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Antimicrobial lubricant formulations containing poly(hydroxybenzene)-trimethoprim conjugates synthesized by tyrosinase

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Abstract

Poly(hydroxybenzene)-trimethoprim conjugates were prepared using methylparaben as substrate of the oxidative enzyme tyrosinase. MALDI-TOF MS analysis showed that the enzymatic oxidation of methylparaben alone leads to the poly(hydroxybenzene) formation. In the presence of trimethoprim, the methylparaben tyrosinase oxidation leads poly(hydroxybenzene)-trimethoprim conjugates. All of these compounds were incorporated into lubricant hydroxyethyl cellulose/glycerol mixtures. Poly(hydroxybenzene)-trimethoprim conjugates were the most effective phenolic structures against the bacterial growth reducing by 96 and 97 % of Escherichia coli and Staphylococcus epidermidis suspensions, respectively (after 24 h). A novel enzymatic strategy to produce antimicrobial poly(hydroxybenzene)-antibiotic conjugates is proposed here for a wide range of applications on the biomedical field.

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Acknowledgments

The authors Idalina Gonçalves and Cláudia Botelho would like to acknowledge the NOVO project (FP7-HEALTH-2011.2.3.1- 5) for funding. Loïc Hilliou acknowledges the financial support by FCT – Foundation for Science and Technology, Portugal (501100001871), through Grant PEst-C/CTM/LA0025/2013 - Strategic Project - LA 25 - 2013–2014, and by Programa Operacional Regional do Norte (ON.2) through the project “Matepro – Optimizing Materials and Processes”, with reference NORTE-07-0124-FEDER-000037 FEDER COMPETE.

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Author notes

  1. Ana S. Abreu

    Present address: IPC - Institute of Polymer and Composites/I3N- Institute of Nanostructures, Nanomodelling and Nanofabrication, University of Minho, 4800-058, Braga, Portugal

  2. Carla Silva

    Present address: 3B’s Research Group, Biomaterials, Biodegradables and Biomimetics, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Ave Park, S. Cláudio de Barco, Taipas, 4806-909, Guimarães, Portugal

Authors and Affiliations

  1. CEB - Centre of Biological Engineering, University of Minho, 4710-057, Braga, Portugal

    Idalina Gonçalves, Cláudia M. Botelho, Ana Teixeira, Ana S. Abreu, Carla Silva & Artur Cavaco-Paulo

  2. Department of Polymer Engineering, University of Minho, 4800-058, Guimarães, Portugal

    Loïc Hilliou

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  1. Idalina Gonçalves
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Correspondence to Artur Cavaco-Paulo.

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Idalina Gonçalves and Cláudia M. Botelho contributed equally to this work.

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Gonçalves, I., Botelho, C.M., Teixeira, A. et al. Antimicrobial lubricant formulations containing poly(hydroxybenzene)-trimethoprim conjugates synthesized by tyrosinase. Appl Microbiol Biotechnol 99, 4225–4235 (2015). https://doi.org/10.1007/s00253-015-6509-1

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