Synthesis of Homoveratric Acid-Imprinted Polymers and Their Evaluation as Selective Separation Materials
Abstract
:1. Introduction
2. Results and Discussion
2.1. Affinity of Imprinted Polymers Towards Homoveratric Acid
2.1.1. Imprinting Factors
Polymer No. | Amount of Homoveratric Acid Bound to Polymer ± S.D. [μmol/g] | Imprinting Factor | |
---|---|---|---|
MIP | NIP | ||
1 | 0.61 ± 0.02 | 0.78 ± 0.02 | 0.78 |
2 | 2.23 ± 0.13 | 2.64 ± 0.12 | 0.84 |
3 | 5.03 ± 0.32 | 5.55 ± 0.46 | 0.91 |
4 | 0.49 ± 0.01 | 0.22 ± 0.01 | 2.23 |
5 | 7.25 ± 0.84 | 8.13 ± 0.89 | 0.89 |
6 | 0.98 ± 0.03 | 0.82 ± 0.03 | 1.20 |
7 | 3.84 ± 0.02 | 3.92 ± 0.18 | 0.98 |
8 | 3.46 ± 0.20 | 1.01 ± 0.06 | 3.43 |
2.1.2. Molecular Modeling of Prepolymerization Complexes
2.2. Evaluation of Imprinting Polymers Using Dynamic Binding Procedure
2.3. Effect of Cross-Linker
Polymer No. | Amount of Homoveratric Acid Bound to Polymer ± S.D. [μmol/g] | Imprinting Factor | |
---|---|---|---|
MIP | NIP | ||
8 | 3.46 ± 0.20 | 1.01 ± 0.06 | 3.43 |
8a | 1.41 ± 0.05 | 1.14 ± 0.06 | 1.24 |
8b | 4.12 ± 0.57 | 4.83 ± 0.64 | 0.85 |
2.4. Binding Characteristics
2.5. Morphology of Particles
2.6. IR Spectra of Selected Polymers
2.7. Molecular Recognition Mechanism
2.8. Selectivity Toward Dopamine and Its Metabolites
2.9. Application of MIP8 to Separation of Homoveratric Acid
Extraction Steps | MIP8 |
---|---|
Found [nmol] | |
1. Conditioning (2 mL, water) | < L.Q.a |
Bound [nmol] | |
2. Loading (total of 10 × 2 mL, 75 μmol/L) | 829 ± 32 |
Found [nmol] | |
3. Washing (1 mL, water) | 69.5 ± 2.7 |
4. Eluting (total of 2 × 2 mL, methanol) | 832 ± 32 |
2.9.1. Preliminary Analysis of Homoveratric Acid Separation from Artificial Urine
Steps | AU1 | AU2 |
---|---|---|
Found [nmol] | ||
1. Conditioning (2 mL, water) | < L.Q.a | < L.Q.a |
Bound [nmol] | ||
2. Loading (total of 10 × 2 mL, 75 μmol/L) | 168.0 ± 6.4 | 317 ± 12 |
Found [nmol] | ||
3. Washing (1 mL, water) | 28.3 ± 1.1 | 36.0 ± 1.4 |
4. Eluting (total of 2 × 2 mL, methanol) | 157 ± 6.0 | 312 ± 12 |
3. Experimental
3.1. General
3.2. Molecular Modeling
3.3. Preparation of Homoveratric Acid Imprinted Polymer
No of MIPs | Template mg [mmol] | Functional Monomermg [mmol] | Cross-linkermL [mmol] | Initiatormg | PorogenmL |
---|---|---|---|---|---|
1 | 2-vinylpyridine (1) | EGDMA | CHC | DMF | |
39.2 [0.2] | 84.1 [0.8] | 0.754 [4.0] | 14.1 | 0.841 | |
2 | 4-vinylpyridine (2) | EGDMA | CHC | DMF | |
39.2 [0.2] | 84.1 [0.8] | 0.754 [4.0] | 14.1 | 0.841 | |
3 | 1-vinylimidazole (3) | EGDMA | CHC | DMF | |
39.2 [0.2] | 75.3 [0.8] | 0.754 [4.0] | 14.1 | 0.827 | |
4 | N-allylaniline (4) | EGDMA | CHC | DMF | |
39.2 [0.2] | 106.6 [0.8] | 0.754 [4.0] | 14.1 | 0.863 | |
5 | N-allylpiperazine (5) | EGDMA | CHC | DMF | |
39.2 [0.2] | 101.0 [0.8] | 0.754 [4.0] | 14.1 | 0.866 | |
6 | allylurea (6) | EGDMA | CHC | DMF | |
39.2 [0.2] | 80.1 [0.8] | 0.754 [4.0] | 14.1 | 0.754 | |
7 | allylthiourea (7) | EGDMA | CHC | DMF | |
39.2 [0.2] | 92.9 [0.8] | 0.754 [4.0] | 14.1 | 0.754 | |
8 | allylamine (8) | EGDMA | CHC | DMF | |
39.2 [0.2] | 45.7 [0.8] | 0.754 [4.0] | 14.1 | 0.814 | |
8a | TGDMA | CHC | DMF | ||
allylamine (8) | 1.145 [4.0] | 14.1 | 1.109 | ||
8b | 39.2 [0.2] | 45.7 [0.8] | TRIM | CHC | DMF |
0.271 [0.8] | 4.7 | 0.331 |
3.4. Binding Experiments
4. Conclusions
Acknowledgements
References and Notes
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Dana, M.; Luliński, P.; Maciejewska, D. Synthesis of Homoveratric Acid-Imprinted Polymers and Their Evaluation as Selective Separation Materials. Molecules 2011, 16, 3826-3844. https://doi.org/10.3390/molecules16053826
Dana M, Luliński P, Maciejewska D. Synthesis of Homoveratric Acid-Imprinted Polymers and Their Evaluation as Selective Separation Materials. Molecules. 2011; 16(5):3826-3844. https://doi.org/10.3390/molecules16053826
Chicago/Turabian StyleDana, Mariusz, Piotr Luliński, and Dorota Maciejewska. 2011. "Synthesis of Homoveratric Acid-Imprinted Polymers and Their Evaluation as Selective Separation Materials" Molecules 16, no. 5: 3826-3844. https://doi.org/10.3390/molecules16053826