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Design of an Amphiphilic Perylene Diimide for Optical Recognition of Anticancer Drug through a Chirality-Induced Helical Structure |
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| Authors: | Hao Zhao Dr Sameer Hussain Xiaoyan Liu Shengliang Li Dr Fengting Lv Dr Libing Liu Prof Shu Wang |
| Institution: | 1. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 P. R. China
College of Chemistry, University of Chinese Academy of Sciences, Beijing, 100049 P. R. China;2. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 P. R. China |
| Abstract: | Introduction of chirality into a supramolecular self-assembly system plays an indispensable role in attaining specific molecular recognition ability. Herein, a chiral anticancer drug 5′-deoxy-5-fluorouridine (5′DFU) was explored for inducing the self-assembly of a cationic perylene diimide derivative containing boronic acid groups (PDI-PBA) into a highly ordered right-handed helical structure. As a result, PDI-PBA exhibited a molecular recognition ability towards 5′DFU among other cis-diols and anticancer drugs. With the help of a dynamic covalent bond and favorable hydrogen-bonding interactions, chirality transfer from chiral 5′DFU to achiral PDI-PBA breaks down the strong π–π stacking of PDI-PBA and makes it reorganize into highly ordered helical supramolecular structures. This work provides an insight into chiral anticancer drug tuning interactions of π-chromophores and the inducement of hierarchical self-assembly to achieve specific molecular recognition. |
| Keywords: | anticancer drug chirality transfer molecular recognition perylene diimide self-assembly |