Novel Perbutyrylated Glucose Derivatives of (–)-Epigallocatechin-3-Gallate Inhibit Cancer Cells Proliferation by Decreasing Phosphorylation of the EGFR: Synthesis, Cytotoxicity, and Molecular Docking
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Evaluation of Anticancer Activity
2.3. EGCG Derivatives Inhibited Phosphorylation of EGFR and Downstream Signaling Protein in A-549 Cells
2.4. Molecular Docking Analysis
3. Experimental
3.1. Materials and Methods
3.2. Chemistry
3.3. Cytotoxicity Assay
3.4. Western Blotting
3.5. Docking Studies
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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Compounds | IC50 (μM) | |||||
---|---|---|---|---|---|---|
HL-60 | SMMC-7721 | A-549 | MCF-7 | SW480 | BEAS-2B | |
4 | >40.0 | >40.0 | >40.0 | >40.0 | >40.0 | NT |
7 | 29.5 ± 0.10 | >40.0 | 38.5 ± 0.08 | >40.0 | >40.0 | NT |
8 | 28.2 ± 0.06 | >40.0 | 34.4 ± 0.43 | 36.1 ± 0.11 | >40.0 | NT |
9 | >40.0 | >40.0 | 39.6 ± 0.02 | >40.0 | >40.0 | NT |
10 | >40.0 | >40.0 | >40.0 | >40.0 | >40.0 | NT |
11 | 28.4 ± 1.00 | 37.9 ± 0.12 | 32.1 ± 0.10 | 28.7 ± 0.38 | >40.0 | >40.0 |
12 | 22.9 ± 0.23 | 30.4 ± 1.00 | 24.4 ± 0.31 | 26.4 ± 0.12 | 39.7 ± 0.01 | >40.0 |
Cisplatin | 0.8 ± 0.03 | 4.7 ± 0.35 | 1.9 ± 0.43 | 14.2 + 0.93 | 10.2 ± 1.20 | 12.9 ± 0.25 |
Molecules | Hydrophobic Interactions | Hydrogen Bonds | π-Stacking | Salt Bridges |
---|---|---|---|---|
11 | PHE723, ALA743, LEU844 | LEU718, MET793 ASN842 | — | LYS745, ARG841 |
12 | ALA722, PHE723, VAL726, LYS745, MET793, ARG841, VAL876 | GLU758, ASP855, VAL876 | LYS745 | ARG841 |
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Wang, Y.; Shen, X.-J.; Su, F.-W.; Xie, Y.-R.; Wang, L.-X.; Zhang, N.; Wu, Y.-L.; Niu, Y.; Zhang, D.-Y.; Zi, C.-T.; et al. Novel Perbutyrylated Glucose Derivatives of (–)-Epigallocatechin-3-Gallate Inhibit Cancer Cells Proliferation by Decreasing Phosphorylation of the EGFR: Synthesis, Cytotoxicity, and Molecular Docking. Molecules 2021, 26, 4361. https://doi.org/10.3390/molecules26144361
Wang Y, Shen X-J, Su F-W, Xie Y-R, Wang L-X, Zhang N, Wu Y-L, Niu Y, Zhang D-Y, Zi C-T, et al. Novel Perbutyrylated Glucose Derivatives of (–)-Epigallocatechin-3-Gallate Inhibit Cancer Cells Proliferation by Decreasing Phosphorylation of the EGFR: Synthesis, Cytotoxicity, and Molecular Docking. Molecules. 2021; 26(14):4361. https://doi.org/10.3390/molecules26144361
Chicago/Turabian StyleWang, Ya, Xiao-Jing Shen, Fa-Wu Su, Yin-Rong Xie, Li-Xia Wang, Ning Zhang, Yi-Long Wu, Yun Niu, Dong-Ying Zhang, Cheng-Ting Zi, and et al. 2021. "Novel Perbutyrylated Glucose Derivatives of (–)-Epigallocatechin-3-Gallate Inhibit Cancer Cells Proliferation by Decreasing Phosphorylation of the EGFR: Synthesis, Cytotoxicity, and Molecular Docking" Molecules 26, no. 14: 4361. https://doi.org/10.3390/molecules26144361