CHEBI:131923 - salubrinal

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ChEBI Name salubrinal
ChEBI ID CHEBI:131923
Definition A member of the class of quinolines that is a mixed aminal resulting from the formal condensation oftrichloroacetaldehyde with the amide nitrogen of trans-cinnamamide and the primary amino group of 1-quinolin-8-ylthiourea. It is a selective inhibitor of cellular complexes that dephosphorylate eukaryotic translation initiation factor 2 subunit α (eIF2α).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ceri
Supplier Information ZINC000058638393
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Salubrinal is a drug which acts as a specific inhibitor of eIF2α phosphatase enzymes 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, resulting in activation of stress response pathways usually triggered by events such as oxidative stress or buildup of unfolded protein in the endoplasmic reticulum. Salubrinal has putative therapeutic value due to its function, but is as yet only used experimentally. Salubrinal is being studied at Indiana University for its potential to fight osteoporosis and accelerate bone healing.
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Formula C21H17Cl3N4OS
Net Charge 0
Average Mass 479.812
Monoisotopic Mass 478.01887
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
SMILES C=1C=2C(C(=CC1)NC(NC(NC(/C=C/C=3C=CC=CC3)=O)C(Cl)(Cl)Cl)=S)=NC=CC2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing salubrinal (CHEBI:131923) has functional parent trans-cinnamamide (CHEBI:76320)
salubrinal (CHEBI:131923) has functional parent trichloroacetaldehyde (CHEBI:48814)
salubrinal (CHEBI:131923) is a aminal (CHEBI:35412)
salubrinal (CHEBI:131923) is a organochlorine compound (CHEBI:36683)
salubrinal (CHEBI:131923) is a quinolines (CHEBI:26513)
salubrinal (CHEBI:131923) is a secondary carboxamide (CHEBI:140325)
salubrinal (CHEBI:131923) is a thioureas (CHEBI:51276)
IUPAC Name
(2E)-3-phenyl-N-{2,2,2-trichloro-1-[(quinolin-8-ylcarbamothioyl)amino]ethyl}acrylamide
Synonym Source
(E)-3-phenyl-N-[2,2,2-trichloro-1-(quinolin-8-ylcarbamothioylamino)ethyl]prop-2-enamide SUBMITTER
Manual Xrefs Databases
EP2589593 Patent
Salubrinal Wikipedia
View more database links
Registry Numbers Types Sources
13925629 Reaxys Registry Number Reaxys
405060-95-9 CAS Registry Number ChemIDplus
Citations
Logsdon AF, Lucke-Wold BP, Nguyen L, Matsumoto RR, Turner RC, Rosen CL, Huber JD (2016)
Salubrinal reduces oxidative stress, neuroinflammation and impulsive-like behavior in a rodent model of traumatic brain injury.
Brain research 1643, 140-151 [PubMed:27131989]
[show Abstract]
Anuncibay-Soto B, Pérez-Rodríguez D, Santos-Galdiano M, Font E, Regueiro-Purriños M, Fernández-López A (2016)
Post-ischemic salubrinal treatment results in a neuroprotective role in global cerebral ischemia.
Journal of neurochemistry 138, 295-306 [PubMed:27123756]
[show Abstract]
Jeon YJ, Kim JH, Shin JI, Jeong M, Cho J, Lee K (2016)
Salubrinal-Mediated Upregulation of eIF2α Phosphorylation Increases Doxorubicin Sensitivity in MCF-7/ADR Cells.
Molecules and cells 39, 129-135 [PubMed:26743901]
[show Abstract]
Nakajima S, Chi Y, Gao K, Kono K, Yao J (2015)
eIF2α-Independent Inhibition of TNF-α-Triggered NF-κB Activation by Salubrinal.
Biological & pharmaceutical bulletin 38, 1368-1374 [PubMed:26328492]
[show Abstract]
Hamamura K, Nishimura A, Iino T, Takigawa S, Sudo A, Yokota H (2015)
Chondroprotective effects of Salubrinal in a mouse model of osteoarthritis.
Bone & joint research 4, 84-92 [PubMed:25977571]
[show Abstract]
Hamamura K, Chen A, Tanjung N, Takigawa S, Sudo A, Yokota H (2015)
In vitro and in silico analysis of an inhibitory mechanism of osteoclastogenesis by salubrinal and guanabenz.
Cellular signalling 27, 353-362 [PubMed:25435425]
[show Abstract]
Hamamura K, Nishimura A, Chen A, Takigawa S, Sudo A, Yokota H (2015)
Salubrinal acts as a Dusp2 inhibitor and suppresses inflammation in anti-collagen antibody-induced arthritis.
Cellular signalling 27, 828-835 [PubMed:25619567]
[show Abstract]
Wang T, Zhang SJ, Cao SL, Guo WZ, Yan B, Fang HB (2015)
Protective effects of salubrinal on liver injury in rat models of brain death.
Chinese medical journal 128, 1523-1528 [PubMed:26021511]
[show Abstract]
Barreda-Manso MA, Yanguas-Casás N, Nieto-Sampedro M, Romero-Ramírez L (2015)
Salubrinal inhibits the expression of proteoglycans and favors neurite outgrowth from cortical neurons in vitro.
