2-Pyridinecarboxaldehyde-Modified Chitosan–Silver Complexes: Optimized Preparation, Characterization, and Antibacterial Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Preparation of PCA-CS-Ag Complex
2.2. Single-Factor Experiment Results and Analysis
2.2.1. Effect of the Additional Amount of Silver Nitrate on the Silver Content
2.2.2. Effect of the Solution pH on the Silver Content
2.2.3. Effect of the Reaction Temperature on the Silver Content
2.3. Optimization Preparation of PCA-CS-Ag Complex
2.3.1. Experimental Design and Results
2.3.2. Regression Modeling and Analysis of Variance (ANOVA)
2.3.3. Optimization Validation
2.4. UV–Vis Analysis
2.5. FT-IR Analysis
2.6. 1H NMR Analysis
2.7. TG Analysis
2.8. Molecular Computation Study
2.9. Antibacterial Activity
3. Materials and Methods
3.1. Materials
3.2. Synthesis of 2-Pyridinecarboxaldehyde-Modified Chitosan (PCA-CS)
3.3. Preparation of PCA-CS-Ag Complex
3.4. Investigation of the Influence of the Preparation Conditions
3.5. Box–Behnken Design
3.6. Ultraviolet–Visible (UV–Vis) Spectroscopy
3.7. Fourier-Transform Infrared (FT-IR) Spectroscopy
3.8. Proton Nuclear Magnetic Resonance (1H NMR) Spectroscopy
3.9. Thermogravimetric (TG) Analysis
3.10. Molecular Computation Study
3.11. Antibacterial Activity Determination
3.11.1. Zone of Inhibition (ZOI) Assay
3.11.2. Determination of Antibacterial Rate with Optical Density Method
3.12. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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No. | A: Additional Amount of AgNO3 (mg) | B: pH | C: Temperature (°C) | Silver Content (mg/g) |
---|---|---|---|---|
1 | 0 (60) | −1 (3) | −1 (60) | 9.92 |
2 | 0 (60) | −1 (3) | 1 (80) | 9.61 |
3 | 0 (60) | 1 (5) | −1 (60) | 10.19 |
4 | 0 (60) | 1 (5) | 1 (80) | 8.92 |
5 | −1 (40) | 0 (4) | −1 (60) | 9.64 |
6 | −1 (40) | 0 (4) | 1 (80) | 8.83 |
7 | 1 (80) | 0 (4) | −1 (60) | 8.93 |
8 | 1 (80) | 0 (4) | 1 (80) | 8.64 |
9 | −1 (40) | −1 (3) | 0 (70) | 10.81 |
10 | −1 (40) | 1 (5) | 0 (70) | 12.42 |
11 | 1 (80) | −1 (3) | 0 (70) | 12.23 |
12 | 1 (80) | 1 (5) | 0 (70) | 9.38 |
13 | 0 (60) | 0 (4) | 0 (70) | 13.34 |
14 | 0 (60) | 0 (4) | 0 (70) | 12.91 |
15 | 0 (60) | 0 (4) | 0 (70) | 13.53 |
16 | 0 (60) | 0 (4) | 0 (70) | 13.31 |
17 | 0 (60) | 0 (4) | 0 (70) | 13.45 |
Source of Variance | Sum of Square | Degree of Freedom | Mean Square | F-Value | p-Value 1 |
---|---|---|---|---|---|
Model | 57.09 | 9 | 6.34 | 109.22 | <0.0001 ** |
A | 0.79 | 1 | 0.79 | 13.67 | 0.0077 ** |
B | 0.34 | 1 | 0.34 | 5.93 | 0.0451 * |
C | 0.90 | 1 | 0.90 | 15.46 | 0.0057 ** |
AB | 4.97 | 1 | 4.97 | 85.63 | <0.001 |
AC | 0.068 | 1 | 0.068 | 1.16 | 0.3164 |
BC | 0.23 | 1 | 0.23 | 3.97 | 0.0867 |
A2 | 7.95 | 1 | 7.95 | 136.87 | <0.0001 ** |
B2 | 2.21 | 1 | 2.21 | 38.00 | 0.0005 ** |
C2 | 36.00 | 1 | 36.00 | 619.86 | <0.0001 ** |
Residual | 0.41 | 7 | 0.058 | — | — |
Lack of fit | 0.18 | 3 | 0.059 | 1.03 | 0.4672 |
Pure error | 0.23 | 4 | 0.057 | — | — |
Cor. total | 57.50 | 16 | — | — | — |
Energy (kcal/mol) | Monomer of PCA-CS | PCA-CS-Ag (Mode I) | PCA-CS-Ag (Mode II) | PCA-CS-Ag (Mode III) |
---|---|---|---|---|
Stretch | 1.2766 | 2.3763 | 17.8308 | 26.6365 |
Bend | 8.9573 | 51.1380 | 62.5756 | 90.8197 |
Stretch-Bend | 0.6058 | −0.0447 | −0.0597 | 0.4352 |
Torsion | 5.3844 | 59.6525 | 29.8432 | 3.9841 |
Non-1,4 VDW | −6.3229 | −6.8230 | −6.8841 | −18.7602 |
1,4 VDW | 18.3978 | 18.6322 | 21.9594 | 17.9010 |
Dipole/Dipole | −1.6975 | −4.0458 | 0.1046 | 0.8527 |
Total Energy | 26.6016 | 120.8853 | 125.3698 | 121.8691 |
Sample | Antibacterial Rates (%) | |
---|---|---|
E. coli | S. aureus | |
CS | 22.9 | 29.8 |
PCA-CS | 45.7 ** | 51.6 ** |
PCA-CS-Ag | 83.1 **## | 89.3 **## |
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Zhang, Z.; Zhao, Y.; Hu, Z.; Si, Z.; Yang, Z. 2-Pyridinecarboxaldehyde-Modified Chitosan–Silver Complexes: Optimized Preparation, Characterization, and Antibacterial Activity. Molecules 2023, 28, 6777. https://doi.org/10.3390/molecules28196777
Zhang Z, Zhao Y, Hu Z, Si Z, Yang Z. 2-Pyridinecarboxaldehyde-Modified Chitosan–Silver Complexes: Optimized Preparation, Characterization, and Antibacterial Activity. Molecules. 2023; 28(19):6777. https://doi.org/10.3390/molecules28196777
Chicago/Turabian StyleZhang, Zhaoyu, Yurong Zhao, Zhang Hu, Zhenyu Si, and Ziming Yang. 2023. "2-Pyridinecarboxaldehyde-Modified Chitosan–Silver Complexes: Optimized Preparation, Characterization, and Antibacterial Activity" Molecules 28, no. 19: 6777. https://doi.org/10.3390/molecules28196777