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Therapeutic Role of Deep Eutectic Solvents Based on Menthol and Saturated Fatty Acids on Wound Healing

  • Joana M. Silva
    Joana M. Silva
    3B’s Research Group—Biomaterials, Biodegradable and Biomimetic, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Avepark Barco, Guimarães 4805-017, Portugal
    ICVS/3B’s PT Government Associated Laboratory, Braga/Guimarães 4806-909, Portugal
  • Carolina V. Pereira
    Carolina V. Pereira
    Nutraceuticals and Bioactives Process Technology Laboratory, Instituto de Biologia Experimental e Tecnológica, Oeiras 2780-157, Portugal
  • Francisca Mano
    Francisca Mano
    LAQV/REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Caparica 2829-516, Portugal
  • Eduardo Silva
    Eduardo Silva
    3B’s Research Group—Biomaterials, Biodegradable and Biomimetic, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Avepark Barco, Guimarães 4805-017, Portugal
    ICVS/3B’s PT Government Associated Laboratory, Braga/Guimarães 4806-909, Portugal
  • Vânia I. B. Castro
    Vânia I. B. Castro
    3B’s Research Group—Biomaterials, Biodegradable and Biomimetic, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Avepark Barco, Guimarães 4805-017, Portugal
    ICVS/3B’s PT Government Associated Laboratory, Braga/Guimarães 4806-909, Portugal
  • Isabel Sá-Nogueira
    Isabel Sá-Nogueira
    Microbial Genetics Laboratory, UCIBIO/REQUIMTE, Departamento de Ciências da Vida, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Caparica 2829-516, Portugal
  • Rui L. Reis
    Rui L. Reis
    3B’s Research Group—Biomaterials, Biodegradable and Biomimetic, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Avepark Barco, Guimarães 4805-017, Portugal
    ICVS/3B’s PT Government Associated Laboratory, Braga/Guimarães 4806-909, Portugal
    The Discoveries Centre for Regenerative and Precision Medicine, Headquarters, University of Minho, Avepark Barco, Guimarães 4805-017, Portugal
    More by Rui L. Reis
  • Alexandre Paiva
    Alexandre Paiva
    LAQV/REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Caparica 2829-516, Portugal
  • Ana A. Matias
    Ana A. Matias
    Nutraceuticals and Bioactives Process Technology Laboratory, Instituto de Biologia Experimental e Tecnológica, Oeiras 2780-157, Portugal
    Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Oeiras 2780-157, Portugal
  • , and 
  • Ana Rita C. Duarte*
    Ana Rita C. Duarte
    3B’s Research Group—Biomaterials, Biodegradable and Biomimetic, University of Minho, Headquarters of the European Institute of Excellence on Tissue Engineering and Regenerative Medicine, Avepark Barco, Guimarães 4805-017, Portugal
    ICVS/3B’s PT Government Associated Laboratory, Braga/Guimarães 4806-909, Portugal
    *E-mail: [email protected]
Cite this: ACS Appl. Bio Mater. 2019, 2, 10, 4346–4355
Publication Date (Web):August 26, 2019
https://doi.org/10.1021/acsabm.9b00598
Copyright © 2019 American Chemical Society
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Abstract

Abstract Image

The breakthroughs achieved in green solvents promote the emergence of therapeutic deep eutectic solvents (THEDES), which possess intriguing possible applications in the biomedical field. Herein, the main aim was to unravel the biomedical potential of hydrophobic THEDES based in menthol and saturated fatty acids with different chain lengths (e.g., stearic acid (SA), myristic acid (MA), and lauric acid (LA)). Our comprehensive strategy resulted in the thermophysical characterization of different formulations, which allow one to identify the most suitable molar ratio, as well as the intermolecular interactions behind the successful formation of THEDES. The evaluation of their biological performance was also performed toward bacteria and HaCaT cells. Among the different formulations of THEDES, the one based on menthol and SA establishes stronger hydrogen bonding interactions, being also the most promising formulation because it did not elicit any relevant cytotoxicity, and potentiated wound healing, while presenting antibacterial properties against Staphylococcus epidermis and Staphylococcus aureus strains, some of which were methicillin resistant. This work provides clues on the future use of THEDES based on menthol:SA in wound dressings.

Cited By


This article is cited by 8 publications.

  1. Dannie J. G. P. van Osch, Carin H. J. T. Dietz, Samah E. E. Warrag, Maaike C. Kroon. The Curious Case of Hydrophobic Deep Eutectic Solvents: A Story on the Discovery, Design, and Applications. ACS Sustainable Chemistry & Engineering 2020, 8 (29) , 10591-10612. https://doi.org/10.1021/acssuschemeng.0c00559
  2. Liliana A. Rodrigues, Carolina V. Pereira, Inês C. Leonardo, Naiara Fernández, Frédéric B. Gaspar, Joana M. Silva, Rui L. Reis, Ana Rita C. Duarte, Alexandre Paiva, Ana A. Matias. Terpene-Based Natural Deep Eutectic Systems as Efficient Solvents To Recover Astaxanthin from Brown Crab Shell Residues. ACS Sustainable Chemistry & Engineering 2020, 8 (5) , 2246-2259. https://doi.org/10.1021/acssuschemeng.9b06283
  3. Filipa Santos, Ana Rita C. Duarte. Therapeutic Deep Eutectic Systems for the Enhancement of Drug Bioavailability. 2021,,, 103-129. https://doi.org/10.1007/978-3-030-53069-3_3
  4. Faisal Al-Akayleh, Samer Adwan, Mai Khanfar, Nasir Idkaidek, Mayyas Al-Remawi. A Novel Eutectic-Based Transdermal Delivery System for Risperidone. AAPS PharmSciTech 2021, 22 (1) https://doi.org/10.1208/s12249-020-01844-4
  5. Cristian Grazioli, Georgina Faura, Nicolò Dossi, Rosanna Toniolo, Franco Tubaro, Fabio Terzi, Gino Bontempelli. A colorimetric paper-based smart label soaked with a deep-eutectic solvent for the detection of malondialdehyde. Sensors and Actuators B: Chemical 2020, , 129174. https://doi.org/10.1016/j.snb.2020.129174
  6. Eduardo Silva, Filipe Oliveira, Joana M. Silva, Ana Matias, Rui L. Reis, Ana Rita C. Duarte. Optimal Design of THEDES Based on Perillyl Alcohol and Ibuprofen. Pharmaceutics 2020, 12 (11) , 1121. https://doi.org/10.3390/pharmaceutics12111121
  7. Filipe Silva Nunes de Oliveira, Ana Rita Cruz Duarte. A look on target-specificity of eutectic systems based on natural bioactive compounds. 2020,,https://doi.org/10.1016/bs.abr.2020.09.008
  8. Joana M. Silva, Eduardo Silva, Rui L. Reis, Ana Rita C. Duarte. A closer look in the antimicrobial properties of deep eutectic solvents based on fatty acids. Sustainable Chemistry and Pharmacy 2019, 14 , 100192. https://doi.org/10.1016/j.scp.2019.100192

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