WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 206183
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.
MedKoo Cat#: 206183
Name: Epothilone F
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
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
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.
|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|
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, HÃ¶fle 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.