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SML0951

Sigma-Aldrich

Salubrinal

≥98% (HPLC), powder, eIF2α dephosphorylation inhibitor

Synonym(s):

(2E)-3-Phenyl-N-[2,2,2-trichloro-1-[[(8-quinolinylamino)thioxomethyl]amino]ethyl] 2-propenamide

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About This Item

Empirical Formula (Hill Notation):
C21H17Cl3N4OS
CAS Number:
405060-95-9
Molecular Weight:
479.81
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Salubrinal, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

, White to brown to grey

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

S=C(NC(NC(=O)\C=C\c3ccccc3)C(Cl)(Cl)Cl)Nc1c2ncccc2ccc1

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+

InChI key

LCOIAYJMPKXARU-VAWYXSNFSA-N

Application

Salubrinal has been used to study the effect of stress-protective genes and pathways on organism development and lifespan. It has also been used to study the therapeutic potential of salubrinal in methamphetamine induced blood–brain barrier disruption.

Biochem/physiol Actions

Salubrinal is a selective Inhibitor of eIF2α (eukaryotic translation initiation factor 2 α-subunit) dephosphorylation, inhibiting global protein translation. Salubrinal is a specific inhibitor of ER Stress induced apoptosis.
Salubrinal is a selective Inhibitor of eIF2α dephosphorylation; specific inhibitor of ER Stress induced apoptosis.
Salubrinal maintains protein phosphorylation in order to offer protection against from the adverse effects of endoplasmic reticulum stress. Salubrinal prevents collagenase-mediated articular cartilage damage promoting downregulation of matrix metalloproteinase 13.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Exclamation mark
GHS07

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Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
116M4757V
125M4725V
045M4711V
094M4724V
024M4715V

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Rescue of a developmental arrest caused by a C. elegans heat-shock transcription-factor mutation by loss of ribosomal S6-kinase activity.
Chisnell P J D, et al.
bioRxiv, 310086-310086 (2018)
K Hamamura et al.
Osteoarthritis and cartilage, 21(5), 764-772 (2013-03-12)
Stress to the endoplasmic reticulum (ER) and inflammatory cytokines induce expression and activity of matrix metalloproteinase 13 (MMP13). Since a synthetic agent, salubrinal, is known to alleviate ER stress and attenuate nuclear factor kappa B (NFκB) signaling, we addressed a
Daphne E Lodes et al.
Journal of neurochemistry, 160(6), 613-624 (2021-12-23)
The neural precursor cell expressed developmentally down-regulated protein 4-like (Nedd4-2) is an E3 ubiquitin ligase critical for neurodevelopment and homeostasis of neural circuit excitability. While dysregulation of Nedd4-2 has been linked to elevated seizure susceptibility through impaired ubiquitination of multiple
Muhammad M Hossain et al.
Toxicological sciences : an official journal of the Society of Toxicology, 167(1), 249-257 (2018-09-25)
Endoplasmic reticulum (ER) stress is a significant contributor to neurodegeneration and cognitive dysfunction. Recently, we reported that repeated exposure to the pyrethroid insecticide deltamethrin caused ER stress in the hippocampus of adult mice, which was accompanied by deficits in learning
Protection of Bcl-2 by salubrinal.
Kessel D.
Biochemical and Biophysical Research Communications, 346(4), 1320-1323 (2006)
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