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Chemical Structure| 1268524-71-5 Chemical Structure| 1268524-71-5

Structure of (R)-(-)-JQ1 Enantiomer
CAS No.: 1268524-71-5

Chemical Structure| 1268524-71-5

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(R)-(-)-JQ1 enantiomer, the stereoisomer(+)-JQ1, showed no significant interaction with any bromodomain. (+)-JQ1 is an inhibitor for the BET which targets the BET bromodomain. The (R)-(-)-JQ1 enantiomer stereoisomer has no appreciable affinity to BET bromodomains, whereas S-enantiomer pure (+)-JQ1 binds to BRD4 bromodomains 1 and 2 with Kd values of ~ 50 and 90 nM, respectively.

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Product Details of (R)-(-)-JQ1 Enantiomer

CAS No. :1268524-71-5
Formula : C23H25ClN4O2S
M.W : 456.99
SMILES Code : 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
MDL No. :MFCD22124456
InChI Key :DNVXATUJJDPFDM-QGZVFWFLSA-N
Pubchem ID :49871818

Safety of (R)-(-)-JQ1 Enantiomer

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Related Pathways of (R)-(-)-JQ1 Enantiomer

epigenetics

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
SKO-007(J3) 0.5 μM 72 h upregulation of MICA expression J Hematol Oncol. 2016 Dec 1;9(1):134.
RPMI-8226 0.5 μM 72 h upregulation of MICA expression J Hematol Oncol. 2016 Dec 1;9(1):134.
CD138+ MM cells 0.5 μM 72 h upregulation of MICA expression J Hematol Oncol. 2016 Dec 1;9(1):134.
JJN3 0.5 μM 72 h upregulation of MICA expression J Hematol Oncol. 2016 Dec 1;9(1):134.
ARP-1 0.5 μM 72 h upregulation of MICA expression J Hematol Oncol. 2016 Dec 1;9(1):134.
U266 0.5 μM 72 h upregulation of MICA expression J Hematol Oncol. 2016 Dec 1;9(1):134.
TY-82 cells 500 nM 9 hr JQ1 treatment increased LC3II levels, indicating enhanced autophagic flux Mol Cell. 2017 May 18;66(4):517-532.e9.
KP-4 cells 500 nM 9 hr JQ1 treatment increased LC3II levels, indicating enhanced autophagic flux Mol Cell. 2017 May 18;66(4):517-532.e9.
NMC 11060 cells 4 nM Confirmed the stereospecific, potent effect of (+)-JQ1 on cellular viability, growth and cell cycle progression Nature. 2010 Dec 23;468(7327):1067-73.
NMC 797 cells 500 nM 48 h Induced squamous differentiation, featuring cell spreading and flattening, open chromatin and striking spindle morphology Nature. 2010 Dec 23;468(7327):1067-73.
cortical neurons 250 nM 10 min JQ1 pretreatment prevented rapid IEG induction after TTX withdrawal Nat Neurosci. 2015 Oct;18(10):1464-73.
cortical neurons 250 nM 10 min JQ1 pretreatment blocked the BDNF-induced increase in Arc, Fos, and Nr4a1 mRNA Nat Neurosci. 2015 Oct;18(10):1464-73.
DMD immortalized myoblasts 200 nM 24 h JQ1 treatment significantly reduced the transcript levels of NADPH oxidase subunits. Nat Commun. 2020 Nov 30;11(1):6108.
C2C12 cells 200 nM 24 h JQ1 pretreatment prevented H2O2-induced oxidative stress, restored LC3II and p62 levels, indicating that JQ1 can rescue autophagy. Nat Commun. 2020 Nov 30;11(1):6108.
adult rat ventricular fibroblasts (ARVFs) 5nM-10μM 72 h To determine the IC50 of JQ1 for inhibition of α-SMA expression. Results showed an IC50 of 94nM. Circ Res. 2019 Sep 13;125(7):662-677.
adult rat ventricular fibroblasts (ARVFs) 500nM 72 h To evaluate the inhibitory effect of JQ1 on TGF-β-induced cardiac fibroblast activation. Results showed that JQ1 significantly reduced collagen gel contraction and α-SMA protein expression. Circ Res. 2019 Sep 13;125(7):662-677.
H2081 cells 1 μM 48 h To evaluate the synergistic effect of JQ1 and IGF-1R inhibitor BMS-754807, results showed combined treatment significantly enhanced apoptosis. Nat Commun. 2019 Jul 19;10(1):3201.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice Male mice Intraperitoneal injection 50 mg/kg Once daily for 3 weeks or 6 weeks To assess the effects of JQ1 on spermatogenesis, results showed significant reduction in testis volume, sperm count and motility without affecting hormone levels. Cell. 2012 Aug 17;150(4):673-84
Mice NMC 797 xenograft model Intraperitoneal injection 50 mg/kg Daily for 4 days JQ1 treatment significantly reduced FDG uptake, slowed tumor growth, effaced NUT nuclear speckles, and induced squamous differentiation Nature. 2010 Dec 23;468(7327):1067-73.
Mice WT adult mice Intraperitoneal injection 50 mg/kg Daily for one week or three weeks JQ1 treatment affected memory formation, resulting in long-term memory deficits and decreased seizure susceptibility Nat Neurosci. 2015 Oct;18(10):1464-73.
Mdx mice Duchenne muscular dystrophy model Intraperitoneal injection 20 mg/kg Daily for two weeks JQ1 treatment reduced muscle damage, improved muscle morphology and function, decreased oxidative stress and inflammation, and rescued autophagy. Nat Commun. 2020 Nov 30;11(1):6108.
Mice H2081 xenograft model Intraperitoneal injection 25 mg/kg Every other day, continuous treatment To evaluate the anti-tumor efficacy of JQ1 and BMS-754807 combination treatment, results showed combined treatment significantly inhibited tumor growth. Nat Commun. 2019 Jul 19;10(1):3201.

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.19mL

0.44mL

0.22mL

10.94mL

2.19mL

1.09mL

21.88mL

4.38mL

2.19mL

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