Salubrinal

Category	Herpes simplex Virus (HSV)
CAS	405060-95-9
Description	Salubrinal is a selective inhibitor of eIF2α dephosphorylation and inhibits ER stress-mediated apoptosis with EC50 of ~15 μM.

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Synonyms	salubrinal\|405060-95-9\|(E)-3-phenyl-N-[2,2,2-trichloro-1-(quinolin-8-ylcarbamothioylamino)ethyl]prop-2-enamide\|N-(2,2,2-trichloro-1-(3-(quinolin-8-yl)thioureido)ethyl)cinnamamide\|(2E)-3-phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl]-2-propenamide\|C21H17N4OSCl3\|CHEMBL180127\|SCHEMBL6477826\|SCHEMBL6477833\|SCHEMBL17360638\|CHEBI:91873\|DTXSID70420852\|CHEBI:131923\|HMS3413G22\|HMS3677G22\|BCP06507\|EX-A2153\|MFCD00548612\|s2923\|STL253110\|AKOS000525027\|AKOS016042385\|CCG-269541\|3-Phenyl-N-[2,2,2-trichloro-1-(3-quinolin-8-yl-thioureido)-ethyl]-acrylamide\|3-Phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl]-2-propenamide\|NCGC00159554-01\|NCGC00159554-09\|AC-33176\|NS-05839\|SW102000-2\|C75050\|Q7406268\|BRD-A77299732-001-01-6\|F0095-1218\|N-(2,2,2-trichloro-1-(3-quinolin-8-ylthioureido)ethyl)cinnamamide\|(E)-N-(2,2,2-Trichloro-1-(3-(quinolin-8-yl)thioureido)ethyl)cinnamamide\|(2E)-3-phenyl-N-{2,2,2-trichloro-1-[(quinolin-8-ylcarbamothioyl)amino]ethyl}acrylamide\|(E)-3-phenyl-N-[2,2,2-trichloro-1-(8-quinolylcarbamothioylamino)ethyl]prop-2-enamide\|(2E)-3-phenyl-N-(2,2,2-trichloro-1-{[(quinolin-8-yl)carbamothioyl]amino}ethyl)prop-2-enamide\|(2E)-3-phenyl-N-{2,2,2-trichloro-1-[(quinolin-8-ylcarbamothioyl)amino]ethyl}prop-2-enamide\|3-Phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl]-2-propen amide
Molecular Weight	479.81
Molecular Formula	C21H17Cl3N4OS
Canonical SMILES	C1=CC=C(C=C1)C=CC(=O)NC(C(Cl)(Cl)Cl)NC(=S)NC2=CC=CC3=C2N=CC=C3
InChI	InChI=1S/C21H17Cl3N4OS/c22-21(23,24)19(27-17(29)12-11-14-6-2-1-3-7-14)28-20(30)26-16-10-4-8-15-9-5-13-25-18(15)16/h1-13,19H,(H,27,29)(H2,26,28,30)/b12-11+
InChIKey	LCOIAYJMPKXARU-VAWYXSNFSA-N
Purity	>98%
Density	1.5±0.1 g/cm3
Solubility	In vitro: 10 mM in DMSO
Appearance	White to brown (Solid)
Storage	4°C, protect from light * In solvent : -80°C, 6 months -20°C, 1 month (protect from light)
Animal Admin	Using Balb/c female mice (~nine weeks old), CAIA is induced by intravenous injection of a 2 mg cocktail of ArthritoMAb antibodies on day 0 followed by intraperitoneal injection of 100 µg LPS on day 3. Mice are randomly divided into a placebo group and a Salubrinal-treated group. Salubrinal (2.0 mg/kg) is intravenously administered daily from day 0, while a solvent (49.5% PEG 400 and 0.5% Tween 80 in PBS) is administered to the placebo group.
Complexity	622
Exact Mass	478.018865
Index Of Refraction	1.732
In Vitro	Salubrinal, a recently identified PP1 inhibitor capable to protect against endoplasmic reticulum (ER) stress in various model systems, strongly synergized with proteasome inhibitors to augment apoptotic death of different leukemic cell lines. Salubrinal preferentially seems to target the PP1/GADD34 complex, Salubrinal is of interest to examine whether the effect of Salubrinal could also be recapitulated by another inhibitor of this phosphatase. For this purpose cantharidin, wis selected, which is less toxic than okadaic acid, but which also blocks PP1 (IC50=1.7 µM) activities.
In Vivo	Salubrinal is a synthetic chemical that inhibits de-phosphorylation of eukaryotic translation initiation factor 2 alpha (eIF2α). Salubrinal significantly suppresses inflammation of the paws of CAIA mice. For instance, the clinical scores are 1.94±1.7 (placebo) and 0.31±0.6 (Salubrinal) on day 6; and 4.63±3.4 (placebo) and 1.09±1.6 (Salubrinal) on day 12. Consistent with the clinical scores, the thickening of the paws is also reduced in the Salubrinal-treated group. Furthermore, Salubrinal reduces the histological scores from 1.47±1.10 (N=16; placebo) to 0.59±0.64 (N=16; Salubrinal) (p=0.01).
PSA	98.14000
Target	IC50: 1.7 µM (PP1)
XLogP3-AA	5.2