Synthesis and Antiproliferative Activity of Novel Dehydroabietic Acid-Chalcone Hybrids
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the DHA-Chalcone Hybrids 31–53
2.2. Biological Evaluation
2.3. Structure-Activity Relationships
3. Materials and Methods
3.1. General Methods
3.2. Experimental Procedures
General Procedure for the Synthesis of the DHA-Chalcone Hybrids
3.3. Biological Assays
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Compound | IC50 (μM) | Selectivity Index for | |||||
---|---|---|---|---|---|---|---|
MDA-MB-231 | MCF-7 | Hs578T | Fibroblasts | MDA-MB-231 | MCF-7 | Hs578T | |
31 | >75 | 23.90 ± 4.47 | >75 | n/a | n/a | n/a | n/a |
32 | >75 | >75 | >75 | n/a | n/a | n/a | n/a |
33 | 5.89 ± 0.77 | 2.21 ± 0.40 | 2.48 ± 0.13 | 8.68 ± 0.88 | 1.47 | 3.93 | 3.50 |
34 | >75 | 21.36 ± 0.60 | 28.09 ± 7.76 | n/a | n/a | n/a | n/a |
35 | 37.05 ± 1.82 | 9.90 ± 0.05 | 8.69 ± 0.55 | 33.83 ± 6.63 | 0.91 | 3.42 | 3.89 |
36 | >75 | >75 | >75 | n/a | n/a | n/a | n/a |
37 | >75 | 11.39 ± 1.55 | >75 | n/a | n/a | n/a | n/a |
38 | 73.00 ± 2.31 | 7.06 ± 1.71 | >75 | 160.65 ± 13.08 | 2.20 | 22.75 | - |
39 | >75 | 11.50 ± 1.02 | 15.71 ± 2.74 | 32.88 ± 2.27 | - | 2.86 | 2.09 |
40 | >75 | >75 | >75 | 92.11 ± 5.47 | - | - | - |
41 | 7.12 ± 0.20 | 3.99 ± 0.15 | 10.31 ± 0.25 | 7.96 ± 0.10 | 1.12 | 1.99 | 0.77 |
42 | >75 | 37.01 ± 6.89 | 43.33 ± 4.32 | n/a | n/a | n/a | n/a |
43 | 29.20 ± 3.26 | 4.29 ± 0.29 | 16.64 ± 2.83 | 33.05 ± 6.10 | 1.13 | 7.70 | 1.99 |
44 | 25.21 ± 0.84 | 3.45 ± 0.36 | 21.48 ± 1.20 | 44.03 ± 1.84 | 1.75 | 12.76 | 2.05 |
45 | >75 | 29.94 ± 5.26 | >75 | n/a | n/a | n/a | n/a |
46 | >75 | >75 | >75 | n/a | n/a | n/a | n/a |
47 | 40.37 ± 0.67 | 12.52 ± 8.43 | >75 | n/a | n/a | n/a | n/a |
48 | >75 | 25.62 ± 0.09 | 23.15 ± 2.50 | n/a | n/a | n/a | n/a |
49 | 22.43 ± 0.81 | 45.93 ± 1.52 | 17.07 ± 2.13 | 23.81 ± 1.07 | 1.06 | 0.52 | 1.39 |
50 | >75 | >75 | >75 | 192.25 ± 51.41 | - | - | - |
51 | 18.01 ± 2.78 | >75 | 23.11 ± 0.04 | 20.47 ± 2.46 | 1.14 | - | 0.88 |
52 | >75 | >75 | 60.21 ± 6.94 | n/a | n/a | n/a | n/a |
53 | 17.12 ± 0.41 | 41.44 ± 1.74 | 28.44 ± 1.97 | n/a | n/a | n/a | n/a |
28 | 115.44 ± 40.11 | 206.95 ± 7.28 | 135.95 ± 2.47 | n/a | n/a | n/a | n/a |
5-FU | 19.17 ± 0.39 | 5.37 ± 1.16 | 7.38 ± 2.49 | 9.43 ± 0.80 | 0.49 | 1.76 | 1.28 |
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Grigoropoulou, S.; Manou, D.; Antoniou, A.I.; Tsirogianni, A.; Siciliano, C.; Theocharis, A.D.; Athanassopoulos, C.M. Synthesis and Antiproliferative Activity of Novel Dehydroabietic Acid-Chalcone Hybrids. Molecules 2022, 27, 3623. https://doi.org/10.3390/molecules27113623
Grigoropoulou S, Manou D, Antoniou AI, Tsirogianni A, Siciliano C, Theocharis AD, Athanassopoulos CM. Synthesis and Antiproliferative Activity of Novel Dehydroabietic Acid-Chalcone Hybrids. Molecules. 2022; 27(11):3623. https://doi.org/10.3390/molecules27113623
Chicago/Turabian StyleGrigoropoulou, Sophia, Dimitra Manou, Antonia I. Antoniou, Artemis Tsirogianni, Carlo Siciliano, Achilleas D. Theocharis, and Constantinos M. Athanassopoulos. 2022. "Synthesis and Antiproliferative Activity of Novel Dehydroabietic Acid-Chalcone Hybrids" Molecules 27, no. 11: 3623. https://doi.org/10.3390/molecules27113623