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MedKoo Cat#: 562501 | Name: Epothilone A
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Description:

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

Epothilone A is a taxol-like microtubule (MT) stabilizing agent.

Chemical Structure

Epothilone A
Epothilone A
CAS#152044-53-6

Theoretical Analysis

MedKoo Cat#: 562501

Name: Epothilone A

CAS#: 152044-53-6

Chemical Formula: C26H39NO6S

Exact Mass: 493.2498

Molecular Weight: 493.65

Elemental Analysis: C, 63.26; H, 7.96; N, 2.84; O, 19.45; S, 6.49

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 weeks
10mg USD 650.00 2 weeks
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Related CAS #
No Data
Synonym
Epothilone A; Epothilone-A; Epothilon A; (-)-Epothilone A; EpoA; Epo A;
IUPAC/Chemical Name
(1R,5S,6S,7R,10S,14S,16S)-6,10-Dihydroxy-5,7,9,9-tetramethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione
InChi Key
HESCAJZNRMSMJG-KKQRBIROSA-N
InChi Code
InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1
SMILES Code
O=C(C(C)(C)[C@@H](O)C1)[C@H](C)[C@@H](O)[C@@H](C)CCC[C@@]2([H])O[C@@]2([H])C[C@@H](/C(C)=C/C3=CSC(C)=N3)OC1=O
Appearance
Solid powder
Purity
>95% (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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 493.65 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.

