One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials
Amino acid-based hydrogels have received widespread attention because of their wide range of sources, biodegradability, and biocompatibility. Despite considerable progress, the development of such hydrogels has been limited by critical problems such as bacterial infection and complex preparation. He...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/8/3334 |
| _version_ | 1827744309912272896 |
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| author | Xianwen Song Shunmei He Jun Zheng Shutong Yang Qiang Li Yi Zhang |
| author_facet | Xianwen Song Shunmei He Jun Zheng Shutong Yang Qiang Li Yi Zhang |
| author_sort | Xianwen Song |
| collection | DOAJ |
| description | Amino acid-based hydrogels have received widespread attention because of their wide range of sources, biodegradability, and biocompatibility. Despite considerable progress, the development of such hydrogels has been limited by critical problems such as bacterial infection and complex preparation. Herein, by using the non-toxic gluconolactone (GDL) to adjust the pH of the solution to induce the rapid self-assembly of N-[(benzyloxy)carbonyl]-L-tryptophan (ZW) to form a three-dimensional (3D) gel network, we developed a stable and effective self-assembled small-molecule hydrogel. Characterization assays and molecular dynamics studies indicate that π–π stacking and hydrogen bonding are the main drivers of self-assembly between ZW molecules. In vitro experiments further confirmed this material’s sustained release properties, low cytotoxicity, and excellent antibacterial activity, particularly against Gram-negative <i>Escherichia coli</i> and Gram-positive <i>Staphylococcus aureus</i>. This study provides a different and innovative perspective for the further development of antibacterial materials based on amino acid derivatives. |
| first_indexed | 2024-03-11T04:42:52Z |
| format | Article |
| id | doaj.art-c7d4189b2f3b4540bacc6a816328ec59 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:42:52Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c7d4189b2f3b4540bacc6a816328ec592023-11-17T20:37:30ZengMDPI AGMolecules1420-30492023-04-01288333410.3390/molecules28083334One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial MaterialsXianwen Song0Shunmei He1Jun Zheng2Shutong Yang3Qiang Li4Yi Zhang5Hunan Provincial Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, ChinaHunan Provincial Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, ChinaHunan Provincial Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, ChinaHunan Provincial Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, ChinaHunan Provincial Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, ChinaHunan Provincial Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, ChinaAmino acid-based hydrogels have received widespread attention because of their wide range of sources, biodegradability, and biocompatibility. Despite considerable progress, the development of such hydrogels has been limited by critical problems such as bacterial infection and complex preparation. Herein, by using the non-toxic gluconolactone (GDL) to adjust the pH of the solution to induce the rapid self-assembly of N-[(benzyloxy)carbonyl]-L-tryptophan (ZW) to form a three-dimensional (3D) gel network, we developed a stable and effective self-assembled small-molecule hydrogel. Characterization assays and molecular dynamics studies indicate that π–π stacking and hydrogen bonding are the main drivers of self-assembly between ZW molecules. In vitro experiments further confirmed this material’s sustained release properties, low cytotoxicity, and excellent antibacterial activity, particularly against Gram-negative <i>Escherichia coli</i> and Gram-positive <i>Staphylococcus aureus</i>. This study provides a different and innovative perspective for the further development of antibacterial materials based on amino acid derivatives.https://www.mdpi.com/1420-3049/28/8/3334antimicrobial materialsamino acid-based hydrogelstryptophanself-assemblyhydrogen bonding |
| spellingShingle | Xianwen Song Shunmei He Jun Zheng Shutong Yang Qiang Li Yi Zhang One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials Molecules antimicrobial materials amino acid-based hydrogels tryptophan self-assembly hydrogen bonding |
| title | One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials |
| title_full | One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials |
| title_fullStr | One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials |
| title_full_unstemmed | One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials |
| title_short | One-Step Construction of Tryptophan-Derived Small Molecule Hydrogels for Antibacterial Materials |
| title_sort | one step construction of tryptophan derived small molecule hydrogels for antibacterial materials |
| topic | antimicrobial materials amino acid-based hydrogels tryptophan self-assembly hydrogen bonding |
| url | https://www.mdpi.com/1420-3049/28/8/3334 |
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