Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases
<i>N</i>-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC), a cationic quaternary ammonium salt polymer exhibiting good solubility in water, is widely used because of its low toxicity and good biocompatibility. Herein, through ion exchange reaction, we prepared <i>N</i&...
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MDPI AG
2022-01-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/2/86 |
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| author | Jingmin Cui Xia Ji Yingqi Mi Qin Miao Fang Dong Wenqiang Tan Zhanyong Guo |
| author_facet | Jingmin Cui Xia Ji Yingqi Mi Qin Miao Fang Dong Wenqiang Tan Zhanyong Guo |
| author_sort | Jingmin Cui |
| collection | DOAJ |
| description | <i>N</i>-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC), a cationic quaternary ammonium salt polymer exhibiting good solubility in water, is widely used because of its low toxicity and good biocompatibility. Herein, through ion exchange reaction, we prepared <i>N</i>-2-hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid Schiff bases with good biological activities. The accuracy of the structures was verified by FT-IR and <sup>1</sup>H NMR. The antibacterial activity, antifungal activity, and scavenging ability of DPPH radical and superoxide radical of HACC derivatives were significantly improved compared with that of HACC. In particular, HACGM (HACC-potassium 2-((2-hydroxy-3-methoxybenzylidene)amino)acetate) and HACGB (HACC-potassium 2-((5-bromo-2-hydroxybenzylidene)amino)acetate) showed good inhibitory effect on bacteria and fungi, including <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, <i>Botrytis cinerea,</i> and <i>Fusarium oxysporum</i> f. sp. <i>cubense</i>. The inhibition rate of HACGB on <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> could reach 100% at the concentration of 0.1 mg/mL, and the inhibition rate of HACGM and HACGB on <i>Botrytis cinerea</i> and <i>Fusarium oxysporum</i> f. sp. <i>cubense</i> could also reach 100% at the concentration of 0.5 mg/mL. Improving antimicrobial and antioxidant activities of HACC could provide ideas and experiences for the development and utilization of chitosan derivatives. |
| first_indexed | 2024-03-09T21:33:13Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T21:33:13Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-42d8227b0a594023b6d8994d07876e052023-11-23T20:49:36ZengMDPI AGMarine Drugs1660-33972022-01-012028610.3390/md20020086Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff BasesJingmin Cui0Xia Ji1Yingqi Mi2Qin Miao3Fang Dong4Wenqiang Tan5Zhanyong Guo6Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, ChinaSchool of Pharmacy, Qilu Medical University, Zibo 255300, ChinaKey Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, ChinaKey Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, ChinaKey Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, ChinaKey Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, ChinaKey Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China<i>N</i>-2-hydroxypropyltrimethyl ammonium chloride chitosan (HACC), a cationic quaternary ammonium salt polymer exhibiting good solubility in water, is widely used because of its low toxicity and good biocompatibility. Herein, through ion exchange reaction, we prepared <i>N</i>-2-hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid Schiff bases with good biological activities. The accuracy of the structures was verified by FT-IR and <sup>1</sup>H NMR. The antibacterial activity, antifungal activity, and scavenging ability of DPPH radical and superoxide radical of HACC derivatives were significantly improved compared with that of HACC. In particular, HACGM (HACC-potassium 2-((2-hydroxy-3-methoxybenzylidene)amino)acetate) and HACGB (HACC-potassium 2-((5-bromo-2-hydroxybenzylidene)amino)acetate) showed good inhibitory effect on bacteria and fungi, including <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, <i>Botrytis cinerea,</i> and <i>Fusarium oxysporum</i> f. sp. <i>cubense</i>. The inhibition rate of HACGB on <i>Staphylococcus aureus</i> and <i>Escherichia coli</i> could reach 100% at the concentration of 0.1 mg/mL, and the inhibition rate of HACGM and HACGB on <i>Botrytis cinerea</i> and <i>Fusarium oxysporum</i> f. sp. <i>cubense</i> could also reach 100% at the concentration of 0.5 mg/mL. Improving antimicrobial and antioxidant activities of HACC could provide ideas and experiences for the development and utilization of chitosan derivatives.https://www.mdpi.com/1660-3397/20/2/86<i>N</i>-2-hydroxypropyltrimethyl ammonium chloride chitosanamino acid Schiff basesantimicrobial activityantioxidant activity |
| spellingShingle | Jingmin Cui Xia Ji Yingqi Mi Qin Miao Fang Dong Wenqiang Tan Zhanyong Guo Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases Marine Drugs <i>N</i>-2-hydroxypropyltrimethyl ammonium chloride chitosan amino acid Schiff bases antimicrobial activity antioxidant activity |
| title | Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases |
| title_full | Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases |
| title_fullStr | Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases |
| title_full_unstemmed | Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases |
| title_short | Antimicrobial and Antioxidant Activities of <i>N</i>-2-Hydroxypropyltrimethyl Ammonium Chitosan Derivatives Bearing Amino Acid Schiff Bases |
| title_sort | antimicrobial and antioxidant activities of i n i 2 hydroxypropyltrimethyl ammonium chitosan derivatives bearing amino acid schiff bases |
| topic | <i>N</i>-2-hydroxypropyltrimethyl ammonium chloride chitosan amino acid Schiff bases antimicrobial activity antioxidant activity |
| url | https://www.mdpi.com/1660-3397/20/2/86 |
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