Synthetic transformations of eleutherobin reveal new features of its microtubule-stabilizing pharmacophore

被引:25
作者
Britton, R
de Silva, ED
Bigg, CM
McHardy, LM
Roberge, M
Andersen, RJ
机构
[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada
[2] Univ British Columbia, Dept EOS, Vancouver, BC V6T 1Z1, Canada
[3] Univ British Columbia, Dept Biochem & Mol Biol, Vancouver, BC V6T 1Z3, Canada
关键词
D O I
10.1021/ja016459q
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:8632 / 8633
页数:2
相关论文
共 14 条
[1]   Antimitotic diterpenoids from Erythropodium caribaeorum:: isolation artifacts and putative biosynthetic intermediates [J].
Britton, R ;
Roberge, M ;
Berisch, H ;
Andersen, RJ .
TETRAHEDRON LETTERS, 2001, 42 (16) :2953-2956
[2]   The total synthesis of eleutherobin [J].
Chen, XT ;
Bhattacharya, SK ;
Zhou, BS ;
Gutteridge, CE ;
Pettus, TRR ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6563-6579
[3]   Solid-state and solution conformations of eleutherobin obtained from X-ray diffraction analysis and solution NOE data [J].
Cinel, B ;
Patrick, BO ;
Roberge, M ;
Andersen, RJ .
TETRAHEDRON LETTERS, 2000, 41 (16) :2811-2815
[4]   Antimitotic diterpenes from Erythropodium caribaeorum test pharmacophore models for microtubule stabilization [J].
Cinel, B ;
Roberge, M ;
Behrisch, H ;
van Ofwegen, LP ;
Castro, CB ;
Andersen, RJ .
ORGANIC LETTERS, 2000, 2 (03) :257-260
[5]   A common pharmacophore for epothilone and taxanes: Molecular basis for drug resistance conferred by tubulin mutations in human cancer cells [J].
Giannakakou, P ;
Gussio, R ;
Nogales, E ;
Downing, KH ;
Zaharevitz, D ;
Bollbuck, B ;
Poy, G ;
Sackett, D ;
Nicolaou, KC ;
Fojo, T .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (06) :2904-2909
[6]   A common pharmacophore for Taxol and the epothilones based on the biological activity of a taxane molecule lacking a C-13 side chain [J].
He, LF ;
Jagtap, PGF ;
Kingston, DGI ;
Shen, HJ ;
Orr, GA ;
Horwitz, SB .
BIOCHEMISTRY, 2000, 39 (14) :3972-3978
[7]  
Jordan A, 1998, MED RES REV, V18, P259, DOI 10.1002/(SICI)1098-1128(199807)18:4<259::AID-MED3>3.3.CO
[8]  
2-T
[9]   Eleutherobin, a new cytotoxin that mimics paclitaxel (Taxol) by stabilizing microtubules [J].
Lindel, T ;
Jensen, PR ;
Fenical, W ;
Long, BH ;
Casazza, AM ;
Carboni, J ;
Fairchild, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (37) :8744-8745
[10]   Solid and solution phase synthesis and biological evaluation of combinatorial sarcodictyin libraries [J].
Nicolaou, KC ;
Winssinger, N ;
Vourloumis, D ;
Ohshima, T ;
Kim, S ;
Pfefferkorn, J ;
Xu, JY ;
Li, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :10814-10826