Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction

doi:10.1007/s40242-020-9063-z

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (2): 281-284.doi: 10.1007/s40242-020-9063-z

Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction

SHI Peijun¹, ZHANG Zhe¹, LIU Mingchun¹, SUN Teng¹, HE Xiaoyan¹, MAO Chengde^1,3, FANG Liang², ZUO Hua¹

1. National Demonstration Center for Experimental Pharmacy Education(Southwest University), College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, P. R. China;
2. Department of Oncology, the Ninth People's Hospital of Chongqing, Chongqing 400700, P. R. China;
3. Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA

收稿日期:2019-11-25 修回日期:2019-12-13 出版日期:2020-04-01 发布日期:2020-03-18
通讯作者: FANG Liang, ZUO Hua E-mail:fangliangkkk@163.com;zuohua@swu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21974111), the Chongqing Research Program of Basic Research and Frontier Technology, China(No.cstc2018jcyjAX0482), the Venture & Innovation Support Program for Chongqing Overseas Returnees, China(No.cx2018088), the Sichuan Applied Basic Research Project, China(No.2019YJ0603) and the Sichuan Financial Innovation Capacity Improvement Project, China(No.2016GYSH-016).

Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction

SHI Peijun¹, ZHANG Zhe¹, LIU Mingchun¹, SUN Teng¹, HE Xiaoyan¹, MAO Chengde^1,3, FANG Liang², ZUO Hua¹

1. National Demonstration Center for Experimental Pharmacy Education(Southwest University), College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, P. R. China;
2. Department of Oncology, the Ninth People's Hospital of Chongqing, Chongqing 400700, P. R. China;
3. Department of Chemistry, Purdue University, West Lafayette, IN, 47907, USA

Received:2019-11-25 Revised:2019-12-13 Online:2020-04-01 Published:2020-03-18
Contact: FANG Liang, ZUO Hua E-mail:fangliangkkk@163.com;zuohua@swu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21974111), the Chongqing Research Program of Basic Research and Frontier Technology, China(No.cstc2018jcyjAX0482), the Venture & Innovation Support Program for Chongqing Overseas Returnees, China(No.cx2018088), the Sichuan Applied Basic Research Project, China(No.2019YJ0603) and the Sichuan Financial Innovation Capacity Improvement Project, China(No.2016GYSH-016).

摘要/Abstract

摘要： Poor water-solubility of hydrophobic drugs greatly hampers drug design and creats delivery problems. The traditional way to improve the solubility is to add hydrotropes or excipients to supress aggregations. Here, a novel mechanisim has been proposed based on supramolecular interactions and demonstrated with a small molecule, pyromellitic diimide(PD). This compound contains thymine-like ‘face’ and can interact with adenines through Watson-Crick and Hoogsteen hydrogen-bonding. Given the high water solubility of polyadenines[poly(A)], it is expected that poly(A) will greatly increase the PD solubility. Indeed, such an increased solubility was confirmed by ultraviolet-visible spectroscopy(UV-Vis) and polyacrylamide gel electrophoresis(PAGE) analysis. We believe that this strategy could be used to improve the solubility of other similar hydrophobic molecules.

关键词: Polyadenine[poly (A)], Pyromellitic diimide, Hydrogen bond force, Increased solubility

Abstract: Poor water-solubility of hydrophobic drugs greatly hampers drug design and creats delivery problems. The traditional way to improve the solubility is to add hydrotropes or excipients to supress aggregations. Here, a novel mechanisim has been proposed based on supramolecular interactions and demonstrated with a small molecule, pyromellitic diimide(PD). This compound contains thymine-like ‘face’ and can interact with adenines through Watson-Crick and Hoogsteen hydrogen-bonding. Given the high water solubility of polyadenines[poly(A)], it is expected that poly(A) will greatly increase the PD solubility. Indeed, such an increased solubility was confirmed by ultraviolet-visible spectroscopy(UV-Vis) and polyacrylamide gel electrophoresis(PAGE) analysis. We believe that this strategy could be used to improve the solubility of other similar hydrophobic molecules.

Key words: Polyadenine[poly (A)], Pyromellitic diimide, Hydrogen bond force, Increased solubility

SHI Peijun, ZHANG Zhe, LIU Mingchun, SUN Teng, HE Xiaoyan, MAO Chengde, FANG Liang, ZUO Hua. Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction[J]. 高等学校化学研究, 2020, 36(2): 281-284.

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Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction

Increasing the Solubility of a Hydrophobic Molecule with Thymine-like Face by DNA via Supramolecular Interaction

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