Design, Synthesis, and Evaluation of Monoamine Oxidase A Inhibitors–Indocyanine Dyes Conjugates as Targeted Antitumor Agents
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Cytotoxicity against PC-3
2.3. MAOA Inhibitory Activity of G10, G11, and G12
2.4. In Silico Molecular Docking
3. Materials and Methods
3.1. Materials
3.2. Molecular Docking
3.3. Cytotoxicity Evaluation
3.4. MAOA Inhibition Activity Assay
3.5. General Procedure for the Synthesis of Compounds G1–G3
3.6. General Procedure for the Synthesis of Compounds G4–G6
3.7. General Procedure for the Synthesis of Compounds G7–G13
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds G1–G13 are available from the authors. |
Compound | R1 | R2 | R3 | R4 | n | Y | IC50 (μM) |
---|---|---|---|---|---|---|---|
G1 | OMe | OMe | Me | (CH2)5COOH | 5 | Br | 18.41 |
G2 | Br | Br | Me | (CH2)5COOH | 5 | Br | 75.00 |
G3 | OMe | OMe | Et | (CH2)5COOH | 5 | Br | 13.29 |
G4 | Me | Me | Me | (CH2)5COOH | 5 | Br | 46.66 |
G5 | OMe | OMe | Me | (CH2)5COOH | 5 | Br | 5.06 |
G6 | OMe | OMe | Et | (CH2)5COOH | 5 | Br | 37.07 |
G7 | Me | OMe | Me | (CH2)4SO3− | 5 | - | 28.59 |
G8 | OMe | OMe | Me | (CH2)4SO3− | 5 | - | 101.80 |
G9 | H | OMe | Me | (CH2)4SO3− | 5 | - | 90.53 |
G10 | Me | OMe | Me | (CH2)3CH3 | 3 | Br | 0.85 |
G11 | Me | OMe | Me | (CH2)3CH3 | 5 | Br | 0.40 |
G12 | Br | OMe | Me | (CH2)3CH3 | 5 | Br | 1.55 |
G13 | - | - | - | - | - | - | 10.54 |
INH | - | - | - | - | - | - | >200 |
DOX | - | - | - | - | - | - | 0.21 |
Compound | G10 | G11 | G12 | Isoniazid | Clorgyline |
---|---|---|---|---|---|
IC50 (nM) | 221.1 | 469.5 | 660.6 | >1000 | 1.8 |
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Yang, X.-G.; Mou, Y.-H.; Wang, Y.-J.; Wang, J.; Li, Y.-Y.; Kong, R.-H.; Ding, M.; Wang, D.; Guo, C. Design, Synthesis, and Evaluation of Monoamine Oxidase A Inhibitors–Indocyanine Dyes Conjugates as Targeted Antitumor Agents. Molecules 2019, 24, 1400. https://doi.org/10.3390/molecules24071400
Yang X-G, Mou Y-H, Wang Y-J, Wang J, Li Y-Y, Kong R-H, Ding M, Wang D, Guo C. Design, Synthesis, and Evaluation of Monoamine Oxidase A Inhibitors–Indocyanine Dyes Conjugates as Targeted Antitumor Agents. Molecules. 2019; 24(7):1400. https://doi.org/10.3390/molecules24071400
Chicago/Turabian StyleYang, Xiao-Guang, Yan-Hua Mou, Yong-Jun Wang, Jian Wang, Yan-Yu Li, Rui-Heng Kong, Meng Ding, Dun Wang, and Chun Guo. 2019. "Design, Synthesis, and Evaluation of Monoamine Oxidase A Inhibitors–Indocyanine Dyes Conjugates as Targeted Antitumor Agents" Molecules 24, no. 7: 1400. https://doi.org/10.3390/molecules24071400