Literature DB >> 27246784

In Vitro and In Vivo Characterization of the Novel Oxabicyclooctane-Linked Bacterial Topoisomerase Inhibitor AM-8722, a Selective, Potent Inhibitor of Bacterial DNA Gyrase.

Christopher M Tan1, Charles J Gill2, Jin Wu2, Nathalie Toussaint2, Jingjun Yin3, Takayuki Tsuchiya4, Charles G Garlisi2, David Kaelin2, Peter T Meinke3, Lynn Miesel2, David B Olsen4, Armando Lagrutta4, Hideyuki Fukuda5, Ryuta Kishii5, Masaya Takei5, Kouhei Oohata5, Tomoko Takeuchi5, Taku Shibue5, Hisashi Takano5, Akinori Nishimura5, Yasumichi Fukuda5, Sheo B Singh1.   

Abstract

Oxabicyclooctane-linked novel bacterial topoisomerase inhibitors (NBTIs) represent a new class of recently described antibacterial agents with broad-spectrum activity. NBTIs dually inhibit the clinically validated bacterial targets DNA gyrase and topoisomerase IV and have been shown to bind distinctly from known classes of antibacterial agents directed against these targets. Herein we report the molecular, cellular, and in vivo characterization of AM-8722 as a representative N-alkylated-1,5-naphthyridone left-hand-side-substituted NBTI. Consistent with its mode of action, macromolecular labeling studies revealed a specific effect of AM-8722 to dose dependently inhibit bacterial DNA synthesis. AM-8722 displayed greater intrinsic enzymatic potency than levofloxacin versus both DNA gyrase and topoisomerase IV from Staphylococcus aureus and Escherichia coli and displayed selectivity against human topoisomerase II. AM-8722 was rapidly bactericidal and exhibited whole-cell activity versus a range of Gram-negative and Gram-positive organisms, with no whole-cell potency shift due to the presence of DNA or human serum. Frequency-of-resistance studies demonstrated an acceptable rate of resistance emergence in vitro at concentrations 16- to 32-fold the MIC. AM-8722 displayed acceptable pharmacokinetic properties and was shown to be efficacious in mouse models of bacterial septicemia. Overall, AM-8722 is a selective and potent NBTI that displays broad-spectrum antimicrobial activity in vitro and in vivo.
Copyright © 2016, American Society for Microbiology. All Rights Reserved.

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Year:  2016        PMID: 27246784      PMCID: PMC4958163          DOI: 10.1128/AAC.00619-16

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


  26 in total

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Journal:  J Med Chem       Date:  2012-07-20       Impact factor: 7.446

2.  Novel hydroxyl tricyclics (e.g., GSK966587) as potent inhibitors of bacterial type IIA topoisomerases.

Authors:  Timothy J Miles; Alan J Hennessy; Ben Bax; Gerald Brooks; Barry S Brown; Pamela Brown; Nathalie Cailleau; Dongzhao Chen; Steven Dabbs; David T Davies; Joel M Esken; Ilaria Giordano; Jennifer L Hoover; Jianzhong Huang; Graham E Jones; Senthill K Kusalakumari Sukmar; Claus Spitzfaden; Roger E Markwell; Elisabeth A Minthorn; Steve Rittenhouse; Michael N Gwynn; Neil D Pearson
Journal:  Bioorg Med Chem Lett       Date:  2013-07-17       Impact factor: 2.823

3.  Kibdelomycin is a bactericidal broad-spectrum aerobic antibacterial agent.

Authors:  Sheo B Singh; Priya Dayananth; Carl J Balibar; Charles G Garlisi; Jun Lu; Ryuta Kishii; Masaya Takei; Yasumichi Fukuda; Sookhee Ha; Katherine Young
Journal:  Antimicrob Agents Chemother       Date:  2015-04-06       Impact factor: 5.191

4.  Hydroxy tricyclic 1,5-naphthyridinone oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents-SAR of RHS moiety (Part-3).

