Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Antiproliferative Effects of Dehydroabietic Acid (DAA) and Its Derivatives
2.3. Cell Cycle Analysis
2.4. Hoechst 33258 Staining Assay
2.5. Annexin V-FITC/PI Dual Staining Assay
3. Experimental Section
3.1. Materials and Methods
3.2. Procedure for the Synthesis of Compound 3
3.3. General Procedures for the Synthesis of Compounds 4a–o
3.4. Cytotoxic Assay
3.5. Cell Cycle Analysis
3.6. Hoechst 33258 Staining Assay
3.7. Annexin V-FITC/PI Dual Staining Assay
3.8. Statistical Analysis
4. Conclusions
Supplementary Materials
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 4a–o are available from the authors. |
Compound | CLogP | IC50 (μM) | |||
---|---|---|---|---|---|
MCF-7 | SMMC-7721 | HeLa | LO2 | ||
1 | − | >50 | >50 | >50 | >50 |
2 | − | >50 | >50 | 43.32 ± 3.26 | >50 |
3 | − | >50 | 45.83 ± 5.28 | 37.72 ± 3.75 | >50 |
4a | 4.69 | 2.36 ± 0.29 | 1.65 ± 0.22 | 2.08 ± 0.43 | 15.72 ± 0.65 |
4b | 6.81 | 1.78 ± 0.36 | 0.72 ± 0.09 | 1.08 ± 0.12 | 11.09 ± 0.57 |
4c | 8.92 | 21.02 ± 1.27 | 10.96 ± 0.58 | 8.67 ± 0.65 | >50 |
4d | 11.04 | 28.13 ± 0.92 | 32.70 ± 2.69 | 25.32 ± 3.01 | >50 |
4e | 5.96 | 20.45 ± 1.51 | 18.64 ± 2.37 | 12.79 ± 1.26 | >50 |
4f | 7.08 | 8.95 ± 0.63 | 7.71 ± 0.82 | 5.98 ± 0.37 | 42.23 ± 2.78 |
4g | 8.20 | >50 | 27.89 ± 2.91 | 32.01 ± 4.21 | >50 |
4h | 4.52 | 12.32 ± 1.03 | 16.28 ± 1.85 | 9.67 ± 1.13 | 36.64 ± 3.12 |
4i | 4.49 | 5.89 ± 0.56 | 4.32 ± 0.64 | 5.05 ± 0.72 | 21.95 ± 2.70 |
4j | 5.40 | 12.21 ± 0.75 | 8.03 ± 0.70 | 6.62 ± 0.59 | 29.52 ± 3.61 |
4k | 6.58 | 38.66 ± 2.87 | 26.45 ± 3.73 | 13.51 ± 2.21 | >50 |
4l | 3.75 | 22.84 ± 3.21 | 15.30 ± 2.06 | 12.73 ± 1.35 | >50 |
4m | 3.21 | 3.73 ± 0.62 | 4.66 ± 0.42 | 2.18 ± 0.37 | 18.36 ± 1.73 |
4n | 3.86 | 15.76 ± 0.81 | 10.88 ± 1.68 | 13.26 ± 2.71 | >50 |
4o | 3.44 | 24.38 ± 1.69 | 16.92 ± 1.95 | 20.46 ± 3.12 | >50 |
Etoposide | − | 0.73 ± 0.07 | 0.69 ± 0.18 | 0.87 ± 0.16 | 8.89 ± 0.38 |
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Gu, W.; Wang, S.; Jin, X.; Zhang, Y.; Hua, D.; Miao, T.; Tao, X.; Wang, S. Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents. Molecules 2017, 22, 1154. https://doi.org/10.3390/molecules22071154
Gu W, Wang S, Jin X, Zhang Y, Hua D, Miao T, Tao X, Wang S. Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents. Molecules. 2017; 22(7):1154. https://doi.org/10.3390/molecules22071154
Chicago/Turabian StyleGu, Wen, Shuang Wang, Xiaoyan Jin, Yaliang Zhang, Dawei Hua, Tingting Miao, Xubing Tao, and Shifa Wang. 2017. "Synthesis and Evaluation of New Quinoxaline Derivatives of Dehydroabietic Acid as Potential Antitumor Agents" Molecules 22, no. 7: 1154. https://doi.org/10.3390/molecules22071154