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p53 and MDM2 proteins-interaction-inhibitor racemic

CAS# 939983-14-9

p53 and MDM2 proteins-interaction-inhibitor racemic

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Chemical structure

p53 and MDM2 proteins-interaction-inhibitor racemic

3D structure

Chemical Properties of p53 and MDM2 proteins-interaction-inhibitor racemic

Cas No. 939983-14-9 SDF Download SDF
PubChem ID 50878542 Appearance Powder
Formula C40H49Cl2N5O4 M.Wt 734.75
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in DMSO
Chemical Name 2-[4-[(4R,5S)-2-(4-tert-butyl-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dimethylimidazole-1-carbonyl]piperazin-1-yl]-1-morpholin-4-ylethanone
SMILES CCOC1=C(C=CC(=C1)C(C)(C)C)C2=NC(C(N2C(=O)N3CCN(CC3)CC(=O)N4CCOCC4)(C)C5=CC=C(C=C5)Cl)(C)C6=CC=C(C=C6)Cl
Standard InChIKey DJZBZZRLUQDRII-PVXQIPPMSA-N
Standard InChI InChI=1S/C40H49Cl2N5O4/c1-7-51-34-26-30(38(2,3)4)12-17-33(34)36-43-39(5,28-8-13-31(41)14-9-28)40(6,29-10-15-32(42)16-11-29)47(36)37(49)46-20-18-44(19-21-46)27-35(48)45-22-24-50-25-23-45/h8-17,26H,7,18-25,27H2,1-6H3/t39-,40+/m1/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 p53 and MDM2 proteins-interaction-inhibitor racemic

Descriptionp53 and MDM2 proteins-interaction-inhibitor (racemic) (Compound 2j) is an inhibitor of the interaction between p53 and MDM2 proteins.

References:
[1]. Vu B, et al. Discovery of RG7112: A Small-Molecule MDM2 Inhibitor in Clinical Development. ACS Med Chem Lett. 2013 Apr 2;4(5):466-9.

p53 and MDM2 proteins-interaction-inhibitor racemic Dilution Calculator

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Preparing Stock Solutions of p53 and MDM2 proteins-interaction-inhibitor racemic

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.361 mL 6.805 mL 13.6101 mL 27.2201 mL 34.0252 mL
5 mM 0.2722 mL 1.361 mL 2.722 mL 5.444 mL 6.805 mL
10 mM 0.1361 mL 0.6805 mL 1.361 mL 2.722 mL 3.4025 mL
50 mM 0.0272 mL 0.1361 mL 0.2722 mL 0.5444 mL 0.6805 mL
100 mM 0.0136 mL 0.0681 mL 0.1361 mL 0.2722 mL 0.3403 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 p53 and MDM2 proteins-interaction-inhibitor racemic

p53 and MDM2 proteins-interaction-inhibitor (racemic) is an inhibitor of the interaction between p53 and MDM2 proteins.

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References on p53 and MDM2 proteins-interaction-inhibitor racemic

Exploration of liquid and supercritical fluid chromatographic chiral separation and purification of Nutlin-3--a small molecule antagonist of MDM2.[Pubmed:17897804]

J Pharm Biomed Anal. 2007 Dec 21;45(5):720-9.

Inhibition of the MDM2-p53 interaction can stabilize the p53 protein and offer a novel strategy for cancer therapy. The imidazoline compound (Nutlin-3) is a promising small molecule antagonist of the MDM2-p53 interaction. This compound was synthesized as a racemic mixture, and one enantiomer is 100-200-fold more active than the other enantiomer. In this study, various enantiomeric separation approaches were explored to resolve the Nutlin-3 enantiomers using chiral supercritical fluid chromatography (SFC) as well as chiral liquid chromatography (LC) under normal phase mode, reversed phase mode and polar organic phase mode. The chiral SFC method based on Chiralcel OD column showed superior separation in terms of selectivity and efficiency. Optimization of the chiral separation method enabled high throughput preparative scale purification. Ultimately, 5 g of racemic mixture were purified on Prep-SFC in 75 min with the recovery rate above 92%.

Organocatalytic, diastereo- and enantioselective synthesis of nonsymmetric cis-stilbene diamines: a platform for the preparation of single-enantiomer cis-imidazolines for protein-protein inhibition.[Pubmed:25017623]

J Org Chem. 2014 Aug 1;79(15):6913-38.

