E-64C

E-64C Property

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

Safety

WGK Germany 

3

RTECS 

RR0404200

HS Code 

29241990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

E-64C Chemical Properties,Usage,Production

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

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