MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 201280 | Name: Epothilone D
Featured New

Description:

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

Epothilone D is a natural polyketide compound isolated from the myxobacterium Sorangium cellulosum. Also known as desoxyepothilone B, epothilone D binds to tubulin and inhibits the disassembly of microtubules, resulting in the inhibition of mitosis, cellular proliferation, and cell motility.

Chemical Structure

Epothilone D
Epothilone D
CAS#189453-10-9

Theoretical Analysis

MedKoo Cat#: 201280

Name: Epothilone D

CAS#: 189453-10-9

Chemical Formula: C27H41NO5S

Exact Mass: 491.2705

Molecular Weight: 491.68

Elemental Analysis: C, 65.95; H, 8.40; N, 2.85; O, 16.27; S, 6.52

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
25mg USD 1,450.00 2 Weeks
50mg USD 2,350.00 2 Weeks
100mg USD 3,750.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
(-)-Desoxyepothilone B; (-)-Epothilone D; 12,13-Deoxyepothilone B; 12,13-Desoxyepothilone B; Desoxyepothilone B; Epo D; Epothilone D; KOS 862; KOS862; KOS-862; NSC 703147; NSC703147; NSC-703147; NSC-721085; NSC721085; NSC 721085
IUPAC/Chemical Name
(4S,7R,8S,9S,16S,Z)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)oxacyclohexadec-13-ene-2,6-dione
InChi Key
XOZIUKBZLSUILX-GIQCAXHBSA-N
InChi Code
InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
SMILES Code
O=C(C[C@@H]1O)O[C@H](/C(C)=C/C2=CSC(C)=N2)C/C=C(C)\CCC[C@H](C)[C@H](O)[C@@H](C)C(C1(C)C)=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, 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
More Info
 Information about this agent The epothilones are a new class of cytotoxic molecules identified as potential chemotherapeutic drugs. As of September 2008[update], epothilones A to F have been identified and characterised. Early studies in cancer cell lines and in human cancer patients indicate superior efficacy to the taxanes. Their mechanism of action is similar, but their chemical structure is simpler. Due to their better water solubility, cremophors (solubilizing agents used for paclitaxel which can affect cardiac function and cause severe hypersensitivity) are not needed. Endotoxin-like properties known from paclitaxel, like activation of macrophages synthesizing inflammatory cytokines and nitric oxide, are not observed for epothilone B. Epothilones were originally identified as metabolites produced by the myxobacterium Sorangium cellulosum. see http://en.wikipedia.org/wiki/Epothilone.     Clinical trials about Epotilones:  Several epothilone analogs are currently undergoing clinical development for treatment of various cancers. One analog, ixabepilone, was approved in October 2007 by the United States Food and Drug Administration for use in the treatment of aggressive metastatic or locally advanced breast cancer no longer responding to currently available chemotherapies.  In November 2008, the EMEA has refused a marketing authorisation for Ixabepilone.  Epothilone B has proven to contain potent in vivo anticancer activities at tolerate dose levels in several human xenograft models.  As a result, epothilone B and its various analogues are currently undergoing various clinical phases (patupilone [EPO906] and sagopilone [SH-Y03757A, ZK-EPO, chemical structure] are in phase II trials; BMS-310705 and BMS-247550 in phase I trials). Results of a phase III trial with ixabepilone in combination with capecitabine in metastatic breast cancer have been announced. see http://en.wikipedia.org/wiki/Epothilone.       
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Epothilone D (KOS 862) is a potent microtubule stabilizer.
In vitro activity:
At 2DIV, 100 nM EpoD (Epothilone D) treated cultures showed significantly (p < 0.05) reduced cell viability by 32%, vehicle treated control neuron (Fig. 1B). By 3DIV (two days of recurrent treatment), the percentage viability was significantly (p < 0.01 and p < 0.001) reduced by 18% in 10 nM EpoD treated cultures and 37% in 100 nM EpoD treated cultures, compared to vehicle treated controls (Fig. 1C). Cell viability decreased further, to 35% in 10 nM EpoD treated cultures and 56% in 100 nM EpoD, when compared to vehicle treated controls (Fig. 1D), suggesting that higher doses of EpoD are detrimental to neuronal cell growth and survival. Reference: Sci Rep. 2020; 10: 918. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6976590/
In vivo activity:
Dendritic spines were analyzed from radially projecting/oblique branches of layer 5 projection neuron apical dendrites at the layer 4/5 boarder (Figures 1A,B). All major morphological spine classes (mushroom, stubby, thin) were represented in all mouse groups (Figure 1C). Initial analysis segregated the total spine population by length – spines (<2.5 μm) and filopodia (>2.5 μm) – and revealed a significant decrease (p < 0.05) in average spine length (Figure 1D), but not filopodial length (Figure 1E), in response to epothilone D treatment relative to vehicle treatment in both brain-injured and sham-operated animals. Furthermore, binning the spines by length showed that epothilone D treatment resulted in a significantly higher proportion (p < 0.05) of shorter (<1.5 μm) spines and significantly lower proportion (p < 0.05) of longer spines (1.5–2.5 μm) (Figure Figure1F1F). With respect to density, spine density was significantly increased (p < 0.05) in sham-operated, but not brain-injured animals (Figure 1G) in response to epothilone D treatment, whereas filopodial density was unaltered in both sham-operated and brain-injured animals (Figure 1H). Analysis of morphological sub-class revealed a significant increase (p < 0.05) specifically in mushroom spines in both brain-injured and sham-operated animals in response to epothilone D treatment (Figure 1I). Reference: Front Cell Neurosci. 2018; 12: 223. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6077201/
Solvent mg/mL mM
Solubility
DMSO 100.0 203.38
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 491.68 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.

