All Photos(1)
Synonym(s):
(R)-(-)-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, (6R)-
Empirical Formula (Hill Notation):
C23H25ClN4O2S
CAS Number:
Molecular Weight:
456.99
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥95% (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-/m1/s1
InChI key
DNVXATUJJDPFDM-QGZVFWFLSA-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. Its core structure is composed of thienodiazepine.
Biochem/physiol Actions
(-)-JQ1 is the negative control probe for (+)-JQ1, the active enantiomer of (+/-)-JQ1, which is a potent and selective BET bromodomain inhibitor. (-)-JQ1 shows no significant interaction with BRD1-4 or other bromodomains.
For characterization details of the active probe, (+)-JQ1, please visit the JQ1 probe summary on the Structural Genomics Consortium (SGC) website.
(+)-JQ1, the active enantiomer, 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
For characterization details of the active probe, (+)-JQ1, please visit the JQ1 probe summary on the Structural Genomics Consortium (SGC) website.
(+)-JQ1, the active enantiomer, 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 a negative control for (+) JQ1, 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.
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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Targeting chromatin readers.
James LI and Frye SV
Clinical Pharmacology and Therapeutics, 93(4), 312-314 (2013)
Epigenetic chemical probes.
Muller S and Brown PJ
Clinical Pharmacology and Therapeutics, 92(6), 689-693 (2012)
Tatsuro Yamamoto et al.
British journal of cancer, 123(4), 580-590 (2020-06-06)
Oral squamous cell carcinoma (OSCC) has increased morbidity, and its high metastatic potential affects patient survival. Bromodomain containing 4 (BRD4) is a chromatin protein that associates with acetylated histone lysines and facilitates transcription. BRD4 has been implicated in cell proliferation
Jiwoon Lee et al.
Glia, 71(12), 2866-2883 (2023-08-16)
The zebrafish retina possesses tremendous regenerative potential. Müller glia underlie retinal regeneration through their ability to reprogram and generate multipotent neuronal progenitors that re-differentiate into lost neurons. Many factors required for Müller glia reprogramming and proliferation have been identified; however
Hilmar Strickfaden et al.
Cell, 183(7), 1772-1784 (2020-12-17)
The association of nuclear DNA with histones to form chromatin is essential for temporal and spatial control of eukaryotic genomes. In this study, we examined the physical state of condensed chromatin in vitro and in vivo. Our in vitro studies demonstrate that self-association
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