(-)-JQ-1

Names

[ Name ]:
(-)-JQ-1

[Synonym ]:
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)-
2-Methyl-2-propanyl [(6R)-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)-(-)-JQ1 Enantiomer

Biological Activity

[Description]:

(-)-JQ-1 is the stereoisomer of (+)-JQ1. (+)-JQ1 potently decreases expression of both BRD4 target genes, whereas (−)-JQ1 has no effect.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> Epigenetic Reader Domain

Research Areas >> Cancer

[Target]

BET bromodomain[1]

[In Vitro]

(−)-JQ1 shows no significant interaction with any bromodomain. Besides, (−)-JQ1 enantiomer is comparatively inactive in nuclear protein in testis (NUT) midline carcinoma (NMC)[1].

[References]

[1]. Filippakopoulos, et al. Selective inhibition of BET bromodomains. Nature. 2010 Dec 23;468(7327):1067-73.

[2]. Mahe M, et al. An FGFR3/MYC positive feedback loop provides new opportunities for targeted therapies in bladder cancers. EMBO Mol Med. 2018 Apr;10(4). pii: e8163.

[Related Small Molecules]

(+)-JQ1 | GSK126 | Tazemetostat (EPZ-6438) | Birabresib (OTX015) | A 485 | Curcumin | ARV-771 | ARV-825 | I-BET762 | BI 2536 | GSK343 | C646 | 3-Deazaneplanocin A (hydrochloride) | I-BET151 | 666-15

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
610.4±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₂₅ClN₄O₂S

[ Molecular Weight ]:
456.988

[ Flash Point ]:
322.9±34.3 °C

[ Exact Mass ]:
456.138672

[ PSA ]:
97.61000

[ LogP ]:
4.49

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.657

[ Storage condition ]:
-20°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Targeting bromodomains: epigenetic readers of lysine acetylation.

Nat. Rev. Drug Discov. 13(5) , 337-56, (2014)

Lysine acetylation is a key mechanism that regulates chromatin structure; aberrant acetylation levels have been linked to the development of several diseases. Acetyl-lysine modifications create dockin...

Epigenetic chemical probes. Müller S and Brown PJ

Clin. Pharmacol. Ther. 92(6) , 689-93, (2012)

Targeting chromatin readers. James LI and Frye SV

Clin. Pharmacol. Ther. 93(4) , 312-4, (2013)