Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry
Abstract
:1. Introduction
2. Results and Discussion
2.1. Cytotoxicity Assay
2.2. Antiviral Activity Screening
3. Experimental
3.1. General Procedures
3.2. Preparation of Derivatives
3.2.1. Starting Compounds
3.2.2. Preparation of Terpene-Alkynyl Esters
3.2.3. Synthesis of Hybrid Derivatives 1–16
3.3. Treatment Solutions
3.4. Cells and Viruses
3.5. Cytotoxicity Assay
3.6. Cytopathic Effect Assay
3.7. Statistical Analysis
4. Conclusions
Author Contributions
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–16 are available from the authors. |
Compound | CC50 (μM) | |||
---|---|---|---|---|
Vero | HEP-2 | C6 | Raw 264.7 | |
1 | 623.9 ± 5 | 229.7 ± 1.8 | >1000 | >1000 |
2 | 216.2 ± 2 | 48.1 ± 1.1 | 354.9 ± 2.5 | 300 ± 1.9 |
3 | 667.5 ± 4.2 | 411.8 ± 2.1 | >1000 | >1000 |
4 | >1000 | >1000 | >1000 | >1000 |
7 | 680 ± 4.8 | 700 ± 5.8 | 552.5 ± 4 | 552.5 ± 3.9 |
8 | >1000 | >1000 | >1000 | >1000 |
Compound | CC50 a (μM) | EC50 (μM) | SI | ||||
---|---|---|---|---|---|---|---|
KOS | Field | B2006 | KOS | Field | B2006 | ||
2 | 216.2 ± 2 | 118.4 ± 2.3 | 157.9 ± 1.9 | 226.3 ± 2.1 | 1.8 | 1.3 | 0.9 |
3 | 667.5 ± 4.2 | 107.9 ± 1.2 | 140.2 ± 1.2 | 122.1 ± 1.2 | 6.2 | 4.76 | 5.5 |
4 | >1000 | 109 ± 1.0 | 137.5 ± 1.9 | 110 ± 1.0 | >9.2 | >7.2 | >9 |
5 | >1000 | 105.1 ± 1.1 | 140.3 ± 2.1 | 112.1 ± 1.1 | >9.5 | >7.1 | >8.9 |
6 | >1000 | 96.2 ± 1.2 | 137.8 ± 1.4 | 120 ± 1.5 | >10.4 | >7.3 | >8.3 |
8 | >1000 | 99.3 ± 1.5 | 132.4 ± 1.1 | 105.9 ± 1.9 | >10 | >7.6 | >9.4 |
ACV b | >1000 | 8.2 ± 1.0 | 73 ± 1.0 | 50 ± 2.0 | >121.9 | >13.7 | >20 |
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Pertino, M.W.; Petrera, E.; Alché, L.E.; Schmeda-Hirschmann, G. Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry. Molecules 2018, 23, 1343. https://doi.org/10.3390/molecules23061343
Pertino MW, Petrera E, Alché LE, Schmeda-Hirschmann G. Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry. Molecules. 2018; 23(6):1343. https://doi.org/10.3390/molecules23061343
Chicago/Turabian StylePertino, Mariano Walter, Erina Petrera, Laura Edith Alché, and Guillermo Schmeda-Hirschmann. 2018. "Synthesis, Antiviral and Cytotoxic Activity of Novel Terpenyl Hybrid Molecules Prepared by Click Chemistry" Molecules 23, no. 6: 1343. https://doi.org/10.3390/molecules23061343