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Psammaplins from the Sponge Pseudoceratina purpurea: Inhibition of Both Histone Deacetylase and DNA Methyltransferase
Abstract
Four novel bisulfide bromotyrosine derivatives, psammaplins E (9), F (10), G (11), and H (12), and two new bromotyrosine derivatives, psammaplins I (13) and J (14), were isolated from the sponge Pseudoceratina purpurea, along with known psammaplins A (4), B (6), C (7), and D (8) and bisaprasin (5). The structures of psammaplins E (9) and F (10), which each contain an oxalyl group rarely found in marine organisms, were determined by spectroscopic analysis. Compounds 4, 5, and 10 are potent histone deacetylase inhibitors and also show mild cytotoxicity. Furthermore, compounds 4, 5, and 11 are potent DNA methyltransferase inhibitors. The biogenetic pathway previously proposed for the psammaplins class is also revisited.
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Citations
Cited by
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Egger, G., Liang, G., Aparicio, A., & Jones, P. A. (2004) · Nature · doi:10.1038/nature02625 · Cited by 3,232
Targeting epigenetic regulators for cancer therapy: mechanisms and advances in clinical trials
Cheng, Y., He, C., Wang, M., Ma, X., Mo, F., Yang, S., Han, J., & Wei, X. (2019) · Signal Transduction and Targeted Therapy · doi:10.1038/s41392-019-0095-0 · Cited by 1,097
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Butler, M. S. (2008) · Natural Product Reports · doi:10.1039/b514294f · Cited by 1,075
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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
Blunt, J. W., Copp, B. R., Hu, W.-P., Munro, M. H. G., Northcote, P. T., & Prinsep, M. R. (2009) · Natural Product Reports · doi:10.1039/b805113p · Cited by 520
Metadata
- Authors
- Piña, I. C., Gautschi, J. T., Wang, G.-Y.-S., Sanders, M. L., Schmitz, F. J., France, D., Cornell-Kennon, S., Sambucetti, L. C., Remiszewski, S. W., Perez, L. B., Bair, K. W., & Crews, P.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-04-18
- Volume
- 68
- Issue
- 10
- Pages
- 3866-3873
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2172496848
- Cited by
- 311
- References
- 0
- FWCI
- 9.33
- Type
- journal article
- Language
- en
- Open access
- closed
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- The paper
- Piña, I. C., Gautschi, J. T., Wang, G.-Y.-S., Sanders, M. L., Schmitz, F. J., France, D., Cornell-Kennon, S., Sambucetti, L. C., Remiszewski, S. W., Perez, L. B., Bair, K. W., & Crews, P. (2003). Psammaplins from the Sponge Pseudoceratina purpurea: Inhibition of Both Histone Deacetylase and DNA Methyltransferase. The Journal of Organic Chemistry. https://doi.org/10.1021/jo034248t
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