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
Formulation protocol:
1. Xue W, Zhang H, Fan Y, Xiao Z, Zhao Y, Liu W, Xu B, Yin Y, Chen B, Li J, Cui Y, Shi Y, Dai J. Upregulation of Apol8 by Epothilone D facilitates the neuronal relay of transplanted NSCs in spinal cord injury. Stem Cell Res Ther. 2021 May 26;12(1):300. doi: 10.1186/s13287-021-02375-w. PMID: 34039405; PMCID: PMC8157417. 2. Clark JA, Chuckowree JA, Dyer MS, Dickson TC, Blizzard CA. Epothilone D alters normal growth, viability and microtubule dependent intracellular functions of cortical neurons in vitro. Sci Rep. 2020 Jan 22;10(1):918. doi: 10.1038/s41598-020-57718-z. PMID: 31969604; PMCID: PMC6976590. 3. Chuckowree JA, Zhu Z, Brizuela M, Lee KM, Blizzard CA, Dickson TC. The Microtubule-Modulating Drug Epothilone D Alters Dendritic Spine Morphology in a Mouse Model of Mild Traumatic Brain Injury. Front Cell Neurosci. 2018 Jul 30;12:223. doi: 10.3389/fncel.2018.00223. PMID: 30104961; PMCID: PMC6077201. 4. Sandner B, Puttagunta R, Motsch M, Bradke F, Ruschel J, Blesch A, Weidner N. Systemic epothilone D improves hindlimb function after spinal cord contusion injury in rats. Exp Neurol. 2018 Aug;306:250-259. doi: 10.1016/j.expneurol.2018.01.018. Epub 2018 Feb 2. PMID: 29408734.
In vitro protocol:
1. Xue W, Zhang H, Fan Y, Xiao Z, Zhao Y, Liu W, Xu B, Yin Y, Chen B, Li J, Cui Y, Shi Y, Dai J. Upregulation of Apol8 by Epothilone D facilitates the neuronal relay of transplanted NSCs in spinal cord injury. Stem Cell Res Ther. 2021 May 26;12(1):300. doi: 10.1186/s13287-021-02375-w. PMID: 34039405; PMCID: PMC8157417. 2. Clark JA, Chuckowree JA, Dyer MS, Dickson TC, Blizzard CA. Epothilone D alters normal growth, viability and microtubule dependent intracellular functions of cortical neurons in vitro. Sci Rep. 2020 Jan 22;10(1):918. doi: 10.1038/s41598-020-57718-z. PMID: 31969604; PMCID: PMC6976590.
In vivo protocol:
1. Chuckowree JA, Zhu Z, Brizuela M, Lee KM, Blizzard CA, Dickson TC. The Microtubule-Modulating Drug Epothilone D Alters Dendritic Spine Morphology in a Mouse Model of Mild Traumatic Brain Injury. Front Cell Neurosci. 2018 Jul 30;12:223. doi: 10.3389/fncel.2018.00223. PMID: 30104961; PMCID: PMC6077201. 2. Sandner B, Puttagunta R, Motsch M, Bradke F, Ruschel J, Blesch A, Weidner N. Systemic epothilone D improves hindlimb function after spinal cord contusion injury in rats. Exp Neurol. 2018 Aug;306:250-259. doi: 10.1016/j.expneurol.2018.01.018. Epub 2018 Feb 2. PMID: 29408734.
