Copper(II) Methacrylate Complexes with Imidazole Derivatives—Structural, Spectral and Antitumor Features
Abstract
:1. Introduction
2. Results and Discussion
2.1. Description of the X-ray Crystal Structures of the Complexes
2.2. Characterization of Complexes
2.2.1. Fourier Transform Infrared Spectroscopy
2.2.2. Electronic Spectroscopy
2.2.3. Voltammetric Studies
2.2.4. Thermal Behaviour
2.3. Antitumor Assay
3. Materials and Methods
3.1. General Information
3.2. Synthesis of Complexes
3.3. Cell Culture Conditions
3.4. In Vitro Viability
3.5. Statistical Analysis
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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(1) | (2) | (3) | (4) | (5) | Assignments |
---|---|---|---|---|---|
- | 3311 m | - | 3441 m | 3450 m | ν(OH) |
3173 m 3151 m 3133 m | 3151 m 3129 m | 3140 w 3059 w | 3140 w 3060 w | 3168 m 3155 m 3138 m | ν(CH) + ν(NH) |
2960 m 2925 m | 2954 m 2924 m | 2969 w | 2979 w | 2970 m 2924 m | νas(CH2) |
2866 m | 2891 m | 2929 w | 2930 w | 2878 m | νs(CH2) |
1644 s | 1644 s | 1648 s | 1645 s | 1644 s | ν(C=N) |
1577 m | overlapped | 1613 vs | 1605 vs | 1581 m | δ(NH) + ν(C=C) + ν(C=N) |
1547 vs | 1590 vs | 1549 vs | 1549 vs | 1547 vs | νas(COO) |
1413 m | 1406 m | 1434 m | 1434 m | 1420 m | νs(COO) |
1297 s | - | 1260 w | 1260 w | 1294 s | δ(CH2) |
1237 s | 1236 m | 1252 w | 1257 w | 1236 m | ν(C−N) + δ(CH) |
1166 w | - | 1163 w | 1163 w | 1158 w | ν(C−C) + ν(C−N) + δ(CH) |
954 m | 969 m | 962 w | 977 w | 929 m | δ(CH) + δ(Im ring) |
861 m | 881 m | 834 w | 873 w | 878 m | π(CH) + δ(Im ring) |
749 m | 780 w | 763 w | 768 w | 760 m | π(CH) |
631 m | 625 m | 618 w | 618 w | 623 w | δ(COO) |
Compound | Epc1 * | Epc2 * | Epa1 * | Epa2 * | E1/2 (V) a Cu(I)/Cu(0) | E1/2 (V) b Cu(II)/Cu(I) |
---|---|---|---|---|---|---|
Cu(Macr)2·H2O | −0.598 | −0.266 | 0.187 | |||
(1) | −0.125 | −0.760 | −0.266 | 0.348 | −0.563 | +0.112 |
(2) | −0.215 | −0.769 | −0.185 | 0.419 | −0.477 | +0.102 |
(3) | −0.679 | −1.031 | −0.366 | 0.438 | −0.699 | −0.121 |
(4) | −0.296 | −0.991 | −0.145 | 0.388 | −0.568 | +0.040 |
(5) | −0.629 | −1.051 | −0.175 | 0.418 | −0.613 | −0.106 |
Complex | Step | Thermal Effect | Temp./°C | Δmexp/% | Δmcalc/% | Process |
---|---|---|---|---|---|---|
[Cu(2-MeIm)2(Macr)2] (1) | 1. | Endothermic | 160 | - | - | melting |
2. | Miscellaneous | 160–282 | 41.7 | 41.3 | -2(2-MeIm) | |
3. | Exothermic | 282–845 | 38.5 | 38.7 | Macr oxidative degradation | |
Residue (CuO) | 19.8 | 20.0 | ||||
[Cu(4-MeIm)2(Macr)2(H2O)] (2) | 1. | Endothermic | 100 | - | - | melting |
2. | Miscellaneous | 120–280 | 39.8 | 39.5 | -H2O, -2(4-MeIm) | |
3. | Exothermic | 280–900 | 36.5 | 37.1 | Macr oxidative degradation | |
Residue (CuO) | 19.3 | 19.1 | ||||
[Cu(2-EtIm)2(Macr)2] (3) | 1. | Endothermic | 120 | - | - | melting |
2. | Miscellaneous | 140–290 | 45.5 | 45.1 | -2(2-EtIm) | |
3. | Exothermic | 290–900 | 35.7 | 36.2 | Macr oxidative degradation | |
Residue (CuO) | 18.8 | 18.7 | ||||
[Cu(2-EtIm)2(Macr)2]·H2O (4) | 1. | Endothermic | 80–125 | 4.2 | 4.1 | -H2O |
2. | Endothermic | 133 | - | - | melting | |
3. | Miscellaneous | 145–300 | 43.9 | 43.3 | -2(2-EtIm) | |
Exothermic | 300–900 | 33.9 | 34.7 | Macr oxidative degradation | ||
Residue (CuO) | 18.0 | 17.9 | ||||
[Cu(2-iPrIm)2(Macr)2]·CH3OH (5) | 1. | Endothermic | 155 | - | - | melting |
2. | Endothermic | 160–190 | 6.7 | 6.6 | -CH3OH | |
3. | Endothermic | 190–380 | 45.3 | 45.5 | -2(2-iPrIm) | |
4. | Exothermic | 390–900 | 31.6 | 31.6 | Macr oxidative degradation | |
Residue (CuO) | 16.4 | 16.3 |
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Teodoru, D.V.; Olar, R.; Maxim, C.; Bacalum, M.; Răileanu, M.; Iorgulescu, E.-E.; Vasile Scăețeanu, G.; Badea, M. Copper(II) Methacrylate Complexes with Imidazole Derivatives—Structural, Spectral and Antitumor Features. Molecules 2024, 29, 4010. https://doi.org/10.3390/molecules29174010
Teodoru DV, Olar R, Maxim C, Bacalum M, Răileanu M, Iorgulescu E-E, Vasile Scăețeanu G, Badea M. Copper(II) Methacrylate Complexes with Imidazole Derivatives—Structural, Spectral and Antitumor Features. Molecules. 2024; 29(17):4010. https://doi.org/10.3390/molecules29174010
Chicago/Turabian StyleTeodoru, Dragoș Vlad, Rodica Olar, Cătălin Maxim, Mihaela Bacalum, Mina Răileanu, Emilia-Elena Iorgulescu, Gina Vasile Scăețeanu, and Mihaela Badea. 2024. "Copper(II) Methacrylate Complexes with Imidazole Derivatives—Structural, Spectral and Antitumor Features" Molecules 29, no. 17: 4010. https://doi.org/10.3390/molecules29174010