Novel Anticancer NHC*-Gold(I) Complexes Inspired by Lepidiline A
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. Structural Discussion
2.3. Biological Evaluation
3. Materials and Methods
3.1. General Conditions
3.2. Synthesis
3.2.1. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) Bromide (2b)
3.2.2. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) Iodide (2c)
3.2.3. 1,3-Dibenzyl-4,5-diphenylimidazolium Hexafluorophosphate (6a)
3.2.4. 1,3-Dibenzyl-4,5-diphenylimidazolium Tetrafluoroborate (6b)
3.2.5. Bis-[1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene]gold(I) Hexafluorophosphate (3a)
3.2.6. Bis-[1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene]gold(I) Tetrafluoroborate (3b)
3.2.7. Triphenylphosphino-(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) Hexafluorophosphate (4a)
3.2.8. Triphenylphosphino-(1,3-dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) Tetrafluoroborate (4b)
3.2.9. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)(ethynyl)gold(I) (5a)
3.2.10. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)(phenylethynyl)gold(I) (5b)
3.2.11. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)(4-methoxyphenylethynyl)gold(I) (5c)
3.2.12. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)(4-fluorophenylethynyl)gold(I) (5d)
3.2.13. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)[4-(trifluoromethyl)phenylethynyl]gold(I) (5e)
3.3. Structure Determination
3.4. Biological Evaluation
3.4.1. Cell Culture Conditions and Stock Solutions
3.4.2. Anti-Proliferative Activity (MTT-assay)
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 2b–5e are not available from the authors. |
C(8)-Au | Au-X | C(8)-Au-X | C(30)-C(31) | C(31)-C(32) | Au···Au Contact | |
---|---|---|---|---|---|---|
2b a | 2.000(3) | 2.4043(3) | 177.379(8) | - | - | 3.5850(3) |
2c b | 2.0057(18) | 2.55545(15) | 174.66(5) | - | - | 3.5449(3) |
3a c | 2.022(2) | 2.021(2) | 176.14(8) | - | - | - |
3b c | 2.022(3) | 2.019(3) | 173.92(10) | - | - | - |
4a d | 2.038(2) | 2.2808(5) | 177.84(6) | - | - | - |
4b d | 2.035(2) | 2.2834(6) | 179.40(6) | - | - | - |
5a e | 2.018(2) | 1.993(3) | 175.94(9) | 1.198(4) | - | 3.5242(3) |
5b e | 2.028(4) | 1.994(4) | 179.65(16) | 1.196(6) | 1.437(5) | - |
5c e | 2.019(2) | 1.994(2) | 173.28(9) | 1.197(4) | 1.442(3) | - |
5d e | 2.021(4) | 1.982(5) | 173.24(18) | 1.217(7) | 1.430(7) | 3.2077(9) 3.2666(9) |
5e e | 2.033(4) | 1.999(4) | 173.46(17) | 1.193(6) | 1.445(6) | 3.3318(5) |
Compound | HCT-116wt | MCF-7topo | Compound | HCT-116wt | MCF-7topo |
---|---|---|---|---|---|
Cisplatin a | 5.42 ± 0.12 | 18.21 ± 0.10 | 4a | 1.3 ± 0.1 | 1.5 ± 0.2 |
Auranofin a | 3.78 ± 0.10 | 2.89 ± 0.05 | 4b | 2.3 ± 0.2 | 2.4 ± 0.2 |
2a | 22.7 ± 1.2 | 20.8 ± 1.9 | 5a | 3.2 ± 0.3 | 7.3 ± 0.8 |
2b | 16.7 ± 2.5 | 12.8 ± 2.4 | 5b | 14.1 ± 1.3 | >50 |
2c | 0.64 ± 0.01 | 1.1 ± 0.2 | 5c | 8.3 ± 0.5 | >50 |
3a | 0.41 ± 0.01 | 0.70 ± 0.06 | 5d | >50 | >50 |
3b | 0.29 ± 0.01 | 0.80 ± 0.04 | 5e | >50 | >50 |
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Curran, D.; Müller-Bunz, H.; Bär, S.I.; Schobert, R.; Zhu, X.; Tacke, M. Novel Anticancer NHC*-Gold(I) Complexes Inspired by Lepidiline A. Molecules 2020, 25, 3474. https://doi.org/10.3390/molecules25153474
Curran D, Müller-Bunz H, Bär SI, Schobert R, Zhu X, Tacke M. Novel Anticancer NHC*-Gold(I) Complexes Inspired by Lepidiline A. Molecules. 2020; 25(15):3474. https://doi.org/10.3390/molecules25153474
Chicago/Turabian StyleCurran, Danielle, Helge Müller-Bunz, Sofia I. Bär, Rainer Schobert, Xiangming Zhu, and Matthias Tacke. 2020. "Novel Anticancer NHC*-Gold(I) Complexes Inspired by Lepidiline A" Molecules 25, no. 15: 3474. https://doi.org/10.3390/molecules25153474