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Key Documents

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S3567

Sigma-Aldrich

SB 415286

≥98% (HPLC)

Sinónimos:

3-[(3-Chloro-4-hydroxyphenyl)­amino]-4-(2-nitrophenyl)-1H-pyrrol-2,5-dione

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About This Item

Fórmula empírica (notación de Hill):
C16H10N3O5Cl
Número de CAS:
264218-23-7
Peso molecular:
359.72
MDL number:
MFCD04039789
UNSPSC Code:
12352200
PubChem Substance ID:
24278412
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

color

yellow to orange

solubility

DMSO: 5 mg/mL, clear
H2O: insoluble

originator

GlaxoSmithKline

storage temp.

−20°C

SMILES string

Oc1ccc(NC2=C(C(=O)NC2=O)c3ccccc3[N+]([O-])=O)cc1Cl

InChI

1S/C16H10ClN3O5/c17-10-7-8(5-6-12(10)21)18-14-13(15(22)19-16(14)23)9-3-1-2-4-11(9)20(24)25/h1-7,21H,(H2,18,19,22,23)

InChI key

PQCXVIPXISBFPN-UHFFFAOYSA-N

Gene Information

human ... GSK3A(2931) , GSK3B(2932)

Application

SB 415286 was used to treat neuroblastoma cells and study the effect of GSK-3 inhibition on cell proliferation.

Biochem/physiol Actions

SB 415286 is a small molecule inhibitor of GSK-3 in muscle and fat cells. SB 415286 induces activation of glycogen synthase and regulates the transport glucose. SB 415286 reduces the systemic inflammation induced by endotoxic shock in rat model of acute colitis. It increases the axonal growth and promotes the recovery of injured adult CNS neurons. SB 415289 is implicated in inducing chromosome instability when used as therapeutic agents.
Glycogen synthase kinase-3 (GSK-3) inhibitor.

Features and Benefits

This compound is featured on the GSK-3 and PKB/Akt pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Sold for research purposes under agreement from GlaxoSmithKline.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Jorge-Tonatiuh Ayala-Sumuano et al.
Scientific reports, 1, 178-178 (2012-02-23)
Adipogenesis is regulated by a complex cascade of transcriptional factors, but little is known about the early events that regulate the adipogenic program. Here, we report the role of the srebf1a gene in the differentiation of fibroblastic 3T3-F442A cells. We
Brendan J R Whittle et al.
British journal of pharmacology, 147(5), 575-582 (2005-11-30)
The effects of the inhibitors of glycogen synthase kinase-3beta (GSK-3beta), TDZD-8 and SB 415286, which can substantially reduce the systemic inflammation associated with endotoxic shock in vivo, have now been investigated on the acute colitis provoked by trinitrobenzene sulphonic acid
John Dill et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 28(36), 8914-8928 (2008-09-05)
Axonal regeneration is minimal after CNS injuries in adult mammals and medical treatments to recover neurological deficits caused by axon disconnection are extremely limited. The failure of axonal elongation is principally attributed to the nonpermissive environment and reduced intrinsic growth
Katrina MacAulay et al.
European journal of biochemistry, 270(18), 3829-3838 (2003-09-03)
Glycogen synthase kinase 3 (GSK3) is inactivated by insulin and lithium and, like insulin, Li also activates glycogen synthase (GS) via inhibition of GSK3. Li also mimics insulin's ability to stimulate glucose transport (GT), an observation that has led to
Daniela Hulcová et al.
Molecules (Basel, Switzerland), 23(4) (2018-03-22)
Glycogen synthase kinase-3β (GSK-3β) is a multifunctional serine/threonine protein kinase that was originally identified as an enzyme involved in the control of glycogen metabolism. It plays a key role in diverse physiological processes including metabolism, the cell cycle, and gene
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