DihydroeponemycinProteasome inhibitor,antitumor reagent,eponemycin ddrivative CAS# 126463-64-7 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 126463-64-7 | SDF | Download SDF |
PubChem ID | 10092400 | Appearance | Powder |
Formula | C20H36N2O6 | M.Wt | 400.51 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | >15.6mg/mL in DMSO | ||
Chemical Name | N-[(2S)-3-hydroxy-1-[[(2S)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]-6-methylheptanamide | ||
SMILES | CC(C)CCCCC(=O)NC(CO)C(=O)NC(CC(C)C)C(=O)C1(CO1)CO | ||
Standard InChIKey | IUDBVFIQSSOIDB-TWOQFEAHSA-N | ||
Standard InChI | InChI=1S/C20H36N2O6/c1-13(2)7-5-6-8-17(25)21-16(10-23)19(27)22-15(9-14(3)4)18(26)20(11-24)12-28-20/h13-16,23-24H,5-12H2,1-4H3,(H,21,25)(H,22,27)/t15-,16-,20+/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. |
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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. |
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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. |
Description | Dihydroeponemycin is an inhibitor of proteasome and antitumor reagent. | |||||
Targets | Proteasome |
Dihydroeponemycin Dilution Calculator
Dihydroeponemycin Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.4968 mL | 12.4841 mL | 24.9682 mL | 49.9363 mL | 62.4204 mL |
5 mM | 0.4994 mL | 2.4968 mL | 4.9936 mL | 9.9873 mL | 12.4841 mL |
10 mM | 0.2497 mL | 1.2484 mL | 2.4968 mL | 4.9936 mL | 6.242 mL |
50 mM | 0.0499 mL | 0.2497 mL | 0.4994 mL | 0.9987 mL | 1.2484 mL |
100 mM | 0.025 mL | 0.1248 mL | 0.2497 mL | 0.4994 mL | 0.6242 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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Description:IC50: 100 nm (antiproliferative IC50) [1]
The proteasome is a member of the growing N-terminal nucleophile (Ntn) hydrolase family, whose aminoterminal side chains act as nucleophiles and free amino groups as proton acceptors. Proteasome inhibitors have been increasingly used to help define the role of the proteasome in cell biology. Dihydroeponemycin labels the catalytic threonine residues of the immunoproteasome subunits LMP2 and LMP7 and the constitutive proteasome subunit X, while epoxomicin covalently modifies the N-terminal catalytic threonine residues of the constitutive proteasome (X and Z) and immunoproteasome (LMP7 and MECL1) subunits.
In vitro: Previoius study reports that dihydroeponemycin, an analogue of the antitumor and antiangiogenic natural product eponemycin, selectively targets the 20S proteasome. Dihydroeponemycin covalently modifies a subset of catalytic proteasomal subunits, binding preferentially to the IFN-g-inducible subunits LMP2 and LMP7. Moreover, the three major peptidolytic activities of the proteasome are inhibited by dihydroeponemycin at different rates. In addition, dihydroeponemycin-mediated proteasome inhibition induces a spindle-like cellular morphological change and apoptosis. These results validate the proteasome as a target for antitumor pharmacological intervention and are relevant for the design of novel chemotherapeutic strategies [2].
In vivo: Recent study in the mouse model of dihydrosterptomycin shows that hair cells are targeted because aminoglycosides enter outer hair cells through large mechanically gated channels in the mechanosensory hair boundles. The aminoglycoside molecules then block the channels through which they entered. When this occurs, the aminoglycoside goes through the channel and effectively traps itself in the hair cell [3].
Clinical trial: Dihydroeponemycin is currently in the preclinical development and non clinical trial is ongoing.
References:
[1] Kim KB, Myung J, Sin N, Crews CM. Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency. Bioorg Med Chem Lett. 1999;9(23):3335-40.
[2] Meng L, Kwok BH, Sin N, Crews CM. Eponemycin exerts its antitumor effect through the inhibition of proteasome function. Cancer Res. 1999;59(12):2798-801.
[3] Marcotti W, van Netten SM, Kros CJ. The aminoglycoside antibiotic dihydrostreptomycin rapidly enters mouse outer hair cells through the mechano-electrical transducer channels. J Physiol. 2005;567(Pt 2):505-21.
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Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency.[Pubmed:10612595]
Bioorg Med Chem Lett. 1999 Dec 6;9(23):3335-40.
While two structurally related epoxyketone-containing antitumor natural products, epoxomicin and eponemycin, share the proteasome as a common intracellular target, they differ in their antiproliferative activity, proteasome subunit binding specificity, and rates of proteasome inhibition. As a first step towards understanding such differences and developing novel proteasome subunit-specific inhibitors, we report here the synthesis and characterization of epoxomicin/Dihydroeponemycin chimerae.