Literature DB >> 27722252

Picolinic acids as β-exosite inhibitors of botulinum neurotoxin A light chain.

Paul T Bremer1, Song Xue1, Kim D Janda1.   

Abstract

In developing small-molecule inhibitors of botulinum neurotoxin serotype A light chain (BoNT/A LC), substituted picolinic acids were identified. Extensive investigation into the SAR of the picolinic acid scaffold revealed 5-(1-butyl-4-chloro-1H-indol-2-yl)picolinic acid (CBIP), which possessed low micromolar activity against BoNT/A. Kinetic and docking studies demonstrated binding of CBIP to the β-exosite: a largely unexplored site on the LC that holds therapeutic relevance for botulism treatment.

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Year:  2016        PMID: 27722252      PMCID: PMC5085802          DOI: 10.1039/c6cc06749b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  31 in total

Review 1.  Botulinum toxin in clinical practice.

Authors:  J Jankovic
Journal:  J Neurol Neurosurg Psychiatry       Date:  2004-07       Impact factor: 10.154

Review 2.  The looming threat of bioterrorism.

Authors:  D A Henderson
Journal:  Science       Date:  1999-02-26       Impact factor: 47.728

3.  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

4.  FRED pose prediction and virtual screening accuracy.

Authors:  Mark McGann
Journal:  J Chem Inf Model       Date:  2011-02-16       Impact factor: 4.956

5.  The binary toxin produced by Clostridium botulinum enters cells by receptor-mediated endocytosis to exert its pharmacologic effects.

Authors:  L I Simpson
Journal:  J Pharmacol Exp Ther       Date:  1989-12       Impact factor: 4.030

6.  Toward the discovery of dual inhibitors for botulinum neurotoxin A: concomitant targeting of endocytosis and light chain protease activity.

Authors:  Hajime Seki; Song Xue; Mark S Hixon; Sabine Pellett; Marek Remes; Eric A Johnson; Kim D Janda
Journal:  Chem Commun (Camb)       Date:  2015-04-11       Impact factor: 6.222

7.  Conformer generation with OMEGA: learning from the data set and the analysis of failures.

Authors:  Paul C D Hawkins; Anthony Nicholls
Journal:  J Chem Inf Model       Date:  2012-11-12       Impact factor: 4.956

8.  Structure- and substrate-based inhibitor design for Clostridium botulinum neurotoxin serotype A.

Authors:  Desigan Kumaran; Richa Rawat; Matthew L Ludivico; S Ashraf Ahmed; Subramanyam Swaminathan
Journal:  J Biol Chem       Date:  2008-04-22       Impact factor: 5.157

9.  Clinical and laboratory comparison of botulism from toxin types A, B, and E in the United States, 1975-1988.

Authors:  B A Woodruff; P M Griffin; L M McCroskey; J F Smart; R B Wainwright; R G Bryant; L C Hutwagner; C L Hatheway
Journal:  J Infect Dis       Date:  1992-12       Impact factor: 5.226

10.  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
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  1 in total

1.  Metal Ions Effectively Ablate the Action of Botulinum Neurotoxin A.

Authors:  Paul T Bremer; Sabine Pellett; James P Carolan; William H Tepp; Lisa M Eubanks; Karen N Allen; Eric A Johnson; Kim D Janda
Journal:  J Am Chem Soc       Date:  2017-05-19       Impact factor: 15.419

  1 in total

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