Enantioselective Labeling of Zebrafish for D-Phenylalanine Based on Graphene-Based Nanoplatform

Author:

He Yuqing1,Ye Ziqi2,Zhu Fei3,Qiu Tianxiang1,Dai Xiyan1,Xie Yue1,Zou Shibiao1,Dong Qingjian4,Zhang Weiying2,Ma Junkai5,Mao Xiaowei1ORCID

Affiliation:

1. Hubei Key Laboratory of Environmental and Health Effects of Persistent Toxic Substances, School of Environment and Health, Jianghan University, Wuhan 430056, China

2. Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, School of Life Science, Jianghan University, Wuhan 430056, China

3. Hubei Key Laboratory of Embryonic Stem Cell Research, School of Basic Medical Science, Hubei University of Medicine, Shiyan 442000, China

4. Department of Nuclear Medicine, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China

5. Hubei Key Laboratory of Wudang Local Chinese Medicine Research, Department of Chemistry, School of Pharmacy, Hubei University of Medicine, Shiyan 442000, China

Abstract

Enantioselective labeling of important bioactive molecules in complex biological environments by artificial receptors has drawn great interest. From both the slight difference of enantiomers’ physicochemical properties and inherently complexity in living organism point of view, it is still a contemporary challenge for preparing practical chiral device that could be employed in the model animal due to diverse biological interference. Herein, we introduce γ-cyclodextrin onto graphene oxide for fabricating γ-cyclodextrin and graphene oxide assemblies, which provided an efficient nanoplatform for chiral labelling of D-phenylalanine with higher chiral discrimination ratio of KD/KL = 8.21. Significantly, the chiral fluorescence quenching effect of this γ-CD-GO nanoplatform for D-phenylalanine enantiomer in zebrafish was 7.0-fold higher than L-isomer, which exhibiting real promise for producing practical enantio-differentiating graphene-based systems in a complex biological sample.

Funder

National Natural Science Foundation of China

State Key Laboratory of Environmental Chemistry and Ecotoxicology, RCEES, CAS

Central Government Guides Local Scientific and Technological Development Special Fund Project of Hubei Province

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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