Salubrinal

Salubrinal
Identifiers
	IUPAC name 3-phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl]-2-propenamide;
CAS Number	405060-95-9 ;
PubChem CID	5717801;
ChemSpider	4654442 ;
ChEBI	CHEBI:131923 ;
ChEMBL	ChEMBL180127 ;
CompTox Dashboard (EPA)	DTXSID70420852 ;
ECHA InfoCard	100.237.268
Chemical and physical data
Formula	C21H17Cl3N4OS
Molar mass	479.81 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)/C=C/C(=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+ ; Key:LCOIAYJMPKXARU-VAWYXSNFSA-N ;
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Salubrinal is a drug which acts as a specific inhibitor of eIF2α phosphatase enzymes^[3]^[4]^[5] and is primarily used experimentally, to study stress responses in eukaryotic cells associated with the action of eIF2. Salubrinal indirectly inhibits eIF2 as a result of reduced dephosphorylation of its α-subunit,^[6] resulting in activation of stress response pathways usually triggered by events such as oxidative stress or buildup of unfolded protein in the endoplasmic reticulum.^[7] Salubrinal has putative therapeutic value due to its function,^[3]^[5] but is as yet only used experimentally. Salubrinal is being studied at Indiana University for its potential to fight osteoporosis and accelerate bone healing.^[8]

References

^ "SALUBRINAL | 405060-95-9". ChemicalBook. Retrieved 2010-10-05.
^ "Salubrinal: sc-202332" (PDF). Santa Cruz Biotechnology, Inc. 2010-07-28. Retrieved 2010-10-05.
^ ^a ^b Lewerenz, Jan; Maher, Pamela (2009-01-09). "Basal Levels of eIF2α Phosphorylation Determine Cellular Antioxidant Status by Regulating ATF4 and xCT Expression". The Journal of Biological Chemistry. 284 (2). The American Society for Biochemistry and Molecular Biology, Inc: 1106. doi:10.1074/jbc.M807325200.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ Kessel, David (2006-08-11). "Protection of Bcl-2 by sulubrinal". Biochemical and Biophysical Research Communications. 346 (4). Elsevier Inc: 1320–3. doi:10.1016/j.bbrc.2006.06.056. PMC 2978664. PMID 16806073. Retrieved 2010-10-05.
^ ^a ^b Boyce M; Bryant KF; Jousse C; Long K; Harding HP; Scheuner D; Kaufman RJ; Ma D; Coen DM; Ron D; Yuan J (February 2005). "A selective inhibitor of eIF2alpha dephosphorylation protects cells from ER stress". Science. 307 (5711): 935–9. doi:10.1126/science.1101902. PMID 15705855. Retrieved 2010-10-05.
^ "Entrez Gene: EIF2S1 eukaryotic translation initiation factor 2, subunit 1 alpha, 35kDa". National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2010-10-05.
^ "Coping with stress: eIF2 kinases and translational control" (PDF). Biochemical Society Transactions. 34 (1). Biochemical Society: 7–11. February 2006. doi:10.1042/BST20060007. PMID 16246168. Retrieved 2010-10-05. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
^ "New compound may accelerate bone healing, prevent osteoporosis". August 2011. Retrieved 2011-08-29.

[cdata1-1] "SALUBRINAL | 405060-95-9". ChemicalBook. Retrieved 2010-10-05.

[cdata2-2] "Salubrinal: sc-202332" (PDF). Santa Cruz Biotechnology, Inc. 2010-07-28. Retrieved 2010-10-05.

[jl1-3] Lewerenz, Jan; Maher, Pamela (2009-01-09). "Basal Levels of eIF2α Phosphorylation Determine Cellular Antioxidant Status by Regulating ATF4 and xCT Expression". The Journal of Biological Chemistry. 284 (2). The American Society for Biochemistry and Molecular Biology, Inc: 1106. doi:10.1074/jbc.M807325200.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[dk1-4] Kessel, David (2006-08-11). "Protection of Bcl-2 by sulubrinal". Biochemical and Biophysical Research Communications. 346 (4). Elsevier Inc: 1320–3. doi:10.1016/j.bbrc.2006.06.056. PMC 2978664. PMID 16806073. Retrieved 2010-10-05.

[bm1-5] Boyce M; Bryant KF; Jousse C; Long K; Harding HP; Scheuner D; Kaufman RJ; Ma D; Coen DM; Ron D; Yuan J (February 2005). "A selective inhibitor of eIF2alpha dephosphorylation protects cells from ER stress". Science. 307 (5711): 935–9. doi:10.1126/science.1101902. PMID 15705855. Retrieved 2010-10-05.

[entrez1-6] "Entrez Gene: EIF2S1 eukaryotic translation initiation factor 2, subunit 1 alpha, 35kDa". National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2010-10-05.

[rw1-7] "Coping with stress: eIF2 kinases and translational control" (PDF). Biochemical Society Transactions. 34 (1). Biochemical Society: 7–11. February 2006. doi:10.1042/BST20060007. PMID 16246168. Retrieved 2010-10-05. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[seet1-8] "New compound may accelerate bone healing, prevent osteoporosis". August 2011. Retrieved 2011-08-29.

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