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Literature DB >> 17951059

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

Katerina Capková¹, Yoshiyuki Yoneda, Tobin J Dickerson, Kim D Janda.

Abstract

Botulinum neurotoxins are the most toxic proteins currently known. Based on a recently identified potent lead structure, 2,4-dichlorocinnamic acid hydroxamate, herein we report on the structure-activity relationship of a series of hydroxamate BoNT/A inhibitors. Among them, 2-bromo-4-chlorocinnamic acid hydroxamate, 2-methyl-4-chlorocinnamic acid hydroxamate, and 2-trifluoromethyl-4-chlorocinnamic acid hydroxamate displayed comparable inhibitory activity to that of the lead structure.

Entities: Chemical

Mesh：

Substances：

Year: 2007 PMID： 17951059 PMCID： PMC2170532 DOI： 10.1016/j.bmcl.2007.09.103

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

21 in total

1. Genetic and immunological comparison of anti-botulinum type A antibodies from immune and non-immune human phage libraries.

Authors: Peter Amersdorfer; Cindy Wong; Theresa Smith; Steven Chen; Sharad Deshpande; Robert Sheridan; James D Marks
Journal: Vaccine Date: 2002-02-22 Impact factor: 3.641

2. Improved solution- and solid-phase preparation of hydroxamic acids from esters.

Authors: Chih Y Ho; Eric Strobel; Janet Ralbovsky; Robert A Galemmo
Journal: J Org Chem Date: 2005-06-10 Impact factor: 4.354

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. Concise and efficient asymmetric synthesis of (S)-2-ethylphenylpropanoic acid derivatives: dual agonists for human peroxisome proliferator-activated receptor alpha and delta.

Authors: Jun-ichi Kasuga; Yuichi Hashimoto; Hiroyuki Miyachi
Journal: Bioorg Med Chem Lett Date: 2006-02-15 Impact factor: 2.823

5. Aromatic sulfide inhibitors of histone deacetylase based on arylsulfinyl-2,4-hexadienoic acid hydroxyamides.

Authors: Charles M Marson; Pascal Savy; Alphonso S Rioja; Thevaki Mahadevan; Catherine Mikol; Arthi Veerupillai; Eva Nsubuga; Angela Chahwan; Simon P Joel
Journal: J Med Chem Date: 2006-01-26 Impact factor: 7.446

Review 6. The use of small molecules to investigate molecular mechanisms and therapeutic targets for treatment of botulinum neurotoxin A intoxication.

Authors: Tobin J Dickerson; Kim D Janda
Journal: ACS Chem Biol Date: 2006-07-21 Impact factor: 5.100

7. Potent neutralization of botulinum neurotoxin by recombinant oligoclonal antibody.

Authors: A Nowakowski; C Wang; D B Powers; P Amersdorfer; T J Smith; V A Montgomery; R Sheridan; R Blake; L A Smith; J D Marks
Journal: Proc Natl Acad Sci U S A Date: 2002-08-12 Impact factor: 11.205

8. Hypersensitivity reactions associated with botulinal antitoxin.

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

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

10. 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 3: Design, synthesis and SAR of orally bioavailable benzamidine-P4 inhibitors.

Authors: Zhaozhong J Jia; Yanhong Wu; Wenrong Huang; Penglie Zhang; Yonghong Song; John Woolfrey; Uma Sinha; Ann E Arfsten; Susan T Edwards; Athiwat Hutchaleelaha; Stanley J Hollennbach; Joseph L Lambing; Robert M Scarborough; Bing-Yan Zhu
Journal: Bioorg Med Chem Lett Date: 2004-03-08 Impact factor: 2.823

17 in total

1. Structural insight into exosite binding and discovery of novel exosite inhibitors of botulinum neurotoxin serotype A through in silico screening.

Authors: Xin Hu; Patricia M Legler; Noel Southall; David J Maloney; Anton Simeonov; Ajit Jadhav
Journal: J Comput Aided Mol Des Date: 2014-06-24 Impact factor: 3.686

2. 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

3. 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

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

1. Genetic and immunological comparison of anti-botulinum type A antibodies from immune and non-immune human phage libraries.

2. Improved solution- and solid-phase preparation of hydroxamic acids from esters.

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

4. Concise and efficient asymmetric synthesis of (S)-2-ethylphenylpropanoic acid derivatives: dual agonists for human peroxisome proliferator-activated receptor alpha and delta.

5. Aromatic sulfide inhibitors of histone deacetylase based on arylsulfinyl-2,4-hexadienoic acid hydroxyamides.

Review 6. The use of small molecules to investigate molecular mechanisms and therapeutic targets for treatment of botulinum neurotoxin A intoxication.

7. Potent neutralization of botulinum neurotoxin by recombinant oligoclonal antibody.

8. Hypersensitivity reactions associated with botulinal antitoxin.

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

10. 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 3: Design, synthesis and SAR of orally bioavailable benzamidine-P4 inhibitors.

1. Structural insight into exosite binding and discovery of novel exosite inhibitors of botulinum neurotoxin serotype A through in silico screening.

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

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

4. Basic tetrapeptides as potent intracellular inhibitors of type A botulinum neurotoxin protease activity.

5. Reexamining hydroxamate inhibitors of botulinum neurotoxin serotype A: extending towards the β-exosite.

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

7. Function-oriented synthesis applied to the anti-botulinum natural product toosendanin.

Review 8. Investigations into small molecule non-peptidic inhibitors of the botulinum neurotoxins.

9. Botulinum neurotoxin serotype A inhibitors: small-molecule mercaptoacetamide analogs.

10. Toosendanin: synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II).