EP 459

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

MedKoo CAT#: 463222

CAS#: 76739-51-0

Description: EP 459 is a thiol and calpain protease inhibitor.

Chemical Structure

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EP 459
CAS# 76739-51-0
Instruction

Theoretical Analysis

MedKoo Cat#: 463222
Name: EP 459
CAS#: 76739-51-0
Chemical Formula: C14H25N3O5
Exact Mass: 315.18
Molecular Weight: 315.370
Elemental Analysis: C, 53.32; H, 7.99; N, 13.32; O, 25.37

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.