Epothilone F

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 206183

CAS#: 208518-52-9

Description: Epothilone F is a derivative or analogue of Epothilone D. Epothilone F is also an active metabolite of Epothilone D. In molecule of Epothilone F, a hydroxymethyl group is on the thiazole ring. Like taxanes, Epothilone F prevents cancer cells from dividing by interfering with tubulin. Early studies in cancer cell lines and in human cancer patients indicate superior efficacy to the taxanes. Epothilone's mechanism of action is similar to taxanes, but their chemical structure is simpler. Due to its better water solubility, cremophors (solubilizing agents used for paclitaxel which can affect cardiac function and cause severe hypersensitivity) are not needed.


Chemical Structure

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Epothilone F
CAS# 208518-52-9

Theoretical Analysis

MedKoo Cat#: 206183
Name: Epothilone F
CAS#: 208518-52-9
Chemical Formula: C27H41NO7S
Exact Mass: 523.26037
Molecular Weight: 523.68
Elemental Analysis: C, 61.92; H, 7.89; N, 2.67; O, 21.39; S, 6.12

Size Price Shipping out time Quantity
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Pricing updated 2021-03-01. Prices are subject to change without notice.

Epothilone F is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: Epothilone F.

IUPAC/Chemical Name: (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-3-((E)-1-(2-(hydroxymethyl)thiazol-4-yl)prop-1-en-2-yl)-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

InChi Key: UKIMCRYGLFQEOE-RGJAOAFDSA-N

InChi Code: InChI=1S/C27H41NO7S/c1-15-8-7-9-27(6)21(35-27)11-19(16(2)10-18-14-36-22(13-29)28-18)34-23(31)12-20(30)26(4,5)25(33)17(3)24(15)32/h10,14-15,17,19-21,24,29-30,32H,7-9,11-13H2,1-6H3/b16-10+/t15-,17+,19-,20-,21-,24-,27+/m0/s1

SMILES Code: O=C(C[C@@H]1O)O[C@H](/C(C)=C/C2=CSC(CO)=N2)C[C@H]3[C@@](O3)(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(C1(C)C)=O

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 523.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Nayeem A, Chiang SJ, Liu SW, Sun Y, You L, Basch J. Engineering enzymes for improved catalytic efficiency: a computational study of site mutagenesis in epothilone-B hydroxylase. Protein Eng Des Sel. 2009 Apr;22(4):257-66. doi: 10.1093/protein/gzn081. Epub 2009 Jan 28. PubMed PMID: 19179341.

2: Basch J, Chiang SJ. Cloning and expression of a cytochrome P450 hydroxylase gene from Amycolatopsis orientalis: hydroxylation of epothilone B for the production of epothilone F. J Ind Microbiol Biotechnol. 2007 Feb;34(2):171-6. Epub 2006 Sep 14. Erratum in: J Ind Microbiol Biotechnol. 2007 Feb;34(2):177. PubMed PMID: 16972046.

3: Mutka SC, Carney JR, Liu Y, Kennedy J. Heterologous production of epothilone C and D in Escherichia coli. Biochemistry. 2006 Jan 31;45(4):1321-30. PubMed PMID: 16430229.

4: Hardt IH, Steinmetz H, Gerth K, Sasse F, Reichenbach H, Höfle G. New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies. J Nat Prod. 2001 Jul;64(7):847-56. PubMed PMID: 11473410.

5: Sinha SC, Sun J, Miller GP, Wartmann M, Lerner RA. Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F. Chemistry. 2001 Apr 17;7(8):1691-702. PubMed PMID: 11349910.

6: Nicolaou KC, Hepworth D, King NP, Finlay MR, Scarpelli R, Pereira MM, Bollbuck B, Bigot A, Werschkun B, Winssinger N. Total synthesis of 16-desmethylepothilone B, epothilone B10, epothilone F, and related side chain modified epothilone B analogues. Chemistry. 2000 Aug 4;6(15):2783-800. PubMed PMID: 10985727.



Additional Information