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Relationships between the structure of taxol analogs and their antimitotic activity
Abstract
A variety of synthetic analogues of taxol, a naturally occurring antitumor diterpene, were examined for their potency to inhibit microtubule disassembly. For some of the compounds, the in vitro cytotoxic properties showed a good correlation with the tubulin assay. This structure-activity relationship study shows that inhibition of microtubule disassembly is quite sensitive to the configuration at C-2' and C-3'. A correlation between the conformation of the side chain at C-13 and the activity is suggested. Of all the compounds examined, one of the most potent in inhibiting microtubule disassembly and in inhibiting murine P388 leukemic cells, N-debenzoyl-N-tert-(butoxycarbonyl)-10-deacetyltaxol, named taxotere, was selected for evaluation as a potential anticancer agent.
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Cited by
Vasey, P. A., Jayson, G. C., Gordon, A., Gabra, H., Coleman, R., Atkinson, R., Parkin, D., Paul, J., Hay, A., Kaye, S. B., et al. (2004) · JNCI Journal of the National Cancer Institute · doi:10.1093/jnci/djh323 · Cited by 632
Chemistry and Biology of Taxol
Nicolaou, K. C., Dai, W., & Guy, R. K. (1994) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199400151 · Cited by 623
Gao, Y., Kuang, Y., Guo, Z.-F., Guo, Z., Krauss, I. J., & Xu, B. (2009) · Journal of the American Chemical Society · doi:10.1021/ja904411z · Cited by 403
Camptothecin and Taxol: Historic Achievements in Natural Products Research
Oberlies, N. H., & Kroll, D. J. (2004) · Journal of Natural Products · doi:10.1021/np030498t · Cited by 353
Taxanes: A New Class of Antitumor Agents
Huizing, M. T., Misser, V. H. S., Pieters, R. C., ten Bokkel Huinink, W. W., Veenhof, C. H. N., Vermorken, J. B., Pinedo, H. M., & Beijnen, J. H. (1995) · Cancer Investigation · doi:10.3109/07357909509031919 · Cited by 285
Metadata
- Authors
- Gueritte-Voegelein, F., Guenard, D., Lavelle, F., Le Goff, M. T., Mangatal, L., & Potier, P.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1991-03
- Volume
- 34
- Issue
- 3
- Pages
- 992-998
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2073533584
- Cited by
- 538
- References
- 0
- FWCI
- 14.68
- Type
- journal article
- Language
- en
- Open access
- closed
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- Gueritte-Voegelein, F., Guenard, D., Lavelle, F., Le Goff, M. T., Mangatal, L., & Potier, P. (1991). Relationships between the structure of taxol analogs and their antimitotic activity. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm00107a017
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Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
