76739-51-0
Chemical Structure
EP-459
- CAS No.: 76739-51-0
- Formula:C14H25N3O5
- Molecular Weight:315.37
IUPAC Name: (2S,3S)-3-(((S)-1-((4-aminobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylic acid
InChIKey: AVTVMICMSRMLMA-DCAQKATOSA-N
SMILES: C(N[C@H](C(NCCCCN)=O)CC(C)C)(=O)[C@@H]1[C@@H](C(O)=O)O1
Biological Activity: EP-459 is a papain inhibitor (IC50=0.4 μg/mL) with no significant inhibitory activity against serine proteases such as trypsin, plasmin, thrombin, and urokinase. The effects of EP-459 are similar to those of E-64C (HY-100227), but differ from the functions of leupeptin and its analogs. EP-459 can serve as a titration reagent for mouse cathepsin L (precursor form/MEP) activity, covalently binding to the cysteine residue at its active site. EP-459 is also a Ca2+-dependent active site-directed inhibitor that can inactivate chicken gizzard smooth muscle calpain II, and can be acetylated to generate Ac-Ep-459, which after radiolabeling can be used to prepare [3H]Ac-Ep-459 for calpain active site labeling[1][2][3].
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EP-459 | EP-459 is a papain inhibitor (IC50=0.4 μg/mL) with no significant inhibitory activity against serine proteases such as trypsin, plasmin, thrombin, and urokinase. The effects of EP-459 are similar to those of E-64C (HY-100227), but differ from the functions of leupeptin and its analogs. EP-459 can serve as a titration reagent for mouse cathepsin L (precursor form/MEP) activity, covalently binding to the cysteine residue at its active site. EP-459 is also a Ca2+-dependent active site-directed inhibitor that can inactivate chicken gizzard smooth muscle calpain II, and can be acetylated to generate Ac-Ep-459, which after radiolabeling can be used to prepare [3H]Ac-Ep-459 for calpain active site labeling. | |||||||||||||||||||||
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References
- [1]. Aoyagi T, et al. Relation between in vivo effects and in vitro effects of serine and thiol proteinase inhibitors. Journal of pharmacobio-dynamics. 1983 Sep;6(9):643-53.
- [2]. Mason RW, et al. The identification of the major excreted protein (MEP) from a transformed mouse fibroblast cell line as a catalytically active precursor form of cathepsin L. The Biochemical journal. 1987 Dec 01;248(2):449-54.
- [3]. Parkes C, et al. Calpain inhibition by peptide epoxides. The Biochemical journal. 1985 Sep 01;230(2):509-16.
