In Vitro Antitumor Active Gold(I) Triphenylphosphane Complexes Containing 7-Azaindoles
Abstract
:1. Introduction
2. Results
2.1. Chemistry
2.2. Single Crystal X-ray Analysis
2.3. Aqueous Chemistry and Interaction Studies
2.3.1. Solution Behaviour in a Water/DMF Mixture
2.3.2. Interaction Studies with Biomolecules
2.4. In Vitro Antitumor Activity
2.5. Cell Cycle Analysis
3. Discussion
4. Materials and Methods
4.1. Materials
4.2. Synthesis
4.3. General Methods
4.4. Single Crystal X-ray Analysis
4.5. Studies of Aqueous Chemistry and Interaction with Biomolecules
4.6. In Vitro Cytotoxicity Testing
4.7. Cell Cycle Analysis
4.8. Statistical Analysis
5. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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7 | 8′ | |
---|---|---|
Empirical Formula | C25H18AuBrIN2P | C52H44Au2Cl2N4OP2 |
Formula weight | 781.16 | 1267.68 |
Temperature (K) | 120(2) | 120(2) |
Wavelength (Å) | 0.71073 | 0.71073 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, C2/c |
Unit cell dimensions | ||
a (Å) | 6.8563(3) | 24.2844(14) |
b (Å) | 24.2482(12) | 15.1186(14) |
c (Å) | 14.7081(8) | 16.3330(14) |
α (°) | 90 | 90 |
β (°) | 101.313(2) | 128.203(4) |
γ (°) | 90 | 90 |
V (Å3) | 2397.8(2) | 4712.3(7) |
Z, Dcalc (g·cm−3) | 4, 2.164 | 4, 1.787 |
Absorption coefficient (mm−1) | 9.172 | 6.444 |
Crystal size (mm) | 0.170 × 0.140 × 0.120 | 0.160 × 0.120 × 0.120 |
F (000) | 1456 | 2456 |
θ range for data collection (°) | 2.825 to 27.513 | 2.500 to 27.940 |
Index ranges (h, k, l) | −7 ≤ h ≤ 8 | −31 ≤ h ≤ 31 |
−31 ≤ k ≤ 31 | −19 ≤ k ≤ 19 | |
−19 ≤ l ≤ 19 | −21 ≤ l ≤ 21 | |
Reflections collected/unique | 56041 | 104819 |
Data/restraints/parameters | 5508/0/280 | 5648/0/289 |
Goodness–of–fit on F2 | 1.071 | 1.012 |
Final R indices [I > 2σ(I)] | R1 = 0.0279, wR2 = 0.0453 | R1 = 0.0193, wR2 = 0.0340 |
R indices (all data) | R1 = 0.0427, wR2 = 0.0485 | R1 = 0.0301, wR2 = 0.0366 |
Largest peak and hole (e Å−3) | 0.900 and −1.237 | 0.550 and −0.702 |
Cambridge Crystallographic Data Centre nos. | 1507789 | 1507790 |
Parameter | 7 | 8′ |
---|---|---|
Au1–N1 | 2.047(3) | 2.030(2) |
Au1–P1 | 2.2349(9) | 2.2277(6) |
P1–Au1–N1 | 176.41(8) | 173.27(6) |
Au1–P1–C10 | 112.34(12) | 107.47(8) |
Au1–P1–C20 | 111.24(12) | 117.05(8) |
Au1–P1–C30 | 115.36(11) | 114.19(8) |
Au1–N1–C2 | 126.1(2) | 125.1(2) |
Au1–N1–C7a | 125.9(2) | 127.7(2) |
Complex | A2780 | A2780R | MRC5 | RF 1 | SI 2 |
---|---|---|---|---|---|
[Au(aza)(PPh3)] (1) | 3.8 ± 1.1 *** | 4.4 ± 0.8 | 7.7 ± 1.7 | 1.2 | 2.0 |
[Au(3Claza)(PPh3)] (2) | 22.4 ± 5.7 | 21.7 ± 0.8 | 31.4 ± 4.9 | 1.0 | 1.4 |
[Au(3Braza)(PPh3)] (3) | 23.3 ± 3.4 | 21.3 ± 0.8 | 27.3 ± 1.7 | 0.9 | 1.2 |
[Au(3Iaza)(PPh3)] (4) | 3.5 ± 0.4 *** | 11.0 ± 4.7 | 29.2 ± 5.9 | 3.1 | 8.3 |
[Au(5Braza)(PPh3)] (5) | 3.1 ± 0.5 *** | 14.4 ± 3.3 | 26.0 ± 4.2 | 4.6 | 8.4 |
[Au(3Cl5Braza)(PPh3)] (6) | 22.9 ± 2.3 | 13.8 ± 2.1 | 26.5 ± 3.7 | 0.6 | 1.2 |
[Au(3I5Braza)(PPh3)] (7) | 20.2 ± 2.5 | 22.1 ± 0.3 | 27.3 ± 2.6 | 1.1 | 1.4 |
[Au(2Me4Claza)(PPh3)] (8) | 2.8 ± 0.7 *** | 8.9 ± 3.8 | 26.9 ± 3.6 | 3.2 | 9.6 |
Cisplatin | 20.3 ± 2.3 | >50.0 | >50.0 | - | - |
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Štarha, P.; Trávníček, Z.; Drahoš, B.; Dvořák, Z. In Vitro Antitumor Active Gold(I) Triphenylphosphane Complexes Containing 7-Azaindoles. Int. J. Mol. Sci. 2016, 17, 2084. https://doi.org/10.3390/ijms17122084
Štarha P, Trávníček Z, Drahoš B, Dvořák Z. In Vitro Antitumor Active Gold(I) Triphenylphosphane Complexes Containing 7-Azaindoles. International Journal of Molecular Sciences. 2016; 17(12):2084. https://doi.org/10.3390/ijms17122084
Chicago/Turabian StyleŠtarha, Pavel, Zdeněk Trávníček, Bohuslav Drahoš, and Zdeněk Dvořák. 2016. "In Vitro Antitumor Active Gold(I) Triphenylphosphane Complexes Containing 7-Azaindoles" International Journal of Molecular Sciences 17, no. 12: 2084. https://doi.org/10.3390/ijms17122084