Antiproliferative and Structure Activity Relationships of Amaryllidaceae Alkaloids
Abstract
:1. Introduction
2. Results and Discussion
Compound | A2780 | SW1573 | T47-D | WiDr |
---|---|---|---|---|
1 | ≥100 | ≥100 | ≥100 | ≥100 |
2 | 8.3 ± 0.5 | 4.3 ± 0.7 | 6.5 ± 2.0 | 9.1 ± 1.0 |
2a | 3.4 ± 1.0 | 3.9 ± 0.7 | 8.8 ± 1.0 | 7.5 ± 2.0 |
2b | 75.2 ± 25.0 | ≥100 | ≥100 | ≥100 |
3 | 16.5 ± 10.0 | 12.5 ± 7.0 | 52.9 ± 14.0 | 39.1 ± 20.0 |
3a | 41.1 ± 3.0 | 90.3 ± 11.0 | ≥ 100 | ≥100 |
3b | 16.8 ± 7.0 | 17.3 ± 9.0 | 26.7 ± 10.0 | 29.1 ± 11.0 |
3c | ≥100 | ≥100 | ≥100 | ≥100 |
3d | 58.7 ± 7.0 | 91.5 ± 10.0 | ≥100 | ≥100 |
3e | ≥100 | ≥100 | ≥100 | ≥100 |
3f | ≥100 | ≥100 | ≥100 | ≥100 |
3g | 14.6 ± 8.0 | 25.0 ± 6.0 | ≥100 | ≥100 |
3h | ≥100 | ≥100 | ≥100 | ≥100 |
3i | 67.2 ± 13.0 | ≥100 | ≥100 | ≥100 |
3j | ≥100 | ≥100 | ≥100 | ≥100 |
3k | 54.9 ± 24.0 | ≥100 | ≥100 | ≥100 |
4 | ≥100 | ≥100 | ≥100 | ≥100 |
5 | 21.0 ± 2.0 | 16.9 ± 4.0 | 12.5 ± 9.0 | 21.1 ± 6.0 |
5a | ≥100 | ≥100 | ≥100 | ≥100 |
5b | 35.9 ± 5.0 | 34.8 ± 4.0 | 51.1 ± 3.0 | 53.8 ± 3.0 |
5c | 100 | 100 | 100 | 100 |
6 | 0.68 ± 0.2 | 2.1 ± 2.0 | 0.87 ± 0.4 | 1.2 ± 0.5 |
6a | ≥100 | ≥100 | ≥100 | ≥100 |
6b | 27.2 ± 10.0 | 29.5 ± 12.0 | 72.3 ± 24.0 | 63.3 ± 35.0 |
6c | 19.1 ± 1.0 | 21.9 ± 4.0 | 46.1 ± 30.0 | 32.8 ± 22.0 |
6d | ≥100 | ≥100 | ≥100 | ≥100 |
6e | ≥100 | ≥100 | ≥100 | ≥100 |
6f | ≥100 | ≥100 | ≥100 | ≥100 |
6g | 1.5 ± 0.1 | 2.7 ± 0.1 | 4.4 ± 1.5 | 3.5 ± 2.0 |
6h | 33.2 ± 2.0 | 39.1 ± 20.0 | 78.6 ± 24.0 | 67.4 ± 34.0 |
6i | 31.4 ± 7.0 | 29.8 ± 3.0 | ≥100 | 58.9 ± 12.0 |
6j | ≥100 | ≥100 | ≥100 | ≥100 |
6k | 27.2 ± 5.0 | 22.0 ± 20.0 | ≥100 | ≥100 |
7 | 1.5 ± 0.1 | 2.0 ± 1.0 | 1.8 ± 1.0 | 2.7 ± 2.0 |
7a | ≥100 | ≥100 | ≥100 | ≥100 |
7b | 6.9 ± 1.0 | 4.5 ± 0.7 | 8.2 ± 1.2 | 10.1 ± 0.5 |
7c | ≥100 | ≥100 | ≥100 | ≥100 |
7d | ≥100 | ≥100 | ≥100 | ≥100 |
7e | ≥100 | ≥100 | ≥100 | ≥100 |
Compound | MW | LogP | H-Bond Donors | H-Bond Acceptors | Rotable Bonds | TPSA |
---|---|---|---|---|---|---|
1 | 331 | 1.53 | 1 | 6 | 1 | 60.40 |
2 | 287 | 0.54 | 2 | 5 | 1 | 62.16 |
2a | 319 | 2.39 | 0 | 4 | 1 | 30.94 |
2b | 349 | 2.55 | 0 | 5 | 2 | 40.17 |
3 | 315 | 1.23 | 1 | 6 | 0 | 68.24 |
3a | 303 | 0.37 | 3 | 6 | 0 | 90.23 |
3b | 314 | 0.59 | 2 | 6 | 0 | 71.03 |
