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Total synthesis and evaluation of 22-(3-azidobenzoyloxy)methyl epothilone C for photoaffinity labeling of β-tubulin
dc.contributor.author | Hutt, Oliver E. | |
dc.contributor.author | Inagaki, Jun | |
dc.contributor.author | Reddy, Bollu S. | |
dc.contributor.author | Nair, Sajiv K. | |
dc.contributor.author | Reiff, Emily A. | |
dc.contributor.author | Henri, John T. | |
dc.contributor.author | Greiner, Jack F. | |
dc.contributor.author | VanderVelde, David G. | |
dc.contributor.author | Chiu, Ting-Lan | |
dc.contributor.author | Amin, Elizabeth A. | |
dc.contributor.author | Himes, Richard H. | |
dc.contributor.author | Georg, Gunda I. | |
dc.date.accessioned | 2017-05-04T19:10:31Z | |
dc.date.available | 2017-05-04T19:10:31Z | |
dc.date.issued | 2009-06-15 | |
dc.identifier.citation | Hutt, O. E., Inagaki, J., Reddy, B. S., Nair, S. K., Reiff, E. A., Henri, J. T., … Georg, G. I. (2009). Total synthesis and evaluation of 22-(3-azidobenzoyloxy)methyl epothilone C for photoaffinity labeling of β-tubulin. Bioorganic & Medicinal Chemistry Letters, 19(12), 3293–3296. http://doi.org/10.1016/j.bmcl.2009.04.077 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/23895 | |
dc.description.abstract | The total synthesis of 22-(3-azidobenzoyloxy)methyl epothilone C is described as a potential photoaffinity probe to elucidate the β-tubulin binding site. A sequential Suzuki-aldol-Yamaguchi macrolactonization strategy was utilized employing a novel derivatized C1–C6 fragment. The C22-functionalized analog exhibited good activity in microtubule assembly assays, but cytotoxicity was significantly reduced. Molecular modeling simulations indicated that excessive steric bulk in the C22 position is accommodated by the large hydrophobic pocket of the binding site. Photoaffinity labeling studies were inconclusive suggesting non-specific labeling. | en_US |
dc.publisher | Elsevier | en_US |
dc.rights | This article is made available under an Attribution-NonCommercial-NoDerivs 3.0 United States (CC BY-NC-ND 3.0 US) License. | en_US |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/3.0/us/ | en_US |
dc.subject | Epothilone | en_US |
dc.subject | Photoaffinity labels | en_US |
dc.subject | Microtubules | en_US |
dc.title | Total synthesis and evaluation of 22-(3-azidobenzoyloxy)methyl epothilone C for photoaffinity labeling of β-tubulin | en_US |
dc.type | Article | en_US |
kusw.kuauthor | Hutt, Oliver E. | |
kusw.kuauthor | Inagaki, Jun | |
kusw.kuauthor | Reddy, Bollu S. | |
kusw.kuauthor | Nair, Sajiv K. | |
kusw.kuauthor | Reiff, Emily A. | |
kusw.kuauthor | Greiner, Jack F. | |
kusw.kuauthor | VanderVelde, David G. | |
kusw.kuauthor | Georg, Gunda I. | |
kusw.kuauthor | Himes, Richard H. | |
kusw.kudepartment | Medicinal Chemistry | en_US |
kusw.kudepartment | Molecular Bioscience | en_US |
dc.identifier.doi | 10.1016/j.bmcl.2009.04.077 | en_US |
kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
dc.identifier.pmid | PMC2803616 | en_US |
dc.rights.accessrights | openAccess |