Literature DB >> 19746976

Function-oriented biosynthesis of beta-lactone proteasome inhibitors in Salinispora tropica.

Markus Nett1, Tobias A M Gulder, Andrew J Kale, Chambers C Hughes, Bradley S Moore.   

Abstract

The natural proteasome inhibitor salinosporamide A from the marine bacterium Salinispora tropica is a promising drug candidate for the treatment of multiple myeloma and mantle cell lymphoma. Using a comprehensive approach that combined chemical synthesis with metabolic engineering, we generated a series of salinosporamide analogues with altered proteasome binding affinity. One of the engineered compounds is equipotent to salinosporamide A in inhibition of the chymotrypsin-like activity of the proteasome yet exhibits superior activity in the cell-based HCT-116 assay.

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Year:  2009        PMID： 19746976      PMCID： PMC2771571          DOI： 10.1021/jm901098m

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  27 in total

Review 1.  Proteolysis: from the lysosome to ubiquitin and the proteasome.

Authors:  Aaron Ciechanover
Journal:  Nat Rev Mol Cell Biol       Date:  2005-01       Impact factor: 94.444

Review 2.  Functions of the proteasome: from protein degradation and immune surveillance to cancer therapy.

Authors:  A L Goldberg
Journal:  Biochem Soc Trans       Date:  2007-02       Impact factor: 5.407

Review 3.  Natural occurrence, syntheses, and applications of cyclopropyl-group-containing alpha-amino acids. 2. 3,4- and 4,5-methanoamino acids.

Authors:  Farina Brackmann; Armin de Meijere
Journal:  Chem Rev       Date:  2007-10-18       Impact factor: 60.622

4.  Engineered biosynthesis of antiprotealide and other unnatural salinosporamide proteasome inhibitors.

Authors:  Ryan P McGlinchey; Markus Nett; Alessandra S Eustáquio; Ratnakar N Asolkar; William Fenical; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2008-05-31       Impact factor: 15.419

5.  Crystal structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in complex with the 20S proteasome reveal important consequences of beta-lactone ring opening and a mechanism for irreversible binding.

Authors:  Michael Groll; Robert Huber; Barbara C M Potts
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

6.  Structure-activity relationship studies of salinosporamide A (NPI-0052), a novel marine derived proteasome inhibitor.

Authors:  Venkat R Macherla; Scott S Mitchell; Rama Rao Manam; Katherine A Reed; Ta-Hsiang Chao; Benjamin Nicholson; Gordafaried Deyanat-Yazdi; Bao Mai; Paul R Jensen; William F Fenical; Saskia T C Neuteboom; Kin S Lam; Michael A Palladino; Barbara C M Potts
Journal:  J Med Chem       Date:  2005-06-02       Impact factor: 7.446

7.  Inhibitors of human histone deacetylase: synthesis and enzyme and cellular activity of straight chain hydroxamates.

Authors:  Stacy W Remiszewski; Lidia C Sambucetti; Peter Atadja; Kenneth W Bair; Wendy D Cornell; Michael A Green; Kobporn Lulu Howell; Manfred Jung; Paul Kwon; Nancy Trogani; Heather Walker
Journal:  J Med Chem       Date:  2002-02-14       Impact factor: 7.446

8.  Antiprotealide is a natural product.

Authors:  Rama Rao Manam; Venkat R Macherla; Ginger Tsueng; Chris W Dring; Jeffrey Weiss; Saskia T C Neuteboom; Kin S Lam; Barbara C Potts
Journal:  J Nat Prod       Date:  2009-02-27       Impact factor: 4.050

Review 9.  Total synthesis of lactacystin and salinosporamide A.

Authors:  Masakatsu Shibasaki; Motomu Kanai; Nobuhisa Fukuda
Journal:  Chem Asian J       Date:  2007-01-08

Review 10.  Advances in and applications of proteasome inhibitors.

Authors:  Bradley S Moore; Alessandra S Eustáquio; Ryan P McGlinchey
Journal:  Curr Opin Chem Biol       Date:  2008-07-24       Impact factor: 8.822
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  27 in total

1.  Translating Nature's Library: The Bryostatins and Function-Oriented Synthesis.

Authors:  Paul A Wender; Brian A Loy; Adam J Schrier
Journal:  Isr J Chem       Date:  2011-03-24       Impact factor: 3.333

Review 2.  Salinosporamide natural products: Potent 20 S proteasome inhibitors as promising cancer chemotherapeutics.

Authors:  Tobias A M Gulder; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

Review 3.  Lessons from the past and charting the future of marine natural products drug discovery and chemical biology.

Authors:  William H Gerwick; Bradley S Moore
Journal:  Chem Biol       Date:  2012-01-27

4.  Bioinspired total synthesis and human proteasome inhibitory activity of (-)-salinosporamide A, (-)-homosalinosporamide A, and derivatives obtained via organonucleophile promoted bis-cyclizations.

Authors:  Henry Nguyen; Gil Ma; Tatiana Gladysheva; Trisha Fremgen; Daniel Romo
Journal:  J Org Chem       Date:  2010-11-03       Impact factor: 4.354

5.  Bacterial self-resistance to the natural proteasome inhibitor salinosporamide A.

Authors:  Andrew J Kale; Ryan P McGlinchey; Anna Lechner; Bradley S Moore
Journal:  ACS Chem Biol       Date:  2011-09-26       Impact factor: 5.100

6.  The carmaphycins: new proteasome inhibitors exhibiting an α,β-epoxyketone warhead from a marine cyanobacterium.

Authors:  Alban R Pereira; Andrew J Kale; Andrew T Fenley; Tara Byrum; Hosana M Debonsi; Michael K Gilson; Frederick A Valeriote; Bradley S Moore; William H Gerwick
Journal:  Chembiochem       Date:  2012-03-01       Impact factor: 3.164

7.  Fundamental reaction pathway for peptide metabolism by proteasome: insights from first-principles quantum mechanical/molecular mechanical free energy calculations.

Authors:  Donghui Wei; Lei Fang; Mingsheng Tang; Chang-Guo Zhan
Journal:  J Phys Chem B       Date:  2013-10-10       Impact factor: 2.991

8.  Proteasome inhibitors prevent caspase-1-mediated disease in rodents challenged with anthrax lethal toxin.

Authors:  Stefan M Muehlbauer; Heriberto Lima; David L Goldman; Lee S Jacobson; Johanna Rivera; Michael F Goldberg; Michael A Palladino; Arturo Casadevall; Jürgen Brojatsch
Journal:  Am J Pathol       Date:  2010-07-01       Impact factor: 4.307

Review 9.  Generating a generation of proteasome inhibitors: from microbial fermentation to total synthesis of salinosporamide a (marizomib) and other salinosporamides.

Authors:  Barbara C Potts; Kin S Lam
Journal:  Mar Drugs       Date:  2010-03-25       Impact factor: 5.118

10.  Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica.

Authors:  Ulrike Groenhagen; Ana Ligia Leandrini De Oliveira; Elisha Fielding; Bradley S Moore; Stefan Schulz
Journal:  Chembiochem       Date:  2016-09-06       Impact factor: 3.164
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