Literature DB >> 20131905

Incorporation of fluorinated phenylalanine generates highly specific inhibitor of proteasome's chymotrypsin-like sites.

Paul P Geurink1, Nora Liu, Michiel P Spaans, Sondra L Downey, Adrianus M C H van den Nieuwendijk, Gijsbert A van der Marel, Alexei F Kisselev, Bogdan I Florea, Herman S Overkleeft.   

Abstract

Proteasomal processing is conducted by three individual catalytic subunits, namely beta1, beta2, and beta5. Subunit-specific inhibitors are useful tools in dissecting the role of these individual subunits and are leads toward the development of antitumor agents. We here report that the presence of fluorinated phenylalanine derivatives in peptide based proteasome inhibitors has a profound effect on inhibitor potency and selectivity. Specifically, compound 4a emerges as one of the most beta5 specific inhibitors known to date.

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Year:  2010        PMID： 20131905      PMCID： PMC3037272          DOI： 10.1021/jm9015685

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


  23 in total

1.  Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency.

Authors:  K B Kim; J Myung; N Sin; C M Crews
Journal:  Bioorg Med Chem Lett       Date:  1999-12-06       Impact factor: 2.823

2.  Global analysis of proteasomal substrate specificity using positional-scanning libraries of covalent inhibitors.

Authors:  T Nazif; M Bogyo
Journal:  Proc Natl Acad Sci U S A       Date:  2001-03-13       Impact factor: 11.205

3.  The caspase-like sites of proteasomes, their substrate specificity, new inhibitors and substrates, and allosteric interactions with the trypsin-like sites.

Authors:  Alexei F Kisselev; Margarita Garcia-Calvo; Herman S Overkleeft; Erin Peterson; Michael W Pennington; Hidde L Ploegh; Nancy A Thornberry; Alfred L Goldberg
Journal:  J Biol Chem       Date:  2003-06-18       Impact factor: 5.157

Review 4.  Bioorthogonal organic chemistry in living cells: novel strategies for labeling biomolecules.

Authors:  Paul F van Swieten; Michiel A Leeuwenburgh; Benedikt M Kessler; Herman S Overkleeft
Journal:  Org Biomol Chem       Date:  2004-11-29       Impact factor: 3.876

5.  Mixing of peptides and electrophilic traps gives rise to potent, broad-spectrum proteasome inhibitors.

Authors:  Martijn Verdoes; Bogdan I Florea; Wouter A van der Linden; Didier Renou; Adrianus M C H van den Nieuwendijk; Gijs A van der Marel; Herman S Overkleeft
Journal:  Org Biomol Chem       Date:  2007-03-23       Impact factor: 3.876

6.  Novel fluorinated pseudopeptides as proteasome inhibitors.

Authors:  Lucia Formicola; Xavier Maréchal; Nicolas Basse; Michelle Bouvier-Durand; Danièle Bonnet-Delpon; Thierry Milcent; Michèle Reboud-Ravaux; Sandrine Ongeri
Journal:  Bioorg Med Chem Lett       Date:  2008-11-07       Impact factor: 2.823

7.  Using a sterically restrictive amino acid as a 19F NMR label to monitor and to control peptide aggregation in membranes.

Authors:  Parvesh Wadhwani; Jochen Bürck; Erik Strandberg; Christian Mink; Sergii Afonin; Anne S Ulrich
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419

8.  Potent and selective inhibitors of the proteasome: dipeptidyl boronic acids.

Authors:  J Adams; M Behnke; S Chen; A A Cruickshank; L R Dick; L Grenier; J M Klunder; Y T Ma; L Plamondon; R L Stein
Journal:  Bioorg Med Chem Lett       Date:  1998-02-17       Impact factor: 2.823

9.  Use of Fluorinated Functionality in Enzyme Inhibitor Development: Mechanistic and Analytical Advantages.

Authors:  David B Berkowitz; Kannan R Karukurichi; Roberto de la Salud-Bea; David L Nelson; Christopher D McCune
Journal:  J Fluor Chem       Date:  2008-09       Impact factor: 2.050

10.  A selective inhibitor of the immunoproteasome subunit LMP7 blocks cytokine production and attenuates progression of experimental arthritis.

