Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier

Bio-based compounds are a leading direction in the context of the increased demand for these materials due to the numerous advantages associated with their use over conventional materials, which hardly degrade in the environment. At the same time, the use of essential oils and their components is ge...

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Main Authors: Aurica P. Chiriac, Alina Gabriela Rusu, Loredana Elena Nita, Ana-Maria Macsim, Nita Tudorachi, Irina Rosca, Iuliana Stoica, Daniel Tampu, Magdalena Aflori, Florica Doroftei
Format: Article
Language:English
Published: MDPI AG 2021-04-01
Series:Pharmaceutics
Subjects:
Online Access:https://www.mdpi.com/1999-4923/13/4/477
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author Aurica P. Chiriac
Alina Gabriela Rusu
Loredana Elena Nita
Ana-Maria Macsim
Nita Tudorachi
Irina Rosca
Iuliana Stoica
Daniel Tampu
Magdalena Aflori
Florica Doroftei
author_facet Aurica P. Chiriac
Alina Gabriela Rusu
Loredana Elena Nita
Ana-Maria Macsim
Nita Tudorachi
Irina Rosca
Iuliana Stoica
Daniel Tampu
Magdalena Aflori
Florica Doroftei
author_sort Aurica P. Chiriac
collection DOAJ
description Bio-based compounds are a leading direction in the context of the increased demand for these materials due to the numerous advantages associated with their use over conventional materials, which hardly degrade in the environment. At the same time, the use of essential oils and their components is generated mainly by finding alternative solutions to antibiotics and synthetic preservatives due to their bioactive characteristics, but also to their synergistic capacity during the manifestation of different biological properties. The present study is devoted to poly(ethylene brassylate-co-squaric acid) (PEBSA), synthesis and its use for thymol encapsulation and antibacterial system formation. The synthesized copolymer, performed through ethylene brassylate macrolactone ring-opening and copolymerization with squaric acid, was physicochemical characterized. Its amphiphilic character allowed the entrapment of thymol (Ty), a natural monoterpenoid phenol found in oil of thyme, a compound with strong antiseptic properties. The copolymer chemical structure was confirmed by spectroscopic analyses. Thermal analysis evidenced a good thermal stability for the copolymer. Additionally, the antimicrobial activity of PEBSA_Ty complex was investigated against eight different reference strains namely: bacterial strains—<i>Staphylococcus aureus</i> ATCC25923, <i>Escherichia coli</i> ATCC25922, <i>Enterococcus faecalis</i> ATCC 29212, <i>Klebsiella pneumonie</i> ATCC 10031 and <i>Salmonella typhimurium</i> ATCC 14028, yeast strains represented by <i>Candida albicans</i> ATCC10231 and <i>Candida glabrata</i> ATCC 2001, and the fungal strain <i>Aspergillus brasiliensis</i> ATCC9642.
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spelling doaj.art-91d93880352a425d9c547c236a2bad1d2023-11-21T13:48:00ZengMDPI AGPharmaceutics1999-49232021-04-0113447710.3390/pharmaceutics13040477Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil CarrierAurica P. Chiriac0Alina Gabriela Rusu1Loredana Elena Nita2Ana-Maria Macsim3Nita Tudorachi4Irina Rosca5Iuliana Stoica6Daniel Tampu7Magdalena Aflori8Florica Doroftei9Department of Natural Polymers, Bioactive and Biocompatible Materials, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Natural Polymers, Bioactive and Biocompatible Materials, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Natural Polymers, Bioactive and Biocompatible Materials, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Polycondensation and Thermostable Polymers, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Natural Polymers, Bioactive and Biocompatible Materials, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaCenter of Advanced Research in Bionanoconjugates and Biopolymers, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Physical Chemistry of Polymers, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Physical Chemistry of Polymers, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Physics of Polymers and Polymeric Materials, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaDepartment of Physics of Polymers and Polymeric Materials, Petru Poni Institute of Macromolecular Chemistry, 41 A Grigore Ghica Voda Alley, 700487 Iasi, RomaniaBio-based compounds are a leading direction in the context of the increased demand for these materials due to the numerous advantages associated with their use over conventional materials, which hardly degrade in the environment. At the same time, the use of essential oils and their components is generated mainly by finding alternative solutions to antibiotics and synthetic preservatives due to their bioactive characteristics, but also to their synergistic capacity during the manifestation of different biological properties. The present study is devoted to poly(ethylene brassylate-co-squaric acid) (PEBSA), synthesis and its use for thymol encapsulation and antibacterial system formation. The synthesized copolymer, performed through ethylene brassylate macrolactone ring-opening and copolymerization with squaric acid, was physicochemical characterized. Its amphiphilic character allowed the entrapment of thymol (Ty), a natural monoterpenoid phenol found in oil of thyme, a compound with strong antiseptic properties. The copolymer chemical structure was confirmed by spectroscopic analyses. Thermal analysis evidenced a good thermal stability for the copolymer. Additionally, the antimicrobial activity of PEBSA_Ty complex was investigated against eight different reference strains namely: bacterial strains—<i>Staphylococcus aureus</i> ATCC25923, <i>Escherichia coli</i> ATCC25922, <i>Enterococcus faecalis</i> ATCC 29212, <i>Klebsiella pneumonie</i> ATCC 10031 and <i>Salmonella typhimurium</i> ATCC 14028, yeast strains represented by <i>Candida albicans</i> ATCC10231 and <i>Candida glabrata</i> ATCC 2001, and the fungal strain <i>Aspergillus brasiliensis</i> ATCC9642.https://www.mdpi.com/1999-4923/13/4/477bio-based copolymersethylene brassylatesquaric acidring-opening copolymerizationthymolantimicrobial activity
spellingShingle Aurica P. Chiriac
Alina Gabriela Rusu
Loredana Elena Nita
Ana-Maria Macsim
Nita Tudorachi
Irina Rosca
Iuliana Stoica
Daniel Tampu
Magdalena Aflori
Florica Doroftei
Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier
Pharmaceutics
bio-based copolymers
ethylene brassylate
squaric acid
ring-opening copolymerization
thymol
antimicrobial activity
title Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier
title_full Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier
title_fullStr Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier
title_full_unstemmed Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier
title_short Synthesis of Poly(Ethylene Brassylate-Co-squaric Acid) as Potential Essential Oil Carrier
title_sort synthesis of poly ethylene brassylate co squaric acid as potential essential oil carrier
topic bio-based copolymers
ethylene brassylate
squaric acid
ring-opening copolymerization
thymol
antimicrobial activity
url https://www.mdpi.com/1999-4923/13/4/477
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