Name: (-)-JQ1
Price: 378.00 USD

- Overview
  - Please contact us at for specific academic pricing.
    
    Background
    
    (-)-JQ1 is the stereoisomer of JQ1, a cell-permeable small-molecule inhibitor of BET bromodomain that competitively binds to acetyl-lysine recognition motifs. JQ1 is a novel thieno-triazolo-1,4-diazepine with an appended and bulky t-butyl ester functional group at C6 position in its chemical structure, which allows for additional pendant group diversity and mitigates binding to the central benzodiazepine receptor. JQ1 competitively binds to the bromodomain displacing the BRD4 fusion oncoprotein from chromatin, which induces squamous differentiation and specific anti-proliferative effect in BRD4-dependent cell lines and patient-derived xenograft models. However, study results have shown that (-)-JQ1 fails to significantly interact with any bromodomain tested and exhibits inhibition against BRD4(1) with 50% inhibition concentration IC50 value of 10,000 nM.
    
    Reference:
    Filippakopoulos P, Qi J, Picaud S, Shen Y, Smith WB, Fedorov O, Morse EM, Keates T, Hickman TT, Felletar I, Philpott M, Munro S, McKeown MR, Wang Y, Christie AL, West N, Cameron MJ, Schwartz B, Heightman TD, La Thangue N, French CA, Wiest O, Kung AL, Knapp S, Bradner JE. Selective inhibition of BET bromodomains. Nature. 2010 Dec 23;468(7327):1067-73. doi: 10.1038/nature09504. Epub 2010 Sep 24.
- Properties
  - Categories
    
    Stereoisomer of (+)-JQ1, used as negative control
    
    Alternative Name
    
    (-)-JQ1; (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
    
    CAS Number
    
    1268524-71-5
    
    Molecular Formula
    
    C23H25ClN4O2S
    
    Molecular Weight
    
    456.99
    
    Appearance
    
    A solid
    
    Purity
    
    98.12%
    
    Solubility
    
    ≥22.85 mg/mL in DMSO; insoluble in H2O; ≥46.9 mg/mL in EtOH with ultrasonic
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    CC1=C(C)SC2=C1C(C3=CC=C(Cl)C=C3)=N[[email protected]](CC(OC(C)(C)C)=O)C4=NN=C(C)N24
    
    * For Research Use Only
- Reference
  - 1. Danhui Liu, Yuzhen Liu, et al. "Trichostatin A promotes esophageal squamous cell carcinoma cell migration and EMT through BRD4/ERK1/2-dependent pathway." Cancer Med. 2021 Aug;10(15):5235-5245. PMID:34160902
    2. Somayeh Layeghi-Ghalehsoukhteh, Shreoshi Pal Choudhuri, et al. "Concerted cell and in vivo screen for pancreatic ductal adenocarcinoma (PDA) chemotherapeutics." Sci Rep. 2020 Nov 26;10(1):20662. PMID:33244070
    3. Te Zhang, Xuming Song, et al. "Aberrant super-enhancer landscape reveals core transcriptional regulatory circuitry in lung adenocarcinoma." Oncogenesis. 2020 Oct 17;9(10):92. PMID:33070167
    4. Wu SY, Lee CF, et al. "Opposing Functions of BRD4 Isoforms in Breast Cancer." Mol Cell. 2020;78(6):1114-1132.e10. PMID:32446320
    5. Alfonso-Dunn R, Turner AW, et al. "Transcriptional Elongation of HSV Immediate Early Genes by the Super Elongation Complex Drives Lytic Infection and Reactivation from Latency." Cell Host Microbe. 2017 Apr 12;21(4):507-517.e5. PMID:28407486
    6. Alonso, Victoria Lucia, et al. "Overexpression of bromodomain factor 3 in Trypanosoma cruzi (TcBDF3) affects differentiation of the parasite and protects it against bromodomain inhibitors." FEBS Journal (2016). PMID:27007774
    7. Peeters, Janneke GC, et al. "Inhibition of Super-Enhancer Activity in Autoinflammatory Site-Derived T Cells Reduces Disease-Associated Gene Expression." Cell reports (2015). PMID:26387944
    8. Sengupta, Surojeet, et al. "Inhibition of BET proteins impairs estrogen-mediated growth and transcription in breast cancers by pausing RNA polymerase advancement." Breast cancer research and treatment (2015): 1-14. PMID:25721606