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Merck
CN

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(s):

DL-Thiorphan, N-[(RS)-2-Benzyl-3-mercaptopropanoyl]-glycine

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About This Item

Empirical Formula (Hill Notation):
C12H15NO3S
CAS Number:
76721-89-6
Molecular Weight:
253.32
MDL number:
MFCD00058435
UNSPSC Code:
12352200

Key Documents

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Quality Level

100

Assay

≥95% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated
protect from light

color

white

solubility

DMSO: 10 mg/mL
ethanol: 10 mg/mL

shipped in

ambient

storage temp.

−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)

InChI key

LJJKNPQAGWVLDQ-UHFFFAOYSA-N

General description

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 Actions

Cell permeable: no
Primary Target
NEP activity
Product does not compete with ATP.
Reversible: no
Target IC50: 2.1 nM for neutral endopeptidase-NEP

Packaging

Packaged under inert gas

Preparation Note

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

Other Notes

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Properties and modulation of excitatory inputs to the locus coeruleus.
Barcomb, et al.
The Journal of physiology, 600, 4897-4916 (2023)

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