Antimicrobial Chitosan Conjugates: Current Synthetic Strategies and Potential Applications
Abstract
:1. Introduction
2. Methodologies for Covalent Bioactive Substances
2.1. Free Radical-Induced Conjugation
2.2. Carbodiimide Chemistry
2.3. Coupling by Forming a Schiff Base
2.4. Functional Group Conversion Strategy
2.5. Enzyme-Assisted Coupling Reaction
2.6. Other Methods
3. Physiochemical Properties, Antimicrobial Activities, and Potential Applications
3.1. Physiochemical Properties and Antimicrobial Activities
3.2. Potential Applications
4. Challenge and Limitations
4.1. How Can Chitosan Conjugates Be Properly Designdesigned and Synthesized to Ensure Their Effectiveness?
4.2. How Can the Structure-Activity Relationship and Mechanism of Action of the Chitosan Conjugates Be Clarified?
5. Conclusions and Outlook
Author Contributions
Funding
Conflicts of Interest
References
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Number | Sample | Active Molecule | Linker | Bond Type | References |
---|---|---|---|---|---|
1 | Chitosan-tannic acid: Conjugate | tannic acid | No | Amide/ester | [33] |
2 | Gallic acid-chitosan conjugate | gallic acid | No | Amide/ester | [55] |
3 | Chitosan–hydroxycinnamic acid conjugates | hydroxycinnamic acid | No | Amide/ester | [54] |
4 | Gibberellin–chitosan conjugate | gibberellin | No | Amide | [38] |
5 | Chitosan-caffeic acid conjugates | caffeic acid | No | Amide | [31] |
6 | Curcuminconjugated chitosan | curcumin | No | Imino | [35] |
7 | Chitosan-isoniazid conjugates | isoniazid | epichlorohydrin | Hydrazo/hydrazide | [112] |
8 | Chitosan–thymine conjugate | thymine | bromoacetic acid | Amide | [74] |
9 | chitosan-PVC conjugates | PVC | bromoacetyl bromide | Alkylamino | [97] |
Sample | Microorganism | Antimicrobial Properties | References |
---|---|---|---|
Chitosan-Catechin Conjugate | Bacillus subtilis | MIC: 64 μg/mL (Conjugate); 128 μg/mL (chitosan) | [34] |
Chitosan-Caffeic Acid Conjugate | Staphylococcus aureus | MIC: 8 μg/mL (Conjugate); 16 μg/m(chitosan) | [116] |
Chitosan–hydroxycinnamic acid conjugates | Bacillus subtilis | MIC: 2 μg/mL (CFA (I)); 128 μg/mL(chitosan) | [54] |
Chitosan thiolated conjugate | E. coli | MIC: 2.9 mg/mL (TCNAC); 4.1 mg/mL(chitosan) | [39] |
Chitosan thiolated conjugate | Bacillus subtilis | MIC: 0.25 mg/mL (CA-g-CS); 2 mg/mL(chitosan) | [69] |
chitosan–lauricacid conjugate | Staphylococcus aureus | Antibacterial rate: 95.6% (Ti-PDOP-Chi–2.5%LA) | [117] |
Cinnamic acids conjugated chitosan | Ralstonia solanacearum−5 | IC50: 0.23 mg/mL (CTS-g-CA)); 0.56 mg/mL(chitosan) | [118] |
Chitosan gallic acid conjugate | C. albicans | Reduction of fungi: 70%(GA); 61%(chitosan) | [100] |
Sulfadiazine—Chitosan Conjugates | Listeria monocytogenes | Inhibition rate: 100% (PEC Lm-SDZ); 58%(chitosan) | [48] |
Polylysine–chitosanconjugates | Beer yeast | Inhibition zone: 1.36 cm (conjugate) 0.96 cm (chitosan) | [109] |
Hydrocaffeic acid conjugated chitosan | S. epidermidis | Enhanced antimicrobial activity compared to pure chitosan. | [119] |
Sample | Potential Applications | Physiochemical Properties | Bio-Functions | Cytotoxicity | References |
---|---|---|---|---|---|
LED 209 conjugated chitosan | Antimicrobial and anti-adhesion material | Increasing solubility with increase in DS | Highly selective activity and anti-adhesion activity against MDR-E. coli | Minor cytotoxicity to mammalian cells. | [114] |
