Epothilone B Antitumor Drugs

English name：Epothilone B

CAS number：152044-54-7

Another name: EpothiloneB(EPO906);EpothiloneBHOUSESTANDARD;EpothiloneB(Patupilone);(3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentaMethyl-3-((E)-1-(2-Methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxa-bicyclo[14.1.0]heptadecan-5,9-dione;EpothiloneB(EPO906,Patupilone);EPOTHILONE;(1S,3S,7S,10R,11S,12S,16R,E)-7,1Chemicalbook1-dihydroxy-8,8,10,12,16-pentamethyl-3-(1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione;Patupilone(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Molecular formula: C27H41NO6S

Molecular weight: 507.68

EINECS number: 604-822-6

Related category

Microbial metabolites; Pharmaceutical intermediates; Antibiotics; Raw materials; Biochemical reagent; Medical raw materials; Intermediate; Analytical reagent standard; Other biochemical reagents; Small molecule inhibitors, natural products; Inhibitors; Chiral Reagents; I Intermediates & Fine Chemicals & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; Fermentative; Ingredients; Pharmaceutical raw materials; Medical raw materials; Chemical reagent; Pharmaceutical raw materials; API; Chemical raw material

Mol file：152044-54-7.mol

Structural formula:

Melting point: 95-97°C

Specific rotation: D21-35°(c=0.7inmethanol)

Boiling point: 680.2±55.0°C(Predicted)

Density: 1.136

Storage condition: Storeat-20°C

Solubility: Soluble in DMSO (up to 40mg/ml) or ethanol (up to 35mg/ml).

Predicted Acidity coefficient (pKa):13.57±0.70

Form: White to white solid

Color: Colorless

Optical activity (opticalactivity): -35.021(methanol)

Biological source: Sorangiumcellulosum

Stability: Can be stored in DMSO or ethanol solution at -20° for up to 1 month.

InChIKey: QXRSDHAAWVKZLJ-PVYNADRNSA-N

CAS database: 152044-54-7

Intro

epothilone (epothilone) is a class of macrolide compounds, which was first reported in 1993 by G. Haofle et al of the German National Biotechnology Center (GBF). Ebomycin can be isolated from the fermentation broth of Myxobacterium suborder cellulus strains, and its main groups are EpothiloneA and B.

Use

Ebomycin B is an organic synthesis intermediate and pharmaceutical intermediate, which can be used in laboratory research and development process and chemical pharmaceutical synthesis process.

Biological activity

Patupilone (EPO906, Epothilone B) is a paclitaxel-like microtubule stabilizer with EC0.01 of 1.8 μM. Phase 2.

Target point

Target Value

Tubulin 1.8 μM(EC0.01)

(Cell-free assay)

In vitro study

EpothiloneB has higher activity than EpothiloneA. EpothiloneB has an EC0.01 of 1.8nM. EpothiloneB effectively inhibited cell proliferation in HCT116 cells with IC50 of 0.8nM. EpothiloneB acts on KB3-1,KBV-1,Hela, and Hs578T cells, inducing cell cycle arrest and is cytotoxic with IC50 ranging from 3nM to 92nM. EpothiloneB and paclitaxel competitively bind to microtubules with IC50 of 3.3μM. 3.5nMEpothiloneB acts on MCF-7 cells that overexpress Gfchemical BookP-α-tubulin, and fully inhibits microtubule dynamics. At the same time, EpothiloneB induced mitotic arrest with an IC50 of 3.5nM. EpothiloneB acts on multiple myeloma (MM) cells, including RPMI8226,U266, MM.1s,LR5, and MR20, directly inhibiting cell proliferation with IC50 ranging from 1nM to 10nM. 10nMEpothiloneB also induced cell cycle arrest and apoptosis. Recent studies have shown that 5nm-100Nmepothiloneb acts on Hey cells of ovarian cancer, enhancing surface epithelial cell adhesion antigen (EpCAM).

In vivo study

EpothiloneB was administered at a dose of 2.5mg/kg to 4mg/kg to mice with RPMI8226 cell grafted tumor, prolonging Chemicalbook life and inhibiting tumor growth. EpothiloneB also inhibited tumor growth in mice with transplanted tumors carrying prostate cancer cells, including DU145 and PC3.

Use

(-) -Ebomycin B is a microtubule (MT) stabilizing drug derived from natural mucous bacteria Sorangiumcellulosum and is a macrolide anti-tumor factor. EpoB and EpoA have similar biological characteristics. However, EpoB was 10 times more effective than EpoA in MDR cells (IC50=2nMforMDRCCRF-CEM/VBL100cells) against P-glycoprotein expression. (-) -Eberomycin B is similar to paclitaxel and can substitute for paclitaxel in cell growth. EpoB leads to cell cycle arrest (IC50=3.5nM).

Safety information

WGK Germany 3

Customs code: 29419090

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