The finding by scientists at Hoffmann-La Roche that cis-imidazolines could disrupt the protein-protein interaction between p53 and MDM2, thereby inducing apoptosis in cancer cells, raised considerable interest in this scaffold over the past decade. Initial routes to these small molecules (i.e., Nutlin-3) provided only the racemic form, with enantiomers being enriched by chromatographic separation using high-pressure liquid chromatography (HPLC) and a chiral stationary phase. Reported here is the first application of an enantioselective aza-Henry approach to nonsymmetric cis-stilbene diamines and cis-imidazolines. Two novel mono(amidine) organocatalysts (MAM) were discovered to provide high levels of enantioselection (>95% ee) across a broad range of substrate combinations. Furthermore, the versatility of the aza-Henry strategy for preparing nonsymmetric cis-imidazolines is illustrated by a comparison of the roles of aryl nitromethane and aryl aldimine in the key step, which revealed unique substrate electronic effects providing direction for aza-Henry substrate-catalyst matching. This method was used to prepare highly substituted cis-4,5-diaryl imidazolines that project unique aromatic rings, and these were evaluated for MDM2-p53 inhibition in a fluorescence polarization assay. The diversification of access to cis-stilbene diamine-derived imidazolines provided by this platform should streamline their further development as chemical tools for disrupting protein-protein interactions.

Stereochemical studies of hexylitaconic acid, an inhibitor of p53-HDM2 interaction.[Pubmed:19414261]

Bioorg Med Chem Lett. 2009 Jun 1;19(11):3027-30.

Hexylitaconic acid (1) is an intriguing natural product possessing a chiral carbon, and both its enantiomers have been found in nature. Enantiomeric pure (+)-(1) and (-)-(1) were successfully prepared by racemic synthesis followed by enantiomeric separation in a chiral HPLC system. Their absolute configurations were clarified by the vibrational circular dichroism technique using their methyl esters 2 and lactones 3. Their inhibitory activities against the interaction of p53-HDM2 were also examined.

Tetrahydroanthraquinone Derivative (+/-)-4-Deoxyaustrocortilutein Induces Cell Cycle Arrest and Apoptosis in Melanoma Cells via Upregulation of p21 and p53 and Downregulation of NF-kappaB.[Pubmed:27053954]

J Cancer. 2016 Mar 12;7(5):555-68.

BACKGROUND: Malignant melanoma is an aggressive type of skin cancer with high risk for metastasis and chemoresistance. Disruption of tightly regulated processes such as cell cycle, cell adhesion, cell differentiation and cell death are predominant in melanoma development. So far, conventional treatment options have been insufficient to treat metastatic melanoma and survival rates are poor. Anthraquinone compounds have been reported to have anti-tumorigenic potential by DNA-interaction, promotion of apoptosis and suppression of proliferation in various cancer cells. METHODS: In the current study, the racemic tetrahydroanthraquinone derivative (+/-)-4-deoxyaustrocortilutein (4-DACL) was synthesized and the cytotoxic activity against melanoma cells and melanoma spheroids determined by CellTiter-Blue viability Assay and phase contrast microscopy. Generation of reactive oxygen species (ROS) was determined with CellROX Green and Deep Red Reagent kit and microplate-based fluorometry. Luciferase reporter gene assays for nuclear factor kappa B (NF-kappaB) and p53 activities and western blotting analysis were carried out to detect the expression of anti-proliferative or pro-apoptotic (p53, p21, p27, MDM2, and GADD45M) and anti-apoptotic (p65, IkappaB-alpha, IKK) proteins. Cell cycle distribution and apoptosis rate were detected by flow cytometry, the morphological changes visualized by fluorescence microscopy and the activation of different caspase cascades distinguished by Caspase Glo 3/7, 8 and 9 Assays. RESULTS: We demonstrated that 4-DACL displayed high activity against different malignant melanoma cells and melanoma spheroids and only low toxicity to melanocytes and other primary cells. In particular, 4-DACL treatment induced mitochondrial ROS, reduced NF-kappaB signaling activity and increased up-regulation of the cell cycle inhibitors cyclin-dependent kinase inhibitor p21 (p21(WAF1/Cip1)) and the tumor suppressor protein p53 in a dose-dependent manner, which was accompanied by decreased cell proliferation and apoptosis via the intrinsic pathway. CONCLUSION: According to these results, we suggest that 4-DACL may be a promising therapeutic agent for the treatment of malignant melanoma.

Solid-phase synthesis of the cyclic peptide portion of chlorofusin, an inhibitor of p53-MDM2 interactions.[Pubmed:14682762]

Org Lett. 2003 Dec 25;5(26):5051-4.

The first solid-phase synthesis of the chlorofusin peptide is described. The synthesis involved side-chain immobilization of N(alpha)-Fmoc-Asp-ODmab. Synthesis of the linear peptide, initially incorporating racemic Ade8 and unsubstituted ornithine in place of the chromophore-bearing residue, was followed by cyclization on resin and peptide release to give a mixture of diastereomers. Resynthesis identified (by HPLC) the second isomer as analogous to the natural product. Initial biological assays, using an immunofluorescence method, suggest that the compounds are not cytotoxic but do not inhibit the p53/mdm2 interaction. [structure: see text]

Description

p53 and MDM2 proteins-interaction-inhibitor (racemic) (Compound 2j) is an inhibitor of the interaction between p53 and MDM2 proteins.

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