Synthesis and Biological Evaluation of Novel Alkyl Amine Substituted Icariside II Derivatives as Potential Anticancer Agents
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Cell Viability Analysis and Discussion on the Preliminary Structure-Activity Relationship (SAR)
2.3. Cell Morphological Assessment
2.4. Cell Cycle Distribution Analysis
2.5. Assessment of Apoptotic Analysis
3. Conclusions
4. Experimental Section
4.1. Materials and Methods
4.2. General Experimental Procedure for Mannich Base Derivatives 4a–d
4.3. General Experimental Procedure for the 7-O-Alkylamino Derivatives 7a–h
4.4. Cell Lines and Cell Culture Conditions
4.5. Cell Viability Inhibition Assay
4.6. Cell Morphological Assessment
4.7. Cell Cycle Distribution Analysis
4.8. Assessment of Apoptotic Analysis
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 4a–d and 7a–h are available from the authors. |
Compound | IC50 (μM) a | |||
---|---|---|---|---|
HCCLM3-LUC | HepG2 | MCF-7 | MDA-MB-231 | |
4a | >50 | >50 | >50 | >50 |
4b | >50 | >50 | >50 | >50 |
4c | >50 | >50 | >50 | >50 |
4d | >50 | >50 | >50 | >50 |
7a | 18.72 ± 0.33 | 15.41 ± 0.60 | 14.97 ± 0.12 | 16.85 ± 0.24 |
7b | 14.23 ± 1.02 | 7.67 ± 0.83 | 10.53 ± 1.34 | 8.42 ± 0.45 |
7c | Nd b | Nd | Nd | Nd |
7d | 13.51 ± 0.93 | 7.67 ± 0.67 | 10.98 ± 0.22 | 10.15 ± 0.74 |
7e | 13.9 ± 1.12 | 7.12 ± 0.83 | 10.94 ± 0.94 | 8.58 ± 0.69 |
7f | 46.82 ± 5.94 | 19.92 ± 1.19 | 31.46 ± 2.37 | 31.08 ± 4.62 |
7g | 13.28 ±0.44 | 3.96 ± 0.37 | 2.44 ± 0.18 | 4.21 ± 0.31 |
7h | 15.31 ± 0.87 | 7.14 ± 0.69 | 14.61 ± 1.05 | 9.57 ± 0.59 |
Icariin | >100 | >100 | >100 | >100 |
Icariside II | 39.04 ± 1.92 | 21.92 ± 2.04 | 30.64 ± 3.46 | 32.53 ± 2.18 |
doxorubicin | 1.97 ± 0.11 | 0.96 ± 0.06 | 16.16 ± 0.47 | 2.36 ± 0.14 |
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Wu, T.; Li, T.; Kang, Y.-N.; Liu, L.; Wang, X.-M.; Lan, J.-S.; Ding, Y.; Zhang, T. Synthesis and Biological Evaluation of Novel Alkyl Amine Substituted Icariside II Derivatives as Potential Anticancer Agents. Molecules 2018, 23, 2146. https://doi.org/10.3390/molecules23092146
Wu T, Li T, Kang Y-N, Liu L, Wang X-M, Lan J-S, Ding Y, Zhang T. Synthesis and Biological Evaluation of Novel Alkyl Amine Substituted Icariside II Derivatives as Potential Anticancer Agents. Molecules. 2018; 23(9):2146. https://doi.org/10.3390/molecules23092146
Chicago/Turabian StyleWu, Tong, Ting Li, Ya-Nan Kang, Li Liu, Xi-Man Wang, Jin-Shuai Lan, Yue Ding, and Tong Zhang. 2018. "Synthesis and Biological Evaluation of Novel Alkyl Amine Substituted Icariside II Derivatives as Potential Anticancer Agents" Molecules 23, no. 9: 2146. https://doi.org/10.3390/molecules23092146