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Ecteinascidin 743: A Minor Groove Alkylator That Bends DNA toward the Major Groove
Abstract
The ecteinascidins (Ets), which are natural products derived from marine tunicates, exhibit potent antitumor activity. Of the numerous Ets isolated, Et 743 is presently being evaluated in phase II clinical trials. Et 743 binds in the minor groove of DNA and alkylates N2 of guanine. Although structurally similar to saframycin, which exhibits poor activity in cellular assays, Et 743 has shown good efficacy as an antitumor agent. In this study, DNA structural distortions induced by Et 743 were examined to provide insight into the molecular basis for the antitumor activity of Et 743. Electrophoretic mobility shifts of ligated oligomers containing site-directed adducts were used to examine the extent and direction of the Et 743-induced bend. Surprisingly, we find that Et 743 bends DNA toward the major groove, which is a unique feature among DNA-interactive agents that occupy the minor groove.
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Cited by
Marine natural products as anticancer drugs
Simmons, T. L., Andrianasolo, E., McPhail, K., Flatt, P., & Gerwick, W. H. (2005) · Molecular Cancer Therapeutics · doi:10.1158/1535-7163.333.4.2 · Cited by 597
Anticancer Activity of Natural Compounds from Plant and Marine Environment
Lichota, A., & Gwozdzinski, K. (2018) · International Journal of Molecular Sciences · doi:10.3390/ijms19113533 · Cited by 473
Development of Yondelis® (trabectedin, ET-743). A semisynthetic process solves the supply problem
Cuevas, C., & Francesch, A. (2009) · Natural Product Reports · doi:10.1039/b808331m · Cited by 323
Garcia-Carbonero, R., Supko, J. G., Manola, J., Seiden, M. V., Harmon, D., Ryan, D. P., Quigley, M. T., Merriam, P., Canniff, J., Goss, G., et al. (2004) · Journal of Clinical Oncology · doi:10.1200/jco.2004.02.098 · Cited by 294
Allavena, P., Signorelli, M., Chieppa, M., Erba, E., Bianchi, G., Marchesi, F., Olimpio, C. O., Bonardi, C., Garbi, A., Lissoni, A., et al. (2005) · Cancer Research · doi:10.1158/0008-5472.can-04-4037 · Cited by 286
Metadata
- Authors
- Zewail-Foote, M., & Hurley, L. H.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-06-25
- Volume
- 42
- Issue
- 14
- Pages
- 2493-2497
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2003174619
- Cited by
- 214
- References
- 0
- FWCI
- 11.67
- Type
- journal article
- Language
- en
- Open access
- closed
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- Zewail-Foote, M., & Hurley, L. H. (1999). Ecteinascidin 743: A Minor Groove Alkylator That Bends DNA toward the Major Groove. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm990241l
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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.
