Biomimetic Recognition-Based Bioorthogonal Host-Guest Pairs for Cell Targeting and Tissue Imaging in Living Animals  

作　　者：Yan-Long Ma Chen Sun Zeshun Li Ziyi Wang Jianwen Wei Qian Cheng Li-Shuo Zheng Xiao-Yong Chang Kai Li Ruibing Wang Wei Jiang 

机构地区：[1]Shenzhen Grubbs Institute,Guangdong Provincial Key Laboratory of Catalysis,and Department of Chemistry,Southern University of Science and Technology,Shenzhen 518055 [2]State Key Laboratory of Quality Research in Chinese Medicine,Institute of Chinese Medical Science,MoE Frontiers Science Center for Precision Oncology,University of Macao,Taipa,Macao 999078 [3]Department of Biomedical Engineering,Southern University of Science and Technology,Shenzhen 518055

出　　处：《CCS Chemistry》2022年第6期1977-1989,共13页中国化学会会刊（英文）

基　　金：financially supported by National Natural Science Foundation of China(nos.21772083 and 21822104);the Shenzhen Special Funds(no.JCYJ20180504165810828);the Guangdong Provincial Key Laboratory of Catalysis(no.2020B121201002);the University of Macao(no.MYRG2019-00059-ICMS);the Shenzhen“Pengcheng Scholar”Program;Guangdong High-Level Personnel of Special Support Program(no.2019TX05C157);SUSTech-CRF for the technical support.

摘　　要：Bioconjugation methods offer very important tools in studying biological systems.Synthetic host-guest pairs provide an alternative and complementary conjugation method to bioorthogonal reactions and biological association pairs.Nevertheless,macrocyclic hosts that can be used for in situ capture are limited and often rely on extremely high binding affinities.Herein,we report an alternative bioorthogonal host-guest pair that relies on highly selective molecular recognition in water.The host,namely amide naphthotube,possesses a biomimetic cavity with inward-directing hydrogen bonding sites and shows selective and strong binding to the guest(2-phenyl pyrimidine)even in biological media.Through anchoring the tetraphenyl ethylene-modi fied hosts to cell surfaces,the bioorthogonal host-guest pair can be applied in cell surface recognition,cell-cell interactions,and tissue imaging in mice.The bioorthogonality is originated from the high binding selectivity of the biomimetic macrocyclic host,which is different from other known host-guest pairs that have been applied in biological systems.This research provides a new noncovalent bioconjugation tool and a new concept for designing bioorthogonal host-guest pairs for biological applications.

关 键 词：cell targeting tissue imaging BIOCONJUGATION bioorthogonal host-guest pair naphthotube 

分 类 号：O62[理学—有机化学]