Leupeptin

(Acetyl-L-leucyl-L-leucyl-L-argininal)
C20H38N6O4·1/2H2SO4Mr 475.6CAS [103476-89-7]

Leupeptin, or N-acetyl-L-leucyl-L-leucyl-L-argininal, is a naturally occurring tripeptide and a reversible Inhibitor of serine and cysteine proteases. Competitively inhibits calpain, cathepsin B, kallikrein, papain, plasmin, and trypsin, but is little or non-inhibiting for pepsin, cathepsin A and D, chymotrypsin, and thrombin.
Leupeptin forms in the active site of serine proteases a covalent hemiacetal adduct between the aldehyde group of leupeptin and the hydroxyl group of a serine residue in the enzyme active site. Inhibition of cysteine proteases is achieved by forming a comparable bond between the electrophilic (aldehyde) carbon of leupeptin with the sulfur atom of a cysteine residue in the enzyme active site.
Due to its aldehyde groups, leupeptin may interfere with protein detection assays (e.g. Bradford).
Stock solution: 5 mg/ml (10 mM) in H2O, ethanol, acetic acid and DMF (stabile at +4 °C for approx. 7 days and at -20 °C for approx. 6 months)
Working concentration: 1 - 100 µM (stabile only for few hours)

Assay (HPLC)
(sum of tautomeric isomers)
min. 96.5 %


References:
  1. Umezawa, H. (1976) Methods Enzymol. 45, 678-83
  2. Carlin, C. et al. (1994) J. Cell. Physiol. 160, 427-34
  3. Savory, P.J. & Rivett, A.J. (1993) Biochem. J. 289, 45-8
  4. Eto, I. & Bandy, M.D. (1990) Mol. Cell. Biochem. 94, 19-36
  5. Benistani, B. et al. (1994) Biochim. Biophys. Acta 1223, 84-90
WARNING
Hazard Statements H302 - H332
Precautions P280
Reaction P301 +P312 - P304 +P340 - P330
Storage P501

WGK: 1HS: 29241900
Storage Temperature: -15 °C to -25 °C

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H302

Deutsch:

Gesundheitsschädlich bei Verschlucken.

English:

Harmful if swallowed.

Français:

Nocif en cas d'ingestion.

Italiano:

Nocivo se ingerito.

Español:

Nocivo en caso de ingestión.

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H332

Deutsch:

Gesundheitsschädlich bei Einatmen.

English:

Harmful if inhaled.

Français:

Nocif par inhalation.

Italiano:

Nocivo se inalato.

Español:

Nocivo en caso de inhalación.

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P280

Deutsch:

Schutzhandschuhe/Schutzkleidung/Augenschutz/Gesichtsschutz tragen.

English:

Wear protective gloves/protective clothing/eye protection/face protection.

Français:

Porter des gants de protection/des vêtements de protection/un équipement de protection des yeux/du visage.

Italiano:

Indossare guanti/indumenti protettivi/Proteggere gli occhi/il viso.

Español:

Llevar guantes/prendas/gafas/máscara de protección.

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P301 +P312

Deutsch:

BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM oder Arzt anrufen.

English:

IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.

Français:

EN CAS D’INGESTION: appeler un CENTRE ANTIPOISON ou un médecin en cas de malaise.

Italiano:

IN CASO DI INGESTIONE accompagnata da malessere: contattare un CENTRO ANTIVELENI o un medico.

Español:

EN CASO DE INGESTIÓN: Llamar a un CENTRO DE INFORMACIÓN TOXICOLÓGICA o a un médico si se encuentra mal.

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P304 +P340

Deutsch:

BEI EINATMEN: An die frische Luft bringen und in einer Position ruhigstellen, die das Atmen erleichtert.

English:

IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.

Français:

EN CAS D’INHALATION: transporter la victime à l’extérieur et la maintenir au repos dans une position où elle peut confortablement respirer.

Italiano:

IN CASO DI INALAZIONE: trasportare l'infortunato all’aria aperta e mantenerlo a riposo in posizione che favorisca la respirazione.

Español:

EN CASO DE INHALACIÓN: Transportar a la víctima al exterior y mantenerla en reposo en una posición confortable para respirar.

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P330

Deutsch:

Mund ausspülen.

English:

Rinse mouth.

Français:

Rincer la bouche.

Italiano:

Sciacquare la bocca.

Español:

Enjuagarse la boca.