Synthesis of isotopically labeled epothilones.
作者： Thota Ganesh , Peggy J. Brodie , Abhijit Banerjee , Susan Bane , David G. I. Kingston
DOI: 10.1002/JLCR.3144
关键词: Epothilones 、 Epothilone B 、 Chemistry 、 Ligand (biochemistry) 、 Stereochemistry 、 Resonance (chemistry) 、 Tubulin Modulators 、 Polymerization 、 Epothilone D 、 Tubulin
摘要: The epothilones, including epothilones B and D, are macrocyclic lactones, which have potent cytotoxicities promote the polymerization of tubulin to mictotubules by binding stabilizing polymer. They a very similar mechanism action paclitaxel (Taxol®). determination microtubule-binding conformation is an important piece information in designing improved analogs for possible clinical use, internuclear distance that will assist this can be obtained rotational echo double resonance (REDOR) NMR studies microtubule-bound with appropriate stable isotope labels. Analogs epothilone D [(2) H3 ] [(19) F] labels were prepared from advanced precursor potential use REDOR determine distances tubulin-bound ligand.
sci-hub.se 参考文章(33)
Edward F. McClay, Taxanes and Epothilones in Cancer Treatment Cancer Management in Man: Chemotherapy, Biological Therapy, Hyperthermia and Supporting Measures. pp. 39- 60 ,(2011) , 10.1007/978-90-481-9704-0_3
Younkee Paik, Chao Yang, Belhu Metaferia, Shoubin Tang, Susan Bane, Rudravajhala Ravindra, Natasha Shanker, Ana A. Alcaraz, Scott A. Johnson, Jacob Schaefer, Robert D. O'Connor, Lynette Cegelski, James P. Snyder, David G. I. Kingston, Rotational-Echo Double-Resonance NMR Distance Measurements for the Tubulin-Bound Paclitaxel Conformation Journal of the American Chemical Society. ,vol. 129, pp. 361- 370 ,(2007) , 10.1021/JA0656604
Robert M. Borzilleri, Gregory D. Vite, Chapter 15 Case History: Discovery of Ixabepilone (IXEMPRATM), a First-in-Class Epothilone Analog for Treatment of Metastatic Breast Cancer Annual Reports in Medicinal Chemistry. ,vol. 44, pp. 301- 322 ,(2009) , 10.1016/S0065-7743(09)04415-7
K.C. Nicolaou, N.P. King, M.R.V. Finlay, Y. He, F. Roschangar, D. Vourloumis, H. Vallberg, F. Sarabia, S. Ninkovic, D. Hepworth, Total synthesis of Epothilone E and related side-chain modified analogues via a stille coupling based strategy1This paper is dedicated with admiration and respect to the memory of Sir Derek H. R. Barton.1 Bioorganic & Medicinal Chemistry. ,vol. 7, pp. 665- 697 ,(1999) , 10.1016/S0968-0896(98)00153-9
KC Nicolaou, R Scarpelli, B Bollbuck, B Werschkun, MMA Pereira, M Wartmann, K-H Altmann, D Zaharevitz, R Gussio, P Giannakakou, Chemical synthesis and biological properties of pyridine epothilones Chemistry & Biology. ,vol. 7, pp. 593- 599 ,(2000) , 10.1016/S1074-5521(00)00006-5
K. C. Nicolaou, Andreas Ritzén, Kenji Namoto, Recent developments in the chemistry, biology andmedicine of the epothilones Chemical Communications. pp. 1523- 1535 ,(2001) , 10.1039/B104949F
Robert Newman, Jun Yang, Raymond Finlay, Fernando Cabral, Dionisios Vourloumis, Clifton Stephens, Patricia Troncoso, Xiaobing Wu, Christopher Logothetis, Nicolaou K., Nora Navone, Antitumor efficacy of 26-fluoroepothilone B against human prostate cancer xenografts. Cancer Chemotherapy and Pharmacology. ,vol. 48, pp. 319- 326 ,(2001) , 10.1007/S002800100323
Thota Ganesh, Jennifer K Schilling, Radha K Palakodety, Rudravajhala Ravindra, Natasha Shanker, Susan Bane, David G.I Kingston, Synthesis and biological evaluation of fluorescently labeled epothilone analogs for tubulin binding studies Tetrahedron. ,vol. 59, pp. 9979- 9984 ,(2003) , 10.1016/J.TET.2003.10.024
Gerhard Höfle, Norbert Bedorf, Heinrich Steinmetz, Dietmar Schomburg, Klaus Gerth, Hans Reichenbach, Epothilone A and B—Novel 16-Membered Macrolides with Cytotoxic Activity: Isolation, Crystal Structure, and Conformation in Solution† Angewandte Chemie. ,vol. 35, pp. 1567- 1569 ,(1996) , 10.1002/ANIE.199615671
Weiqiang Zhan, Yi Jiang, Shubhada Sharma, Peggy J. Brodie, Susan Bane, David G. I. Kingston, Dennis C. Liotta, James P. Snyder, C6-C8 bridged epothilones: consequences of installing a conformational lock at the edge of the macrocycle. Chemistry: A European Journal. ,vol. 17, pp. 14792- 14804 ,(2011) , 10.1002/CHEM.201102630