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Epothilone D - CAS 189453-10-9

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Category
Inhibitor
Product Name
Epothilone D
Catalog Number
189453-10-9
Synonyms
Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)-; Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl -16-(1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-,(4S-(4R*,7S,8R*,9R*,1 3Z,16R*(E)))-; (3S,7S,14S,15S,16R)-3,15-Dihydroxy-2,2,10,14,16-pentamethyl-7-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-6-oxacyclohexadec-9-ene-1,5-dione; Epothilone D; Desoxyepothilone B; (4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentaMethyl-16-[(1E)-1-Methyl-2-(2-Methyl-4-thiazolyl)ethenyl]oxacyclohexadec-13-ene-2,6-dione; 12,13-Desoxyepothilone B; Epo D
CAS Number
189453-10-9
Description
Epothilone D is a natural polyketide compound isolated from the myxobacterium Sorangium cellulosum. Also known as desoxyepothilone B, epothilone D binds to tubulin and inhibits the disassembly of microtubules, resulting in the inhibition of mitosis, cellular proliferation, and cell motility.
Molecular Weight
491.68
Molecular Formula
C27H41NO5S
Quantity
Grams-Kilos
Quality Standard
In-house Standard
COA
Certificate of Analysis-Epothilone D 189453-10-9 B15JA0722  
MSDS
Inquire
Canonical SMILES
CC1CCCC(=CCC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC2=CSC(=N2)C)C)C
InChI
1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19-,22-,23-,25-/m0/s1
InChIKey
XOZIUKBZLSUILX-XWIMUJDOSA-N
Target
Microtubule/Tubulin
Current Developer
Kosan.
Structure
CAS 189453-10-9 Epothilone D
Specification
Purity
≥ 98.0%
Boiling Point
663.658 °C at 760 mmHg
Melting Point
63-66ºC
Density
1.085 g/cm3
Appearance
White solid
Application
Anti-neoplastic
Storage
Store at -20ºC Freezer
Solubility
Chloroform (Slightly), DMSO (Slightly)
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Reference Reading
1.Nanomolar concentrations of epothilone D inhibit the proliferation of glioma cells and severely affect their tubulin cytoskeleton
Dietzmann, D. Kanakis, E. Kirches, S. Kropf, C. Mawrin and K. Dietzmann. Journal of Neuro-Oncology 65: 99–106, 2003
Since a long time, colchizine, podophyllotoxins and vinblastin are known to cause cell death by destabilizing microtubules. However, not only agents promoting microtubule degradation might be used as antiproliferative and cytotoxic drugs, but also microtubule stabilizing agents. Microtubules are small hollow cylinders composed of 13 parallel rows of globular proteins, α- and β-tubulin. These cylinders can grow on one edge and melt down at the other by non-enzymatic addition or removal of tubulin heterodimers. The balance between polymerization and depolymerization depends on the accessible concentration of free, soluble tubulin, but is modulated by some accessory proteins and strongly influenced by certain drugs, which can bind to specific sites of the β-tubulin molecule. The drug taxol, which was discovered in the early 80s, was the first example of such a compound, which binds β-tubulin and thereby inhibits tubulin depolymerization. In the presence of taxol, microtubule turnover is disturbed by this stabilizing effect.
2.Synthesis of Epothilone D with the Forced Application of Oxycyclopropane Intermediates
L. Hurski and O. G. Kulinkovich. Russian Journal of Organic Chemistry, 2011, Vol. 47, No. 11, pp. 1653−1674.
The yields of epothilone D (I) in the synthesis we developed in the longest linear successions of 23 stages proceeding from diethyl adipate and 24 stages, from (R)-methyl 2,3-О-isopropylidene glycerate (XX) were 2 and 1.6% respectively. It is close to the average number of stages and overall yield (2.3%) in the previously described approaches. The overall number of stages of the synthesis of epothilone D (I) carried out in this study was as expected considerably larger than the average number in the known syntheses. Yet as the advantages of the used approach should be mentioned the experimental simplicity of performing the reactions of cyclopropanols preparation and the reactions of the cleavage of the three-membered ring of hydroxycyclopropane intermediates, and also the low price of the corresponding reagents and catalysts. The latter statement was quantitatively illustrated by the estimation from the catalog data the average price of the molar amounts of reagents and the corresponding proportional quantities of catalysts. In the previously published syntheses of epothilone D it equaled 37 × 103 € ·mol–1, whereas in this work it was 11×103 € ·mol–1. The latter value had the smallest absolute magnitude, and calculated per 1% of epothilone D (I) yield this approach was in the first five “profitable” procedures.
3.Building Blocks for (C15–C3)-Modified Epothilone D Analogs
R. F. Valeev, R. F. Bikzhanov, and M. S. Miftakhov. Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 10, pp. 1511–1519
We previously planned to synthesize new metabolically and chemically more stable epothilone D (I) analogs, compounds II and III with isosterically displaced methylene unit in the C15–C3 fragment. We presumed that, unlike readily hydrolyzable in vivo macrolide I, its analogs II and III contain more stable lactam and lactone fragments, respectively (the C1=O carbonyl group is sterically hindered and is stabilized by the C1=O···HO–C2 hydrogen bond, and elimination of the C2-hydroxy group is impossible). Such isosteric rearrangement of the C15–C3 fragment of natural epothilone I has not been reported. This structural modification should affect the stability of the resulting compounds and change their conformation upon binding to tubulin, so that their biological activity should change. The above considerations determined the choice of compounds II and III as target structures. Compound III is an isostere of epothilone D (I), which is important from the viewpoint of estimation of the effect of modification of the C15–C3 fragment on the biological activity of epothilones.
4.Alternative Synthesis of Thiazole-Substituted Fragment С10–С21 of Epothilone D Analog
R. F. Valeev, R. F. Bikzhanov, and M. S. Miftakhov. Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 5, pp. 660–663.
Epothilones, especially their analogs, are very promising objects for designing and synthesis of anticancer compounds of tubulin-polymerizing (taxol-like) action. In our planned synthetic approach to analogs of epothilone D 1a and 1b a block 2 with thiazole substituent is one of the key synthons.
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