Antioxidant Activity of Metal Nanoparticles Coated with Tocopherol-Like Residues—The Importance of Studies in Homo- and Heterogeneous Systems
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Reagents
2.2. General Information
2.3. Synthesis Procedures
2.3.1. 2,2′-Diaminodiethyl disulfide dihydrochloride (2)
2.3.2. N,N’-(disulfanediylbis(ethane-2,1-diyl))bis(6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxamide) (3)
2.3.3. 6-hydroxy-N-(2-mercaptoethyl)-5,7,8-trimethylchromane-2-carboxamide (4)
2.3.4. AuNPs Stabilized with TOAB (5)
2.3.5. AuNPs 5 Functionalized with Chromanol Derivative (1A)
2.3.6. AuNPs Functionalized with Chromanol Derivative (1B)
2.4. Preparation of Micelles
2.5. Preparation of Liposomes—Large Unilamellar Vesicles (LUVs)
2.6. Methodology of Autoxidation Measurements
3. Results and Discussion
3.1. Synthesis
3.2. Methodology of Calculation of Kinetic Parameters
3.3. Antioxidant Activity in Homogeneous System
3.4. Antioxidant Activity in Heterogeneous Systems
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations:
ABAP | 2:2’-azobis(2-amidinopropane) |
AgNPs | silver nanoparticles |
AIBN | α,α’-azobisisobutyronitrile |
AuNPs | gold nanoparticles |
BOP | benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate |
DLS | Dynamic Light Scattering |
DMAP | 4-dimethylaminopyridine |
DMPC | 1,2-dimyristoyl-sn-glycero-3-phosphocholine |
dpph• | 2,2-diphenyl-1-picrylhydrazyl radical |
HOBt | hydroxybenzotriazole |
LinMe | methyl linoleate |
NPs | nanoparticles |
PMHC | 2,2,5,7,8-pentamethylchroman-6-ol |
R• | alkyl radical |
ROO• | peroxyl radical |
ROS | Reactive Oxygen Species |
TEM | transmission electron microscopy |
TGA | thermogravimetric analysis |
TOAB | tetraoctylammonium bromide |
Triton X-100 | polyethylene glycol p-(1,1,3,3-tetramethylbutyl)-phenyl ether |
Trolox | 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid |
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Compound | Concentration | τ/min | 10−5 × kinh/M−1 s−1 |
---|---|---|---|
3 | 5 µM | 48 ± 5 a | 6.93 ± 0.31 |
1A | 10.3 ppm b | 40 ± 3 a | 6.95 ± 0.36 |
Experimental System | τ/min | Ria/nMs−1 | Rinh/nMs−1 | Rox/Rinhb | 10−3 × kinh/M−1 s−1 |
---|---|---|---|---|---|
micelles | |||||
PMHC | 7.6 ± 0.7 | 4.4 ± 0.4 | 37 ± 5 | 9.0 | 18.8 ± 3.8 |
Trolox | 9.6 ± 0.4 | 4.4 ± 0.4 | 47 ± 8 | 7.4 | 4.5 ± 0.9 |
1B | 9.3 ± 0.6 | 4.4 ± 0.4 | 87 ± 5 | 4.0 | 2.2 ± 0.4 |
liposomes | |||||
PMHC | 8.6 ± 0.6 | 3.8 ± 0.4 | 20 ± 6 | 5.0 | 13.9 ± 2.7 |
Trolox | 8.7 ± 0.3 | 3.8 ± 0.4 | 24 ± 2 | 4.2 | 13.4 ± 2.7 |
1B | - | 3.8 ± 0.4 | 67 ± 3 c | 1.5 | - |
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Konopko, A.; Kusio, J.; Litwinienko, G. Antioxidant Activity of Metal Nanoparticles Coated with Tocopherol-Like Residues—The Importance of Studies in Homo- and Heterogeneous Systems. Antioxidants 2020, 9, 5. https://doi.org/10.3390/antiox9010005
Konopko A, Kusio J, Litwinienko G. Antioxidant Activity of Metal Nanoparticles Coated with Tocopherol-Like Residues—The Importance of Studies in Homo- and Heterogeneous Systems. Antioxidants. 2020; 9(1):5. https://doi.org/10.3390/antiox9010005
Chicago/Turabian StyleKonopko, Adrian, Jaroslaw Kusio, and Grzegorz Litwinienko. 2020. "Antioxidant Activity of Metal Nanoparticles Coated with Tocopherol-Like Residues—The Importance of Studies in Homo- and Heterogeneous Systems" Antioxidants 9, no. 1: 5. https://doi.org/10.3390/antiox9010005