Enantiopure Corral[4]BINOLs as Ultrastrong Receptors for Recognition and Differential Sensing of Steroids
Rong Fu
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
These authors contributed equally: Rong Fu, Dai-Yuan Li
Search for more papers by this authorDai-Yuan Li
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
These authors contributed equally: Rong Fu, Dai-Yuan Li
Search for more papers by this authorJia-Hong Tian
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorYi-Lin Lin
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorQing-Yu Zhao
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorWen-Li Li
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorFang-Yuan Chen
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorProf. Dr. Dong-Sheng Guo
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Kang Cai
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorRong Fu
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
These authors contributed equally: Rong Fu, Dai-Yuan Li
Search for more papers by this authorDai-Yuan Li
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
These authors contributed equally: Rong Fu, Dai-Yuan Li
Search for more papers by this authorJia-Hong Tian
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorYi-Lin Lin
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorQing-Yu Zhao
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorWen-Li Li
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorFang-Yuan Chen
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorProf. Dr. Dong-Sheng Guo
College of Chemistry, Key Laboratory of Functional Polymer Materials (Ministry of Education), State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Kang Cai
College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071 China
Search for more papers by this authorGraphical Abstract
A pair of enantiomeric macrocycles, RRRR- and SSSS-C[4]BINOL, demonstrated exceptionally high recognition affinities (up to 1012 M−1) towards 16 important steroidal compounds in aqueous solutions, establishing them the most effective known steroid receptors. The two C[4]BINOL enantiomers were employed to compose a fluorescent sensor array which achieved discrimination and sensing of 16 structurally similar steroids in biofluids.
Abstract
The precise recognition and sensing of steroids, a type of vital biomolecules, hold immense practical value across various domains. In this study, we introduced corral[4]BINOLs (C[4]BINOLs), a pair of enantiomeric conjugated deep-cavity hosts, as novel synthetic receptors for binding steroids. Due to the strong hydrophobic effect of their deep nonpolar, chiral cavities, the two enantiomers of C[4]BINOLs demonstrated exceptionally high recognition affinities (up to 1012 M−1) for 16 important steroidal compounds as well as good enantioselectiviy (up to 15.5) in aqueous solutions, establishing them as the most potent known steroid receptors. Harnessing their ultrahigh affinity, remarkable enantioselectivity, and fluorescence emission properties, the two C[4]BINOL enantiomers were employed to compose a fluorescent sensor array which achieved discrimination and sensing of 16 structurally similar steroids at low concentrations.
Conflict of interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
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