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E2656

Sigma-Aldrich

(−)-Epothilone B

from Sorangium cellulosum, ≥98% (HPLC)

Sinónimos:

EPO906, EpoB, Patupilone

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About This Item

Fórmula empírica (notación de Hill):
C27H41NO6S
Número de CAS:
152044-54-7
Peso molecular:
507.68
MDL number:
MFCD02101921
UNSPSC Code:
12352200
PubChem Substance ID:
24724475
NACRES:
NA.77

biological source

Sorangium cellulosum

Quality Level

100

assay

≥98% (HPLC)

form

lyophilized powder

storage condition

desiccated
protect from light

color

white to off-white

storage temp.

−20°C

SMILES string

[H][C@]1(C[C@]2([H])O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)\C(C)=C\c3csc(C)n3

InChI

1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1

InChI key

QXRSDHAAWVKZLJ-PVYNADRNSA-N

General description

Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).

Biochem/physiol Actions

(-)-Epothilone B is a microtubule (MT) stabilizing drug and natural macrolide antitumor from myxobacteria Sorangium cellulosum. EpoB has similar biological properties to EpoA. However, EpoB is 10-fold more potent than EpoA against P-glycoprotein-expressing multidrug resistant (MDR) cells (IC50 = 2 nM for MDR CCRF-CEM/VBL100 cells). (-)-Epothilone B is similar to paclitaxel in binding displacement, and a substitution for paclitaxel in dependent cell growth. EpoB causes cell cycle arrest (IC50 = 3.5 nM).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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BMS-247550: a novel epothilone analog with a mode of action similar to paclitaxel but possessing superior antitumor efficacy
Lee FYF, et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 7(5), 1429-1437 (2001)
Phase II clinical trial of ixabepilone (BMS-247550), an epothilone B analog, as first-line therapy in patients with metastatic breast cancer previously treated with anthracycline chemotherapy
Roche H, et al.
Journal of Clinical Oncology, 25(23), 3415-3420 (2007)
Christoph Grohmann et al.
Cell death & disease, 12(3), 268-268 (2021-03-14)
Targeting cell division by chemotherapy is a highly effective strategy to treat a wide range of cancers. However, there are limitations of many standard-of-care chemotherapies: undesirable drug toxicity, side-effects, resistance and high cost. New small molecules which kill a wide
Colette J Shen et al.
BMC cancer, 14, 532-532 (2014-07-24)
Ionizing radiation (IR) is a mainstay of cancer therapy, but irradiation can at times also lead to stress responses, which counteract IR-induced cytotoxicity. IR also triggers cellular secretion of vascular endothelial growth factor, transforming growth factor β and matrix metalloproteinases

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