1: Cheng H, Huang G. Synthesis and Activity of Epothilone D. Curr Drug Targets. 2018;19(15):1866-1870. doi: 10.2174/1389450119666180803122118. PMID: 30073925. 2: Kolman A. Epothilone D (Kosan/Roche). Curr Opin Investig Drugs. 2004 Jun;5(6):657-67. PMID: 15242255. 3: Ke YD, Ittner LM. Epothilone D - correct drug, wrong disease. Neuropathol Appl Neurobiol. 2018 Oct;44(6):548-549. doi: 10.1111/nan.12478. Epub 2018 Mar 27. PMID: 29437244. 4: Zhao M, Chang Q, Yang H, Wang M, Liu Y, Lv N, Lei Q, Wei H. Epothilone D Modulates Autism-like Behaviors in the BTBR Mouse Model of Autism Spectrum Disorder. Neuroscience. 2022 May 10;490:171-181. doi: 10.1016/j.neuroscience.2022.02.025. Epub 2022 Feb 25. PMID: 35227832. 5: Wang P, Luo S, Shen C, Yu Z, Nie Z, Li Z, Wen J, Li M, Cao X. [Protective effect of Epothilone D against traumatic optic nerve injury in rats]. Nan Fang Yi Ke Da Xue Xue Bao. 2022 Apr 20;42(4):575-583. Chinese. doi: 10.12122/j.issn.1673-4254.2022.04.14. PMID: 35527494; PMCID: PMC9085595. 6: Ye W, Liu T, Zhang WM, Zhang W, Li S. The Improvement of Epothilone D Yield by the Disruption of epoK Gene in Sorangium cellulosum Using TALEN System. Mol Biotechnol. 2023 Feb;65(2):282-289. doi: 10.1007/s12033-022-00602-0. Epub 2022 Nov 19. PMID: 36401710. 7: Xue W, Zhang H, Fan Y, Xiao Z, Zhao Y, Liu W, Xu B, Yin Y, Chen B, Li J, Cui Y, Shi Y, Dai J. Upregulation of Apol8 by Epothilone D facilitates the neuronal relay of transplanted NSCs in spinal cord injury. Stem Cell Res Ther. 2021 May 26;12(1):300. doi: 10.1186/s13287-021-02375-w. PMID: 34039405; PMCID: PMC8157417. 8: Clark JA, Chuckowree JA, Dyer MS, Dickson TC, Blizzard CA. Epothilone D alters normal growth, viability and microtubule dependent intracellular functions of cortical neurons in vitro. Sci Rep. 2020 Jan 22;10(1):918. doi: 10.1038/s41598-020-57718-z. PMID: 31969604; PMCID: PMC6976590. 9: Valdinocci D, Grant GD, Dickson TC, Pountney DL. Epothilone D inhibits microglia-mediated spread of alpha-synuclein aggregates. Mol Cell Neurosci. 2018 Jun;89:80-94. doi: 10.1016/j.mcn.2018.04.006. Epub 2018 Apr 16. PMID: 29673913. 10: Killinger BA, Moszczynska A. Epothilone D prevents binge methamphetamine- mediated loss of striatal dopaminergic markers. J Neurochem. 2016 Feb;136(3):510-25. doi: 10.1111/jnc.13391. Epub 2015 Dec 10. PMID: 26465779; PMCID: PMC5398202. 11: Sandner B, Puttagunta R, Motsch M, Bradke F, Ruschel J, Blesch A, Weidner N. Systemic epothilone D improves hindlimb function after spinal cord contusion injury in rats. Exp Neurol. 