Literature DB >> 28223393

Novel Bacterial Topoisomerase Inhibitors with Potent Broad-Spectrum Activity against Drug-Resistant Bacteria.

Cédric Charrier1, Anne-Marie Salisbury2, Victoria J Savage1, Thomas Duffy1, Emmanuel Moyo1, Nathan Chaffer-Malam1, Nicola Ooi1, Rebecca Newman1, Jonathan Cheung1, Richard Metzger1, David McGarry1, Mark Pichowicz1, Ralph Sigerson1, Ian R Cooper1, Gary Nelson1, Hayley S Butler1, Mark Craighead1, Andrew J Ratcliffe1, Stuart A Best1, Neil R Stokes1.   

Abstract

The novel bacterial topoisomerase inhibitor class is an investigational type of antibacterial inhibitor of DNA gyrase and topoisomerase IV that does not have cross-resistance with the quinolones. Here, we report the evaluation of the in vitro properties of a new series of this type of small molecule. Exemplar compounds selectively and potently inhibited the catalytic activities of Escherichia coli DNA gyrase and topoisomerase IV but did not block the DNA breakage-reunion step. Compounds showed broad-spectrum inhibitory activity against a wide range of Gram-positive and Gram-negative pathogens, including biodefence microorganisms and Mycobacterium tuberculosis No cross-resistance with fluoroquinolone-resistant Staphylococcus aureus and E. coli isolates was observed. Measured MIC90 values were 4 and 8 μg/ml against a panel of contemporary multidrug-resistant isolates of Acinetobacter baumannii and E. coli, respectively. In addition, representative compounds exhibited greater antibacterial potency than the quinolones against obligate anaerobic species. Spontaneous mutation rates were low, with frequencies of resistance typically <10-8 against E. coli and A. baumannii at concentrations equivalent to 4-fold the MIC. Compound-resistant E. coli mutants that were isolated following serial passage were characterized by whole-genome sequencing and carried a single Arg38Leu amino acid substitution in the GyrA subunit of DNA gyrase. Preliminary in vitro safety data indicate that the series shows a promising therapeutic index and potential for low human ether-a-go-go-related gene (hERG) inhibition (50% inhibitory concentration [IC50], >100 μM). In summary, the compounds' distinct mechanism of action relative to the fluoroquinolones, whole-cell potency, low potential for resistance development, and favorable in vitro safety profile warrant their continued investigation as potential broad-spectrum antibacterial agents.
Copyright © 2017 American Society for Microbiology.

Entities:  

Keywords:  DNA gyrase; ESKAPE; antibiotic; topoisomerase

Mesh:

Substances:

Year:  2017        PMID: 28223393      PMCID: PMC5404544          DOI: 10.1128/AAC.02100-16

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  35 in total

1.  Target preference of 15 quinolones against Staphylococcus aureus, based on antibacterial activities and target inhibition.

Authors:  M Takei; H Fukuda; R Kishii; M Hosaka
Journal:  Antimicrob Agents Chemother       Date:  2001-12       Impact factor: 5.191

2.  Novel N-linked aminopiperidine inhibitors of bacterial topoisomerase type II with reduced pK(a): antibacterial agents with an improved safety profile.

Authors:  Folkert Reck; Richard A Alm; Patrick Brassil; Joseph V Newman; Paul Ciaccio; John McNulty; Herbert Barthlow; Kosalaram Goteti; John Breen; Janelle Comita-Prevoir; Mark Cronin; David E Ehmann; Bolin Geng; Andrew Aydon Godfrey; Stewart L Fisher
Journal:  J Med Chem       Date:  2012-07-20       Impact factor: 7.446

3.  A method for measuring the lipophilicity of compounds in mixtures of 10.

Authors:  Mark C Wenlock; Tim Potter; Patrick Barton; Rupert P Austin
Journal:  J Biomol Screen       Date:  2011-02-22

Review 4.  Challenges of antibacterial discovery.

Authors:  Lynn L Silver
Journal:  Clin Microbiol Rev       Date:  2011-01       Impact factor: 26.132

Review 5.  Designing drugs that overcome antibacterial resistance: where do we stand and what should we do?

Authors:  Robert Penchovsky; Martina Traykovska
Journal:  Expert Opin Drug Discov       Date:  2015-05-18       Impact factor: 6.098

Review 6.  Confronting the challenges of discovery of novel antibacterial agents.

Authors:  Sheo B Singh
Journal:  Bioorg Med Chem Lett       Date:  2014-06-26       Impact factor: 2.823

7.  3-aminoquinazolinediones as a new class of antibacterial agents demonstrating excellent antibacterial activity against wild-type and multidrug resistant organisms.

Authors:  Edmund L Ellsworth; Tuan P Tran; H D Hollis Showalter; Joseph P Sanchez; Brian M Watson; Michael A Stier; John M Domagala; Stephen J Gracheck; E Themis Joannides; Martin A Shapiro; Steve A Dunham; Debra L Hanna; Michael D Huband; Jeffrey W Gage; Joel C Bronstein; Jia Yeu Liu; Dai Q Nguyen; Rajeshwar Singh
Journal:  J Med Chem       Date:  2006-11-02       Impact factor: 7.446

8.  Target-based resistance in Pseudomonas aeruginosa and Escherichia coli to NBTI 5463, a novel bacterial type II topoisomerase inhibitor.

