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Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units

New polymer-bioactive compound systems were obtained by immobilization of triazole derivatives onto grafted copolymers and grafted copolymers carrying betaine units based on gellan and N-vinylimidazole. For preparation of bioactive compound, two new types of heterocyclic thio-derivatives with differ...

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Autores principales: Baranov, Nicolae, Racovita, Stefania, Vasiliu, Silvia, Macsim, Ana Maria, Lionte, Catalina, Sunel, Valeriu, Popa, Marcel, Desbrieres, Jacques, Cheptea, Corina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199293/
https://www.ncbi.nlm.nih.gov/pubmed/34206015
http://dx.doi.org/10.3390/molecules26113330
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author Baranov, Nicolae
Racovita, Stefania
Vasiliu, Silvia
Macsim, Ana Maria
Lionte, Catalina
Sunel, Valeriu
Popa, Marcel
Desbrieres, Jacques
Cheptea, Corina
author_facet Baranov, Nicolae
Racovita, Stefania
Vasiliu, Silvia
Macsim, Ana Maria
Lionte, Catalina
Sunel, Valeriu
Popa, Marcel
Desbrieres, Jacques
Cheptea, Corina
author_sort Baranov, Nicolae
collection PubMed
description New polymer-bioactive compound systems were obtained by immobilization of triazole derivatives onto grafted copolymers and grafted copolymers carrying betaine units based on gellan and N-vinylimidazole. For preparation of bioactive compound, two new types of heterocyclic thio-derivatives with different substituents were combined in a single molecule to increase the selectivity of the biological action. The 5-aryl-amino-1,3,4 thiadiazole and 5-mercapto-1,2,4-triazole derivatives, each containing 2-mercapto-benzoxazole nucleus, were prepared by an intramolecular cyclization of thiosemicarbazides-1,4 disubstituted in acidic and basic medium. The structures of the new bioactive compounds were confirmed by elemental and spectral analysis (FT-IR and (1)H-NMR). The antimicrobial activity of 1,3,4 thiadiazoles and 1,2,4 triazoles was tested on gram-positive and gram-negative bacteria. The triazole compound was chosen to be immobilized onto polymeric particles by adsorption. The Langmuir, Freundlich, and Dubinin–Radushkevich adsorption isotherm were used to describe the adsorption equilibrium. Also, the pseudo-first and pseudo-second models were used to elucidate the adsorption mechanism of triazole onto grafted copolymer based on N-vinylimidazole and gellan (PG copolymer) and grafted copolymers carrying betaine units (PGB1 copolymer). In vitro release studies have shown that the release mechanism of triazole from PG and PGB1 copolymers is characteristic of an anomalous transport mechanism.
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spelling pubmed-81992932021-06-14 Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units Baranov, Nicolae Racovita, Stefania Vasiliu, Silvia Macsim, Ana Maria Lionte, Catalina Sunel, Valeriu Popa, Marcel Desbrieres, Jacques Cheptea, Corina Molecules Article New polymer-bioactive compound systems were obtained by immobilization of triazole derivatives onto grafted copolymers and grafted copolymers carrying betaine units based on gellan and N-vinylimidazole. For preparation of bioactive compound, two new types of heterocyclic thio-derivatives with different substituents were combined in a single molecule to increase the selectivity of the biological action. The 5-aryl-amino-1,3,4 thiadiazole and 5-mercapto-1,2,4-triazole derivatives, each containing 2-mercapto-benzoxazole nucleus, were prepared by an intramolecular cyclization of thiosemicarbazides-1,4 disubstituted in acidic and basic medium. The structures of the new bioactive compounds were confirmed by elemental and spectral analysis (FT-IR and (1)H-NMR). The antimicrobial activity of 1,3,4 thiadiazoles and 1,2,4 triazoles was tested on gram-positive and gram-negative bacteria. The triazole compound was chosen to be immobilized onto polymeric particles by adsorption. The Langmuir, Freundlich, and Dubinin–Radushkevich adsorption isotherm were used to describe the adsorption equilibrium. Also, the pseudo-first and pseudo-second models were used to elucidate the adsorption mechanism of triazole onto grafted copolymer based on N-vinylimidazole and gellan (PG copolymer) and grafted copolymers carrying betaine units (PGB1 copolymer). In vitro release studies have shown that the release mechanism of triazole from PG and PGB1 copolymers is characteristic of an anomalous transport mechanism. MDPI 2021-06-01 /pmc/articles/PMC8199293/ /pubmed/34206015 http://dx.doi.org/10.3390/molecules26113330 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Baranov, Nicolae
Racovita, Stefania
Vasiliu, Silvia
Macsim, Ana Maria
Lionte, Catalina
Sunel, Valeriu
Popa, Marcel
Desbrieres, Jacques
Cheptea, Corina
Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units
title Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units
title_full Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units
title_fullStr Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units
title_full_unstemmed Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units
title_short Immobilization and Release Studies of Triazole Derivatives from Grafted Copolymer Based on Gellan-Carrying Betaine Units
title_sort immobilization and release studies of triazole derivatives from grafted copolymer based on gellan-carrying betaine units
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8199293/
https://www.ncbi.nlm.nih.gov/pubmed/34206015
http://dx.doi.org/10.3390/molecules26113330
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