SML1525

Sigma-Aldrich

(-)-JQ1

≥95% (HPLC)

Synonym(s):
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)-, (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
Empirical Formula (Hill Notation):
C23H25ClN4O2S
CAS Number:
Molecular Weight:
456.99
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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.

Packaging

5, 25 mg in glass bottle

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

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.

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

Targeting chromatin readers.
James LI and Frye SV
Clinical Pharmacology and Therapeutics, 93(4), 312-314 (2013)
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...
Epigenetic chemical probes.
Muller S and Brown PJ
Clinical Pharmacology and Therapeutics, 92(6), 689-693 (2012)
null
Leiming Wang et al.
The Journal of clinical investigation, 130(4), 1782-1792 (2019-12-25)
Recent findings have shown that inhibitors targeting bromodomain and extraterminal domain (BET) proteins, such as the small molecule JQ1, are potent growth inhibitors of many cancers and hold promise for cancer therapy. However, some reports have also revealed that JQ1...

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