Salinosporamide

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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[edit]

References[edit]

  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. PMID 12548698. doi:10.1002/anie.200390115. 
  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. PMID 16050677. doi:10.1021/jo050511+. 
  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. PMID 17243724. doi:10.1021/np0603471. 
  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. PMC 3088357Freely accessible. PMID 21154492. doi:10.1002/cbic.201000564. 
  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. PMC 2814440Freely accessible. PMID 19022674. 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. ISBN 978-0-85404-193-0. doi:10.1039/9781847559890-00355.  |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. PMC 3103133Freely accessible. PMID 20927786. 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. PMC 2771571Freely accessible. PMID 19746976. doi:10.1021/jm901098m. 

External links[edit]