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L8511

Sigma-Aldrich

Leupeptin

synthetic, ≥85% (HPLC)

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Synonym(s):
Leupeptin hemisulfate salt, Acetyl-Leu-Leu-Arg-al, N-Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate salt
Linear Formula:
C20H38N6O4 · 1/2H2SO4
CAS Number:
Molecular Weight:
475.59
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

assay

≥85% (HPLC)

form

powder

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

OS(O)(=O)=O.CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C=O.CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C=O

InChI

1S/2C20H38N6O4.H2O4S/c2*1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;1-5(2,3)4/h2*11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H2,1,2,3,4)/t2*15-,16-,17-;/m00./s1

InChI key

CIPMKIHUGVGQTG-VFFZMTJFSA-N

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1 of 4

This Item
L2884L5793L0649
vibrant-m

L8511

Leupeptin

vibrant-m

L2884

Leupeptin

vibrant-m

L5793

Leupeptin

vibrant-m

L0649

Leupeptin hydrochloride

biological source

synthetic

biological source

microbial

biological source

microbial

biological source

microbial

assay

≥85% (HPLC)

assay

≥90% (HPLC)

assay

≥95% (HPLC)

assay

≥70% (HPLC)

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 50 mg/mL

solubility

H2O: 10 mM (Solutions are stable for a week at 4 °C. Stock solutions are stable up to 6 months at −20 °C.), H2O: 50 mg/mL

solubility

H2O: 50 mg/mL

solubility

water: 50 mg/mL, clear, colorless to yellow

form

powder

form

powder

form

powder

form

powder

Application

Leupeptin has been used as a protease inhibitor: in ice-cold lysis buffer to harvest cells for western immunoblotting and immunoprecipitation,in chromatin immunoprecipitation (ChIP) lysis buffer for the isolation of fragmented chromatin samples in lysis buffer I to lyse the cells for tandem affinity purification (TAP)

Biochem/physiol Actions

Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin. (Loss of cochlear hair cells is believed to be mediated by calpain.)
Leupeptin helps to protect motoneurons from apoptosis. It also helps to enhance muscle function following nerve injury. It possesses neurotrophic action and has a growth-stimulating effect.

Analysis Note

Leupeptin gives multiple peaks on HPLC due to equilibria among three forms in solution. Purity determined using three main peaks. Majority of contaminating peptide is racemized leupeptin.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Neurotrophic action of leupeptin, a protease inhibitor on ventral spinal cord in culture
Iwasaki Y, et al.
The International Journal of Neuroscience, 46(3-4), 97-100 (1989)
LAMTOR/Ragulator is a negative regulator of Arl8b-and BORC-dependent late endosomal positioning
Filipek PA, et al.
The Journal of Cell Biology, 216(12), 4199-4215 (2017)
Inhibition of calpains, by treatment with leupeptin, improves motoneuron survival and muscle function in models of motoneuron degeneration
Kieran D and Greensmith L
Neuroscience, 125(2), 427-439 (2004)
RCAN1. 4 regulates VEGFR-2 internalisation, cell polarity and migration in human microvascular endothelial cells
Alghanem AF, et al.
Angiogenesis, 20(3), 341-358 (2017)
An Improved Method for Measuring Chromatin-binding Dynamics Using Time-dependent Formaldehyde Crosslinking
Hoffman EA, et al.
Bio-protocol, 8(4) (2018)

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