ChemicalBook CAS DataBase List 147859-80-1

147859-80-1

Name	CA-074 ME
CAS	147859-80-1
Molecular Formula	C19H31N3O6
MDL Number	MFCD00797532
Molecular Weight	397.47
MOL File	147859-80-1.mol

Synonyms

CA-074 ME CA-074(OME) CA-074 methyl ester CATHEPSIN B INHIBITOR IV CA-074 methyl ester (CA-074 Me) L-trans-Epoxysuccinyl(propylamide)-Ile-P (L-3-Trans-(propylcarbamoyl)oxirane-2-carbony L-TRANS-EPOXYSUCCINYL-ILE-PRO-OME PROPYLAMIDE L-TRANS-EPOXYSUCCINYL (PROPYLAMIDE)-ILE-PRO-OME L-trans-Epoxysuccinic Ile-Pro-OMe Propylamide L-trans-Epoxysuccinyl-isoleucyl-proline methyl ester propylamide N-((L-3-TRANS-(PROPYLAMINO)CARBONYL)-OXIRANE-2-CARBONYL)-ILE-PRO-OME [L-3-TRANS-(POLYCARBAMOYL)OXIRANE-2-CARBONYL]-L-ISOLEUCYL-L-PROLINE METHYL ESTER (L-3-trans-(Propylcarbamyl)oxirane-2-carbonyl)-L-isoleucyl-L-proline methyl ester (L-3-TRANS-(PROPYLCARBAMOYL)OXIRANE-2-CARBONYL)-L-ISOLEUCYL-L-PROLINE METHYL ESTER [L-3-TRANS-(PROPYLCARBAMOYL)OXYRANE-2-CARBONYL]-L-ISOLEUCYL-L-PROLINE METHYL ESTER N-(L-3-TRANS-PROPYLCARBONYL-OXIRANE-2-CARBONYL)-L-ISOLEUCYL-L-PROLINE METHYL ESTER (S)-Methyl 1-((2S,3S)-3-methyl-2-((2S,3S)-3-(propylcarbamoyl)oxirane-2-carboxamido)pentanoyl)p L-Proline, N-[[(2S,3S)-3-[(propylamino)carbonyl]-2-oxiranyl]carbonyl]-L-isoleucyl-, methyl ester (S)-Methyl 1-((2S,3S)-3-methyl-2-((2S,3S)-3-(propylcarbamoyl)oxirane-2-carboxamido)pentanoyl)pyrrolidine-2-carboxylate L-trans-Epoxysuccinyl(propylaMide)-Ile-Pro-OMe, CA-074Me, N-(L-3-trans-(PropylaMino)carbonyl)-oxirane-2-carbonyl)-Ile-Pro-OMe

Chemical Properties

Melting point	153-155°C
Boiling point	666.3±55.0 °C(Predicted)
density	1.212±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	Soluble in DMSO
form	Solid
pka	13.38±0.40(Predicted)
color	White to Off-White
biological source	synthetic (organic)
InChIKey	XGWSRLSPWIEMLQ-YTFOTSKYSA-N
SMILES	C(OC)(=O)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)CC)NC([C@@H]1[C@@H](C(NCCC)=O)O1)=O

Safety Data

WGK Germany	3
Storage Class	11 - Combustible Solids

Hazard Information

Uses

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

Uses

CA-074 methyl ester is a cell-permeable cathepsin B inhibitor.

Biological Activity

ca-074 me is a membrane-permeable and selective inhibitor of cathepsin b with ic50 value of 36.3 nm [1, 2].ca-074 me is a methyl ester derivative of ca-074. in cultured human gingival fibroblasts, ca-074 me exerted a 95% inhibition of cathepsin b and partial inhibition (54%) of the combined activities of cathepsins b and l. ca-074 me was also found to inhibit cathespin l under reducing conditions. it inhibited the activity of purified human cathepsin l by more than 90% when the enzyme had been pre-incubated with 1.4 mm dtt or 4.2 mm gsh for 2 hours. besides that, ca-074 me completely inhibited cathepsin b in the presence of 1.4 mm dtt [2, 3].

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.

in vivo

Hippocampal CA1 neuronal programmed necrosis induced by global cerebral I/R injury is prevented by CA074-me (1 μg, 10 μg) both pre-treatment and post-treatment. The rupture of lysosomal membrane and the leakage of cathepsin-B, and this is strongly inhibited by CA074-me pre-treatment. The overexpression and nuclear translocation of RIP3 and the reduction of NAD⁺ level after I/R injury are also inhibited, while the upregulation of Hsp70 is strengthened by CA074-me pre-treatment^[1].
CA-074Me (30 mg/kg) is capable of inhibiting osteoclastogenesis and bone degradation in vivo^[2].
In the CVB+CA-074Me (4 mg/kg/day i.m.) guinea pigs group, the scores of inflammation significantly decrease in comparison with the CVB+None group. In CVB+CA-074Me group, the number of CD8⁺T cells decrease in comparison with the sham group^[3].

target

cathepsin B

IC 50

Cathepsin B

storage

Store at -20°C

References

[1] wu x, zhang l, gurley e, et al. prevention of free fatty acid–induced hepatic lipotoxicity by 18β-glycyrrhetinic acid through lysosomal and mitochondrial pathways. hepatology, 2008, 47(6): 1905-1915.
[2] steverding d. the cathepsin b-selective inhibitors ca-074 and ca-074me inactivate cathepsin l under reducing conditions. open enzyme inhibition journal, 2011, 4: 11-16.
[3] buttle d j, murata m, knight c g, et al. ca074 methyl ester: a proinhibitor for intracellular cathepsin b. archives of biochemistry and biophysics, 1992, 299(2): 377-380.

Spectrum Detail

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