SML0974

Sigma-Aldrich

(+/-)-JQ1

≥98% (HPLC)

Synonym(s):
N-(2′,5′-Dimethoxy[1,1′-biphenyl]-4-yl)-3-fluoro-4-pyridinecarboxamide, (+/-)-SGCBD01, [(R,S)-4-(4-Chlorophenyl)-2,3,9-trimethyl-6H-1-thia-5,7,8,9a-tetraaza-cyclopenta[e]azulen-6-yl]-acetic acid tert-butyl ester
Empirical Formula (Hill Notation):
C23H25ClN4O2S
CAS Number:
Molecular Weight:
456.99
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CC1=NN=C2N1C3=C(C(C)=C(C)S3)C(C4=CC=C(Cl)C=C4)=NC2CC(OC(C)(C)C)=O

InChI

1S/C23H25ClN4O2S/c1-12-13(2)31-22-19(12)20(15-7-9-16(24)10-8-15)25-17(11-18(29)30-23(4,5)6)21-27-26-14(3)28(21)22/h7-10,17H,11H2,1-6H3

InChI key

DNVXATUJJDPFDM-UHFFFAOYSA-N

Application

(±)-JQ1 has been used to study its effect on adipogenesis, by analysing the its impact on the regulation of genes involved in this process especially peroxisome proliferator-activated receptor (PPAR-g), the CCAAT/enhancer-binding protein (C/EBPa) and, STAT5A and B. JQ1 has been used in drug binding assays as a chemical inhibitor of BRD4 to study the CRBN′s substrate recruiting function in mouse and human.

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

(±)-JQ1 is a Brd4 inhibitor. JQ1 is known to suppress cell proliferation and therefore, can be used as a therapeutic drug for a number of cancers including multiple myeloma and acute myeloid leukemia.
The human BET family, which includes BRD2, BRD3, BRD4 and BRDT, play a role in regulation of gene transcription. (+/-)-JQ1 ((+/-)SGCBD01) is a selective BET bromodomain (BRD) inhibitor that inhibits Brd4 (Bromodomain-containing 4). Brd4 forms complexes with chromatin via two tandem bromodomains (BD1 and BD2) that bind to acetylated lysine residues in histones and Brd4 association with acetylated chromatin is believed to regulate the recruitment of elongation factor b and additional transcription factors to specific promoter regions. The nuclear protein in testis (NUT) gene is known to form fusions with Brd4 that create a potent oncogene, leading to rare, but highly lethal tumors referred to as NUT midline carcinomas (NMC). JQ1 inhibits recruitment and binding of Brd4 to TNFα and E-selectin promoter elements, and accelerates recovery time in FRAP (fluorescence recovery after photobleaching) assays using GFP-Brd4. Thus JQ1/SGCBD01 is a useful tool to study the role of Brd4 in transcriptional initiation. For full characterization details, please visit the SGCBD01/JQ1 probe summary on the Structural Genomics Consortium (SGC) website.

To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc

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.
(+/-) JQ-1 is an epigenetic chemical probe available through a partnership with the Structural Genomics Consortium (SGC). To learn more and view other SGC epigenetic probes, visit sigma.com/SGC.

Other Notes

JQ1 has been expertly reviewed and recommended by the Chemical Probes Portal. For more information, please visit the JQ1 probe summary on the Chemical Probes Portal website.
Racemic mixture

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Panagis Filippakopoulos et al.
Nature, 468(7327), 1067-1073 (2010-09-28)
Epigenetic proteins are intently pursued targets in ligand discovery. So far, successful efforts have been limited to chromatin modifying enzymes, or so-called epigenetic 'writers' and 'erasers'. Potent inhibitors of histone binding modules have not yet been described. Here we report...
Yunlu Jia et al.
Blood cancer journal, 11(2), 32-32 (2021-02-14)
Multiple myeloma (MM) is an aggressive plasma cell neoplasm characterized by genomic heterogeneity. Superenhancers (SEs) are defined as large clusters of enhancers in close genomic proximity, which regulate genes for maintaining cellular identity and promote oncogenic transcription to which cancer...
Ligand-mediated protein degradation reveals functional conservation among sequence variants of the CUL4-type E3 ligase substrate receptor cereblon.
Akuffo A A, et al.
The Journal of Biological Chemistry (2018)
Inhibition of the acetyl lysine-binding pocket of bromodomain and extraterminal domain proteins interferes with adipogenesis.
Goupille O, et al.
Biochemical and Biophysical Research Communications, 472(4), 624-630 (2016)
Hiroki Michida et al.
Cell reports, 31(9), 107724-107724 (2020-06-04)
NF-κB is a transcription factor that activates super enhancers (SEs) and typical enhancers (TEs) and triggers threshold and graded gene expression, respectively. However, the mechanisms by which NF-κB selectively participates in these enhancers remain unclear. Here we show using mouse...

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