Literature DB >> 20092262

Chirality holds the key for potent inhibition of the botulinum neurotoxin serotype a protease.

G Neil Stowe1, Peter Silhár, Mark S Hixon, Nicholas R Silvaggi, Karen N Allen, Scott T Moe, Alan R Jacobson, Joseph T Barbieri, Kim D Janda.   

Abstract

Botulinum neurotoxin serotype A (BoNT/A) is the most toxic protein known to man and also a bioterrorism agent. As defined by our previous research targeting the etiological agent responsible for BoNT/A intoxication, a protease, we now report on the asymmetric synthesis of four new BoNT/A inhibitors; the most potent of this series is roughly 2-fold more active than the best small molecule inhibitor currently known.

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Year:  2010        PMID： 20092262      PMCID： PMC2821465          DOI： 10.1021/ol902820z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  20 in total

1.  Identification of a potent botulinum neurotoxin a protease inhibitor using in situ lead identification chemistry.

Authors:  Grant E Boldt; Jack P Kennedy; Kim D Janda
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

2.  Vorinostat.

Authors:  Steven Grant; Chris Easley; Peter Kirkpatrick
Journal:  Nat Rev Drug Discov       Date:  2007-01       Impact factor: 84.694

3.  Catalytic features of the botulinum neurotoxin A light chain revealed by high resolution structure of an inhibitory peptide complex.

Authors:  Nicholas R Silvaggi; David Wilson; Saul Tzipori; Karen N Allen
Journal:  Biochemistry       Date:  2008-05-06       Impact factor: 3.162

4.  Synthesis and structure-activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors.

Authors:  Katerina Capková; Yoshiyuki Yoneda; Tobin J Dickerson; Kim D Janda
Journal:  Bioorg Med Chem Lett       Date:  2007-10-09       Impact factor: 2.823

5.  Hypersensitivity reactions associated with botulinal antitoxin.

Authors:  R E Black; R A Gunn
Journal:  Am J Med       Date:  1980-10       Impact factor: 4.965

6.  Synthesis of analogues of the carboxyl protease inhibitor pepstatin. Effects of structure on inhibition of pepsin and renin.

Authors:  D H Rich; E T Sun; E Ulm
Journal:  J Med Chem       Date:  1980-01       Impact factor: 7.446

Review 7.  Investigations into small molecule non-peptidic inhibitors of the botulinum neurotoxins.

Authors:  Katerina Capková; Nicholas T Salzameda; Kim D Janda
Journal:  Toxicon       Date:  2009-03-25       Impact factor: 3.033

8.  Wittig reactions in water media employing stabilized ylides with aldehydes. Synthesis of alpha,beta-unsaturated esters from mixing aldehydes, alpha-bromoesters, and Ph3P in aqueous NaHCO3.

Authors:  Amer El-Batta; Changchun Jiang; Wen Zhao; Robert Anness; Andrew L Cooksy; Mikael Bergdahl
Journal:  J Org Chem       Date:  2007-06-09       Impact factor: 4.354

9.  Structures of Clostridium botulinum Neurotoxin Serotype A Light Chain complexed with small-molecule inhibitors highlight active-site flexibility.

Authors:  Nicholas R Silvaggi; Grant E Boldt; Mark S Hixon; Jack P Kennedy; Saul Tzipori; Kim D Janda; Karen N Allen
Journal:  Chem Biol       Date:  2007-05

Review 10.  The design, structure, and clinical update of small molecular weight matrix metalloproteinase inhibitors.

Authors:  Jerry W Skiles; Nina C Gonnella; Arco Y Jeng
Journal:  Curr Med Chem       Date:  2004-11       Impact factor: 4.530
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  14 in total

1.  Synthesis and evaluation of library of betulin derivatives against the botulinum neurotoxin A protease.

Authors:  Peter Šilhár; Sami Alakurtti; Kateřina Čapková; Feng Xiaochuan; Charles B Shoemaker; Jari Yli-Kauhaluoma; Kim D Janda
Journal:  Bioorg Med Chem Lett       Date:  2011-03-04       Impact factor: 2.823

2.  Targeting botulinum A cellular toxicity: a prodrug approach.

Authors:  Peter Silhár; Lisa M Eubanks; Hajime Seki; Sabine Pellett; Sacha Javor; William H Tepp; Eric A Johnson; Kim D Janda
Journal:  J Med Chem       Date:  2013-10-15       Impact factor: 7.446

Review 3.  Targeting Metalloenzymes for Therapeutic Intervention.

