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208719

ALLN

Name: ALLN
Brand: MM

≥95% (HPLC), solid, calpain inhibitor, Calbiochem^®

Synonym(s):

ALLN, LLNL, MG 101, Calpain Inhibitor I, Proteasome Inhibitor V

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₃₇N₃O₄

CAS Number:

110044-82-1

Molecular Weight:

383.53

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00065505

Assay:

≥95% (HPLC)

Form:

solid

Storage condition:

OK to freeze

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Properties

Product Name

ALLN, Cell-permeable inhibitor of calpain I (Ki = 190 nM), calpain II (Ki = 220 nM), cathepsin B (Ki = 150 nM), and cathepsin L (Ki = 500 pM).

Quality Segment

100

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze

color

white to off-white

solubility

DMSO: 10 mg/mL, ethanol: 5 mg/mL

shipped in

ambient

storage temp.

2-8°C

SMILES string

N([C@@H](CC(C)C)C(=O)N[C@@H](CCCC)C=O)C(=O)[C@@H](NC(=O)C)CC(C)C

InChI

1S/C20H37N3O4/c1-7-8-9-16(12-24)22-19(26)18(11-14(4)5)23-20(27)17(10-13(2)3)21-15(6)25/h12-14,16-18H,7-11H2,1-6H3,(H,21,25)(H,22,26)(H,23,27)/t16-,17-,18-/m0/s1

InChI key

FMYKJLXRRQTBOR-BZSNNMDCSA-N

Description

General description

Cell-permeable inhibitor of calpain I (K_i= 190 nM), calpain II (K_i= 220 nM), cathepsin B (K_i= 150 nM), and cathepsin L (K_i= 500 pM). Inhibits neutral cysteine proteases and the proteasome (K_i = 6 µM). Modulates the processing of the β-amyloid precursor protein (βAPP) to β-amyloid (Aβ). Protects against neuronal damage caused by hypoxia and ischemia. Inhibits apoptosis in thymocytes and metamyelocytes. Also inhibits reovirus-induced apoptosis in L929 cells. Inhibits the proteolysis of IκB-α and IκB-β by the ubiquitin-proteasome complex. Inhibits cell cycle progression at G₁/S and metaphase/anaphase in CHO cells by inhibiting cyclin B degradation. Also prevents nitric oxide production by activated macrophages by interfering with transcription of the inducible nitric oxide synthase gene. A 10 mM (5 mg/1.30 ml) solution of ALLN (Cat. No. 208750 ) in DMSO is also available.

Inhibitor of calpain I (K_i = 190 nM), calpain II (K_i = 220 nM), cathepsin B (K_i = 150 nM), and cathepsin L (K_i = 500 pM). Inhibits neutral cysteine proteases and proteasome (K_i = 6 µM). Protects against neuronal damage caused by hypoxia and ischemia. Inhibits apoptosis in thymocytes and metamyelocytes. Inhibits cell cycle progression at the G1/S border and metaphase/anaphase in CHO cells by inhibiting cyclin B degradation. Also prevents nitric oxide production by activated macrophages by interfering with transcription of the inducible nitric oxide synthase gene. Inhibits the proteolysis of IκBα and IκBβ by the ubiquitin-proteasome complex.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Calpain-1

Product does not compete with ATP.

Reversible: no

Target K_i: 190 nM, 220 nM, 150 nM, 500 pM, against calpain I, calpain II, cathepsin B, and cathepsin L, respectively

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Debiasi, R.L., et al. 1999. J. Virol. 73, 695.
Zhang, L., et al. 1999. J. Biol. Chem.274, 8966.
Milligan, S.A., et al. 1996. Arch. Biochem. Biophys. 335, 388.
Griscavage, J.M., et al. 1995. Biochem. Biophys. Res. Commun. 215, 721.
Squier, M.K., et al. 1994. J. Cell Physiol.159, 229.
Rami, J., and Kreiglstein, J. 1993. Brain Res.609, 67.
Sherwood, S.W., et al. 1993. Proc. Natl. Acad. Sci.USA90, 3353.
Vinitsky, A., et al. 1992. Biochemistry31, 9421.
Sasaki, T., et al. 1990. J. Enzyme Inhib. 3, 195.

N-Acetyl-Leu-Leu-Nle-CHO

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c