Authors:  Asha S Nayar; Thomas J Dougherty; Folkert Reck; Jason Thresher; Ning Gao; Adam B Shapiro; David E Ehmann
Journal:  Antimicrob Agents Chemother       Date:  2014-10-27       Impact factor: 5.191

9.  A New-Class Antibacterial-Almost. Lessons in Drug Discovery and Development: A Critical Analysis of More than 50 Years of Effort toward ATPase Inhibitors of DNA Gyrase and Topoisomerase IV.

Authors:  Gregory S Bisacchi; John I Manchester
Journal:  ACS Infect Dis       Date:  2014-12-23       Impact factor: 5.084

10.  Genetic Resistance Determinants, In Vitro Time-Kill Curve Analysis and Pharmacodynamic Functions for the Novel Topoisomerase II Inhibitor ETX0914 (AZD0914) in Neisseria gonorrhoeae.

Authors:  Sunniva Foerster; Daniel Golparian; Susanne Jacobsson; Lucy J Hathaway; Nicola Low; William M Shafer; Christian L Althaus; Magnus Unemo
Journal:  Front Microbiol       Date:  2015-12-10       Impact factor: 5.640

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  9 in total

1.  Bimodal Actions of a Naphthyridone/Aminopiperidine-Based Antibacterial That Targets Gyrase and Topoisomerase IV.

Authors:  Elizabeth G Gibson; Alexandria A Oviatt; Monica Cacho; Keir C Neuman; Pan F Chan; Neil Osheroff
Journal:  Biochemistry       Date:  2019-10-28       Impact factor: 3.162

2.  Mechanistic and Structural Basis for the Actions of the Antibacterial Gepotidacin against Staphylococcus aureus Gyrase.

Authors:  Elizabeth G Gibson; Ben Bax; Pan F Chan; Neil Osheroff
Journal:  ACS Infect Dis       Date:  2019-02-28       Impact factor: 5.084

3.  1,3-Dioxane-Linked Novel Bacterial Topoisomerase Inhibitors: Expanding Structural Diversity and the Antibacterial Spectrum.

Authors:  Yanran Lu; Chelsea A Mann; Sheri Nolan; Jessica A Collins; Elizabeth Parker; Jonathan Papa; Sandip Vibhute; Seyedehameneh Jahanbakhsh; Mary Thwaites; David Hufnagel; Manzour H Hazbón; Jane Moreno; Timothy T Stedman; Thomas Wittum; Daniel J Wozniak; Neil Osheroff; Jack C Yalowich; Mark J Mitton-Fry
Journal:  ACS Med Chem Lett       Date:  2022-05-09       Impact factor: 4.632

4.  Novel Bacterial Topoisomerase Inhibitors Exploit Asp83 and the Intrinsic Flexibility of the DNA Gyrase Binding Site.

Authors:  Sebastian Franco-Ulloa; Giuseppina La Sala; Gian Pietro Miscione; Marco De Vivo
Journal:  Int J Mol Sci       Date:  2018-02-03       Impact factor: 5.923

Review 5.  Two Decades of Successful SAR-Grounded Stories of the Novel Bacterial Topoisomerase Inhibitors (NBTIs).

Authors:  Anja Kolarič; Marko Anderluh; Nikola Minovski
Journal:  J Med Chem       Date:  2020-02-17       Impact factor: 7.446

6.  Rare-Earth Metal Complexes of the Antibacterial Drug Oxolinic Acid: Synthesis, Characterization, DNA/Protein Binding and Cytotoxicity Studies.

Authors:  Ana-Madalina Maciuca; Alexandra-Cristina Munteanu; Mirela Mihaila; Mihaela Badea; Rodica Olar; George Mihai Nitulescu; Cristian V A Munteanu; Marinela Bostan; Valentina Uivarosi
Journal:  Molecules       Date:  2020-11-19       Impact factor: 4.411

Review 7.  The Structural Features of Novel Bacterial Topoisomerase Inhibitors That Define Their Activity on Topoisomerase IV.

Authors:  Maja Kokot; Marko Anderluh; Martina Hrast; Nikola Minovski
Journal:  J Med Chem       Date:  2022-05-03       Impact factor: 8.039

8.  A Study on Repositioning Nalidixic Acid via Lanthanide Complexation: Synthesis, Characterization, Cytotoxicity and DNA/Protein Binding Studies.

Authors:  Ana-Madalina Maciuca; Alexandra-Cristina Munteanu; Mirela Mihaila; Mihaela Badea; Rodica Olar; George Mihai Nitulescu; Cristian V A Munteanu; Valentina Uivarosi
Journal:  Pharmaceuticals (Basel)       Date:  2022-08-17

Review 9.  Quinolone Complexes with Lanthanide Ions: An Insight into their Analytical Applications and Biological Activity.

Authors:  Ana-Mădălina Măciucă; Alexandra-Cristina Munteanu; Valentina Uivarosi
Journal:  Molecules       Date:  2020-03-16       Impact factor: 4.411

  9 in total

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