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C5732

Sigma-Aldrich

CA-074

≥99% (TLC)

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C18H29N3O6
Číslo CAS:
134448-10-5
Molekulová hmotnost:
383.44
MDL number:
MFCD00797531
UNSPSC Code:
12352200
PubChem Substance ID:
24892580
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

assay

≥99% (TLC)

form

powder

solubility

methanol: 1 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

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

InChI

1S/C18H29N3O6/c1-4-8-19-15(22)13-14(27-13)16(23)20-12(10(3)5-2)17(24)21-9-6-7-11(21)18(25)26/h10-14H,4-9H2,1-3H3,(H,19,22)(H,20,23)(H,25,26)/t10?,11-,12-,13-,14-/m0/s1

InChI key

ZEZGJKSEBRELAS-NSIINPIOSA-N

Application

CA-074 has been used as a cathepsin B inhibitor:
  • to study its effect on pseudotyped viruses bearing S proteins harboring R642M and N714K using HeLa cells
  • to determine the role of autophagy in glucose deprivation (GD)-induced damage
  • to study its effects on neuronal function upon exposure to His-cathepsin B (CATB)

Biochem/physiol Actions

CA-074 is a potent and a selective inhibitor of cathepsin B. It is useful to study the biological function of cathepsin B in vivo. Studies show that CA-074 can also inhibit cathepsin L under reducing conditions.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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Clément Naudin et al.
PloS one, 6(9), e25577-e25577 (2011-10-08)
Cysteine cathepsins have emerged as new players in inflammatory lung disorders. Their activities are dramatically increased in the sputum of cystic fibrosis (CF) patients, suggesting that they are involved in the pathophysiology of CF. We have characterized the cathepsins in
The cathepsin B-selective inhibitors CA-074 and CA-074Me inactivate cathepsin L under reducing conditions
Steverding D
Open enzyme inhibition Journal, 4, 11-16 (2011)
M Murata et al.
FEBS letters, 280(2), 307-310 (1991-03-25)
A series of new epoxysuccinyl peptides were designed and synthesized to develop a specific inhibitor of cathepsin B. Of these compounds, N-(L-3-trans-ethoxycarbonyloxirane-2-carbonyl)-L-isoleucyl-L-proli ne (compound CA-030) and N-(L-3-trans-propylcarbamoyloxirane-2-carbonyl)-L-isoleucyl-L-prol ine (compound CA-074) were the most potent and specific inhibitors of cathepsin B
Kazuya Shirato et al.
Journal of virology, 91(1) (2016-11-01)
Human coronavirus 229E (HCoV-229E), a causative agent of the common cold, enters host cells via two distinct pathways: one is mediated by cell surface proteases, particularly transmembrane protease serine 2 (TMPRSS2), and the other by endosomal cathepsin L. Thus, specific
Masashi Asai et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(10), 3720-3730 (2011-07-13)
γ-Secretase catalyzes the cleavage of the intramembrane region of the Alzheimer amyloid precursor protein (APP), generating p3, amyloid-β peptide (Aβ), and the APP intracellular domain (AICD). Although a γ-secretase inhibitor has been shown to cause an accumulation of the APP
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