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SML1524

Sigma-Aldrich

(+)-JQ1

≥98% (HPLC), powder, BET bromodomain protein inhibitor

Synonym(s):

(S)-(+)-tert-Butyl 2-(4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl)acetate, 6H-Thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine-6-acetic acid, 4-(4-chlorophenyl)-2,3,9-trimethyl-, 1,1-dimethylethyl ester, (6S)-

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About This Item

Empirical Formula (Hill Notation):
C23H25ClN4O2S
CAS Number:
1268524-70-4
Molecular Weight:
456.99
MDL number:
MFCD22683748
UNSPSC Code:
41106609
PubChem Substance ID:
329825941
NACRES:
NA.77

product name

(+)-JQ1, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(OC(C)(C)C)C[C@H]1C2=NN=C(C)N2C(SC(C)=C3C)=C3C(C4=CC=C(Cl)C=C4)=N1

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/t17-/m0/s1

InChI key

DNVXATUJJDPFDM-KRWDZBQOSA-N

Related Categories

General description

JQ1 is a member of the triazolo-diazepine compound family, which functions as a pan-BET (bromodomain and extra-terminal motif) family 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.

Application

(+)-JQ1 has been used in flow cytometry assay, cell viability assay and quantitative PCR assay in order to investigate on the reversal of HIV-1 latency.

Biochem/physiol Actions

(+)-JQ1 is a high affinity, potent and selective inhibitor of BET bromodomain proteins, including BRD2, BRD3, BRD4 and BRDT. (+)-JQ1 (also known as SGCBD01), the active enantiomer of (+/-)-JQ1, inhibits Brd4 (bromodomain-containing 4), which 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 TNFa and E-selectin promoter elements, and accelerates recovery time in FRAP (fluorescence recovery after photobleaching) assays using GFP-Brd4. Thus (+)-JQ1 is a useful tool to study the role of Brd4 in transcriptional initiation.

For characterization details of (+)-JQ1, please visit the JQ-1 probe summary on the Structural Genomics Consortium (SGC) website.

(-)-JQ1 is the negative control for the active enantiomer, (+)-JQ1. (-)-JQ1 is available from Sigma. To learn more about and purchase (-)-JQ1, click here.

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hunter R Gibbons et al.
Scientific reports, 9(1), 10280-10280 (2019-07-18)
As a class, 'BET' inhibitors disrupt binding of bromodomain and extra-terminal motif (BET) proteins, BRD2, BRD3, BRD4 and BRDT, to acetylated histones preventing recruitment of RNA polymerase 2 to enhancers and promoters, especially super-enhancers, to inhibit gene transcription. As such
Cong Wang et al.
iScience, 25(1), 103719-103719 (2022-01-25)
The BET-bromodomain protein BRD4 uses two bromodomains to target acetyl-histones and other domains to recruit P-TEFb and other transcription factors to stimulate transcription of proto-oncogenes and key cell identity genes. Recent studies show that its ability to form phase-separated condensates
A novel bromodomain inhibitor reverses HIV-1 latency through specific binding with BRD4 to promote Tat and P-TEFb association.
Huang H, et al.
Frontiers in Microbiology, 8, 1035-1035 (2017)
Jianjian Yu et al.
Cell death discovery, 8(1), 224-224 (2022-04-25)
Diabetes is a potential risk factor for gastric cancer (GC). Pin1, a peptidyl-prolyl cis/trans isomerase, promotes GC cell proliferation and migration. The role and underlying mechanism of the Pin1/BRD4 axis in hyperglycemia-induced proliferation and migration of GC cells were analyzed
Yaping Wu et al.
Theranostics, 9(6), 1777-1793 (2019-05-01)
The bromodomain and extraterminal family members are epigenetic readers and transcriptional coactivators which are critically involved in various biological processes including tumorigenesis. BRD4 has been increasingly appreciated as a key oncogene and promising anticancer target. Here, we sought to characterize
View All Related Papers

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