L8511

Sigma-Aldrich

Leupeptin

synthetic, ≥85% (HPLC)

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

Quality Level

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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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_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
An Improved Method for Measuring Chromatin-binding Dynamics Using Time-dependent Formaldehyde Crosslinking
Hoffman EA, et al.
Bio-protocol, 8(4) (2018)
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)
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)
Nathalia Moraes de Vasconcelos et al.
Cell reports, 32(4), 107959-107959 (2020-07-30)
Pyroptosis has emerged as a key mechanism by which inflammasomes promote host defense against microbial pathogens and sterile inflammation. Gasdermin D (GSDMD)-mediated cell lysis is a hallmark of pyroptosis, but our understanding of cell death signaling during pyroptosis is fragmented....

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