Literature DB >> 31654265

A computational study of the molecular basis of antibiotic resistance in a DXR mutant.

Fanny S Krebs1, Jérémy Esque1,2, Roland H Stote3.   

Abstract

Proteins of the independent mevalonate pathway for isoprenoid biosynthesis are important targets for the development of new antibacterial compounds as this pathway is present in most pathogenic organisms such as Mycobacterium tuberculosis, DPlasmodium falciparum and Escherichia coli, but is not present in mammalian species, including humans. Deoxy-D-xylulose 5-phosphate reductoisomerase (DXR) is an important target in this pathway and the most effective DXR inhibitor to date is fosmidomycin, which is used to treat malaria and, more recently, tuberculosis. Recently, Armstrong C. M. et al. showed that a mutant of DXR, S222T, induces a loss of the fosmidomycin inhibition efficiency, even though the bacteria culture is still viable and able to produce isoprenoids. As this represents a potential fosmidomycin-resistant mutation, it is important to understand the mechanism of this apparent mutation-induced resistance to fosmidomycin. Here, we used molecular dynamics simulations and Molecular Mechanics/Poisson Boltzmann Surface Area analysis to understand the structural and energetic basis of the resistance. Our results suggest that the point mutation results in changes to the structural dynamics of an active site loop that probably protects the active site and facilitates enzymatic reaction. From the simulation analysis, we also showed that the mutation results in changes in the interaction energy profiles in a way that can explain the observed activity of the mutant protein toward the natural inhibitor deoxy-D-xylulose 5-phosphate. These results should be taken into consideration in future efforts to develop new therapeutic antibiotic compounds that target DXR.

Entities:  

Keywords:  DXR; Drug design; Free energy binding; MEP; MM/PBSA; Molecular dynamics simulations; Mutation

Year:  2019        PMID: 31654265     DOI: 10.1007/s10822-019-00229-5

Source DB:  PubMed          Journal:  J Comput Aided Mol Des        ISSN: 0920-654X            Impact factor:   3.686


  44 in total

Review 1.  Mutation frequencies and antibiotic resistance.

Authors:  J L Martinez; F Baquero
Journal:  Antimicrob Agents Chemother       Date:  2000-07       Impact factor: 5.191

2.  Biosynthesis of terpenoids: 1-deoxy-D-xylulose-5-phosphate reductoisomerase from Escherichia coli is a class B dehydrogenase.

Authors:  T Radykewicz; F Rohdich; J Wungsintaweekul; S Herz; K Kis; W Eisenreich; A Bacher; M H Zenk; D Arigoni
Journal:  FEBS Lett       Date:  2000-01-14       Impact factor: 4.124

Review 3.  Inhibition of 1-deoxy-D-xylulose-5-phosphate reductoisomerase (Dxr): a review of the synthesis and biological evaluation of recent inhibitors.

Authors:  Emily R Jackson; Cynthia S Dowd
Journal:  Curr Top Med Chem       Date:  2012       Impact factor: 3.295

4.  Critical role of desolvation in the binding of 20-hydroxyecdysone to the ecdysone receptor.

Authors:  Christopher Browning; Elyette Martin; Caroline Loch; Jean-Marie Wurtz; Dino Moras; Roland H Stote; Annick P Dejaegere; Isabelle M L Billas
Journal:  J Biol Chem       Date:  2007-09-11       Impact factor: 5.157

5.  Rapid parameterization of small molecules using the Force Field Toolkit.

Authors:  Christopher G Mayne; Jan Saam; Klaus Schulten; Emad Tajkhorshid; James C Gumbart
Journal:  J Comput Chem       Date:  2013-09-02       Impact factor: 3.376

6.  Mechanistic studies with 2-C-methyl-D-erythritol 4-phosphate synthase from Escherichia coli.

Authors:  David T Fox; C D Poulter
Journal:  Biochemistry       Date:  2005-06-14       Impact factor: 3.162

7.  The crystal structure of E.coli 1-deoxy-D-xylulose-5-phosphate reductoisomerase in a ternary complex with the antimalarial compound fosmidomycin and NADPH reveals a tight-binding closed enzyme conformation.

Authors:  Aengus Mac Sweeney; Roland Lange; Roberta P M Fernandes; Henk Schulz; Glenn E Dale; Alice Douangamath; Philip J Proteau; Christian Oefner
Journal:  J Mol Biol       Date:  2005-01-07       Impact factor: 5.469

8.  E. coli MEP synthase: steady-state kinetic analysis and substrate binding.

Authors:  Andrew T Koppisch; David T Fox; Brian S J Blagg; C D Poulter
Journal:  Biochemistry       Date:  2002-01-08       Impact factor: 3.162

9.  Perturbation of the Conformational Dynamics of an Active-Site Loop Alters Enzyme Activity.

Authors:  Donald Gagné; Rachel L French; Chitra Narayanan; Miljan Simonović; Pratul K Agarwal; Nicolas Doucet
Journal:  Structure       Date:  2015-11-19       Impact factor: 5.006

10.  Conformational dynamics of the flexible catalytic loop in Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase.

Authors:  Sarah L Williams; J Andrew McCammon
Journal:  Chem Biol Drug Des       Date:  2009-01       Impact factor: 2.817

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