Galabiose-chitosan Conjugate | Anti-adhesion agents | Showed good solubility in neutral water (1.0 mg/mL) | The highest inhibitory effect at the DP of 1839 (MIC:1.7 nM) | n.d | [120] |
Gibberellin–chitosan | Fungicide release | Good water solubility and stability | n.d | n.d | [38] |
Dhvar-5-chitosan conjugate | Antimicrobial surfaces | lower viscosity values | Displayed bactericidal effect. | No cytotoxic potential. | [96] |
Curcumin conjugated chitosan | Anti-skin infection agent | n.d | Be effective against E. coli and S. Auerus | Cyto and hemo-compatible | [35] |
Inulin–LCS Conjugate | Anti-biofilm reagent | Good water solubility | Showed similar biofilm eradication with florfenicol at 500 μg/mL | Low cellular toxicity to mammalian | [83] |
Gallic acid-grafted-chitosan | Biomaterials in food packaging | An increase in water solubility; exhibited darker appearance and weaker transmittance | Significantly enhanced antibacterial ability | n.d | [72] |
Gallic acid grafted chitin-glucan complex | Biomedical areas | n.d | Completely inhibited the growth of Bacillus subtilis and Escherichia coli | Non-hazardous and biocompatible | |
Chitosan–hydroxycinnamic acid conjugates | Food and pharmaceutical industries | n.d | Exhibited better antimicrobial activity than chitosan | No cytotoxic activity | [56] |
Chitosan–lysozyme conjugates | Ingredient with emulsifying properties | Greatly improved solubility and emulsion stability | Enhanced bactericidal action against Escherichia coil K-12, | n.d | [54] |
lysozyme-chitosan oligosaccharide conjugates | Refractory infection drugs | n.d | Exhibited antibacterial activity and low drug resistance | Low hemolytic activity | [110] |
Cefuroxime conjugated chitosan | Anti-chronic wound infection drugs | Decrease in the rate of swelling and degradation rate | Showed an efficient antibacterial activity over a longer period. | Have good blood compatibility | [106] |
Chitosan-phenolic acid conjugates | Food preservatives | Improved water solubility | Showed broad spectrum antibacterial activity | n.d | [42] |
Chitosan-isoniazid conjugates | Antituberculosis drugs | Enhanced solubility under physi-ological conditions | Comparable or slightly higher minimum inhibitory concentration for conjugates than for INH itself | Reduced biodegradability and decreased toxicity | [121] |
Proanthocyanidin-chitosan conjugate | Food nutraceutical, and Biomedicine filed | Had lower crystallinity and thermal stability than chitosan | Showed bacterial strain-depended behavior in the antibacterial activity compared with chitosan | n.d | [112] |
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Qin, Y.; Li, P. Antimicrobial Chitosan Conjugates: Current Synthetic Strategies and Potential Applications. Int. J. Mol. Sci. 2020, 21, 499. https://doi.org/10.3390/ijms21020499
Qin Y, Li P. Antimicrobial Chitosan Conjugates: Current Synthetic Strategies and Potential Applications. International Journal of Molecular Sciences. 2020; 21(2):499. https://doi.org/10.3390/ijms21020499
Chicago/Turabian StyleQin, Yukun, and Pengcheng Li. 2020. "Antimicrobial Chitosan Conjugates: Current Synthetic Strategies and Potential Applications" International Journal of Molecular Sciences 21, no. 2: 499. https://doi.org/10.3390/ijms21020499