Epothilon B
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| Category | New Products |
| Catalog number | BBF-00852 |
| CAS | 152044-54-7 |
| Molecular Weight | 507.68 |
| Molecular Formula | C27H41NO6S |
| Purity | >98% |
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Description
Epothilons B is a 16-membered macrolide antibiotic produced by the myxobacterium Sorangium cellulosum, which is used as a microtubule stabilization agent (EC0.01 = 1.8 μM). It has strong cytotoxicity and has the effect of resisting plant pathogenic fungi.
Specification
| Synonyms | Patupilone; (-)-Epothilone B |
| Storage | Store at -20°C |
| IUPAC Name | (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione |
| Canonical SMILES | CC1CCCC2(C(O2)CC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)C |
| InChI | 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 |
| Source | Sorangium cellulosum |
Properties
| Appearance | White Crystals |
| Application | Antineoplastic Agents |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 680.2°C at 760 mmHg |
| Melting Point | 95-97°C |
| Flash Point | 365.2ºC |
| Density | 1.136 g/cm3 |
| Solubility | Soluble in DMSO |
| LogP | 4.47750 |
Reference Reading
1. Radiosensitizing effect of epothilone B on human epithelial cancer cells
T.Baumgart, G.Klautke, S.Kriesen, S.A.Kuznetsov. Strahlenther Onkol 2012 • 188:177–184
Epothilone B induced a concentration- and application-dependent antiproliferative effect on the cells, with IC50 values in the low nanomolar range. Colony forming assays showed a synergistic radiosensitive effect on both cell lines which was dependent on incubation time and applied concentration of epothilone B. The γH2AX assays demonstrated that ionizing radiation combined with the drug resulted in a concentration-dependent increase in the number of double-strand breaks and suggested a reduction in DNA repair capacity. Epothilone B produced enhanced microtubule bundling and abnormal spindle formation as revealed by immunofluo-rescence microscopy and caused microtubule formation from purified tubulin.
2. A Ph-responsive High Density Lipoprotein-like Nanoparticle of Epothilone B
Ji-Chun Lee, Byoung-Jae Kong, Jae Yoon Shin. Biotechnology and Bioprocess Engineering 20: 249-258 (2015
Therefore, various pH-responsive drug delivery systems have been designed to release enclosed drugs at the target site before lysosomal degradation occurs. Recently, we have shown that rHDL can be composed to release paclitaxel (PTX) in a pH-responsive manner. Perhaps because endosomal escape of the PTX was facilitated, the pH-responsive PTX-rHDL was more potent than normal PTX-rHDL. Inspired by this success, we determined to assemble the pH-responsive rHDL of epothilone B (EpoB), which is extremely more potent than PTX. epothilone B (EpoB) is a member of the epothilone class, which is a group of microtubule-stabilizing agents. epothilone B (EpoB) binds to β-tubulin subunits of microtubules with higher affinity than other taxanes. Most cancer cells overexpressing human epidermal growth factor receptor 2 (HER2) are resistant to taxane chemotherapy.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