Authors:  Sheo B Singh; David E Kaelin; Jin Wu; Lynn Miesel; Christopher M Tan; Charles Gill; Todd Black; Ravi Nargund; Peter T Meinke; David B Olsen; Armando Lagrutta; Changqing Wei; Xuanjia Peng; Xiu Wang; Hideyuki Fukuda; Ryuta Kishii; Masaya Takei; Tomoko Takeuchi; Taku Shibue; Kohei Ohata; Hisashi Takano; Shizuka Ban; Akinori Nishimura; Yasumichi Fukuda
Journal:  Bioorg Med Chem Lett       Date:  2015-04-28       Impact factor: 2.823

5.  Novel quinoline derivatives as inhibitors of bacterial DNA gyrase and topoisomerase IV.

Authors:  Mark J Mitton-Fry; Steven J Brickner; Judith C Hamel; Lori Brennan; Jeffrey M Casavant; Michael Chen; Tao Chen; Xiaoyuan Ding; James Driscoll; Joel Hardink; Thuy Hoang; Erbing Hua; Michael D Huband; Meghan Maloney; Anthony Marfat; Sandra P McCurdy; Dale McLeod; Michael Plotkin; Usa Reilly; Shaughn Robinson; John Schafer; Richard M Shepard; James F Smith; Gregory G Stone; Chakrapani Subramanyam; Kwansik Yoon; Wei Yuan; Richard P Zaniewski; Christopher Zook
Journal:  Bioorg Med Chem Lett       Date:  2013-03-21       Impact factor: 2.823

6.  Antibacterial agents that inhibit lipid A biosynthesis.

Authors:  H R Onishi; B A Pelak; L S Gerckens; L L Silver; F M Kahan; M H Chen; A A Patchett; S M Galloway; S A Hyland; M S Anderson; C R Raetz
Journal:  Science       Date:  1996-11-08       Impact factor: 47.728

7.  Structure activity relationship of pyridoxazinone substituted RHS analogs of oxabicyclooctane-linked 1,5-naphthyridinyl novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents (Part-6).

Authors:  Sheo B Singh; David E Kaelin; Jin Wu; Lynn Miesel; Christopher M Tan; Peter T Meinke; David B Olsen; Armando Lagrutta; Changqing Wei; Yonggang Liao; Xuanjia Peng; Xiu Wang; Hideyuki Fukuda; Ryuta Kishii; Masaya Takei; Masanobu Yajima; Taku Shibue; Takeshi Shibata; Kohei Ohata; Akinori Nishimura; Yasumichi Fukuda
Journal:  Bioorg Med Chem Lett       Date:  2015-06-19       Impact factor: 2.823

8.  Tetrahydroindazole inhibitors of bacterial type II topoisomerases. Part 2: SAR development and potency against multidrug-resistant strains.

Authors:  John J M Wiener; Laurent Gomez; Hariharan Venkatesan; Alejandro Santillán; Brett D Allison; Kimberly L Schwarz; Shirin Shinde; Liu Tang; Michael D Hack; Brian J Morrow; S Timothy Motley; Raul M Goldschmidt; Karen Joy Shaw; Todd K Jones; Cheryl A Grice
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9.  New norfloxacin resistance gene in Pseudomonas aeruginosa PAO.

Authors:  H Fukuda; M Hosaka; K Hirai; S Iyobe
Journal:  Antimicrob Agents Chemother       Date:  1990-09       Impact factor: 5.191

10.  Structure activity relationship of C-2 ether substituted 1,5-naphthyridine analogs of oxabicyclooctane-linked novel bacterial topoisomerase inhibitors as broad-spectrum antibacterial agents (Part-5).

Authors:  Sheo B Singh; David E Kaelin; Peter T Meinke; Jin Wu; Lynn Miesel; Christopher M Tan; David B Olsen; Armando Lagrutta; Hideyuki Fukuda; Ryuta Kishii; Masaya Takei; Tomoko Takeuchi; Hisashi Takano; Kohei Ohata; Haruaki Kurasaki; Akinori Nishimura; Takeshi Shibata; Yasumichi Fukuda
Journal:  Bioorg Med Chem Lett       Date:  2015-06-23       Impact factor: 2.823

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  4 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.  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

3.  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 4.  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

  4 in total

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