Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. UV–Vis Titration
2.3. DNA Binding Selectivity
2.4. Viscosity Studies
2.5. Cytotoxicity Assay
2.6. Morphology Observation
3. Materials and Methods
3.1. Chemistry
3.1.1. Synthesis of N-Epsilon-1,8-naphthalimido-lysine (1)
3.1.2. Synthesis of N-Alpha-(tert-Butoxycarbonyl)-N-epsilon-1,8-naphthalimido-lysine (2)
3.1.3. Synthesis of 3
3.1.4. Synthesis of 4
3.2. UV–Vis Titration
3.3. Viscosity Study
3.4. Cytotoxicity Assay
3.5. Morphology Observation
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 1–4 are available from the authors. |
Compound | Kb (M−1) |
---|---|
4a | 3.40 × 104 |
4b | 2.78 × 104 |
4c | 1.54 × 104 |
4d | 7.29 × 103 |
4e | 1.00 × 104 |
DNA Duplex | Kb (M−1) |
---|---|
[Poly(dA)-Poly(dT)] | 9.08 × 103 |
[Poly(dG)-Poly(dC)] | 1.15 × 103 |
AT Box | 9.71 × 103 |
GC Box | 1.91 × 103 |
Cell Lines | IC50 Value (μmol∙L−1) | |||||
---|---|---|---|---|---|---|
Fluorouracil | 4a | 4b | 4c | 4d | 4e | |
EC109 | 45.82 | 694.59 | 456.35 | 330.38 | 142.45 | 354.48 |
BGC823 | 49.88 | N.T. 1 | N.T. | 193.65 | 77.99 | N.T. |
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Share and Cite
Huang, Y.; Wu, C.-X.; Song, Y.; Huang, M.; Tian, D.-N.; Yang, X.-B.; Fan, Y.-R. Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers. Molecules 2018, 23, 266. https://doi.org/10.3390/molecules23020266
Huang Y, Wu C-X, Song Y, Huang M, Tian D-N, Yang X-B, Fan Y-R. Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers. Molecules. 2018; 23(2):266. https://doi.org/10.3390/molecules23020266
Chicago/Turabian StyleHuang, Yu, Chun-Xia Wu, Yu Song, Min Huang, Da-Nian Tian, Xin-Bin Yang, and Yan-Ru Fan. 2018. "Synthesis, DNA Binding, and Anticancer Properties of Bis-Naphthalimide Derivatives with Lysine-Modified Polyamine Linkers" Molecules 23, no. 2: 266. https://doi.org/10.3390/molecules23020266