Synthesis, Structure, Electrochemical Properties, and Antioxidant Activity of Organogermanium(IV) Catecholate Complexes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. X-ray Structure
2.2.1. The Molecular Structures in the Crystal State
2.2.2. The Features of Crystal Packing
2.3. Electrochemistry
2.4. Radical Scavenging and Antioxidant Activity
3. Materials and Methods
3.1. General
3.2. Spectroscopic Studies
3.3. Single-Crystal X-ray Analysis
3.4. Synthesis and Characterization
3.5. Electrochemistry
3.6. DPPH Assay
3.7. ABTS Assay
3.8. CUPRAC Assay
3.9. Lipid Peroxidation Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Bond | 1 | 2 * | 3 | 6 ** | 8 *, *** |
---|---|---|---|---|---|
Ge1–O1 | 1.8130(8) | 1.801(1)/1.800(1) | 1.805(1) | 1.800(1) | 1.816(2)/1.812(2) |
Ge1–O2 | 1.8099(9) | 1.802(1)/1.804(1) | 1.813(2) | 1.812(1) | 1.817(2)/1.815(2) |
Ge1–C | Ge1–C15 1.928(1) | Ge1–C15 1.913(2)/1.922(2) | Ge1–C19 1.913(2) | Ge1–C20 1.912(2) | Ge1–C22 1.910(2)/1.914(3) |
Ge1–C17 1.930(1) | Ge1–C21 1.909(2)/1.924(2) | Ge1–C25 1.916(2) | Ge1–C26 1.918(2) | Ge1–C28 1.916(3)/1.915(2) | |
O1–C1 | 1.378(1) | 1.376(2)/1.387(2) | 1.387(2) | 1.385(2) | 1.382(2)/1.380(3) |
O2–C2 | 1.379(1) | 1.384(2)/1.388(2) | 1.371(2) | 1.374(2) | 1.372(3)/1.365(3) |
C1–C2 | 1.406(2) | 1.407(3)/1.401(3) | 1.406(2) | 1.406(2) | 1.401(4)/1.401(3) |
C2–C3 | 1.399(2) | 1.395(2)/1.397(2) | 1.402(3) | 1.394(3) | 1.390(3)/1.397(3) |
C3–C4 | 1.400(2) | 1.397(2)/1.396(3) | 1.424(2) | 1.413(3) | 1.424(3)/1.418(4) |
C4–C5 | 1.392(2) | 1.388(3)/1.389(3) | 1.403(2) | 1.400(2) | 1.390(4)/1.399(3) |
C5–C6 | 1.399(2) | 1.396(2)/1.397(2) | 1.410(3) | 1.404(3) | 1.405(3)/1.401(3) |
C1–C6 | 1.401(2) | 1.396(2)/1.394(2) | 1.390(2) | 1.384(3) | 1.393(3)/1.389(3) |
S1–C3 | - | - | 1.786(2) | 1.778(2) | 1.781(3)/1.784(2) |
S1–C7 | - | - | 1.875(2) | 1.827(2) | 1.747(2)/1.748(2) |
№ | Compound | Eox11/2, V | Ic/Ia | Eox2p, V | Eox3p, V |
---|---|---|---|---|---|
1 | Et2Ge(3,6-Cat) | 1.03 | 1.0 | 1.46 | - |
2 | Ph2Ge(3,6-Cat) | 1.13 | 0.6 | 1.45 | - |
3 | Ph2Ge(4,6-sCat-tBu) | 1.15 | 0.4 | 1.47 | 1.78 |
4 | Ph2Ge(4,6-sCat-Ad) | 1.17 | 0.6 | 1.45 | 1.86 |
5 | Ph2Ge(4,6-sCat-BuOH) | 1.08 | 0.8 | 1.38 | 1.70 |
6 | Ph2Ge(4,6-sCat-Fur) | 1.23 * | - | 1.43 | 1.82 |
7 | Ph2Ge(4,6-sCat-Ver) | 1.18 | 0.5 | 1.42 ** | 1.72 |
8 | Ph2Ge(4,6-sCat-Het) | 1.22 * | - | 1.48 | - |
