SGC-CBP30

Inhibitor of CREBBP/EP300 bromodomain,potent CAS# 1613695-14-9

SGC-CBP30

2D Structure

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SGC-CBP30

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Chemical Properties of SGC-CBP30

Cas No. 1613695-14-9 SDF Download SDF
PubChem ID 72201027 Appearance Powder
Formula C28H33ClN4O3 M.Wt 509.04
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 31 mg/mL (60.90 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 4-[(2S)-1-[2-[2-(3-chloro-4-methoxyphenyl)ethyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-1-yl]propan-2-yl]morpholine
SMILES CC1=C(C(=NO1)C)C2=CC3=C(C=C2)N(C(=N3)CCC4=CC(=C(C=C4)OC)Cl)CC(C)N5CCOCC5
Standard InChIKey GEPYBHCJBORHCE-SFHVURJKSA-N
Standard InChI InChI=1S/C28H33ClN4O3/c1-18(32-11-13-35-14-12-32)17-33-25-8-7-22(28-19(2)31-36-20(28)3)16-24(25)30-27(33)10-6-21-5-9-26(34-4)23(29)15-21/h5,7-9,15-16,18H,6,10-14,17H2,1-4H3/t18-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of SGC-CBP30

DescriptionSGC-CBP30 is a potent inhibitor of CREBBP/EP300 with IC50 values of 21 nM and 38 nM, respectively.
TargetsCREBBPEP300    
IC5021 nM38 nM    

Protocol

Cell experiment [1]:

Cell lines

HeLa cells and RKO cells

Preparation method

Limited solubility. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

37oC

Applications

In HeLa cells, treatment of SAHA-treated cells with 0.1 μM SGC-CBP30 reduces FRAP recovery times back to unstimulated levels. In RKO cells, SGC-CBP30 effectively inhibits the Doxorubicin induced p53 activity in a dose-dependent manner.

References:

1. Hay DA, Fedorov O, Martin S et al. Discovery and optimization of small-molecule ligands for the CBP/p300 bromodomains. J Am Chem Soc. 2014 Jul 2;136(26):9308-19.

SGC-CBP30 Dilution Calculator

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SGC-CBP30 Molarity Calculator

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Preparing Stock Solutions of SGC-CBP30

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9645 mL 9.8224 mL 19.6448 mL 39.2896 mL 49.1121 mL
5 mM 0.3929 mL 1.9645 mL 3.929 mL 7.8579 mL 9.8224 mL
10 mM 0.1964 mL 0.9822 mL 1.9645 mL 3.929 mL 4.9112 mL
50 mM 0.0393 mL 0.1964 mL 0.3929 mL 0.7858 mL 0.9822 mL
100 mM 0.0196 mL 0.0982 mL 0.1964 mL 0.3929 mL 0.4911 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on SGC-CBP30

SGC-CBP 30 is a selective inhibitor of CREBBP and EP300 with IC50 value of 21 nM and 38 nM, respectively [1].
EP300 (E1A binding protein p300) is encoded by EP300 gene and plays an important role in regulating cell growth and division, prompting cells mature and assume specialized functions, and preventing tumor cells growth. CREBBP (CREB-binding protein) is encoded by CREBBP gene and involves in the transcriptional coactivation of many different transcription factors [2].
References:
[1]. Duncan A. Hay, Oleg Fedorov, Sarah Martin, et al. Discovery and Optimization of Small-Molecule Ligands for the CBP/p300 Bromodomains [J]. J. Am. Chem. Soc., 2014, 136 (26), pp 9308–9319.
[2]. van Belzen M, Bartsch O, Lacombe D, et al. Rubinstein-Taybi syndrome (CREBBP, EP300) [J]. Eur J Hum Genet. 2011 Jan; 19(1):preceeding 118-20.

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References on SGC-CBP30

Discovery and optimization of 1-(1H-indol-1-yl)ethanone derivatives as CBP/EP300 bromodomain inhibitors for the treatment of castration-resistant prostate cancer.[Pubmed:29448139]

Eur J Med Chem. 2018 Mar 10;147:238-252.

The CREB (cAMP responsive element binding protein) binding protein (CBP) and its homolog EP300 have emerged as new therapeutic targets for the treatment of cancer and inflammatory diseases. Here we report the identification, optimization and evaluation of 1-(1H-indol-1-yl)ethanone derivatives as CBP/EP300 inhibitors starting from fragment-based virtual screening (FBVS). A cocrystal structure of the inhibitor (22e) in complex with CBP provides a solid structural basis for further optimization. The most potent compound 32h binds to the CBP bromodomain and has an IC50 value of 0.037muM in the AlphaScreen assay which was 2 times more potent than the reported CBP bromodomain inhibitor SGC-CBP30 in our hands. 32h also exhibit high selectivity for CBP/EP300 over other bromodomain-containing proteins. Notably, the ester derivative (29h) of compound 32h markedly inhibits cell growth in several prostate cancer cell lines including LNCaP, 22Rv1 and LNCaP derived C4-2B. Compound 29h suppresses the mRNA expression of full length AR (AR-FL), AR target genes and other oncogene in LNCaP cells. 29h also reduces the expression of PSA, the biomarker of prostate cancer. CBP/EP300 inhibitor 29h represents a promising lead compound for the development of new therapeutics for the treatment of castration-resistant prostate cancer.

Activity of bromodomain protein inhibitors/binders against asexual-stage Plasmodium falciparum parasites.[Pubmed:29631126]

Int J Parasitol Drugs Drug Resist. 2018 Aug;8(2):189-193.

Bromodomain-containing proteins (BDPs) are involved in the regulation of eukaryotic gene expression. Compounds that bind and/or inhibit BDPs are of interest as tools to better understand epigenetic regulation, and as possible drug leads for different diseases, including malaria. In this study, we assessed the activity of 42 compounds demonstrated or predicted (using virtual screening of a pharmacophore model) to bind/inhibit eukaryotic BDPs for activity against Plasmodium falciparum malaria parasites. In silico docking studies indicated that all compounds are predicted to participate in a typical hydrogen bond interaction with the conserved asparagine (Asn1436) of the P. falciparum histone acetyltransferase (PfGCN5) bromodomain and a conserved water molecule. Only one compound (the dimethylisoxazole SGC-CBP30; a selective inhibitor of CREBBP (CBP) and EP300 bromodomains) is also predicted to have a salt-bridge between the morpholine nitrogen and Glu1389. When tested for in vitro activity against asynchronous asexual stage P. falciparum Dd2 parasites, all compounds displayed 50% growth inhibitory concentrations (IC50) >10muM. Further testing of the three most potent compounds using synchronous parasites for 72h showed that SGC-CBP30 was the most active (IC50 3.2muM). In vitro cytotoxicity assays showed that SGC-CBP30 has approximately 7-fold better selectivity for the parasites versus a human cell line (HEK 293). Together these data provide a possible starting point for future investigation of these, or related compounds, as tools to understand epigenetic regulation or as potential new drug leads.

Description

SGC-CBP30 is a potent and highly selective CBP/p300 bromodomain (Kds of 21 nM and 32 nM for CBP and p300, respectively) inhibitor, displaying 40-fold selectivity over the first bromodomain of BRD4 [BRD4(1)] bound. SGC-CBP30 strongly reduces secretion of IL-17A in Th17 cells and has anti-inflammatory effects.

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