Authors:  Tony Muchamuel; Michael Basler; Monette A Aujay; Erika Suzuki; Khalid W Kalim; Christoph Lauer; Catherine Sylvain; Eileen R Ring; Jamie Shields; Jing Jiang; Peter Shwonek; Francesco Parlati; Susan D Demo; Mark K Bennett; Christopher J Kirk; Marcus Groettrup
Journal:  Nat Med       Date:  2009-06-14       Impact factor: 53.440
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  9 in total

Review 1.  Proteasome inhibitors: an expanding army attacking a unique target.

Authors:  Alexei F Kisselev; Wouter A van der Linden; Herman S Overkleeft
Journal:  Chem Biol       Date:  2012-01-27

2.  Discovery of a potent and highly β1 specific proteasome inhibitor from a focused library of urea-containing peptide vinyl sulfones and peptide epoxyketones.

Authors:  Wouter A van der Linden; Lianne I Willems; Tamer B Shabaneh; Nan Li; Mark Ruben; Bogdan I Florea; Gijs A van der Marel; Markus Kaiser; Alexei F Kisselev; Herman S Overkleeft
Journal:  Org Biomol Chem       Date:  2011-11-22       Impact factor: 3.876

3.  Specific cell-permeable inhibitor of proteasome trypsin-like sites selectively sensitizes myeloma cells to bortezomib and carfilzomib.

Authors:  Anne C Mirabella; Alexandre A Pletnev; Sondra L Downey; Bogdan I Florea; Tamer B Shabaneh; Matthew Britton; Martijn Verdoes; Dmitri V Filippov; Herman S Overkleeft; Alexei F Kisselev
Journal:  Chem Biol       Date:  2011-05-27

4.  Janus All-Cis 2,3,4,5,6-Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry.

Authors:  Joshua L Clark; Rifahath M Neyyappadath; Cihang Yu; Alexandra M Z Slawin; David B Cordes; David O'Hagan
Journal:  Chemistry       Date:  2021-10-06       Impact factor: 5.020

5.  Incorporation of non-natural amino acids improves cell permeability and potency of specific inhibitors of proteasome trypsin-like sites.

Authors:  Paul P Geurink; Wouter A van der Linden; Anne C Mirabella; Nerea Gallastegui; Gerjan de Bruin; Annet E M Blom; Mathias J Voges; Elliot D Mock; Bogdan I Florea; Gijs A van der Marel; Christoph Driessen; Mario van der Stelt; Michael Groll; Herman S Overkleeft; Alexei F Kisselev
Journal:  J Med Chem       Date:  2013-01-28       Impact factor: 7.446

Review 6.  Subunit specific inhibitors of proteasomes and their potential for immunomodulation.

Authors:  Alexei F Kisselev; Marcus Groettrup
Journal:  Curr Opin Chem Biol       Date:  2014-09-15       Impact factor: 8.822

7.  Fluorescent Probes with Unnatural Amino Acids to Monitor Proteasome Activity in Real-Time.

Authors:  Breanna L Zerfas; Rachel A Coleman; Andres F Salazar-Chaparro; Nathaniel J Macatangay; Darci J Trader
Journal:  ACS Chem Biol       Date:  2020-08-26       Impact factor: 5.100

8.  Downregulation of 26S proteasome catalytic activity promotes epithelial-mesenchymal transition.

Authors:  Asoka Banno; Daniel A Garcia; Eric D van Baarsel; Patrick J Metz; Kathleen Fisch; Christella E Widjaja; Stephanie H Kim; Justine Lopez; Aaron N Chang; Paul P Geurink; Bogdan I Florea; Hermen S Overkleeft; Huib Ovaa; Jack D Bui; Jing Yang; John T Chang
Journal:  Oncotarget       Date:  2016-04-19

Review 9.  Site-Specific Proteasome Inhibitors.

Authors:  Alexei F Kisselev
Journal:  Biomolecules       Date:  2021-12-31
  9 in total

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