Design and Antioxidant Properties of Bifunctional 2H-Imidazole-Derived Phenolic Compounds—A New Family of Effective Inhibitors for Oxidative Stress-Associated Destructive Processes
Abstract
:1. Introduction
2. Results
2.1. Study of Electrochemical Behavior of Synthesized Compounds
2.2. Study of Antioxidant Properties of Polyphenols and Aynthesized Compounds
- Electron-transfer (ET);
- Hydrogen atom transfer (HAT);
- Metal chelating mechanism.
2.3. Evaluation of the Reaction Half-Life (t1/2) by Using Potentiometric Method
3. Materials and Methods
3.1. Apparatus
3.2. Reagents and Chemicals
3.3. Experimental
3.3.1. General Procedure for the Synthesis of Hydrochloride Salt of Imidazole-Derived Polyphenolic Compounds Im(1–5)Phl, Im5Pyr, Im5Hyd
3.3.2. General Procedure for the Synthesis of 2H-imidazoles Im1–2
3.4. Procedures
3.4.1. Cyclic Voltammetry
3.4.2. Potentiometric Assay of Determining Antioxidant Capacity
3.5. Potentiometric Assay of Determining Antiradical Capacity
3.6. Folin Assay
3.7. DPPH Assay
3.8. Data Treatment
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Polyphenol Scaffold Imidazole Scaffold | | | | |
---|---|---|---|---|
| Phl a | Pyr a | Hyd a | |
| Im1H (72%) | Im1Phl (94%) | Im1Pyr (85%) b | Im1Hyd (93%) b |
| Im2H (80%) | Im2Phl (95%) | Im2Pyr (75%) b | Im2Hyd (88%) b |
| - | Im3Phl (92%) | Im3Pyr (90%) b | Im3Hyd (91%) b |
| - | Im4Phl (87%) | Im4Pyr (87%) b | Im4Hyd (90%) b |
| - | Im5Phl (88%) | Im5Pyr (91%) | Im5Hyd (93%) |
Polyphenol | Imidazolylpolyphenols | Eox, V | iox, 106 A |
---|---|---|---|
Phloroglucinol | Phl | 0.64 | 2.80 |
Im1Phl | 1.02 | 3.27 | |
Im2Phl | 1.02 | 1.85 | |
Im3Phl | 0.99 | 4.69 | |
Im4Phl | 1.02 | 4.45 | |
Im5Phl | 0.98 | 5.09 | |
Pyrogallol | Pyr | 0.18 0.60 | 2.90 1.63 |
Im1Pyr | 0.57 1.09 | 6.61 1.93 | |
Im2Pyr | 0.45 1.00 | 8.78 3.10 | |
Im3Pyr | 0.45 0.98 | 7.82 3.23 | |
Im4Pyr | 0.52 1.03 | 9.35 3.51 | |
Im5Pyr | 0.18 0.64 | 5.59 7.00 | |
Hydroxyquinol | Hyd | −0.02 1.08 | 9.80 2.20 |
Im1Hyd | 0.36 1.11 | 10.41 11.41 | |
Im2Hyd | 0.54 1.20 | 7.26 6.64 | |
Im3Hyd | 0.38 1.12 | 8.62 7.97 | |
Im4Hyd | 0.38 1.15 | 14.40 12.37 | |
Im5Hyd | 0.14 1.20 | 1.27 6.46 |
Substrates | AOC | ARC | Folin Assay | DPPH Assay | ||||
---|---|---|---|---|---|---|---|---|
104 mol-eq/dm3 | RSD (%) | 104 mol-eq/dm3 | RSD (%) | C(GA) 104 mol-eq/dm3 | RSD (%) | C(AA) 104 mol-eq/dm3 | RSD (%) | |
Phl | 2.84 ± 0.23 | 8.1 | 2.26 ± 0.04 | 2.2 | - | - | 1.22 ± 0.02 | 1.4 |
Pyr | 5.15 ± 0.11 | 1.9 | 2.84 ± 0.03 | 3.2 | 2.08 ± 0.02 | 0.9 | 1.47 ± 0.03 | 1.2 |
Hyd | 1.92 ± 0.04 | 1.9 | 1.89 ± 0.02 | 0.9 | 0.74 ± 0.01 | 1.3 | 1.40 ± 0.01 | 1.5 |
Im1Phl | 1.95 ± 0.04 | 1.9 | 4.01 ± 0.08 | 1.9 | - | - | 0.78 ± 0.01 | 1.4 |
Im2Phl | 2.74 ± 0.08 | 3.1 | 4.02 ± 0.16 | 3.8 | - | - | 0.71 ± 0.03 | 3.3 |
Im3Phl | 1.89 ± 0.02 | 0.9 | * | - | - | - | - | |
Im4Phl | 1.87 ± 0.04 | 2.1 | * | - | - | 0.69 ± 0.01 | 2.4 | |
