| Identification | Back Directory | [Name]
(±)-JQ1 | [CAS]
1268524-69-1 | [Synonyms]
rac JQ-1
(+/-)-JQ1
(+/-)-SGCBD01
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
[(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
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
tert-butyl
2-[7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11
,12-tetraazatricyclo[8.3.0.0,2,6]trideca-2(6),4,7,10,1
2-pentaen-9-yl]acetate | [Molecular Formula]
C23H25ClN4O2S | [MDL Number]
MFCD23726614 | [MOL File]
1268524-69-1.mol | [Molecular Weight]
456.99 |
| Chemical Properties | Back Directory | [Boiling point ]
610.4±65.0 °C(Predicted) | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble2mg/mL, clear (warmed) | [form ]
powder | [pka]
2.05±0.60(Predicted) | [color ]
white to beige | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months. | [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 | [InChIKey]
DNVXATUJJDPFDM-UHFFFAOYSA-N | [SMILES]
CC1=NN=C2N1C3=C(C(C)=C(C)S3)C(C4=CC=C(Cl)C=C4)=NC2CC(OC(C)(C)C)=O |
| Hazard Information | Back Directory | [Description]
(±) JQ1 (1268524-69-1) is a potent BET bromodomain inhibitor. IC50 = 17.7, 32.6, 76.9 and 12942 nM respectively for BRD2 (N-terminal (N)), BRD4 (C-terminal (C)), BRD4 (N) and CREBBP respectively. Competitive binding by (±) JQ1 displaces the BRD4 fusion oncoprotein from chromatin, prompting squamous differentiation and specific antiproliferative effects in BRD4-dependent cell lines and patient-derived xenograft models establishing proof-of-concept for targeting protein-protein interactions of epigenetic readers.1 Chiral version is available for purchase (Cat#10-1584). | [Uses]
(±)-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. | [Uses]
rac-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 is the isomer of (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 (T117580), which is BET bromodomain inhibitor, also activates HIV latency through antagonizing Brd4 inhibition of Tat-transactivation. | [Definition]
ChEBI: LSM-6732 is an organonitrogen heterocyclic compound, an organosulfur heterocyclic compound and a tert-butyl ester. | [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. | [References]
1) Filippakopoulos et al. (2010), Selective inhibition of BET bromodomains; Nature, 468 1067 |
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https://www.sigmaaldrich.cn |
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Energy Chemical
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http://www.energy-chemical.com |
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