9 | Ph2Ge(4,6-Cat-PhOH) | 1.12 * | - | 1.51 | - |
10 | Ph2Ge(3,5-Cat) | 1.14 | 0.6 | 1.36 | - |
a Ph3Sb(4,6-Cat-PhOH) | 0.89 | 0.8 | 1.39 | - | |
a Ph3Sb(4,6-sCat-Bu) | 0.94 | 0.7 | 1.40 | 1.69 | |
a Ph3Sb(3,6-Cat) | 0.89 | 0.8 | 1.40 | - |
N | Compound | IC50 (DPPH), µM | TEC50, Min | IC50 (ABTS+), µM | ABTSTEAC |
---|---|---|---|---|---|
1 | Et2Ge(3,6-Cat) | 80.2 ± 2.7 | 55 | 115.5 ± 3.2 | 0.20 ± 0.02 |
2 | Ph2Ge(3,6-Cat) | 59.0 ± 0.5 | 60 | 37.3 ± 0.8 | 0.39 ± 0.09 |
3 | Ph2Ge(4,6-sCat-tBu) | 60.1 ± 0.9 | 37 | 113.0 ± 4.5 | 0.21 ± 0.01 |
4 | Ph2Ge(4,6-sCat-Ad) | 178.0 ± 3.6 | 120 | 76.6 ± 1.8 | 0.33 ± 0.01 |
5 | Ph2Ge(4,6-sCat-BuOH) | 76.4 ± 1.0 | 80 | 32.0 ± 1.5 | 0.54 ± 0.04 |
6 | Ph2Ge(4,6-sCat-Fur) | 85.6 ± 3.2 | 110 | 60.3 ± 1.9 | 0.29 ± 0.03 |
7 | Ph2Ge(4,6-sCat-Ver) | 156.0 ± 4.2 | 180 | 34.1 ± 0.7 | 0.52 ± 0.03 |
8 | Ph2Ge(4,6-sCat-Het) | 12.0 ± 0.5 | 57 | 29.2 ± 0.9 | 0.58 ± 0.02 |
9 | Ph2Ge(4,6-Cat-PhOH) | 7.5 ± 0.3 | 50 | 35.2 ± 0.5 | 0.42 ± 0.08 |
10 | Ph2Ge(3,5-Cat) | 130.4 ± 2.0 | 150 | 45.2 ± 0.9 | 0.35 ± 0.03 |
Trolox | 12.0 ± 0.50 | 10 | 16.0 ± 1.0 | 1.00 ± 0.03 | |
a Ph3Sb(4,6-sCat-Bu) | 29.5 ± 1.20 | 170 | - | - | |
a Ph3Sb(3,6-Cat) | 17.3 ± 0.50 | 60 | - | - |
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Burmistrova, D.A.; Pomortseva, N.P.; Voronina, Y.K.; Kiskin, M.A.; Dolgushin, F.M.; Berberova, N.T.; Eremenko, I.L.; Poddel’sky, A.I.; Smolyaninov, I.V. Synthesis, Structure, Electrochemical Properties, and Antioxidant Activity of Organogermanium(IV) Catecholate Complexes. Int. J. Mol. Sci. 2024, 25, 9011. https://doi.org/10.3390/ijms25169011
Burmistrova DA, Pomortseva NP, Voronina YK, Kiskin MA, Dolgushin FM, Berberova NT, Eremenko IL, Poddel’sky AI, Smolyaninov IV. Synthesis, Structure, Electrochemical Properties, and Antioxidant Activity of Organogermanium(IV) Catecholate Complexes. International Journal of Molecular Sciences. 2024; 25(16):9011. https://doi.org/10.3390/ijms25169011
Chicago/Turabian StyleBurmistrova, Daria A., Nadezhda P. Pomortseva, Yulia K. Voronina, Mikhail A. Kiskin, Fedor M. Dolgushin, Nadezhda T. Berberova, Igor L. Eremenko, Andrey I. Poddel’sky, and Ivan V. Smolyaninov. 2024. "Synthesis, Structure, Electrochemical Properties, and Antioxidant Activity of Organogermanium(IV) Catecholate Complexes" International Journal of Molecular Sciences 25, no. 16: 9011. https://doi.org/10.3390/ijms25169011