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Key Documents

SML0666

Sigma-Aldrich

GSK1210151A

≥98% (HPLC)

Synonym(s):

7-(3,5-Dimethyl-4-isoxazolyl)-8-(methyloxy)-1-[(1R)-1-(2-pyridinyl)ethyl]-1,3-dihydro-2H-imidazo[4,5-c]quinolin-2-one, I-BET151

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About This Item

Empirical Formula (Hill Notation):
C23H21N5O3
CAS Number:
1300031-49-5
Molecular Weight:
415.44
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

originator

GlaxoSmithKline

relevant disease(s)

cancer

storage temp.

2-8°C

SMILES string

[n]2(c3c([nH][c]2=O)cnc4c3cc(c(c4)c5c(n[o]c5C)C)OC)[C@H](C)c1ncccc1

InChI

1S/C23H21N5O3/c1-12-21(14(3)31-27-12)16-9-18-15(10-20(16)30-4)22-19(11-25-18)26-23(29)28(22)13(2)17-7-5-6-8-24-17/h5-11,13H,1-4H3,(H,26,29)/t13-/m1/s1

InChI key

VUVUVNZRUGEAHB-CYBMUJFWSA-N

Application

GSK1210151A or I-BET151 has been used to study its inhibitory effect on BET (bromodomain and extra terminal) recruitment to chromatin in treating MLL (mixed-lineage leukemia)-fusion leukemia.

Biochem/physiol Actions

GSK1210151A (I-BET151) is an inhibitor of the BET (bromodomain and extra terminal domain protein) family of acetyl-lysine recognizing, chromatin ′adaptor′ proteins.
GSK1210151A (I-BET151) is an inhibitor of the BET (bromodomain and extra terminal domain protein) family of acetyl-lysine recognizing, chromatin ′adaptor′ proteins. GSK1210151A displaces BRD3 and BRD4, PAFc and SEC components from chromatin resulting in inhibition of transcription at key genes (BCL2, C-MYC and CDK6) involved in the initiation of mixed lineage leukemia (MLL). GSK1210151A (I-BET151) showed good efficacy in 2 MLL animal models.

Other Notes

GSK1210151A has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the GSK1210151A probe summary on the Chemical Probes Portal website.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
046M4721V
105M4733V
084M4722V
033M4620V

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Replication Study: Inhibition of BET recruitment to chromatin as an effective treatment for MLL-fusion leukaemia.
Shan X, et al.
eLife, 6, e25306-e25306 (2017)
Zhongyuan Gao et al.
Cancer biology & therapy, 19(5), 407-415 (2018-01-16)
Lung cancer is the leading cause of cancer-related death worldwide. Bromodomain and extraterminal domain (BET) proteins act as epigenome readers for gene transcriptional regulation. Among BET family members, BRD4 was well studied, but for its mechanism in non-small cell lung
Yan-Yi Jiang et al.
Gastroenterology, 159(4), 1311-1327 (2020-07-04)
We investigated the transcriptome of esophageal squamous cell carcinoma (ESCC) cells, activity of gene regulatory (enhancer and promoter regions), and the effects of blocking epigenetic regulatory proteins. We performed chromatin immunoprecipitation sequencing with antibodies against H3K4me1, H3K4me3, and H3K27ac and

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