Enantiopure Corral[4]BINOLs as Ultrastrong Receptors for Recognition and Differential Sensing of Steroids

• Published in: Angewandte Chemie International Edition Vol. 63; no. 24; pp. e202406233 - n/a
• Main Authors: Fu, Rong, Li, Dai‐Yuan, Tian, Jia‐Hong, Lin, Yi‐Lin, Zhao, Qing‐Yu, Li, Wen‐Li, Chen, Fang‐Yuan, Guo, Dong‐Sheng, Cai, Kang
• Format: Journal Article
• Language: English
• Published: Germany 10.06.2024
• Subjects: Chiral macrocycles; fluorescent sensor array; molecular recognition; steroid receptors; Chiral macrocycles; molecular recognition; fluorescent sensor array; steroid receptors
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202406233

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. 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.