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JQ1

CAT: 0013-GTR19164129-02Size: 200 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19164129-02Size:200 mg
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Description
(+) -JQ-1 (JQ1) is a potent, selective, cell-permeable BET bromodomain inhibitor with IC50 of 77 nM/33 nM for BRD4 BD1 and BD2, respectively; induces rapid expression of keratin in treated NMC 797 cells, displaces the BRD4 fusion oncoprotein from chromatin, prompting squamous differentiation and specific antiproliferative effects in BRD4-dependent cell lines and patient-derived xenograft models. (In Vitro) : (+) -JQ-1 represents a potent, highly specific and Kac competitive inhibitor for the BET family of bromodomains. (+) -JQ-1 (100 nM, 48 h) prompts squamous differentiation exhibited by cell spindling, flattening and increased expression of keratin. (+) -JQ-1 (250 nM) induces rapid expression of keratin in treated NMC 797 cells compared to (-) -JQ1 (250 nM) and vehicle controls, as determined by quantitative immunohistochemistry. (+) -JQ-1 (250 nM) elicits a time-dependent induction of strong (3+) keratin staining of treated NMC 797 cells, compared to (-) -JQ1 (250 nM) . De-repression of autophagy genes is observed almost immediately after (+) -JQ-1 addition. (+) -JQ-1 is a potent thienodiazepine inhibitor (Kd=90 nM) of the BET family coactivator protein BRD4, which is implicated in the pathogenesis of cancer via transcriptional control of the MYC oncogene. Dose-ranging studies of (+) -JQ-1 demonstrates potent inhibition of H4Kac4 binding with a IC50 value of 10 nM for murine BRDT and 11 nM for human BRDT. (In Vivo) :Matched cohorts of mice with established tumors are randomized to treatment with (+) -JQ1 (50 mg/kg) or vehicle, administered by daily intraperitoneal injection. Prior to randomization, and after four days of therapy, mice are evaluated by FDG-PET imaging. A marked reduction in FDG uptake is observed with (+) -JQ1 treatment. Tumor-volume measurements confirm a reduction in tumor growth with JQ1 treatment. Pharmacokinetic studies of (+) -JQ1 are performed in CD1 mice following intravenous and oral administration. Mean plasma concentration-time profiles of (+) -JQ1 after intravenous dosing (5 mg/kg) . The pharmacokinetic parameters for intravenous (+) -JQ1 demonstrate excellent drug exposure (AUC=2090 hr*ng/mL) and an approximately one hour half-life (T1/2) . Mean plasma concentration-time profiles of (+) -JQ1 after oral dosing (10 mg/kg) . The pharmacokinetic parameters for oral (+) -JQ1 demonstrate excellent oral bioavailability (F=49%), peak plasma concentration (Cmax=1180 ng/mL) and drug exposure (AUC=2090 hr*ng/mL) .
CAS Number
1268524-70-4
Product Name Alternative
JQ-1 | (+) -JQ-1
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 45 mg/mL
Smiles
O=C (OC (C) (C) C) C[C@H]1C2=NN=C (C) N2C3=C (C (C) =C (C) S3) C (C4=CC=C (Cl) C=C4) =N1
Molecular Formula
C23H25ClN4O2S
Molecular Weight
456.9882
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
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, (6S) -

Chemical Information

JQ1 compound

JQ1 is a member of the class of thienotriazolodiazepines that is the tert-butyl ester of [(6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-6-yl]acetic acid. An inhibitor of bromodomain-containing protein 4 that exhibits anti-cancer and cardioprotective properties. It has a role as a bromodomain-containing protein 4 inhibitor, a ferroptosis inducer, an antineoplastic agent, an angiogenesis inhibitor, an anti-inflammatory agent, an apoptosis inducer and a cardioprotective agent. It is a tert-butyl ester, a carboxylic ester, an organochlorine compound and a thienotriazolodiazepine.

CAS Number1268524-70-4
PubChem CID46907787
IUPAC Nametert-butyl 2-[(9S)-7-(4-chlorophenyl)-4,5,13-trimethyl-3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaen-9-yl]acetate
Molecular FormulaC23H25ClN4O2S
Molecular Weight457.0
XLogP4.9
Topological Polar Surface Area97.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Heavy Atom Count31
Formal Charge0
Complexity706
SMILES
CC1=C(SC2=C1C(=N[C@H](C3=NN=C(N32)C)CC(=O)OC(C)(C)C)C4=CC=C(C=C4)Cl)C
InChI
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-/m0/s1
InChIKey
DNVXATUJJDPFDM-KRWDZBQOSA-N
Chemical Structure
2D Structure
2D structure of JQ1 compound
CAS: 1268524-70-4
CID: 46907787
Formula: C23H25ClN4O2S
MW: 457.0
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight457.0
XLogP34.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass456.1386749
Monoisotopic Mass456.1386749
Topological Polar Surface Area97.6 Ų
Heavy Atom Count31
Formal Charge0
Complexity706
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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