Salinosporamide

The salinosporamides are a group of closely related chemical compounds isolated from marine bacteria in the genus Salinispora.[1][2][3][4] They possess a densely functionalized γ-lactam-β-lactone bicyclic core.

Salinosporamide A has attracted interest for its potential use in treating various types of cancer.[5][6][7][8]

In addition, a variety of synthetic analogs have been prepared.[9]

Chemical structures

References

  1. ↑ Feling, Robert H.; Buchanan, Greg O.; Mincer, Tracy J.; Kauffman, Christopher A.; Jensen, Paul R.; Fenical, William (2003). "Salinosporamide A: A Highly Cytotoxic Proteasome Inhibitor from a Novel Microbial Source, a Marine Bacterium of the New Genus Salinospora". Angewandte Chemie International Edition 42 (3): 355–7. doi:10.1002/anie.200390115. PMID 12548698.
  2. ↑ Philip G. Williams, Greg O. Buchanan, Robert H. Feling, Christopher A. Kauffman, Paul R. Jensen, and William Fenical (2005). "New Cytotoxic Salinosporamides from the Marine Actinomycete Salinispora tropica". J. Org. Chem. 70 (16): 6196–6203. doi:10.1021/jo050511+. PMID 16050677.
  3. ↑ Reed, Katherine A.; Manam, Rama Rao; Mitchell, Scott S.; Xu, Jianlin; Teisan, Sy; Chao, Ta-Hsiang; Deyanat-Yazdi, Gordafaried; Neuteboom, Saskia T. C. et al. (2007). "Salinosporamides D−J from the Marine ActinomyceteSalinispora tropica, Bromosalinosporamide, and Thioester Derivatives Are Potent Inhibitors of the 20S Proteasome". Journal of Natural Products 70 (2): 269–76. doi:10.1021/np0603471. PMID 17243724.
  4. ↑ Eustáquio, Alessandra S.; Nam, Sang-Jip; Penn, Kevin; Lechner, Anna; Wilson, Micheal C.; Fenical, William; Jensen, Paul R.; Moore, Bradley S. (2011). "The Discovery of Salinosporamide K from the Marine Bacterium "Salinispora pacifica" by Genome Mining Gives Insight into Pathway Evolution". ChemBioChem 12 (1): 61–4. doi:10.1002/cbic.201000564. PMC 3088357. PMID 21154492.
  5. ↑ Fenical, William; Jensen, Paul R.; Palladino, Michael A.; Lam, Kin S.; Lloyd, G. Kenneth; Potts, Barbara C. (2009). "Discovery and development of the anticancer agent salinosporamide A (NPI-0052)". Bioorganic & Medicinal Chemistry 17 (6): 2175. doi:10.1016/j.bmc.2008.10.075.
  6. ↑ Lam, Kin S.; Lloyd, G. Kenneth; Neuteboom, Saskia T. C.; Palladino, Michael A.; Sethna, Kobi M.; Spear, Matthew A.; Potts, Barbara C. (2009). "Natural Product Chemistry for Drug Discovery". p. 355. doi:10.1039/9781847559890-00355. ISBN 978-0-85404-193-0. |chapter= ignored (help)
  7. ↑ Gulder, Tobias A. M.; Moore, Bradley S. (2010). "Salinosporamide Natural Products: Potent 20 S Proteasome Inhibitors as Promising Cancer Chemotherapeutics". Angewandte Chemie International Edition 49 (49): 9346. doi:10.1002/anie.201000728.
  8. ↑ WO 2006118973
  9. ↑ Nett, Markus; Gulder, Tobias A. M.; Kale, Andrew J.; Hughes, Chambers C.; Moore, Bradley S. (2009). "Function-Oriented Biosynthesis of β-Lactone Proteasome Inhibitors inSalinispora tropica". Journal of Medicinal Chemistry 52 (19): 6163–7. doi:10.1021/jm901098m. PMC 2771571. PMID 19746976.

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