Evaluation of Novel Epothilone Analogues by means of a Common Pharmacophore and a QSAR Pseudoreceptor Model for Taxanes and Epothilones

被引：17

作者：

Forli, Stefano ^{[2
]}

Manetti, Fabrizio ^{[2
]}

Altmann, Karl-Heinz ^{[1
]}

Botta, Maurizio ^{[2
]}

机构：

[1] ETH Honggerberg, Dept Chem & Appl Biosci, Inst Pharmaceut Sci, CH-8093 Zurich, Switzerland

[2] Univ Siena, Dipartimento Farmaco Chim Tecnol, I-53100 Siena, Italy

来源：

CHEMMEDCHEM | 2010年 / 5卷 / 01期

关键词：

antitumor agents; epothilones; molecular modeling; pharmacophores; taxanes; NONNATURAL NATURAL-PRODUCTS; BETA-TUBULIN; 12-AZA-EPOTHILONES AZATHILONES; MICROTUBULE STABILIZATION; CHEMICAL-SYNTHESIS; BINDING; DESIGN; TAXOL; PACLITAXEL; DISCOVERY;

D O I：

10.1002/cmdc.200900303

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Taxanes and epothilones: New insights into the binding mode of epothilone B with tubulin support a previous hypothesis based on a pseudoreceptor model, in which taxanes and epothilones binding in the β-tubulin binding pocket share several pharmacophoric elements. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：35 / 40

页数：6

共 35 条

[1] The chemistry and biology of epothilones - The wheel keeps turning [J].

Altmann, Karl-Heinz ;

Pfeiffer, Bernhard ;

Arseniyadis, Stellios ;

Pratt, Benjamin A. ;

Nicolaou, K. C. .

CHEMMEDCHEM, 2007, 2 (04) :396-423

[2] Natural product-based drug discovery -: Epothilones as lead structures for the discovery of new anticancer agents [J].

Altmann, KH ;

Flörsheimer, A ;

Bold, G ;

Caravatti, G ;

Wartmann, M .

CHIMIA, 2004, 58 (10) :686-690

[3]

Altmann KH, 2000, CHIMIA, V54, P612

[4] Structure-activity relationships in side-chain-modified epothilone analogues - How important is the position of the nitrogen atom? [J].

Bold, Guido ;

Wojeik, Severine ;

Caravatti, Giorgio ;

Lindauer, Renate ;

Stierlin, Claire ;

Gertsch, Juerg ;

Wartmann, Markus ;

Altmann, Karl-Heinz .

CHEMMEDCHEM, 2006, 1 (01) :37-40

[5] Interaction of epothilone analogs with the paclitaxel binding site:: Relationship between binding affinity, microtubule stabilization, and cytotoxicity [J].

Buey, RM ;

Díaz, JF ;

Andreu, JM ;

O'Brate, A ;

Giannakakou, P ;

Nicolaou, KC ;

Sasmal, PK ;

Ritzén, A ;

Namoto, K .

CHEMISTRY & BIOLOGY, 2004, 11 (02) :225-236

[6] Total synthesis and biological assessment of benzimidazole-based analogues of epothilone A: Ambivalent effects on cancer cell growth inhibition [J].

Cachoux, F ;

Isarno, T ;

Wartmann, M ;

Altmann, KH .

CHEMBIOCHEM, 2006, 7 (01) :54-57

[7] Scaffolds for microtubule inhibition through extensive modification of the epothilone template [J].

Cachoux, F ;

Isarno, T ;

Wartmann, M ;

Altmann, KH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7469-7473

[8]

CACHOUX F, 2005, ANGEW CHEM, V117, P7636

[9] Therapeutic cure against human tumor xenografts in nude mice by a microtubule stabilization agent, fludelone, via parenteral or oral route [J].

Chou, TC ;

Dong, HJ ;

Zhang, XG ;

Tong, WP ;

Danishefsky, SJ .

CANCER RESEARCH, 2005, 65 (20) :9445-9454

[10] Conformational preferences of natural and C3-modified epothilones in aqueous solution [J].

Erdelyi, Mate ;

Pfeiffer, Bernhard ;

Hauenstein, Kurt ;

Fohrer, Joerg ;

Gertsch, Juerg ;

Altmann, Karl-Heinz ;

Carlomagno, Teresa .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (05) :1469-1473

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