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Molecules 2018, 23(12), 3170; https://doi.org/10.3390/molecules23123170

Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives

1
Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung 40201, Taiwan
2
Department of Medical Education, Chung Shan Medical University Hospital, Taichung 40201, Taiwan
3
Master Program for Pharmaceutical Manufacture, China Medical University, Taichung 40402, Taiwan
4
School of Pharmacy, China Medical University, Taichung 40402, Taiwan
*
Authors to whom correspondence should be addressed.
Received: 7 November 2018 / Revised: 27 November 2018 / Accepted: 30 November 2018 / Published: 1 December 2018
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Abstract

Two camptothecin derivatives, 10-cyclohexyl-7-methyl-20(S)-camptothecin and 7-methyl-10-morpholino-20(S)-camptothecin, were synthesized and their differences in solubility were investigated using four chosen solvent systems. Based on our results, 10-cyclohexyl-7-methyl-20(S)-camptothecin exhibited higher solubilities than 7-methyl-10-morpholino-20(S)-camptothecin in polar aprotic solvents. However, these two camptothecin derivatives did not exhibit apparent differences in solubility between 5% dimethyl sulfoxide (DMSO)/95% normal saline co-solvent system and 5% dimethylacetamide (DMAC)/95% normal saline co-solvent system. To rationalize their differences in solubility, we also tried to perform a DFT-B3LYP study to investigate their interaction with one water molecule. View Full-Text
Keywords: acid-catalyzed; condensation; camptothecin; solubility; DFT acid-catalyzed; condensation; camptothecin; solubility; DFT
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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MDPI and ACS Style

Lai, C.-H.; Chang, C.-C.; Weng, Y.-L.; Chuang, T.-H. Synthesis, Experimental and Density Functional Theory (DFT) Studies on Solubility of Camptothecin Derivatives. Molecules 2018, 23, 3170.

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