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I-BET151

Item № 11181
CAS № 1300031-49-5
Purity ≥98%
product image
                (CAS 1300031-49-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $35.00 0.00
     5 mg $96.00 0.00
     10 mg $175.00 0.00
     50 mg $595.00 0.00

Pricing updated 2019-06-26. Prices are subject to change without notice.

Description
Synonyms
  • GSK1210151A

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.1 I-BET151 is an isoxazole class pan-BET family inhibitor, blocking BRD2, BRD3, and BRD4 with IC50 values of 0.5, 0.25, and 0.79 µM, respectively.2,3,4,5 Through this action, it blocks the growth of leukemic cell lines driven by mixed lineage leukemia (MLL) fusions at nanomolar concentrations, whereas tyrosine kinase activated cells were much less sensitive.6 Specifically, I-BET151 induces apoptosis via reduced expression of BCL2 or triggers G0/G1 cell cycle arrest in MLL-fusion cell lines.6 I-BET151 is effective in vivo, suppressing MLL leukemia progression in two different mouse models.6

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Technical Information
Formal Name
7,3,5-dimethyl-4-isoxazolyl-1,3-dihydro-8-methoxy-1-[1R-1-(2-pyridinyl)ethyl]-2H-imidazo[4,5-c]quinolin-2-one
CAS Number
1300031-49-5
Synonyms
  • GSK1210151A
Molecular Formula
C23H21N5O3
Formula Weight
415.5
Purity
≥98%
Formulation
A crystalline solid
λmax
259, 317 nm
SMILES
CC(ON=C1C)=C1C2=CC(N=CC(N3)=C4N([C@H](C)C5=CC=CC=N5)C3=O)=C4C=C2OC
InChI Code
InChI=1S/C23H21N5O3/c1-12-21(14(3)31-27-12)16-9-18-15(10-20(16)30-4)22-19(11-25-18)26-23(29)28(22)13(2)17-7-5-6-8-24-17/h5-11,13H,1-4H3,(H,26,29)/t13-/m1/s1
InChI Key
VUVUVNZRUGEAHB-CYBMUJFWSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

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References & Product Citations
Product Description References

1. Gallenkamp, D., Gelato, K.A., Haendler, B., et al. Bromodomains and their pharmacological inhibitors ChemMedChem 9(3), 438-464 (2014).

2. Kline, T.B., Benington, F., Morin, R.D., et al. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: Photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives Journal of Medicinal Chemistry 25(11), 1381-1383 (1982).

3. Vidler, L.R., Brown, N., Knapp, S., et al. Druggability analysis and structural classification of bromodomain acetyl-lysine binding sites Journal of Medicinal Chemistry 55(17), 7346-7359 (2012).

4. Hewings, D.S., Fedorov, O., Filippakopoulos, P., et al. Optimization of 3,5-dimethylisoxazole derivatives as potent bromodomain ligands Journal of Medicinal Chemistry 56(8), 3217-3227 (2013).

5. Dawson, M.A., Kouzarides, T., and Huntly, B.J. Targeting epigenetic readers in cancer N. Engl. J. Med. 367(7), 647-657 (2012).

6. Dawson, M.A., Prinjha, R.K., Dittmann, A., et al. Inhibition of BET recruitment to chromatin as an effective treatment for MLL-fusion leukaemia Nature 478, 529-533 (2011).

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