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C5857

Sigma-Aldrich

CA-074 methyl ester

≥99% (TLC)

Synonym(s):

(L-3-trans-(Propylcarbamyl)oxirane-2-carbonyl)-L-isoleucyl-L-proline methyl ester

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About This Item

Empirical Formula (Hill Notation):
C19H31N3O6
CAS Number:
147859-80-1
Molecular Weight:
397.47
MDL number:
MFCD03452890
UNSPSC Code:
12352108
PubChem Substance ID:
329775104
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

Assay

≥99% (TLC)

form

solid

storage temp.

−20°C

SMILES string

CCCNC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](C(C)CC)C(=O)N2CCC[C@H]2C(=O)OC

InChI

1S/C19H31N3O6/c1-5-9-20-16(23)14-15(28-14)17(24)21-13(11(3)6-2)18(25)22-10-7-8-12(22)19(26)27-4/h11-15H,5-10H2,1-4H3,(H,20,23)(H,21,24)/t11?,12-,13-,14-,15-/m0/s1

InChI key

XGWSRLSPWIEMLQ-RQLZCWDZSA-N

Application

CA-074 methyl ester has been used as cathepsin B inhibitor in cardiomyocytes, HeLa cells and human pancreatic cancer PANC-1 cells.

Biochem/physiol Actions

CA-074 methyl ester is a cell-permeable analog of CA-074. It is an inhibitor of cathepsin B especially the intracellular type. and undergoes intracellular transition into active CA-074 by the action of esterases. CA-074 methyl ester also inhibits cathepsin L.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An intracellular form of cathepsin B contributes to invasiveness in cancer
Szpaderska AM and Frankfater A
Cancer Research, 61(8), 3493-3500 (2001)
Chee Fan Tan et al.
Cells, 9(5) (2020-05-30)
Studies have shown that the process of extracellular vesicles (EVs) secretion and lysosome status are linked. When the lysosome is under stress, the cells would secrete more EVs to maintain cellular homeostasis. However, the process that governs lysosomal activity and
The cathepsin B-selective inhibitors CA-074 and CA-074Me inactivate cathepsin L under reducing conditions
Steverding D
Open enzyme inhibition Journal, 4(1), 3493-3500 (2011)
Cathepsin B deficiency attenuates cardiac remodeling in response to pressure overload via TNF-alpha/ASK1/JNK pathway
Wu QQ, et al.
American Journal of Physiology. Heart and Circulatory Physiology, 308(9), H1143-H1154 (2015)
D J Buttle et al.
Archives of biochemistry and biophysics, 299(2), 377-380 (1992-12-01)
The specificity of compound CA074 [N-(L-3-trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-pro line] for the inactivation of cathepsin B was quantified in in vitro measurements with cysteine endopeptidases from cattle, it being found that the compound is a very rapid inactivator of cathepsin B (rate constant
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