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

• 
  Salinosporamide A
• 
  Salinosporamide B
• 
  Salinosporamide C
• 
  Salinosporamide D
• 
  Salinosporamide E
• 
  Salinosporamide F
• 
  Salinosporamide G
• 
  Salinosporamide H
• 
  Salinosporamide I
• 
  Salinosporamide J
• 
  Salinosporamide K

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 & 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": 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.

External links

• Media related to Salinosporamides at Wikimedia Commons