103476-89-7 Usage
Description
Leupeptin, or N-acetyl-L-leucyl-L-leucyl-L-argininal, is a naturally occurring tripeptide that acts particularly as a serine protease inhibitor and as a cysteine protease inhibitor. It is a reversible protease inhibitor, which inhibits cathepsin B, calpain, and trypsin. Its mechanism of action involves structurally similar covalent binding reactions in the active sites of serine and cysteine proteases. Leupeptin hemisulfate is a reversible inhibitor of trypsin-like proteases and cysteine proteases, inhibiting trypsin, plasmin, papain, and cathepsin B, H, and L. It is a white to off-white lyophilized powder and is commonly used in cell lysis buffers to protect proteins from degradation.
Uses
Leupeptin is used as a pharmaceutical composition for its anti-malarial properties. It is employed in the treatment of noise-induced hearing loss and protects the heart from myocardial stunning. Additionally, it is used to inhibit serine, cysteine proteases, plasmin, trypsin, papain, kallikrein, and cathepsin B.
Used in Research Applications:
Leupeptin is used as a protease inhibitor in ice-cold lysis buffer to harvest cells for western immunoblotting and immunoprecipitation. It is also used in chromatin immunoprecipitation (ChIP) lysis buffer for the isolation of fragmented chromatin samples and in lysis buffer I to lyse the cells for tandem affinity purification (TAP).
Used in Protease Inhibitor Sets:
Leupeptin, along with other protease inhibitors like antipain, chymostatin, pepstatin, and phosphoramidon, is useful for the protection of proteins during their isolation from tissues or membranes. Leupeptin can be removed from the reaction by dialysis. It is included in the Protease Inhibitor Set, which also contains Antipain Dihydrochloride, Aprotinin, Bestatin, Chymostatin, E-64, EDTA-Na2, Leupeptin, Pefabloc SC, Pepstatin, and Phosphoramidon.
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.)
References
1) Aoyagi?et al.?(1969),?Leupeptins, new protease inhibitors from Actinomycetes; J. Antibiot.,?22?283
2) Barrett?et al.?(1981),?Cathepsin B, Cathepsin H and Cathepsin L; Methods Enzymol., Pt C,?80?535
3) Knight?et al. (1980),?Human cathepsin B. Application of the substrate N-benzyloxycarbonyl-L-arginyl-L-arginine 2-naphthylamide to a study of the inhibition by leupeptin; Biochem. J.,?189?447
4) Sarin?et al. (1995),?A protease-dependent TCR-induced death pathway in mature lymphocytes; J. Immunol.,?154?5806
Check Digit Verification of cas no
The CAS Registry Mumber 103476-89-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,3,4,7 and 6 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 103476-89:
(8*1)+(7*0)+(6*3)+(5*4)+(4*7)+(3*6)+(2*8)+(1*9)=117
117 % 10 = 7
So 103476-89-7 is a valid CAS Registry Number.
InChI:InChI=1/C20H38N6O4/c1-12(2)9-16(24-14(5)28)18(29)26-19(30)17(10-13(3)4)25-15(11-27)7-6-8-23-20(21)22/h11-13,15-17,25H,6-10H2,1-5H3,(H,24,28)(H4,21,22,23)(H,26,29,30)/t15?,16-,17-/m0/s1
