Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation

doi:10.1016/j.cjche.2023.01.005

中国化学工程学报 ›› 2023, Vol. 59 ›› Issue (7): 160-168.DOI: 10.1016/j.cjche.2023.01.005

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Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation

Wen Yu, Yiyang Bo, Yiling Luo, Xiyan Huang, Rixiang Zhang, Jiaheng Zhang

Research Centre of Printed Flexible Electronics, School of Materials Science and Engineering, Harbin Institute of Technology, Shenzhen 518055, China

收稿日期:2022-09-06 修回日期:2023-01-03 出版日期:2023-07-28 发布日期:2023-10-14
通讯作者: Wen Yu,E-mail:yuwen@hit.edu.cn;Jiaheng Zhang,E-mail:zhangjiaheng@hit.edu.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (21905069, U21A20307, 22208073), the Shenzhen Science and Technology Innovation Committee (ZDSYS20190902093220279, KQTD20170809110344233, GXWD20201230155427003-20200821181245001, GXWD20201230155427003-202008211 81809001, ZX20200151), the Department of Science and Technology of Guangdong Province (2020A1515110879).

Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation

Wen Yu, Yiyang Bo, Yiling Luo, Xiyan Huang, Rixiang Zhang, Jiaheng Zhang

Research Centre of Printed Flexible Electronics, School of Materials Science and Engineering, Harbin Institute of Technology, Shenzhen 518055, China

Received:2022-09-06 Revised:2023-01-03 Online:2023-07-28 Published:2023-10-14
Contact: Wen Yu,E-mail:yuwen@hit.edu.cn;Jiaheng Zhang,E-mail:zhangjiaheng@hit.edu.cn
Supported by:
This work was financially supported by the National Natural Science Foundation of China (21905069, U21A20307, 22208073), the Shenzhen Science and Technology Innovation Committee (ZDSYS20190902093220279, KQTD20170809110344233, GXWD20201230155427003-20200821181245001, GXWD20201230155427003-202008211 81809001, ZX20200151), the Department of Science and Technology of Guangdong Province (2020A1515110879).

摘要/Abstract

摘要： The development of green solvents for enhancing aqueous solubility of drug curcumin remains a challenge. This study explores the enhancing effect of deep eutectic solvents (DESs) on the aqueous solubility of curcumin (CUR) via experiment and theoretical calculation. Choline chloride-based DESs with polyols 1,2-propanediol (1,2-PDO), 1,3-propanediol, ethylene glycol, and glycerol as hydrogen bond donors were prepared and used as co-solvents. The CUR aqueous solubility increased with increasing the DESs content at temperature of 303.15-318.15 K, especially in aqueous ChCl/1,2-PDO (mole ratio 1:4) solutions. The positive apparent molar volume values and reduced density gradient analysis confirmed the existence of strong interactions between CUR and solvent. The van der Waals interactions and hydrogen bonding coexisted in DESs monomer retained the stability of DESs structure after introducing CUR. Moreover, the lower interaction energy of DESs…CUR system than that of the counterpart DESs further proved the strong interaction between CUR and DESs. The lowest interaction energy of ChCl/1,2-PDO…CUR system indicated that this system was the most stable and ChCl/1,2-PDO was promising for CUR dissolution. This work provides efficient solvents for utilizing curcumin, contributing to a deep insight into the interactions between DES and CUR at the molecular level, and the role of DESs on enhancing drugs solubility.

关键词: Choline chloride-polyol, Deep eutectic solvents, Curcumin, Aqueous solubility, Theoretical calculation

Abstract: The development of green solvents for enhancing aqueous solubility of drug curcumin remains a challenge. This study explores the enhancing effect of deep eutectic solvents (DESs) on the aqueous solubility of curcumin (CUR) via experiment and theoretical calculation. Choline chloride-based DESs with polyols 1,2-propanediol (1,2-PDO), 1,3-propanediol, ethylene glycol, and glycerol as hydrogen bond donors were prepared and used as co-solvents. The CUR aqueous solubility increased with increasing the DESs content at temperature of 303.15-318.15 K, especially in aqueous ChCl/1,2-PDO (mole ratio 1:4) solutions. The positive apparent molar volume values and reduced density gradient analysis confirmed the existence of strong interactions between CUR and solvent. The van der Waals interactions and hydrogen bonding coexisted in DESs monomer retained the stability of DESs structure after introducing CUR. Moreover, the lower interaction energy of DESs…CUR system than that of the counterpart DESs further proved the strong interaction between CUR and DESs. The lowest interaction energy of ChCl/1,2-PDO…CUR system indicated that this system was the most stable and ChCl/1,2-PDO was promising for CUR dissolution. This work provides efficient solvents for utilizing curcumin, contributing to a deep insight into the interactions between DES and CUR at the molecular level, and the role of DESs on enhancing drugs solubility.

Key words: Choline chloride-polyol, Deep eutectic solvents, Curcumin, Aqueous solubility, Theoretical calculation

Wen Yu, Yiyang Bo, Yiling Luo, Xiyan Huang, Rixiang Zhang, Jiaheng Zhang. Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation[J]. 中国化学工程学报, 2023, 59(7): 160-168.

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Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation

Enhancing effect of choline chloride-based deep eutectic solvents with polyols on the aqueous solubility of curcumin-insight from experiment and theoretical calculation

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