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AB146612

(+)-JQ1 (DMSO solution), BET bromodomain inhibitor

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(1 Publication)

MW 457 Da, Purity >99%. Potent, selective and cell-permeable BET bromodomain inhibitor (Kd values are 50 and 90 nM at BRD4 first and second bromodomains, respectively).

View Alternative Names

(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, BRD 6, BRD2_HUMAN, BRD3_HUMAN, BRD4-NUT FUSION, BRD4-NUT fusion oncoprotein, BRD4_HUMAN, BRDT protein, BRDT_HUMAN, Bromodomain containing 2, Bromodomain containing 3, Bromodomain containing 4, Bromodomain testis specific, Bromodomain testis-specific protein, Bromodomain-containing protein 2, Bromodomain-containing protein 3, Bromodomain-containing protein 4, CAP, CBP_HUMAN, CP2C9_HUMAN, CPC9, CREB-binding protein, CT9, CYP2C, CYP2C10, CYP2C19, CYPIIC17, CYPIIC19, CYPIIC9, Cancer/testis antigen 9, Cyclic AMP responsive enhancer binding protein, Cytochrome P-450MP, Cytochrome P450 2C19, Cytochrome P450 2C9, Cytochrome P450 MP-4, Cytochrome P450 MP-8, Cytochrome P450 PB-1, Cytochrome P450, family 2, subfamily C, polypeptide 9, Cytochrome P450-11A, Cytochrome P450-254C, D6S113E, DKFZp686N0336, FLJ31942, FSH, FSRG1, Female sterile homeotic related gene 1, Female sterile homeotic related gene 1, mouse, homolog of, HUNK1, HUNKI, KAT3A, KIAA0043, KIAA9001, MCAP, MGC149605, MGC88320, Mephenytoin 4-hydroxylase, Microsomal monooxygenase, Mitotic chromosome-associated protein, NAT, O27.1.1, ORFX, OTTHUMP00000020135, Open reading frame X, P450 MP, P450 PB 1, P450IIC9, Protein HUNK1, RING3, RING3 PROTEIN, RING3 like gene, RING3-like protein, RING3L, RNF3, RSTS, RTS, Really interesting new gene 3 protein, Rubinstein Taybi syndrome, S-mephenytoin 4-hydroxylase, Testis specific bromodomain protein, Xenobiotic monooxygenase, chromosome associated protein, cytochrome P-450 S-mephenytoin 4-hydroxylase, flavoprotein-linked monooxygenase

1 Images
Chemical Structure - (+)-JQ1 (DMSO solution), BET bromodomain inhibitor (AB146612)
  • Chemical Structure

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Chemical Structure - (+)-JQ1 (DMSO solution), BET bromodomain inhibitor (AB146612)

2D chemical structure image of ab146612, (+)-JQ1 (DMSO solution), BET bromodomain inhibitor

Key facts

CAS number

1268524-70-4

Purity

>99%

Form

Liquid

form

Molecular weight

457 Da

Molecular formula

C<sub>2</sub><sub>3</sub>H<sub>2</sub><sub>5</sub>ClN<sub>4</sub>O<sub>2</sub>S

PubChem

46907787

Nature

Synthetic

Biochemical name

(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

Biological description

Potent, selective and cell-permeable BET bromodomain inhibitor (Kd values are 50 and 90 nM at BRD4 first and second bromodomains, respectively).

Canonical smiles

CC1=C(SC2=C1C(=NC(C3=NN=C(N32)C)CC(=O)OC(C)(C)C)C4=CC=C(C=C4)Cl)C

Isomeric 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

IUPAC Name

tert-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

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store in the dark|Store under desiccating conditions|This product is air and light sensitive and impurities can occur as a result of air oxidation or due to metabolism by microbes

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

CREBBP also known as CBP BRD2 BRDT BRD3 and Brd4 are key proteins that function as transcriptional co-activators and acetyltransferases. CREBBP has a molecular mass of about 265 kDa and is expressed in multiple tissues such as the brain lungs and immune cells. It contains a bromodomain which enables it to bind acetylated lysines on histone tails influencing chromatin structure and transcription. BRD2 BRD3 BRDT and Brd4 collectively known as BET (bromodomain and extra-terminal domain) proteins weigh between 75 and 100 kDa and are mainly expressed in the nucleus participating in the regulation of transcription by recognizing acetylated histones.
Biological function summary

These proteins play significant roles in transcriptional regulation and chromatin remodeling. CREBBP exists as part of a transcriptional co-activator complex modifying chromatin structure to facilitate transcription factor binding. BRD2 BRD3 BRDT and Brd4 through their bromodomains recognize and bind acetylated lysines on histones recruiting transcriptional complexes to specific gene promoters. These actions impact gene expression critical for cell cycle progression differentiation and apoptosis.

Pathways

These proteins integrate into large transcriptional and signaling frameworks. They are vital participants in the Notch and Wnt signaling pathways. CREBBP interacts with proteins like p300 functioning in histone acetylation and gene transcription activation. BET proteins such as Brd4 associate with transcription factors and mediate cell cycle transitions by regulating cyclin and c-myc expression. Their roles in these pathways underline their importance in cellular proliferation and development.

Both CREBBP and BET proteins implicate important roles in various conditions including cancer and neurological disorders. CREBBP mutations associate with Rubinstein-Taybi syndrome characterized by developmental abnormalities. Additionally BET proteins like Brd4 show strong connections to cancer by promoting oncogene expression and are targets for bromodomain inhibitors like JQ1. BET inhibitors including JQ1 show promising results in therapeutic strategies for diseases involving dysregulated transcription impacting both oncogenesis and metabolic disorders.

Product protocols

Publications (1)

Recent publications for all applications. Explore the full list and refine your search

Cancer discovery 11:384-407 PubMed33158843

2020

Genetically Defined Syngeneic Mouse Models of Ovarian Cancer as Tools for the Discovery of Combination Immunotherapy.

Applications

Unspecified application

Species

Unspecified reactive species

Sonia Iyer,Shuang Zhang,Simge Yucel,Heiko Horn,Sean G Smith,Ferenc Reinhardt,Esmee Hoefsmit,Bimarzhan Assatova,Julia Casado,Marie-Charlotte Meinsohn,M Inmaculada Barrasa,George W Bell,Fernando Pérez-Villatoro,Kaisa Huhtinen,Johanna Hynninen,Jaana Oikkonen,Pamoda M Galhenage,Shailja Pathania,Paula T Hammond,Benjamin G Neel,Anniina Farkkila,David Pépin,Robert A Weinberg
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