Design of an Amphiphilic Perylene Diimide for Optical Recognition of Anticancer Drug through a Chirality‐Induced Helical Structure. Issue 42 (1st July 2019)

• Record Type: Journal Article
• Authors: Zhao, Hao; Hussain, Sameer; Liu, Xiaoyan; Li, Shengliang; Lv, Fengting; Liu, Libing; Wang, Shu
• Is Part Of: Chemistry. Volume 25:Issue 42(2019)
• Page Start: 9834
• Page End: 9839
• Publication Date: 2019-07-01
• Subjects: anticancer drug -- chirality transfer -- molecular recognition -- perylene diimide -- self-assembly; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201901948
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : A cationic perylene diimide derivative containing boronic acid groups (PDI‐PBA) was designed and synthesized. A chiral anticancer drug 5′‐deoxy‐5‐fluorouridine (5′DFU) could induce the self‐assembly of PDI‐PBA into an ordered right‐handed helical structure, thus PDI‐PBA exhibited a molecular recognition ability towards 5′DFU (see scheme).