Im5Phl | 1.88 ± 0.08 | 4.1 | 5.16 ± 0.17 | 2.9 | - | - | 0.70 ± 0.02 | 2.1 |
Im1Pyr | 2.24 ± 0.09 | 3.8 | 2.15 ± 0.02 | 0.9 | 0.50 ± 0.05 | 9.1 | 1.17 ± 0.02 | 2.1 |
Im2Pyr | 2.46 ± 0.02 | 1.2 | 1.51 ± 0.02 | 1.9 | 0.44 ± 0.004 | 1.1 | 1.17 ± 0.01 | 1.2 |
Im3Pyr | 1.76 ± 0.07 | 3.9 | 2.52 ± 0.07 | 3.2 | 0.40 ± 0.02 | 5.5 | 0.93 ± 0.04 | 4.2 |
Im4Pyr | 1.94 ± 0.04 | 1.7 | 2.97 ± 0.03 | 0.8 | 0.41 ± 0.03 | 7.9 | 1.22 ± 0.01 | 1.1 |
Im5Pyr | 4.19 ± 0.34 | 7.8 | 1.26 ± 0.06 | 4.7 | 0.61 ± 0.07 | 10.6 | 1.22 ± 0.01 | 1.1 |
Im1Hyd | 0.98 ± 0.03 | 2.7 | 0.41 ± 0.01 | 1.6 | 0.68 ± 0.05 | 6.9 | 1.12 ± 0.02 | 1.9 |
Im2Hyd | 0.75 ± 0.05 | 6.7 | 0.40 ± 0.02 | 3.8 | 0.78 ± 0.05 | 6.1 | 1.06 ± 0.01 | 1.3 |
Im3Hyd | 0.72 ± 0.01 | 1.7 | 0.81 ± 0.02 | 2.9 | 1.15 ± 0.06 | 5.1 | 1.12 ± 0.07 | 5.9 |
Im4Hyd | 1.58 ± 0.03 | 1.8 | 1.13 ± 0.06 | 4.6 | 0.75 ± 0.09 | 11.0 | 0.95 ± 0.02 | 1.9 |
Im5Hyd | 2.78 ± 0.25 | 8.8 | 0.34 ± 0.06 | 2.3 | 0.92 ± 0.09 | 10.1 | 1.22 ± 0.00 | 0 |
Substance | t1/2 (s) | RSD (%) |
---|---|---|
Phloroglucinol | 133 ± 6 | 4.8 |
Pyrogallol | 5.2 ± 0.3 | 4.6 |
Hydroxyquinol | 1.3 ± 0.1 | 7.6 |
Im1Phl | 42 ± 2 | 4.7 |
Im2Phl | 86 ± 3 | 4.0 |
Im3Phl | 52 ± 2 | 4.6 |
Im4Phl | 46 ± 3 | 8.1 |
Im5Phl | 73 ± 7 | 9.2 |
Im1Pyr | 9.2 ± 0.3 | 2.4 |
Im2Pyr | 5.5 ± 0.4 | 6.9 |
Im3Pyr | 15.3 ± 0.7 | 4.7 |
Im4Pyr | 7.2 ± 0.1 | 3.0 |
Im5Pyr | 11.3 ± 0.64 | 5.9 |
Im1Hyd | 4.5 ± 0.2 | 4.2 |
Im2Hyd | 6.4 ± 0.2 | 3.9 |
Im3Hyd | 5.5 ± 0.3 | 4.7 |
Im4Hyd | 11.1 ± 0.5 | 4.8 |
Im5Hyd | 4.5 ± 0.1 | 2.3 |
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Gerasimova, E.L.; Gazizullina, E.R.; Borisova, M.V.; Igdisanova, D.I.; Nikiforov, E.A.; Moseev, T.D.; Varaksin, M.V.; Chupakhin, O.N.; Charushin, V.N.; Ivanova, A.V. Design and Antioxidant Properties of Bifunctional 2H-Imidazole-Derived Phenolic Compounds—A New Family of Effective Inhibitors for Oxidative Stress-Associated Destructive Processes. Molecules 2021, 26, 6534. https://doi.org/10.3390/molecules26216534
Gerasimova EL, Gazizullina ER, Borisova MV, Igdisanova DI, Nikiforov EA, Moseev TD, Varaksin MV, Chupakhin ON, Charushin VN, Ivanova AV. Design and Antioxidant Properties of Bifunctional 2H-Imidazole-Derived Phenolic Compounds—A New Family of Effective Inhibitors for Oxidative Stress-Associated Destructive Processes. Molecules. 2021; 26(21):6534. https://doi.org/10.3390/molecules26216534
Chicago/Turabian StyleGerasimova, Elena L., Elena R. Gazizullina, Maria V. Borisova, Dinara I. Igdisanova, Egor A. Nikiforov, Timofey D. Moseev, Mikhail V. Varaksin, Oleg N. Chupakhin, Valery N. Charushin, and Alla V. Ivanova. 2021. "Design and Antioxidant Properties of Bifunctional 2H-Imidazole-Derived Phenolic Compounds—A New Family of Effective Inhibitors for Oxidative Stress-Associated Destructive Processes" Molecules 26, no. 21: 6534. https://doi.org/10.3390/molecules26216534