Ruthenium-p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline Ligands with –Br (Br-Qpy) and –Phenoxy (OH-Ph-Qpy) Groups for Cytotoxicity and Catalytic Transfer Hydrogenation Studies: Synthesis and Characterization
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis and Characterization
2.1.1. Synthesis of [Ru(η6-p-cymene)(Br-Qpy)Cl][Cl] (1a)
2.1.2. Synthesis of [Ru(η6-p-cymene)(Br-Qpy)Cl][PF6] (1b)
2.1.3. Synthesis of [Ru(η6-p-cymene)(OH-Ph-Qpy)Cl][Cl] (2a)
2.1.4. Synthesis of [Ru(η6-p-cymene)(OH-Ph-Qpy)Cl][PF6] (2b)
2.2. Single-Crystal X-ray Structural Determination
2.3. Biological Evaluation
2.3.1. Cell Lines
2.3.2. MTT Assay
2.4. Transfer Hydrogenation of Benzophenone Catalyzed by 1a, 1b
3. Results and Discussion
3.1. Chemistry
Electronic Spectra
3.2. Evaluation of Biological Activity
Cell Viability Assay
3.3. Catalytic Transfer Hydrogenation Studies
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | 2b |
---|---|
Color, habit | Orange, Plate |
Size/mm | 0.411 × 0.127 × 0.072 |
Empirical formula | C36H32ClF6N2OPRu × 0.25C3H6O |
FW | 807.11 |
Crystal system | Monoclinic |
Space group | P21/c |
a/Å | 13.6107(5) |
b/Å | 10.5278(3) |
c/Å | 25.8896(11) |
α/° | 90 |
β/° | 92.702(2) |
γ/° | 90 |
V/Å3 | 3705.6(2) |
Z | 4 |
μ/mm−1 | 0.628 |
T/K | 100 |
θmin/max/full (°) | 2.089/28.294/25.242 |
Completeness to θmax/full (%) | 99.9/99.9 |
Reflections Total/ Independent | 95,535/8017 |
Parameters/restraints | 726/340 |
Rint | 0.0517 |
Final R1, wR2 | 0.0586/0.1787 |
Goodness-of-fit | 1.077 |
Largest peak, hole/e.Å−3 | 1.9/−0.9 |
ρcalc/g.cm−3 | 1.447 |
Compounds | HEK293T (IC50 in μM) | HeLa (IC50 in μM) |
---|---|---|
Br-Qpy | 13.7 ± 0.3 | 108.5 ± 3.6 |
OH-Ph-Qpy | 23.4 ± 0.7 | 84.5 ± 2.2 |
[Ru(p-cymene)Cl2]2 | 48.3 ± 1.7 | 48.9 ± 1.7 |
1a | 102.9 ± 3.4 | 106.9 ± 1.1 |
1b | 36.2 ± 1.2 | 109.6 ± 1.5 |
2a | 35.2 ± 4.6 | 75.0 ± 1.0 |
2b | 22.7 ± 1.2 | 85.1 ± 1.8 |
cisplatin | 20.8 ± 0.0 | 9.5 ± 0.0 |
Catalyst | Conversion (%) b | Time (h) | TOF (h−1) |
---|---|---|---|
1a * | 73 | 1 | 73 |
76 | 3 | 25 | |
92 | 24 | 4 | |
1a ** | 81 | 1 | 324 |
94 | 3 | 125 | |
2a * | 45 | 1 | 45 |
70 | 3 | 23 | |
94 | 24 | 4 | |
2a ** | 42 | 1 | 168 |
73 | 3 | 97 |
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Dritsopoulos, A.; Zacharopoulos, N.; Peyret, A.-E.; Karampella, E.; Tsoureas, N.; Cheilari, A.; Machalia, C.; Emmanouilidou, E.; Andreopoulou, A.K.; Kallitsis, J.K.; et al. Ruthenium-p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline Ligands with –Br (Br-Qpy) and –Phenoxy (OH-Ph-Qpy) Groups for Cytotoxicity and Catalytic Transfer Hydrogenation Studies: Synthesis and Characterization. Chemistry 2024, 6, 773-793. https://doi.org/10.3390/chemistry6040046
Dritsopoulos A, Zacharopoulos N, Peyret A-E, Karampella E, Tsoureas N, Cheilari A, Machalia C, Emmanouilidou E, Andreopoulou AK, Kallitsis JK, et al. Ruthenium-p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline Ligands with –Br (Br-Qpy) and –Phenoxy (OH-Ph-Qpy) Groups for Cytotoxicity and Catalytic Transfer Hydrogenation Studies: Synthesis and Characterization. Chemistry. 2024; 6(4):773-793. https://doi.org/10.3390/chemistry6040046
Chicago/Turabian StyleDritsopoulos, Alexandros, Nikolaos Zacharopoulos, Aigli-Eleonora Peyret, Eftychia Karampella, Nikolaos Tsoureas, Antigoni Cheilari, Christina Machalia, Evangelia Emmanouilidou, Aikaterini K. Andreopoulou, Joannis K. Kallitsis, and et al. 2024. "Ruthenium-p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline Ligands with –Br (Br-Qpy) and –Phenoxy (OH-Ph-Qpy) Groups for Cytotoxicity and Catalytic Transfer Hydrogenation Studies: Synthesis and Characterization" Chemistry 6, no. 4: 773-793. https://doi.org/10.3390/chemistry6040046