Epothilone D

Epothilone D Basic information
Product Name:Epothilone D
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:189453-10-9
MF:C27H41NO5S
MW:491.68
EINECS:
Product Categories:Inhibitors;Chiral Reagents;Intermediates & Fine Chemicals;Anti-cancer&immunity;Pharmaceuticals;Sulfur & Selenium Compounds
Mol File:189453-10-9.mol
Epothilone D Structure
Epothilone D Chemical Properties
Melting point 63-66°C
alpha D22 -61.3° (c = 2.5 in methanol)
Boiling point 663.7±55.0 °C(Predicted)
density 1.084±0.06 g/cm3(Predicted)
storage temp. -20°C Freezer
solubility Soluble in DMSO
form solid
pka13.47±0.70(Predicted)
color white to off-white
Safety Information
MSDS Information
Epothilone D Usage And Synthesis
DescriptionEpothilones are microtubule-stabilizing agents with potential anti-neoplastic actions. They are natural macrolides that have high potency in both taxane-sensitive and taxane-resistant models. Epothilone D is a desoxy form of epothilone B (Item No. 10924) that inhibits the growth of a variety of cancer cells both in vitro (IC50 values range from 0.97 to 21 nM) and in mice. Epothilone D is brain penetrant and reduces neurodegeneration in aged tau transgenic mice. Effects include improved axonal transport, decreased tau neuropathology, and reduced hippocampal neuron loss. Epothilone D also rescues microtubule defects and attenuates nigrostriatal degeneration in a mouse model of Parkinson’s disease.
Chemical PropertiesWhite Foam
UsesEpothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.
UsesEpothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone D is in phase I clinical testing of in patients with advanced solid tumours. Epothilone D is a cytotoxic macrolide that stabilises malignant cells'' microtubules and arrests mitosis, a characteristic it shares with other epothilones. They bind to the same hepatic sites as does paclitaxel (Taxol) in a 1:1 stoichiometric ratio of a, b-tubulin heterodimers.
DefinitionChEBI: An epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group.
in vitroepothilone d is a more potent microtubule stabilizer in vitro than epothilone a or b. in vitro, epothilone d showed potent cytotoxicity in a panel of human tumor cell lines, with similar potency to paclitaxel. it also showed definite advantage over paclitaxel in drug-resistant cell lines, and retained its cytotoxicity against a multidrug resistant cell line over-expressing p-glycoprotein [1].
in vivoin vivo, antitumor efficacy of epothilone d has been observed in both paclitaxel sensitive and resistant xenografts, as well as certain multidrug resistant xenografts including a doxorubinresistant ccrf-cem leukemic cell xenograft [1].
targetTubulin
IC 502.9 nm for mcf-7 cell line; 2.7 nm for kb-31 cell line; 9.5 nm for ccrf-cem cell line
references[1] konner j, grisham rn, park j, o'connor oa, cropp g, johnson r, hannah al, hensley ml, sabbatini p, mironov s, danishefsky s, hyman d, spriggs dr, dupont j, aghajanian c. phase i clinical, pharmacokinetic, and pharmacodynamic study of kos-862 (epothilone d) in patients with advanced solid tumors and lymphoma. invest new drugs. 2012 dec;30(6):2294-302. doi: 10.1007/s10637-011-9765-7.
Epothilone D Preparation Products And Raw materials
Preparation ProductsEpothilone B
4-[(1E,3S,5Z,8R/S,10S)-3,11-Bis-{[tert-butyl(dimethyl)silyl]oxy}-2,6,10-trimethyl-8-(phenylsulfonyl)undeca-1,5-dienyl]-2-methyl-1,3-thiazole BOC-3-ENDO-AMINOBICYCLO[2.2.1]HEPTANE-2-ENDO-CARBOXYLIC ACID (αR,βS)-β-[[(1,1-DiMethylethoxy)carbonyl]aMino]-α-hydroxy-4-(phenylMethoxy)-benzenepropanoic Acid Ethyl Ester 2'-O-tert-Butyl(diMethyl)silyl-7-O-triethylsilyl-2-debenzoyl-4-desacetyl Paclitaxel Epothilone B 6-CHLORO-4-CHLOROMETHYL-7-HYDROXY-CHROMEN-2-ONE (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid 2'-O-(Benzyloxycarbonyl) Taxol N-Desbenzoyl-N-tert-butoxycarbonyl-N,O-isopropylidene-3a€-p-O-benzyl-6,7-dehydro Paclitaxel Paclitaxel Impurity 9 Epothilone A Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9-tetramethyl-16-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (4S,7R,8S,9S,13Z,16S)- Vinorelbine tartrate PEARLATE Epothilone D ethyl 5-oxodecanoate (4S,7R,8S,9S,13Z,16S)-4,8-BIS-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-5,5,7,9,13-PENTAMETHYL-16-[(E)-1-METHYL-2-(2-METHYL-1,3-THIAZOL-4-YL)ETHENYL]OXOCYCLOHEXADEC-13-ENE-2,6-DIONE CIS-3-HEXENYL CAPRYLATE

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