Literature DB >> 27994740

Dipeptidyl Nitroalkenes as Potent Reversible Inhibitors of Cysteine Proteases Rhodesain and Cruzain.

Antonio Latorre1, Tanja Schirmeister2, Jochen Kesselring2, Sascha Jung2, Patrick Johé2, Ute A Hellmich3, Anna Heilos4, Bernd Engels4, R Luise Krauth-Siegel5, Natalie Dirdjaja5, Lledó Bou-Iserte1, Santiago Rodríguez1, Florenci V González1.   

Abstract

Dipeptidyl nitroalkenes are potent reversible inhibitors of cysteine proteases. Inhibitor 11 resulted to be the most potent one with Ki values of 0.49 and 0.44 nM against rhodesain and cruzain, respectively. According to enzymatic dilution and dialysis experiments, as well as computational and NMR studies, dipeptidyl nitroalkenes are tightly binding covalent reversible inhibitors.

Entities:  

Keywords:  Chagas’ disease; Rhodesain; cruzain; inhibitors; sleeping sickness

Year:  2016        PMID： 27994740      PMCID： PMC5150692          DOI： 10.1021/acsmedchemlett.6b00276

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  14 in total

Review 1.  Human and parasitic papain-like cysteine proteases: their role in physiology and pathology and recent developments in inhibitor design.

Authors:  Fabien Lecaille; Jadwiga Kaleta; Dieter Brömme
Journal:  Chem Rev       Date:  2002-12       Impact factor: 60.622

Review 2.  Enzyme kinetics and hit validation in fluorimetric protease assays.

Authors:  Stephanie Ludewig; Markus Kossner; Markus Schiller; Knut Baumann; Tanja Schirmeister
Journal:  Curr Top Med Chem       Date:  2010       Impact factor: 3.295

3.  High throughput screening against the peroxidase cascade of African trypanosomes identifies antiparasitic compounds that inactivate tryparedoxin.

Authors:  Florian Fueller; Britta Jehle; Kerstin Putzker; Joe D Lewis; R Luise Krauth-Siegel
Journal:  J Biol Chem       Date:  2012-01-23       Impact factor: 5.157

4.  Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy.

Authors:  Florian Weigend; Reinhart Ahlrichs
Journal:  Phys Chem Chem Phys       Date:  2005-08-04       Impact factor: 3.676

5.  Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors: 
Journal:  Phys Rev B Condens Matter       Date:  1988-01-15

6.  DOCKTITE-a highly versatile step-by-step workflow for covalent docking and virtual screening in the molecular operating environment.

Authors:  Christoph Scholz; Sabine Knorr; Kay Hamacher; Boris Schmidt
Journal:  J Chem Inf Model       Date:  2015-01-16       Impact factor: 4.956

7.  Quantum Chemical-Based Protocol for the Rational Design of Covalent Inhibitors.

Authors:  Tanja Schirmeister; Jochen Kesselring; Sascha Jung; Thomas H Schneider; Anastasia Weickert; Johannes Becker; Wook Lee; Denise Bamberger; Peter R Wich; Ute Distler; Stefan Tenzer; Patrick Johé; Ute A Hellmich; Bernd Engels
Journal:  J Am Chem Soc       Date:  2016-07-01       Impact factor: 15.419

Review 8.  Use of cysteine-reactive small molecules in drug discovery for trypanosomal disease.

Authors:  Deborah A Nicoll-Griffith
Journal:  Expert Opin Drug Discov       Date:  2012-03-06       Impact factor: 6.098

9.  The use of ATP bioluminescence as a measure of cell proliferation and cytotoxicity.

Authors:  S P Crouch; R Kozlowski; K J Slater; J Fletcher
Journal:  J Immunol Methods       Date:  1993-03-15       Impact factor: 2.303

10.  Production of crystallizable cruzain, the major cysteine protease from Trypanosoma cruzi.

Authors:  A E Eakin; M E McGrath; J H McKerrow; R J Fletterick; C S Craik
Journal:  J Biol Chem       Date:  1993-03-25       Impact factor: 5.157
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  6 in total

1.  Benzimidazole inhibitors of the major cysteine protease of Trypanosoma brucei.

Authors:  Glaécia An Pereira; Lucianna H Santos; Steven C Wang; Luan C Martins; Filipe S Villela; Weiting Liao; Marco A Dessoy; Luiz C Dias; Adriano D Andricopulo; Mariana Af Costa; Ronaldo Ap Nagem; Conor R Caffrey; Klaus R Liedl; Ernesto R Caffarena; Rafaela S Ferreira
Journal:  Future Med Chem       Date:  2019-07       Impact factor: 3.808

2.  Development of Urea-Bond-Containing Michael Acceptors as Antitrypanosomal Agents Targeting Rhodesain.

Authors:  Santo Previti; Roberta Ettari; Elsa Calcaterra; Carla Di Chio; Rahul Ravichandran; Collin Zimmer; Stefan Hammerschmidt; Annika Wagner; Marta Bogacz; Sandro Cosconati; Tanja Schirmeister; Maria Zappalà
Journal:  ACS Med Chem Lett       Date:  2022-06-30       Impact factor: 4.632

3.  Development of Reduced Peptide Bond Pseudopeptide Michael Acceptors for the Treatment of Human African Trypanosomiasis.

Authors:  Santo Previti; Roberta Ettari; Carla Di Chio; Rahul Ravichandran; Marta Bogacz; Ute A Hellmich; Tanja Schirmeister; Sandro Cosconati; Maria Zappalà
Journal:  Molecules       Date:  2022-06-11       Impact factor: 4.927

4.  Mechanism of inhibition of SARS-CoV-2 Mpro by N3 peptidyl Michael acceptor explained by QM/MM simulations and design of new derivatives with tunable chemical reactivity.

Authors:  Kemel Arafet; Natalia Serrano-Aparicio; Alessio Lodola; Adrian J Mulholland; Florenci V González; Katarzyna Świderek; Vicent Moliner
Journal:  Chem Sci       Date:  2020-11-27       Impact factor: 9.825

5.  Tryparedoxin peroxidase-deficiency commits trypanosomes to ferroptosis-type cell death.

Authors:  Marta Bogacz; R Luise Krauth-Siegel
Journal:  Elife       Date:  2018-07-26       Impact factor: 8.140

6.  Multiparameter Optimization of Trypanocidal Cruzain Inhibitors With In Vivo Activity and Favorable Pharmacokinetics.

Authors:  Ivani Pauli; Celso de O Rezende; Brian W Slafer; Marco A Dessoy; Mariana L de Souza; Leonardo L G Ferreira; Abraham L M Adjanohun; Rafaela S Ferreira; Luma G Magalhães; Renata Krogh; Simone Michelan-Duarte; Ricardo Vaz Del Pintor; Fernando B R da Silva; Fabio C Cruz; Luiz C Dias; Adriano D Andricopulo
Journal:  Front Pharmacol       Date:  2022-01-05       Impact factor: 5.810
  6 in total

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