(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

Description

The bromodomain and extra terminal domain (BET) family of proteins, including BRD2, BRD3, and BRD4, play a key role in many cellular processes, including inflammatory gene expression, mitosis, and viral/host interaction by controlling the assembly of histone acetylation-dependent chromatin complexes. (±)-JQ1 displaces BET proteins from chromatin by competitively binding to the acetyl-lysine recognition pocket of BET bromodomains. The (−)-JQ1 stereoisomer has no appreciable affinity to BET bromodomains, whereas enantiomerically pure (+)-JQ1 binds to BRD4 bromodomains 1 and 2 with K_d values of ~50 and 90 nM, respectively.

Uses

(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 is the enantiomer 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-6333 is an organonitrogen heterocyclic compound, an organosulfur heterocyclic compound and a tert-butyl ester.

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

storage

Store at -20°C