Monoterpenes as nitrofurantoin resistance modulating agents: minimal structural requirements, molecular dynamics simulations, and the effect of piperitone on the emergence of nitrofurantoin resistance in Enterobacteriaceae

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• 作者：Ahmad R. Shahverdi ; Sako Mirzaie ; Fatemeh Rafii…
• 关键词：Molecular dynamics ; Monoterpenes ; Nitrofurantoin ; Resistance modulating activity ; Structural activity relationships
• 刊名：Journal of Molecular Modeling
• 出版年：2015
• 出版时间：August 2015
• 年：2015
• 卷：21
• 期：8
• 全文大小：3,294 KB
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• 作者单位：Ahmad R. Shahverdi (1)
  Sako Mirzaie (2)
  Fatemeh Rafii (3)
  Marjan Kakavand (1)
  Alireza Foroumadi (4)
  
  1. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, 1417614411, Iran
  2. Department of Biochemistry, Sanandaj Branch, Islamic Azad University, Sanandaj, Iran
  3. Division of Microbiology, National Center for Toxicological Research, U. S. FDA, Jefferson, AR, 72079, USA
  4. Drug Design and Development Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 1417614411, Iran
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Computer Applications in Chemistry
  Biomedicine
  Molecular Medicine
  Health Informatics and Administration
  Life Sciences
  Computer Application in Life Sciences
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：0948-5023

文摘

The effects of different monoterpenes and 2-cyclohexen-1-one on the antibacterial activity of nitrofurantoin against resistant Enterobacter cloacae, were compared and the minimal structural component of monoterpene required for the highest level of resistance-modulating activity was determined. Subinhibitory concentrations of all compounds tested enhanced the antibacterial activity of nitrofurantoin against E. cloacae to different extents. The highest synergistic effect was observed for the monoterpenes, like piperitone, which contained a conjugated ketone and C=C bond in their carbon ring structure. Piperitone also suppressed the emergence of nitrofurantoin-resistant strains of Enterobacteriaceae that were mutagenized by ethyl methanesulfonate. The modes of interaction of carvone, piperitone, and an enzyme inhibitor, benzoate, with nitroreductase were investigated by molecular docking and molecular dynamic (MD) simulation for 20?ns. MD simulation supported greater stability of the benzoate and monoterpene–nitroreductase (NR) complexes than of free NR. The results of this investigation are promising for the synthesis of more effective lead compounds to enhance the antibacterial activity of nitro drugs against resistant Enterobacter strains.