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328501

Sigma-Aldrich

ERO1 Inhibitor II, EN460

Synonym(s):

ERO1 Inhibitor II, EN460, ( Z)-2-Chloro-5-(4,5-dihydro-5-oxo-4-((5-phenyl-2-furanyl)methylene)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzoic acid, ( Z)-2-Chloro-5-(5-oxo-4-((5-phenylfuran-2-yl)methylene)-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid, (Z)-2-Chloro-5-(4,5-dihydro-5-oxo-4-((5-phenyl-2-furanyl)methylene)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzoic acid, (Z)-2-Chloro-5-(5-oxo-4-((5-phenylfuran-2-yl)methylene)-3-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid

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About This Item

Empirical Formula (Hill Notation):
C22H12ClF3N2O4
Molecular Weight:
460.79
UNSPSC Code:
12352200
NACRES:
NA.28

assay

≥99% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

red

solubility

DMSO: 50 mg/mL

shipped in

ambient

storage temp.

2-8°C

General description

A cell-permeable thiol reactive enone (EN) compound that selectively interacts with the active-site cysteine of reduced, active form of ERO1α and inhibits its activity (IC50 = 1.9 µM). Also prevents ERO1 re-oxidation both in vitro and in mouse embryonic fibroblasts. Activates the unfolded protein response and protects ER-stressed 293T cells. Can inhibit ERO1α even in the presence of an excess amount of competing thiols. Can inhibit ERO1α even in the presence of an excess amount of competing thiols. EN460 binding to ERO1α is shown to promote the loss of flavin adenine dinucleotide (FAD) from the holoenzyme. Its inhibitory action appears to be irreversible, however addition of FAD and tris(hydroxypropyl)phosphine (Cat. No. 598250) can restore some enzyme activity.
A cell-permeable thiol reactive enone (EN) compound that selectively interacts with the active-site cysteine of reduced, active form of ERO1α and inhibits its activity (IC50 = 1.9 µM). Also prevents ERO1 re-oxidation both in vitro and in mouse embryonic fibroblasts. Activates the unfolded protein response and protects ER-stressed 293T cells. Can inhibit ERO1α even in the presence of an excess amount of competing thiols. Can inhibit ERO1α even in the presence of an excess amount of competing thiols. EN460 binding to ERO1α is shown to promote the loss of flavin adenine dinucleotide (FAD) from the holoenzyme. Its inhibitory action appears to be irreversible, however addition of FAD and tris(hydroxypropyl)phosphine (Cat. No. 598250) can restore some enzyme activity.

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Other Notes

Chu, Y., et al. 2011. Bioorg. Med. Chem. Lett.21, 1118.
Blais, J.D., et al. 2010. J. Biol. Chem.285, 20993.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Brennan D Johnson et al.
ACS bio & med chem Au, 2(2), 161-170 (2022-07-28)
The flavin adenine dinucleotide containing Endoplasmic Reticulum Oxidoreductase-1 α (ERO1α) catalyzes the formation of de novo disulfide bond formation of secretory and transmembrane proteins and contributes towards proper protein folding. Recently, increased ERO1α expression has been shown to contribute to

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