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MedKoo Cat#: 463222 | Name: EP-459

Description:

WARNING: This product is for research use only, not for human or veterinary use.

EP-459 (E 64a) is a thiol and calpain protease inhibitor. Ep-459 is an E-64 analogue. EP-459 acts selectively on lysosomal protein degradation. Treatment with Ep459 significantly reduced protein degradation and total activity of cathepsins B and L in the infarcted tissue, compared with the findings in the untreated group. The electrophoretic pattern of the infarcted myocardium was similar to that of myofibrillar proteins degraded by cathepsins B and L.

Chemical Structure

EP-459
EP-459
CAS#76739-51-0

Theoretical Analysis

MedKoo Cat#: 463222

Name: EP-459

CAS#: 76739-51-0

Chemical Formula: C14H25N3O5

Exact Mass: 315.1794

Molecular Weight: 315.37

Elemental Analysis: C, 53.32; H, 7.99; N, 13.32; O, 25.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
EP 459; EP459; EP-459; E-64a; E64a; E 64a;
IUPAC/Chemical Name
(2S,3S)-3-(((S)-1-((4-aminobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylic acid
InChi Key
AVTVMICMSRMLMA-DCAQKATOSA-N
InChi Code
InChI=1S/C14H25N3O5/c1-8(2)7-9(12(18)16-6-4-3-5-15)17-13(19)10-11(22-10)14(20)21/h8-11H,3-7,15H2,1-2H3,(H,16,18)(H,17,19)(H,20,21)/t9-,10-,11-/m0/s1
SMILES Code
CC(C[C@@H](C(NCCCCN)=O)NC([C@H]1O[C@@H]1C(O)=O)=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 315.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Nikawa T, Ikemoto M, Watanabe C, Kitano T, Kano M, Yoshimoto M, Towatari T, Katunuma N, Shizuka F, Kishi K. A cysteine protease inhibitor prevents suspension-induced declines in bone weight and strength in rats. J Physiol Anthropol Appl Human Sci. 2002 Jan;21(1):51-7. doi: 10.2114/jpa.21.51. PMID: 11938609. 2: Qi Y, Dawson G. Hypoxia induces synthesis of a novel 22-kDa protein in neonatal rat oligodendrocytes. J Neurochem. 1992 Nov;59(5):1709-16. doi: 10.1111/j.1471-4159.1992.tb11002.x. PMID: 1383425. 3: Paulesu L, Pessina GP, Bocci V. Human beta-interferon incubated with muscle homogenate is protected by albumin but not by proteinase inhibitors. Proc Soc Exp Biol Med. 1992 Jul;200(3):414-7. doi: 10.3181/00379727-200-43450. PMID: 1615016. 4: Johnson KF, Hancock LW, Dawson G. Synthesis and processing of lysosomal alpha-fucosidase in cultured human fibroblasts. Biochim Biophys Acta. 1991 Jan 23;1073(1):120-8. doi: 10.1016/0304-4165(91)90191-i. PMID: 1899340. 5: Reichelt R, Möhler H, Hebebrand J. Calpain inhibitor I prevents rapid postmortem degradation of benzodiazepine binding proteins: fluorographic and immunological evidence. J Neurochem. 1990 Nov;55(5):1711-5. doi: 10.1111/j.1471-4159.1990.tb04960.x. PMID: 2170581. 6: Ito M, Sato A, Tanabe F, Ishida E, Takami Y, Shigeta S. The thiol proteinase inhibitors improve the abnormal rapid down-regulation of protein kinase C and the impaired natural killer cell activity in (Chediak-Higashi syndrome) beige mouse. Biochem Biophys Res Commun. 1989 Apr 28;160(2):433-40. doi: 10.1016/0006-291x(89)92451-0. PMID: 2541700. 7: Zerda KS, Dresden MH, Chappell CL. Schistosoma mansoni: expression and role of cysteine proteinases in developing schistosomula. Exp Parasitol. 1988 Dec;67(2):238-46. doi: 10.1016/0014-4894(88)90071-9. PMID: 3056735. 8: Mason RW. Species variations amongst lysosomal cysteine proteinases. Biomed Biochim Acta. 1986;45(11-12):1433-40. Erratum in: Biomed Biochim Acta 1987;46(7):following 650. PMID: 3555468. 9: Tsuchida K, Aihara H, Isogai K, Hanada K, Shibata N. Degradation of myocardial structural proteins in myocardial infarcted dogs is reduced by Ep459, a cysteine proteinase inhibitor. Biol Chem Hoppe Seyler. 1986 Jan;367(1):39-45. doi: 10.1515/bchm3.1986.367.1.39. PMID: 3006724. 10: den Tandt WR, Scharpe S. Methylumbelliferyl-N-acetylneuraminic acid sialidase in human liver. Biochem Med. 1984 Jun;31(3):287-93. doi: 10.1016/0006-2944(84)90084-x. PMID: 6477533. 11: Yanagisawa K, Sato S, Amaya N, Miyatake T. Degradation of myelin basic protein by calcium-activated neutral protease (CANP) in human brain and inhibition by E-64 analogue. Neurochem Res. 1983 Oct;8(10):1285-93. doi: 10.1007/BF00963998. PMID: 6197665. 12: Aoyagi T, Wada T, Umezawa K, Kojima F, Nagai M, Umezawa H. Relation between in vivo effects and in vitro effects of serine and thiol proteinase inhibitors. J Pharmacobiodyn. 1983 Sep;6(9):643-53. doi: 10.1248/bpb1978.6.643. PMID: 6361230. 13: Blest AD, Stowe S, Eddey W, Williams DS. The local deletion of a microvillar cytoskeleton from photoreceptors of tipulid flies during membrane turnover. Proc R Soc Lond B Biol Sci. 1982 Jul 22;215(1201):469-79. doi: 10.1098/rspb.1982.0054. PMID: 6127716. 14: Grinde B. Selective inhibition of lysosomal protein degradation by the thiol proteinase inhibitors E-64, Ep-459 and Ep-457 in isolated rat hepatocytes. Biochim Biophys Acta. 1982 Mar 4;701(3):328-33. doi: 10.1016/0167-4838(82)90235-7. PMID: 7039681. 15: Barrett AJ, Kembhavi AA, Brown MA, Kirschke H, Knight CG, Tamai M, Hanada K. L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L. Biochem J. 1982 Jan 1;201(1):189-98. doi: 10.1042/bj2010189. PMID: 7044372; PMCID: PMC1163625.