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152044-53-6,MFCD09970958
Catalog No.:AA006UH3

152044-53-6 | Epothilone A

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1mg
≥95%
in stock  
$63.00   $44.00
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5mg
≥95%
in stock  
$169.00   $118.00
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10mg
≥95%
in stock  
$306.00   $214.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA006UH3
Chemical Name:
Epothilone A
CAS Number:
152044-53-6
Molecular Formula:
C26H39NO6S
Molecular Weight:
493.6560
MDL Number:
MFCD09970958
SMILES:
O=C1O[C@@H](C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1csc(n1)C)/C
NSC Number:
684362
Properties
Properties
 
Form:
Solid  
MP:
>82ºC (dec.)  
Storage:
-20 ℃;  

Computed Properties
 
Complexity:
770  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
34  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
4  

Literature

Title: 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.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20180301

Title: Induction of apoptosis in human ovarian cancer cells by new anticancer compounds, epothilone A and B.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20130201

Title: Overexpression of mitotic centromere-associated Kinesin stimulates microtubule detachment and confers resistance to paclitaxel.

Journal: Molecular cancer therapeutics 20110601

Title: Extended and clustered conformers of epothilone A.

Journal: The journal of physical chemistry. B 20110407

Title: Synthesis and SAR of C12-C13-oxazoline derivatives of epothilone A.

Journal: Bioorganic & medicinal chemistry letters 20090715

Title: Differential responses of mitotic spindle pole formation to microtubule-stabilizing agents epothilones A and B at low concentrations.

Journal: Cell cycle (Georgetown, Tex.) 20080215

Title: Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites.

Journal: Nature chemical biology 20070201

Title: Prostaglandins from a zoanthid: paclitaxel-like neurite-degenerating and microtubule-stabilizating activities.

Journal: Bioscience, biotechnology, and biochemistry 20060301

Title: Total synthesis and biological assessment of benzimidazole-based analogues of epothilone A: ambivalent effects on cancer cell growth inhibition.

Journal: Chembiochem : a European journal of chemical biology 20060101

Title: beta-Amyloid and endoplasmic reticulum stress responses in primary neurons: effects of drugs that interact with the cytoskeleton.

Journal: Journal of molecular neuroscience : MN 20060101

Title: Studies towards the synthesis of epothilone A via organoboranes.

Journal: Organic & biomolecular chemistry 20051021

Title: Much anticipated--the bioactive conformation of epothilone and its binding to tubulin.

Journal: Angewandte Chemie (International ed. in English) 20050218

Title: EpoK, a cytochrome P450 involved in biosynthesis of the anticancer agents epothilones A and B. Substrate-mediated rescue of a P450 enzyme.

Journal: Biochemistry 20041123

Title: The binding mode of epothilone A on alpha,beta-tubulin by electron crystallography.

Journal: Science (New York, N.Y.) 20040806

Title: What makes epothilones stick?

Journal: Chemistry & biology 20040201

Title: Polyketide-nonribosomal peptide epothilone antitumor agents: the EpoA, B, C subunits.

Journal: Journal of industrial microbiology & biotechnology 20030801

Title: Flavopiridol down-regulates antiapoptotic proteins and sensitizes human breast cancer cells to epothilone B-induced apoptosis.

Journal: Cancer research 20030101

Title: Total synthesis of epothilone a through stereospecific epoxidation of the p-methoxybenzyl ether of epothilone C.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20020816

Title: Studies on the biosynthesis of epothilones: hydroxylation of Epo A and B to epothilones E and F.

Journal: The Journal of antibiotics 20020101

Title: Gene expression profiling of epothilone A-resistant cells.

Journal: Novartis Foundation symposium 20020101

Title: Anticancer therapy with novel tubulin-interacting drugs.

Journal: Drug resistance updates : reviews and commentaries in antimicrobial and anticancer chemotherapy 20011201

Title: Stereoselective syntheses of epothilones A and B via nitrile oxide cycloadditions and related studies.

Journal: The Journal of organic chemistry 20010921

Title: The epothilones, eleutherobins, and related types of molecules.

Journal: Current pharmaceutical design 20010901

Title: Epothilone biosynthesis: assembly of the methylthiazolylcarboxy starter unit on the EpoB subunit.

Journal: Chemistry & biology 20010901

Title: New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies.

Journal: Journal of natural products 20010701

Title: Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition.

Journal: Journal of the American Chemical Society 20010418

Title: Catalytic antibody route to the naturally occurring epothilones: total synthesis of epothilones A-F.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20010417

Title: Studies on the biosynthesis of epothilones: the PKS and Epothilone C/D monooxygenase.

Journal: The Journal of antibiotics 20010201

Title: Solid phase synthesis of complex natural products and libraries thereof.

Journal: Biopolymers 20010101

Title: Kowalski RJ, et al. Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol(R)). J Biol Chem. 1997 Jan 24;272(4):2534-41.

Title: Cheng KL, et al. Novel microtubule-targeting agents - the epothilones. Biologics. 2008 Dec;2(4):789-811.

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Tags:152044-53-6 Molecular Formula|152044-53-6 MDL|152044-53-6 SMILES|152044-53-6 Epothilone A