E-64C
E-64C Basic information
- Product Name:
- E-64C
- Synonyms:
-
- (2S,3S)-TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-3-METHYLBUTANE
- (2S,3S)-L-TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-3-METHYLBUTANE
- (2S,3S)-3-(((S)-1-(isopentylaMino)-4-Methyl-1-oxopentan-2-yl)carbaMoyl)oxirane-2-carboxylic acid
- 2-Oxiranecarboxylicacid,3-[[[(1S)-3-methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-,(2S,3S)-
- Loxistatin Acid (E-64C)
- NSC 694279
- E-64c, EP 475
- (1S,2S)-2-(((S)-1-(Isopentylamino)-4-methyl-1-oxopentan-2-yl)carbamoyl)cyclopropanecarboxylic
- CAS:
- 76684-89-4
- MF:
- C15H26N2O5
- MW:
- 314.38
- Product Categories:
-
- Pepetides
- Inhibitors
- peptides
- Mol File:
- 76684-89-4.mol
E-64C Chemical Properties
- storage temp.
- Sealed in dry,Store in freezer, under -20°C
- solubility
- ≥31.4 mg/mL in DMSO; insoluble in H2O; ≥111.8 mg/mL in EtOH
- form
- White to off-white solid
- color
- White to off-white
- biological source
- synthetic (organic)
- InChI
- InChI=1S/C15H26N2O5/c1-8(2)5-6-16-13(18)10(7-9(3)4)17-14(19)11-12(22-11)15(20)21/h8-12H,5-7H2,1-4H3,(H,16,18)(H,17,19)(H,20,21)/t10-,11-,12-/m0/s1
- InChIKey
- SCMSYZJDIQPSDI-SRVKXCTJSA-N
- SMILES
- O1[C@H](C(N[C@H](C(NCCC(C)C)=O)CC(C)C)=O)[C@H]1C(O)=O
MSDS
- Language:English Provider:SigmaAldrich
E-64C Usage And Synthesis
Description
E-64c is an active metabolite of the protease inhibitor E-64d . E-64c inhibits the cysteine proteases cathepsin B, cathepsin H, and papain but not the serine proteases trypsin, chymotrypsin, or elastase. It reduces the autocatalytic activity of the foot-and-mouth-disease virus (FMDV) leader protease when used at concentrations ranging from 0.1 to 1 mg/ml. E-64c reduces infection of HEK293T cells by an HIV-based virus system pseudotyped with severe acute respiratory syndrome coronavirus (SARS-CoV) surface glycoprotein, also known as the spike glycoprotein, in a concentration-dependent manner.
Uses
E-64c is a cysteine protease inhibitor used for detecting autophagy in plants.
Definition
ChEBI: E-64c is a leucine derivative.
in vivo
The t-1/2 of plasma E-64c is 0.48 hours. The hemodynamic effects of E-64c are absent at this dose. Using two way analysis of variance, the effects of reperfusion (p=0.0016) or E-64c (p=0.0226) per se on infarct size are significant. In comparing Group A with Group B and Group C with Group D, the depletion of CPK in the E-64c treated groups (Groups A and C) is slightly less than in the vehicle-injected groups (Groups B and D). The insufficient effect of E-64c alone may be explained by the early administration and relatively short t-1/2. Since the effectiveness of NCO-700 has been established,6),7) our findings might indicate a small but beneficial effect of E-64c on infarct size and CPK content[2].
target
cathepsins B
IC 50
Cathepsin C
References
[1] Y SHOJI-KASAI. Thiol protease-specific inhibitor E-64 arrests human epidermoid carcinoma A431 cells at mitotic metaphase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 1: 146-150. DOI: 10.1073/pnas.85.1.146
[2] WILLIAM R ROUSH . Design, Synthesis and Evaluation of d-Homophenylalanyl Epoxysuccinate Inhibitors of the Trypanosomal Cysteine Protease Cruzain[J]. Tetrahedron, 2000, 56 50: Pages 9747-9762. DOI: 10.1016/s0040-4020(00)00882-6
[3] L G KLEINA M J G. Antiviral effects of a thiol protease inhibitor on foot-and-mouth disease virus.[J]. Journal of Virology, 1992, 66 12: 7168-7175. DOI: 10.1128/jvi.66.12.7168-7175.1992
[4] GRAHAM SIMMONS. Inhibitors of cathepsin L prevent severe acute respiratory syndrome coronavirus entry.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2005: 11876-11881. DOI: 10.1073/pnas.0505577102
[5] A J BARRETT. L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L.[J]. Biochemical Journal, 1982, 201 1: 189-198. DOI: 10.1042/bj2010189
[6] M TAMAI. In vitro and in vivo inhibition of cysteine proteinases by EST, a new analog of E-64.[J]. Journal of pharmacobio-dynamics, 1986, 9 8: 672-677. DOI: 10.1248/bpb1978.9.672
E-64CSupplier
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E-64C(76684-89-4)Related Product Information
- 2-Hydroxy-4-amino butanoic acid
- (S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID
- BUTTPARK 37\11-64
- GLYCIDAMIDE
- EST
- BUTTPARK 45\03-64
- BUTTPARK 44\01-64
- BUTTPARK 36\08-64
- BUTTPARK 45\03-64
- BUTTPARK 43\57-64
- (2-amino-2-oxoethoxy)acetic acid
- E-64C
- (2-AMINO-ETHOXY)-ACETIC ACID
- 2(2-HYDROXYETHOXY)ACETAMIDE
- BUTTPARK 62\07-64
- BUTTPARK 51\09-64
- BUTTPARK 64\41-01
- BUTTPARK 46\18-64