A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells

• Published in: Chinese chemical letters 2024-10, Vol.35 (10), p.109862, Article 109862
• Main Authors: Ni, Chuan-Zhi, Li, Ruo-Ming, Zhang, Fang-Qi, Li, Qu-Ao-Wei, Zhu, Yuan-Yuan, Zeng, Jie, Gu, Shuang-Xi
• Format: Article
• Language: English
• Subjects: Basic amino acids; Cell imaging; Chemoselectivity; Chiral recognition; Enantioselectivity; Fluorescent probe
• ISSN: 1001-8417
• DOI: 10.1016/j.cclet.2024.109862

A novel and readily available binaphthyl-based fluorescent probe (S)-1 was designed and synthesized. (S)-1 can be used to not only chemoselectively discriminate 3 basic amino acids out of common amino acids, but also enantioselectively recognize histidine. Encouragingly, enantioselective imaging of histidine in cells was achieved for the first time by the probe (S)-1. These performances endowed it potential application in the chiral analysis of basic amino acids in asymmetric synthesis and cell imaging for diagnosis of diseases caused by racemization of histidine. Nuclear magnetic resonance (NMR) and mass spectrometry investigations suggested that different reaction extent of (S)-1 with l/d-histidine and different product structures generated the observed enantioselective fluorescent response. The molecular structures and thermodynamic stability of the complexes, formed from (S)-1 + Zn2+ and enantiomers of histidine, were calculated by Gaussian 16 based on density functional theory (DFT) to validate the above action mechanism. A novel fluorescent probe has been successfully applied to chemoselectively discriminate 3 basic amino acids out of common amino acids, and enantioselectively recognize histidine for the first time in both solutions and cells. These endowed it potential application in the chiral analysis of basic amino acids in asymmetric synthesis and cell imaging for diagnosis of diseases. [Display omitted]