SML0974
(+/-)-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
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About This Item
Empirical Formula (Hill Notation):
C23H25ClN4O2S
CAS Number:
Molecular Weight:
456.99
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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
Related Categories
Application
(±)-JQ1 has been used to study its effect on adipogenesis, by analyzing 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.
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
To learn about other SGC chemical probes for epigenetic targets, visit sigma.com/sgc
Features and Benefits
(+/-) 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.
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.
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
related product
Product No.
Description
Pricing
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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