Recalculate based on batch purity %
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: Altmann KH. Epothilone B and its analogs - a new family of anticancer agents. Mini Rev Med Chem. 2003 Mar;3(2):149-58. doi: 10.2174/1389557033405269. PMID: 12570848. 2: Herwerth M, Kenet S, Schifferer M, Winkler A, Weber M, Snaidero N, Wang M, Lohrberg M, Bennett JL, Stadelmann C, Hemmer B, Misgeld T. A new form of axonal pathology in a spinal model of neuromyelitis optica. Brain. 2022 Jun 3;145(5):1726-1742. doi: 10.1093/brain/awac079. PMID: 35202467; PMCID: PMC9166560. 3: Parajuli P, Pandey RP, Koirala N, Yoon YJ, Kim BG, Sohng JK. Enzymatic synthesis of epothilone A glycosides. AMB Express. 2014 Mar 20;4:31. doi: 10.1186/s13568-014-0031-1. PMID: 24949266; PMCID: PMC4052672. 4: Pandey RP, Dhakal D, Thapa SB, Bashyal P, Kim TS, Sohng JK. UPLC-PDA coupled HR-TOF ESI/MS2 -based identification of derivatives produced by whole-cell biotransformation of epothilone A using Nocardia sp. CS692 and a cytochrome P450 overexpressing strain. Biotechnol Appl Biochem. 2022 Aug;69(4):1723-1732. doi: 10.1002/bab.2241. Epub 2021 Sep 2. PMID: 34415071. 5: Parajuli P, Pandey RP, Gurung RB, Shin JY, Jung HJ, Kim DH, Sohng JK. Enzymatic synthesis of lactosylated and sialylated derivatives of epothilone A. Glycoconj J. 2016 Apr;33(2):137-46. doi: 10.1007/s10719-015-9646-y. Epub 2016 Feb 6. PMID: 26852037. 6: Xiao CF, Li K, Huang R, He GJ, Zhang JQ, Zhu L, Yang QY, Jiang KM, Jin Y, Lin J. Investigation of inclusion complex of epothilone A with cyclodextrins. Carbohydr Polym. 2014 Feb 15;102:297-305. doi: 10.1016/j.carbpol.2013.11.049. Epub 2013 Dec 4. PMID: 24507285. 7: Zhu B, Panek JS. Total synthesis of epothilone A. Org Lett. 2000 Aug 24;2(17):2575-8. doi: 10.1021/ol006104w. PMID: 10990400. 8: Wolff A, Technau A, Brandner G. Epothilone A induces apoptosis in neuroblastoma cells with multiple mechanisms of drug resistance. Int J Oncol. 1997 Jul;11(1):123-6. doi: 10.3892/ijo.11.1.123. PMID: 21528189. 9: Rogalska A, Gajek A, Marczak A. Suppression of autophagy enhances preferential toxicity of epothilone A and epothilone B in ovarian cancer cells. Phytomedicine. 2019 Aug;61:152847. doi: 10.1016/j.phymed.2019.152847. Epub 2019 Jan 31. PMID: 31029905. 10: Rogalska A, Bukowska B, Marczak A. Metformin and epothilone A treatment up regulate pro-apoptotic PARP-1, Casp-3 and H2AX genes and decrease of AKT kinase level to control cell death of human hepatocellular carcinoma and ovary adenocarcinoma cells. Toxicol In Vitro. 2018 Mar;47:48-62. doi: 10.1016/j.tiv.2017.11.001. Epub 2017 Nov 5. PMID: 29117515. 11: Giannakakou P, Gussio R, Nogales E, Downing KH, Zaharevitz D, Bollbuck B, Poy G, Sackett D, Nicolaou KC, Fojo T. A common pharmacophore for epothilone and taxanes: molecular basis for drug resistance conferred by tubulin mutations in human cancer cells. Proc Natl Acad Sci U S A. 2000 Mar 14;97(6):2904-9. doi: 10.1073/pnas.040546297. PMID: 10688884; PMCID: PMC16028. 12: Kamel K, Kolinski A. Computational study of binding of epothilone A to β-tubulin. Acta Biochim Pol. 2011;58(2):255-60. Epub 2011 Jun 2. PMID: 21633729. 13: Dolenc J, van Gunsteren WF, Prota AE, Steinmetz MO, Missimer JH. Conformational Properties of the Chemotherapeutic Drug Analogue Epothilone A: How to Model a Flexible Protein Ligand Using Scarcely Available Experimental Data. J Chem Inf Model. 2019 May 28;59(5):2218-2230. doi: 10.1021/acs.jcim.9b00171. Epub 2019 Mar 25. PMID: 30855963. 14: Passarella D, Comi D, Cappelletti G, Cartelli D, Gertsch J, Quesada AR, Borlak J, Altmann KH. Synthesis and biological evaluation of epothilone A dimeric compounds. Bioorg Med Chem. 2009 Nov 1;17(21):7435-40. doi: 10.1016/j.bmc.2009.09.032. Epub 2009 Sep 20. PMID: 19804980. 15: Shi G, Wang Y, Jin Y, Chi S, Shi Q, Ge M, Wang S, Zhang X, Xu S. Structural insight into the mechanism of epothilone A bound to beta-tubulin and its mutants at Arg282Gln and Thr274Ile. J Biomol Struct Dyn. 2012;30(5):559-73. doi: 10.1080/07391102.2012.687522. Epub 2012 Jun 25. PMID: 22731768. 16: Bertinato P, Sorensen EJ, Meng D, Danishefsky SJ. Studies toward a Synthesis of Epothilone A: Stereocontrolled Assembly of the Acyl Region and Models for Macrocyclization. J Org Chem. 1996 Nov 15;61(23):8000-8001. doi: 10.1021/jo961674o. PMID: 11667778. 17: Borrelli S, Christodoulou MS, Ficarra I, Silvani A, Cappelletti G, Cartelli D, Damia G, Ricci F, Zucchetti M, Dosio F, Passarella D. New class of squalene- based releasable nanoassemblies of paclitaxel, podophyllotoxin, camptothecin and epothilone A. Eur J Med Chem. 2014 Oct 6;85:179-90. doi: 10.1016/j.ejmech.2014.07.035. Epub 2014 Jul 27. PMID: 25084144. 18: Meng D, Sorensen EJ, Bertinato P, Danishefsky SJ. Studies toward a Synthesis of Epothilone A: Use of Hydropyran Templates for the Management of Acyclic Stereochemical Relationships. J Org Chem. 1996 Nov 15;61(23):7998-7999. doi: 10.1021/jo961673w. PMID: 11667777. 19: Rogalska A, Sliwinska A, Kasznicki J, Drzewoski J, Marczak A. Effects of Epothilone A in Combination with the Antidiabetic Drugs Metformin and Sitagliptin in HepG2 Human Hepatocellular Cancer Cells: Role of Transcriptional Factors NF-κB and p53. Asian Pac J Cancer Prev. 2016;17(3):993-1001. doi: 10.7314/apjcp.2016.17.3.993. PMID: 27039825. 20: Ramachandran PV, Chandra JS, Prabhudas B, Pratihar D, Reddy MV. Studies towards the synthesis of epothilone A via organoboranes. Org Biomol Chem. 2005 Oct 21;3(20):3812-24. doi: 10.1039/b508001k. Epub 2005 Sep 15. PMID: 16211118.