Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating
Improving medical implants with functional polymer coatings is an effective way to further improve the level of medical care. Antibacterial and biofilm-preventing properties are particularly desirable in the area of wound healing, since there is a generally high risk of infection, often with a chron...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-10-01
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| Series: | Pharmaceutics |
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| Online Access: | https://www.mdpi.com/1999-4923/13/10/1647 |
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| author | Max Borgolte Oliver Riester Tereza Kacerova Simone Rentschler Magnus S. Schmidt Susanne Jacksch Markus Egert Stefan Laufer René Csuk Hans-Peter Deigner |
| author_facet | Max Borgolte Oliver Riester Tereza Kacerova Simone Rentschler Magnus S. Schmidt Susanne Jacksch Markus Egert Stefan Laufer René Csuk Hans-Peter Deigner |
| author_sort | Max Borgolte |
| collection | DOAJ |
| description | Improving medical implants with functional polymer coatings is an effective way to further improve the level of medical care. Antibacterial and biofilm-preventing properties are particularly desirable in the area of wound healing, since there is a generally high risk of infection, often with a chronic course in the case of biofilm formation. To prevent this we here report a polymeric design of polymer-bound <i>N</i>-acetyl-glucosamine-oligoethylene glycol residues that mimic a cationic, antibacterial, and biocompatible chitosan surface. The combination of easy to use, crosslinkable, thin, potentially 3D-printable polymethacrylate layering with antibacterial and biocompatible functional components will be particularly advantageous in the medical field to support a wide range of implants as well as wound dressings. Different polymers containing a <i>N</i>-acetylglucosamine-methacryloyl residue with oligoethylene glycol linkers and a methacryloyl benzophenone crosslinker were synthesized by free radical polymerization. The functional monomers and corresponding polymers were characterized by <sup>1</sup>H, <sup>13</sup>C NMR, and infrared (IR) spectroscopy. The polymers showed no cytotoxic or antiadhesive effects on fibroblasts as demonstrated by extract and direct contact cell culture methods. Biofilm formation was reduced by up to 70% and antibacterial growth by 1.2 log, particularly for the 5% GlcNAc-4EG polymer, as observed for Escherichia coli and Staphylococcus aureus as clinically relevant Gram-negative and Gram-positive model pathogens. |
| first_indexed | 2024-03-10T06:16:21Z |
| format | Article |
| id | doaj.art-880efccff5274eeaa1b42efd26771edb |
| institution | Directory Open Access Journal |
| issn | 1999-4923 |
| language | English |
| last_indexed | 2024-03-10T06:16:21Z |
| publishDate | 2021-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj.art-880efccff5274eeaa1b42efd26771edb2023-11-22T19:39:08ZengMDPI AGPharmaceutics1999-49232021-10-011310164710.3390/pharmaceutics13101647Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible CoatingMax Borgolte0Oliver Riester1Tereza Kacerova2Simone Rentschler3Magnus S. Schmidt4Susanne Jacksch5Markus Egert6Stefan Laufer7René Csuk8Hans-Peter Deigner9Institute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyInstitute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyDepartment of Chemistry, Czech University of Life Sciences, Kamýcká 129, 16500 Prague, Czech RepublicInstitute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyInstitute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyInstitute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyInstitute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyDepartment of Pharmaceutical and Medicinal Chemistry, Institute of Pharmaceutical Sciences, Eberhard Karls University Tuebingen, Auf der Morgenstelle 8, 72076 Tübingen, GermanyDepartment of Organic Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str. 2, 06120 Halle (Saale), GermanyInstitute of Precision Medicine, Furtwangen University, Jakob-Kienzle Str. 17, 78054 Villingen-Schwenningen, GermanyImproving medical implants with functional polymer coatings is an effective way to further improve the level of medical care. Antibacterial and biofilm-preventing properties are particularly desirable in the area of wound healing, since there is a generally high risk of infection, often with a chronic course in the case of biofilm formation. To prevent this we here report a polymeric design of polymer-bound <i>N</i>-acetyl-glucosamine-oligoethylene glycol residues that mimic a cationic, antibacterial, and biocompatible chitosan surface. The combination of easy to use, crosslinkable, thin, potentially 3D-printable polymethacrylate layering with antibacterial and biocompatible functional components will be particularly advantageous in the medical field to support a wide range of implants as well as wound dressings. Different polymers containing a <i>N</i>-acetylglucosamine-methacryloyl residue with oligoethylene glycol linkers and a methacryloyl benzophenone crosslinker were synthesized by free radical polymerization. The functional monomers and corresponding polymers were characterized by <sup>1</sup>H, <sup>13</sup>C NMR, and infrared (IR) spectroscopy. The polymers showed no cytotoxic or antiadhesive effects on fibroblasts as demonstrated by extract and direct contact cell culture methods. Biofilm formation was reduced by up to 70% and antibacterial growth by 1.2 log, particularly for the 5% GlcNAc-4EG polymer, as observed for Escherichia coli and Staphylococcus aureus as clinically relevant Gram-negative and Gram-positive model pathogens.https://www.mdpi.com/1999-4923/13/10/1647carbohydratesglycosidesantibacterialantibiofilmMRSA<i>E. coli</i> |
| spellingShingle | Max Borgolte Oliver Riester Tereza Kacerova Simone Rentschler Magnus S. Schmidt Susanne Jacksch Markus Egert Stefan Laufer René Csuk Hans-Peter Deigner Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating Pharmaceutics carbohydrates glycosides antibacterial antibiofilm MRSA <i>E. coli</i> |
| title | Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating |
| title_full | Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating |
| title_fullStr | Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating |
| title_full_unstemmed | Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating |
| title_short | Methacryloyl-GlcNAc Derivatives Copolymerized with Dimethacrylamide as a Novel Antibacterial and Biocompatible Coating |
| title_sort | methacryloyl glcnac derivatives copolymerized with dimethacrylamide as a novel antibacterial and biocompatible coating |
| topic | carbohydrates glycosides antibacterial antibiofilm MRSA <i>E. coli</i> |
| url | https://www.mdpi.com/1999-4923/13/10/1647 |
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