E-64A broad spectrum cysteine proteinase and calpain activation inhibitor

E-64 (CAS 66701-25-5)

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Synonym: trans-Epoxysuccinyl-L-leucylamido(4-guanidino)butane; L-trans-3-Carboxyoxiran-2-carbonyl-L-leucylagmatine; N-(trans-Epoxysuccinyl)-L-leucine 4-guanidinobutylamide
Application: A broad spectrum cysteine proteinase and calpain activation inhibitor
CAS Number: 66701-25-5
Molecular Weight: 357.40
Molecular Formula: C15H27N5O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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E-64 is a broad spectrum cysteine proteinase and calpain activation inhibitor. E-64 has been reported to inhibit intracellular cathepsin B, cathepsin L, cathepsin H, Bax protease activity, and reduces oxidative stress, which includes a decrease in MDA levels, ICAM-1 expression and MOP acitivity. Additionally, Prevotella intermedia studies report that E-64 blocks the breakdown of methaemoglobin and the oxidation of oxyhaemoglobin by InpA. E-64 has also been used to study excystation in Giardia lamblia. E-64 is an inhibitor of Calpain, cathepsin K and cathepsin S.


References

1. Tamai, M., et al. 1987. Chem. Pharm. Bull. 35: 1098-1104. PMID: 3301019
2. Wood, D.E., et al. 1998. Oncogene. 17: 1069-1078. PMID: 9764817
3. Szpaderska, A.M. and Frankfater, A. 2001. Cancer Res. 61: 3493-3500. PMID: 11309313
4. Chatterjee, P.K., et al. 2005. Biochem. Pharmacol. 69: 1121-1131. PMID: 15763548
5. Hussein, E.M., et al. 2009. J Egypt Soc Parasitol. 39: 111-119. PMID: 19530614
6. Byrne, D.P., et al. 2010. Biochem. J. 425: 257-264. PMID: 19814715

Physical State :
Solid
Solubility :
Soluble in DMSO, 50% acetic acid, 0.9% sodium chloride, saturated sodium bicarbonate, and water (1 mM).
Storage :
Store at -20° C
Melting Point :
265.96° C (Predicted)
Boiling Point :
614.23° C (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.62
Optical Activity :
α20/D +25°, c = 0.5 in 0.1N HCl; α20/D +24.5°±1.5°, c = 1 in 0.1M HCl
IC50 :
cathepsins K: IC50 = 1.4 nM; cathepsins S: IC50 = 4.1 nM; cathepsins L: IC50 = 2.5 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
RR0390000
PubChem CID :
439487
MDL Number :
MFCD00080261
Beilstein Registry :
1405664
SMILES :
CC(C)C[C@@H](C(=O)NCCCCN=C(N)N)NC(=O)[C@H]1[C@@H](O1)C(=O)O

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E-64  Product Citations

See how others have used E-64. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 10 total

PMID: # 28223427  Noguchi, F. et al. 2017. Mol. Cancer Ther. 16: 936-947.

PMID: # 19736309  Chandra, M. et al. 2009. J. Biol. Chem. 284: 30889-30896.

PMID: # 19483081  Kobayashi, T. et al. 2009. J. Biol. Chem. 284: 20052-20060.

PMID: # 19632994  Alencastre, IS. et al. 2009. J. Biol. Chem. 284: 27243-27251.

PMID: # 15514105  Fernandez-Twinn, D.S. et al. 2005. Am J Physiol Regul Integr Comp Physiol. 288: R368-R373.

PMID: # 11781373  Niiro, H. et al. 2002. J. Exp. Med. 195: 143-149.

PMID: # 11202906  Roshak, AK. et al. 2000. Cell. Signal. 12: 405-411.

PMID: # 9342364  Langenfeld, J. et al. 1997. Proc. Natl. Acad. Sci. USA. 94: 12070-12074.

PMID: # 3988775  Ahlberg, J. et al. 1985. J. Biol. Chem. 260: 5847-5854.

PMID: # 6309806  Mykles, DL. et al. 1983. J. Biol. Chem. 258: 10474-10480.

Citations 1 to 10 of 10 total
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