Authors:  Allie Y Chen; Rebecca N Adamek; Benjamin L Dick; Cy V Credille; Christine N Morrison; Seth M Cohen
Journal:  Chem Rev       Date:  2018-09-07       Impact factor: 60.622

4.  A cross-over inhibitor of the botulinum neurotoxin light chain B: a natural product implicating an exosite mechanism of action.

Authors:  Nicholas T Salzameda; Lisa M Eubanks; Joseph S Zakhari; Kyoji Tsuchikama; Nicholas J DeNunzio; Karen N Allen; Mark S Hixon; Kim D Janda
Journal:  Chem Commun (Camb)       Date:  2011-01-04       Impact factor: 6.222

5.  Catch and Anchor Approach To Combat Both Toxicity and Longevity of Botulinum Toxin A.

Authors:  Lucy Lin; Margaret E Olson; Takashi Sugane; Lewis D Turner; Margarita A Tararina; Alexander L Nielsen; Elbek K Kurbanov; Sabine Pellett; Eric A Johnson; Seth M Cohen; Karen N Allen; Kim D Janda
Journal:  J Med Chem       Date:  2020-09-18       Impact factor: 7.446

6.  Separation of Betti Reaction Product Enantiomers: Absolute Configuration and Inhibition of Botulinum Neurotoxin A.

Authors:  John H Cardellina; Rebecca C Vieira; Vanessa Eccard; Janet Skerry; Vicki Montgomery; Yvette Campbell; Virginia Roxas-Duncan; William Leister; Christopher A Leclair; David J Maloney; Daniele Padula; Gennaro Pescitelli; Ilja Khavrutskii; Xin Hu; Anders Wallqvist; Leonard A Smith
Journal:  ACS Med Chem Lett       Date:  2011-03-10       Impact factor: 4.345

7.  Enhancing the Pharmacokinetic Properties of Botulinum Neurotoxin Serotype A Protease Inhibitors Through Rational Design.

Authors:  Petr Capek; Yan Zhang; Deborah J Barlow; Karen L Houseknecht; Garry R Smith; Tobin J Dickerson
Journal:  ACS Chem Neurosci       Date:  2011-06-15       Impact factor: 4.418

8.  Structural characterization of three novel hydroxamate-based zinc chelating inhibitors of the Clostridium botulinum serotype A neurotoxin light chain metalloprotease reveals a compact binding site resulting from 60/70 loop flexibility.

Authors:  Aaron A Thompson; Guan-Sheng Jiao; Seongjin Kim; April Thai; Lynne Cregar-Hernandez; Stephen A Margosiak; Alan T Johnson; Gye Won Han; Sean O'Malley; Raymond C Stevens
Journal:  Biochemistry       Date:  2011-04-21       Impact factor: 3.162

9.  Synthesis/biological evaluation of hydroxamic acids and their prodrugs as inhibitors for Botulinum neurotoxin A light chain.

Authors:  Hajime Seki; Sabine Pellett; Peter Silhár; G Neil Stowe; Beatriz Blanco; Matthew A Lardy; Eric A Johnson; Kim D Janda
Journal:  Bioorg Med Chem       Date:  2013-12-08       Impact factor: 3.641

10.  Evaluation of adamantane hydroxamates as botulinum neurotoxin inhibitors: synthesis, crystallography, modeling, kinetic and cellular based studies.

Authors:  Peter Šilhár; Nicholas R Silvaggi; Sabine Pellett; Kateřina Čapková; Eric A Johnson; Karen N Allen; Kim D Janda
Journal:  Bioorg Med Chem       Date:  2012-12-20       Impact factor: 3.641
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