = 2.1 nM for neutral endopeptidase-NEP).

• Synonym(e): DL-Thiorphan, N-[(RS)-2-Benzyl-3-mercaptopropanoyl]-glycine
• Empirische Formel (Hill-System): C₁₂H₁₅NO₃S
• CAS-Nummer: 76721-89-6
• Molekulargewicht: 253.32
• MDL-Nummer: MFCD00058435
• UNSPSC-Code: 12352200

Eigenschaften

• Qualitätsniveau: 100
• Assay: ≥95% (TLC)
• Form: solid
• Hersteller/Markenname: Calbiochem^®
• Lagerbedingungen: OK to freeze; desiccated; protect from light
• Farbe: white
• Löslichkeit: DMSO: 10 mg/mL; ethanol: 10 mg/mL
• Versandbedingung: ambient
• Lagertemp.: −20°C
• InChI: 1S/C12H15NO3S/c14-11(15)7-13-12(16)10(8-17)6-9-4-2-1-3-5-9/h1-5,10,17H,6-8H2,(H,13,16)(H,14,15)
• InChIKey: LJJKNPQAGWVLDQ-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

A thiol containing amido-acid that selectively binds to the active site zinc of metalloproteinases and blocks their activity (IC₅₀ = 2.1 nM for neutral endopeptidase-NEP). Although it is shown to inhibit the activity for Aβ peptide degrading enzyme neprilysin in vitro, it has no effect on the secretion of Aβ peptide or amyloid β precursor protein (APP). Also reported to inhibit the activity of angiotensin-converting enzyme (ACE) at much higher concentrations (IC₅₀ = 140 nM); however, it does not affect the activity of endothelin-converting enzyme.

A thiol-containing amido-acid that selectively binds to the active site zinc of neprilysin (also known as neutral endopeptidase and NEP) and inhibits its activity (IC₅₀ = 2.1 nM). Inhibits the β-amyloid (Aβ) degrading activity of neprilysin in vivo, but does not affect the secretion of either Aβ peptide or amyloid precursor protein (APP). Also shown to inhibit other neprilysin-related family members, such as mouse NL1 (IC₅₀ = 47 nM) and the neprilysin homolog from Ascaris suum (IC₅₀ = 22 µM). Inhibits the activity of angiotensin-converting enzyme (ACE) (IC₅₀ = 140 nM), but has no effect on the activity of endothelin-converting enzyme (ECE).

Biochem./physiol. Wirkung

Cell permeable: no

Primary Target
NEP activity

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 2.1 nM for neutral endopeptidase-NEP

Verpackung

Packaged under inert gas

Warnhinweis

Toxicity: Standard Handling (A)

Rekonstituierung

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 2 weeks at -20°C.

Sonstige Hinweise

Eckman, E.A., et al. 2001. J. Bio. Chem.276, 24540.
Iwata, N., et al. 2001. Science292, 1550.
Shirotani, K., et al. 2001. J. Biol. Chem.276, 21895.
Ghaddar, G., et al. 2000. Biochem. J.347, 419.
Iwata, N., et al. 2000. Nature Med.6, 143.
Takaki, Y., et al. 2000. J. Biochem.128, 897.
Fuller, S.J., et al. 1995. Biochemistry34, 8091.
Sajid, M., et al. 1995. Parasitology.111, 599.
Gomez-Monterrey, I., et al. 1994. J. Med. Chem.37, 1865.
Takahashi, M., et al. 1993. J. Biol. Chem.268, 21394.
Roderick, S.L., et al. 1989. Biochemistry28, 1493.

Rechtliche Hinweise

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable