Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues
Biodegradable polyester fibers have been loaded with two engineered analogues of gramicidin soviet. In these cyclic peptide derivatives, which were designed in a previous work to stabilize the bioactive conformation while enhancing the antimicrobial activity, the D-Phe was replaced by D-Pro, and the...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2017-09-01
|
| Series: | Fibers |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2079-6439/5/3/34 |
| _version_ | 1818015373574799360 |
|---|---|
| author | Silvana Maione Luis Javier del Valle Maria M. Pérez-Madrigal Carlos Cativiela Jordi Puiggalí Carlos Alemán |
| author_facet | Silvana Maione Luis Javier del Valle Maria M. Pérez-Madrigal Carlos Cativiela Jordi Puiggalí Carlos Alemán |
| author_sort | Silvana Maione |
| collection | DOAJ |
| description | Biodegradable polyester fibers have been loaded with two engineered analogues of gramicidin soviet. In these cyclic peptide derivatives, which were designed in a previous work to stabilize the bioactive conformation while enhancing the antimicrobial activity, the D-Phe was replaced by D-Pro, and the L-Pro was changed by 1-aminocyclopropanecarboxylic acid (Ac3c) or by an Ac3c derivative with two vicinal phenyl substituents in a trans relative disposition (S,S-c3diPhe). The diameter, topography, thermal stability and wettability of the polyester fibers, which have been obtained by electrospinning, strongly depend on the molecular constraints and stability of the loaded peptides. More specifically, unloaded and linear gramicidin-loaded fibers (used as control) are hydrophobic, rough and micrometric, while fibers loaded with the cyclic peptides are hydrophilic, ultra-smooth, nanometric and less thermally stable. The activity of the two cyclic peptides increases when loaded into polyester fibers, suggesting that the polymeric matrix stabilizes the bioactive β-sheet structure. The peptide with S,S-c3diPhe displays higher antibiotic potency and biocompatibility than that with Ac3c, which indicates not only that the bioactive conformation is better preserved by the former but also the significant role played by the phenyl rings in the recognition by living cells. |
| first_indexed | 2024-04-14T06:56:59Z |
| format | Article |
| id | doaj.art-5f9775046c22421bbd1aec6221771e4d |
| institution | Directory Open Access Journal |
| issn | 2079-6439 |
| language | English |
| last_indexed | 2024-04-14T06:56:59Z |
| publishDate | 2017-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Fibers |
| spelling | doaj.art-5f9775046c22421bbd1aec6221771e4d2022-12-22T02:06:52ZengMDPI AGFibers2079-64392017-09-01533410.3390/fib5030034fib5030034Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin AnaloguesSilvana Maione0Luis Javier del Valle1Maria M. Pérez-Madrigal2Carlos Cativiela3Jordi Puiggalí4Carlos Alemán5Departament d’Enginyeria Química, EEBE, Universitat Politècnica de Catalunya, Edifici I.2, C/Eduard Maristany, 10-14, 08019 Barcelona, SpainDepartament d’Enginyeria Química, EEBE, Universitat Politècnica de Catalunya, Edifici I.2, C/Eduard Maristany, 10-14, 08019 Barcelona, SpainDepartament d’Enginyeria Química, EEBE, Universitat Politècnica de Catalunya, Edifici I.2, C/Eduard Maristany, 10-14, 08019 Barcelona, SpainDepartamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea-ISQCH, CSIC-Universidad de Zaragoza, C/Pedro Cerbuna, 12, 50009 Zaragoza, SpainDepartament d’Enginyeria Química, EEBE, Universitat Politècnica de Catalunya, Edifici I.2, C/Eduard Maristany, 10-14, 08019 Barcelona, SpainDepartament d’Enginyeria Química, EEBE, Universitat Politècnica de Catalunya, Edifici I.2, C/Eduard Maristany, 10-14, 08019 Barcelona, SpainBiodegradable polyester fibers have been loaded with two engineered analogues of gramicidin soviet. In these cyclic peptide derivatives, which were designed in a previous work to stabilize the bioactive conformation while enhancing the antimicrobial activity, the D-Phe was replaced by D-Pro, and the L-Pro was changed by 1-aminocyclopropanecarboxylic acid (Ac3c) or by an Ac3c derivative with two vicinal phenyl substituents in a trans relative disposition (S,S-c3diPhe). The diameter, topography, thermal stability and wettability of the polyester fibers, which have been obtained by electrospinning, strongly depend on the molecular constraints and stability of the loaded peptides. More specifically, unloaded and linear gramicidin-loaded fibers (used as control) are hydrophobic, rough and micrometric, while fibers loaded with the cyclic peptides are hydrophilic, ultra-smooth, nanometric and less thermally stable. The activity of the two cyclic peptides increases when loaded into polyester fibers, suggesting that the polymeric matrix stabilizes the bioactive β-sheet structure. The peptide with S,S-c3diPhe displays higher antibiotic potency and biocompatibility than that with Ac3c, which indicates not only that the bioactive conformation is better preserved by the former but also the significant role played by the phenyl rings in the recognition by living cells.https://www.mdpi.com/2079-6439/5/3/34biocompatibilityconformational restrictionsencapsulationelectrospinningengineered peptideshydrophobic peptides |
| spellingShingle | Silvana Maione Luis Javier del Valle Maria M. Pérez-Madrigal Carlos Cativiela Jordi Puiggalí Carlos Alemán Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues Fibers biocompatibility conformational restrictions encapsulation electrospinning engineered peptides hydrophobic peptides |
| title | Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues |
| title_full | Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues |
| title_fullStr | Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues |
| title_full_unstemmed | Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues |
| title_short | Antimicrobial Electrospun Fibers of Polyester Loaded with Engineered Cyclic Gramicidin Analogues |
| title_sort | antimicrobial electrospun fibers of polyester loaded with engineered cyclic gramicidin analogues |
| topic | biocompatibility conformational restrictions encapsulation electrospinning engineered peptides hydrophobic peptides |
| url | https://www.mdpi.com/2079-6439/5/3/34 |
| work_keys_str_mv | AT silvanamaione antimicrobialelectrospunfibersofpolyesterloadedwithengineeredcyclicgramicidinanalogues AT luisjavierdelvalle antimicrobialelectrospunfibersofpolyesterloadedwithengineeredcyclicgramicidinanalogues AT mariamperezmadrigal antimicrobialelectrospunfibersofpolyesterloadedwithengineeredcyclicgramicidinanalogues AT carloscativiela antimicrobialelectrospunfibersofpolyesterloadedwithengineeredcyclicgramicidinanalogues AT jordipuiggali antimicrobialelectrospunfibersofpolyesterloadedwithengineeredcyclicgramicidinanalogues AT carlosaleman antimicrobialelectrospunfibersofpolyesterloadedwithengineeredcyclicgramicidinanalogues |