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Chiral-functionalized membranes for chiral drugs sieving

用于手性药物筛分的手性功能化膜

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  • Special Topic: Biomaterials and Bioinspired Materials
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Abstract

Current trend that integrates chiral designs into robust membrane systems is providing distinct horizons for the development of chiral separation technology. However, creating chiral sites in-between membrane laminates is still an open issue. Herein, we demonstrate a decorated layered chitosan/graphene oxide (CG) membrane via non-covalent interactions with L-tryptophan derivatives (LPWM), yielding materials with chiral functionality and superior mechanical strength. LPWM introduces chiral environment into the membrane, giving rise to visual recognition sensitivity and decent enantioseparation performance toward chiral drug molecules, with optical isomeric excess value exceeding 80% for pseudoephedrine (PEP). The chiral discrimination is associated with preferential binding of one of the isomers due to stronger or additional H-bonds with chiral assemblies. This work not only paves a new way for the fabrication of chiral membranes via a simple non-covalent interaction, but also guides a potential direction to realize enantioseparation employing decorated laminated membranes.

摘要

将手性整合到薄膜体系中为手性分离技术的发展提供了独特的方向. 然而, 在膜层之间创建手性位点仍是一个有待解决的问题. 在此, 我们制作了一种壳聚糖/氧化石墨烯(CG)基薄膜, 通过与L-色氨酸衍生物(LPWM)的非共价相互作用, CG-LPWM薄膜不仅保持优异的机械强度, 同时具有手性功能. LPWM在薄膜中引入了手性环境, 使得薄膜不仅能够视觉识别手性分子, 而且对手性药物具有一定的分离性能: 伪麻黄碱的光学异构体过量值超过80%. 手性识别源于手性组装体与其中一种异构体具有更强或更多的氢键作用导致的优先结合. 这项工作通过简单的非共价相互作用制作了手性薄膜, 为手性修饰的层状膜实现对映体识别与分离指引了方向.

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Acknowledgements

This work was supported by the Leading Talents in Science and Technology Innovation under the National Ten Thousand Talents Plan, the National Natural Science Foundation of China (51833006 and 52003154), the Innovation Program of Shanghai Municipal Education Commission (201701070002E00061), the Science and Technology Commission of Shanghai Municipality (19441903000 and 19ZR1425400), Shanghai Jiao Tong University (SJTU) Trans-med Awards Research (WF540162603), Shanghai Pujiang Program (20PJ1407400), and the Natural Science Foundation of Shanghai (20ZR1425500).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. State Key Lab of Metal Matrix Composites, School of Materials Science and Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China

    Sijia He  (何思佳), Yaqian Zhang  (张雅倩), Sravan Baddi, Changli Zhao  (赵常利), Xiaoqiu Dou  (窦晓秋) & Chuanliang Feng  (冯传良)

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  1. Sijia He  (何思佳)
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  2. Yaqian Zhang  (张雅倩)
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  3. Sravan Baddi
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  4. Changli Zhao  (赵常利)
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  5. Xiaoqiu Dou  (窦晓秋)
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  6. Chuanliang Feng  (冯传良)
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Contributions

Author contributions He S performed the experiments, analyzed the data, and revised the manuscript. Zhang Y carried out the experiments and wrote the original draft. Baddi S revised the manuscript. Feng C and Zhao C supervised the project. All authors contributed to the general discussion.

Corresponding authors

Correspondence to Changli Zhao  (赵常利) or Chuanliang Feng  (冯传良).

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Conflict of interest The authors declare that they have no conflict of interest.

Additional information

Supplementary information Supporting data are available in the online version of the paper.

Sijia He received her Bachelor degree from Tianjin University in 2020. She is currently a PhD student at the laboratory of Prof. Chuanliang Feng, Shanghai Jiao Tong University. Her research interests include the development of stimuli-responsive chiral supramolecular assemblies for biomedical applications.

Chuanliang Feng received his PhD degree from the University of Twente (the Netherlands) in 2005, and then he worked at the Max-Planck Institute for Polymer Research as a postdoctoral researcher (Mainz, Germany). From 1998 to 2009, he was a research scientist at Biomade Technology Foundation (Groningen, the Netherlands). Now he is a distinguished professor at the School of Materials Science and Technology, Shanghai Jiao Tong University. His research mainly focuses on functionalized polymeric nanomaterials, bioadhesion materials, and supramolecular hydrogels. Important topics are the synthesis and characterization of stimuli-sensitive polymers and biomimetic materials as well as applications of biomaterials in regenerative medicine.

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He, S., Zhang, Y., Baddi, S. et al. Chiral-functionalized membranes for chiral drugs sieving. Sci. China Mater. (2024). https://doi.org/10.1007/s40843-023-2806-8

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