Experimental cell research 335, 82-90 [PubMed:25882497]
[show Abstract]
Gong N, Wu JH, Liang ZS, Jiang WH, Wang XW (2015)
Role of salubrinal in protecting cardiomyocytes from doxorubicin-induced apoptosis.
Genetics and molecular research : GMR 14, 12377-12385 [PubMed:26505387]
[show Abstract]
Matsuoka M, Komoike Y (2015)
Experimental Evidence Shows Salubrinal, an eIF2α Dephosphorylation Inhibitor, Reduces Xenotoxicant-Induced Cellular Damage.
International journal of molecular sciences 16, 16275-16287 [PubMed:26193263]
[show Abstract]
Li RJ, He KL, Li X, Wang LL, Liu CL, He YY (2015)
Salubrinal protects cardiomyocytes against apoptosis in a rat myocardial infarction model via suppressing the dephosphorylation of eukaryotic translation initiation factor 2α.
Molecular medicine reports 12, 1043-1049 [PubMed:25816071]
[show Abstract]
Romero-Ramírez L, Nieto-Sampedro M, Barreda-Manso MA (2015)
All roads go to Salubrinal: endoplasmic reticulum stress, neuroprotection and glial scar formation.
Neural regeneration research 10, 1926-1927 [PubMed:26889171]
Rubovitch V, Barak S, Rachmany L, Goldstein RB, Zilberstein Y, Pick CG (2015)
The neuroprotective effect of salubrinal in a mouse model of traumatic brain injury.
Neuromolecular medicine 17, 58-70 [PubMed:25582550]
[show Abstract]
Wu L, Luo N, Zhao HR, Gao Q, Lu J, Pan Y, Shi JP, Tian YY, Zhang YD (2014)
Salubrinal protects against rotenone-induced SH-SY5Y cell death via ATF4-parkin pathway.
Brain research 1549, 52-62 [PubMed:24418467]
[show Abstract]
Guo H, Jiang C, Sun X (2014)
Therapeutical effects and mechanism of salubrinal combined with ulinastatin on treating paraquat poisoning.
Cell biochemistry and biophysics 70, 1559-1563 [PubMed:25030410]
[show Abstract]
Niknejad N, Gorn-Hondermann I, Ma L, Zahr S, Johnson-Obeseki S, Corsten M, Dimitroulakos J (2014)
Lovastatin-induced apoptosis is mediated by activating transcription factor 3 and enhanced in combination with salubrinal.
International journal of cancer 134, 268-279 [PubMed:23824972]
[show Abstract]
Kim JS, Heo RW, Kim H, Yi CO, Shin HJ, Han JW, Roh GS (2014)
Salubrinal, ER stress inhibitor, attenuates kainic acid-induced hippocampal cell death.
Journal of neural transmission (Vienna, Austria : 1996) 121, 1233-1243 [PubMed:24728926]
[show Abstract]
Wan Q, Xu W, Yan JL, Yokota H, Na S (2014)
Distinctive subcellular inhibition of cytokine-induced SRC by salubrinal and fluid flow.
PloS one 9, e105699 [PubMed:25157407]
[show Abstract]
Li H, Xing B, Quan Y, Sun M (2014)
[The effect of selective phosphatase inhibitors Salubrinal on autophagy and apoptosis in the lung tissue of rats with acute paraquat poisoning].
Zhonghua wei zhong bing ji jiu yi xue 26, 671-675 [PubMed:25230871]
[show Abstract]
Gao B, Zhang XY, Han R, Zhang TT, Chen C, Qin ZH, Sheng R (2013)
The endoplasmic reticulum stress inhibitor salubrinal inhibits the activation of autophagy and neuroprotection induced by brain ischemic preconditioning.
Acta pharmacologica Sinica 34, 657-666 [PubMed:23603983]
[show Abstract]
Yokota H, Hamamura K, Chen A, Dodge TR, Tanjung N, Abedinpoor A, Zhang P (2013)
Effects of salubrinal on development of osteoclasts and osteoblasts from bone marrow-derived cells.
BMC musculoskeletal disorders 14, 197 [PubMed:23816340]
[show Abstract]
He L, Lee J, Jang JH, Sakchaisri K, Hwang J, Cha-Molstad HJ, Kim KA, Ryoo IJ, Lee HG, Kim SO, Soung NK, Lee KS, Kwon YT, Erikson RL, Ahn JS, Kim BY (2013)
Osteoporosis regulation by salubrinal through eIF2α mediated differentiation of osteoclast and osteoblast.
Cellular signalling 25, 552-560 [PubMed:23178987]
[show Abstract]
Hamamura K, Lin CC, Yokota H (2013)
Salubrinal reduces expression and activity of MMP13 in chondrocytes.
Osteoarthritis and cartilage 21, 764-772 [PubMed:23473976]
[show Abstract]
Zhang P, Hamamura K, Jiang C, Zhao L, Yokota H (2012)
Salubrinal promotes healing of surgical wounds in rat femurs.
Journal of bone and mineral metabolism 30, 568-579 [PubMed:22610062]
[show Abstract]
Boyce M, Bryant KF, Jousse C, Long K, Harding HP, Scheuner D, Kaufman RJ, Ma D, Coen DM, Ron D, Yuan J (2005)
A selective inhibitor of eIF2alpha dephosphorylation protects cells from ER stress.
Science (New York, N.Y.) 307, 935-939 [PubMed:15705855]
[show Abstract]
Last Modified
07 March 2018