2018 Aug;306:250-259. doi: 10.1016/j.expneurol.2018.01.018. Epub 2018 Feb 2. PMID: 29408734. 12: Burrell RC, Turley WA, Bonacorsi SJ Jr. Synthesis of stable isotope-labeled epothilone D using a degradation-reconstruction approach. J Labelled Comp Radiopharm. 2015 Jul;58(9):361-9. doi: 10.1002/jlcr.3312. Epub 2015 Jul 8. PMID: 26158758. 13: Clark JA, Blizzard CA, Breslin MC, Yeaman EJ, Lee KM, Chuckowree JA, Dickson TC. Epothilone D accelerates disease progression in the SOD1G93A mouse model of amyotrophic lateral sclerosis. Neuropathol Appl Neurobiol. 2018 Oct;44(6):590-605. doi: 10.1111/nan.12473. Epub 2018 Mar 27. PMID: 29380402. 14: Bakota L, Brandt R. Tau Biology and Tau-Directed Therapies for Alzheimer's Disease. Drugs. 2016 Mar;76(3):301-13. doi: 10.1007/s40265-015-0529-0. PMID: 26729186; PMCID: PMC4757605. 15: Cheng H, Huang G. Synthesis & antitumor activity of epothilones B and D and their analogs. Future Med Chem. 2018 Jun 1;10(12):1483-1496. doi: 10.4155/fmc-2017-0320. Epub 2018 May 23. PMID: 29788770. 16: Hause G, Lischewski S, Wessjohann LA, Hause B. Epothilone D affects cell cycle and microtubular pattern in plant cells. J Exp Bot. 2005 Aug;56(418):2131-7. doi: 10.1093/jxb/eri211. Epub 2005 Jun 20. PMID: 15967777. 17: Kim TJ, Lim Y, Kim DW, Kwon JS, Son JH, Jin YR, Son DJ, Jung JC, Avery MA, Hong JT, Yun YP. Epothilone D, a microtubule-stabilizing compound, inhibits neointimal hyperplasia after rat carotid artery injury by cell cycle arrest via regulation of G1-checkpoint proteins. Vascul Pharmacol. 2007 Oct;47(4):229-37. doi: 10.1016/j.vph.2007.06.009. Epub 2007 Jul 5. PMID: 17706465. 18: Ruschel J, Bradke F. Systemic administration of epothilone D improves functional recovery of walking after rat spinal cord contusion injury. Exp Neurol. 2018 Aug;306:243-249. doi: 10.1016/j.expneurol.2017.12.001. Epub 2017 Dec 7. PMID: 29223322. 19: Griffin JM, Hingorani Jai Prakash S, Bockemühl T, Benner JM, Schaffran B, Moreno-Manzano V, Büschges A, Bradke F. Rehabilitation enhances epothilone- induced locomotor recovery after spinal cord injury. Brain Commun. 2023 Jan 13;5(1):fcad005. doi: 10.1093/braincomms/fcad005. Erratum in: Brain Commun. 2023 Feb 17;5(1):fcad029. PMID: 36744011; PMCID: PMC9893225. 20: Brizuela M, Blizzard CA, Chuckowree JA, Dawkins E, Gasperini RJ, Young KM, Dickson TC. The microtubule-stabilizing drug Epothilone D increases axonal sprouting following transection injury in vitro. Mol Cell Neurosci. 2015 May;66(Pt B):129-40. doi: 10.1016/j.mcn.2015.02.006. Epub 2015 Feb 12. PMID: 25684676.