3c | 314 | −2.91 | 1 | 6 | 0 | 68.01 |
3d | 357 | 1.93 | 0 | 7 | 2 | 74.32 |
3e | 420 | 2.37 | 0 | 8 | 3 | 87.21 |
3f | 498 | 4.47 | 0 | 7 | 3 | 74.32 |
3g | 313 | 1.04 | 0 | 6 | 0 | 65.08 |
3h | 317 | 1.41 | 1 | 6 | 0 | 68.24 |
3i | 475 | 2.29 | 1 | 6 | 0 | 68.24 |
3j | 297 | 2.12 | 0 | 5 | 0 | 48.01 |
3k | 333 | 2.60 | 0 | 5 | 0 | 48.01 |
4 | 271 | 1.59 | 1 | 4 | 0 | 41.93 |
5 | 287 | 0.67 | 2 | 5 | 0 | 62.16 |
5a | 371 | 2.08 | 0 | 7 | 4 | 74.32 |
5b | 497 | 2.38 | 0 | 9 | 6 | 100.10 |
5c | 653 | 7.15 | 0 | 7 | 6 | 74.32 |
6 | 301 | 1.29 | 1 | 5 | 1 | 51.17 |
6a | 343 | 1.99 | 0 | 6 | 3 | 57.25 |
6b | 406 | 2.14 | 0 | 7 | 4 | 70.14 |
6c | 484 | 4.52 | 0 | 6 | 4 | 57.25 |
6d | 383 | 3.46 | 0 | 6 | 4 | 57.25 |
6e | 275 | −0.19 | 4 | 5 | 0 | 84.15 |
6f | 299 | 1.74 | 0 | 5 | 1 | 43.47 |
6g | 299 | 1.10 | 0 | 5 | 1 | 48.01 |
6h | 314 | 1.55 | 1 | 6 | 1 | 63.53 |
6i | 301 | 1.29 | 1 | 5 | 1 | 51.17 |
6j | 461 | 2.22 | 1 | 5 | 1 | 51.17 |
6k | 317 | 1.25 | 1 | 6 | 1 | 65.00 |
7 | 317 | 0.83 | 2 | 6 | 1 | 71.40 |
7a | 401 | 2.23 | 0 | 8 | 5 | 83.55 |
7b | 422 | 1.68 | 1 | 8 | 4 | 90.37 |
7c | 683 | 7.30 | 0 | 8 | 7 | 83.55 |
7d | 481 | 5.17 | 0 | 8 | 7 | 83.55 |
7e | 291 | −0.65 | 5 | 6 | 0 | 104.38 |
3. Experimental Section
3.1. Natural and Semisynthetic Amaryllidaceae Alkaloids
3.2. Antiproliferative Assay
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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- Sample Availability: Not available.
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Cedrón, J.C.; Ravelo, Á.G.; León, L.G.; Padrón, J.M.; Estévez-Braun, A. Antiproliferative and Structure Activity Relationships of Amaryllidaceae Alkaloids. Molecules 2015, 20, 13854-13863. https://doi.org/10.3390/molecules200813854
Cedrón JC, Ravelo ÁG, León LG, Padrón JM, Estévez-Braun A. Antiproliferative and Structure Activity Relationships of Amaryllidaceae Alkaloids. Molecules. 2015; 20(8):13854-13863. https://doi.org/10.3390/molecules200813854
Chicago/Turabian StyleCedrón, Juan C., Ángel G. Ravelo, Leticia G. León, José M. Padrón, and Ana Estévez-Braun. 2015. "Antiproliferative and Structure Activity Relationships of Amaryllidaceae Alkaloids" Molecules 20, no. 8: 13854-13863. https://doi.org/10.3390/molecules200813854