A fluorescent probe for enantioselective recognition of amino acids in solutions, cells and zebrafishes

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2025-03-06 DOI:10.1016/j.dyepig.2025.112739

Shi-Wei Fu , Zong-Xing Huang , Chuan-Zhi Ni , Fang-Qi Zhang , Yang Li , Yuan-Yuan Zhu , Qi Sun , Shuang-Xi Gu

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Abstract

Binaphthyl-based chiral fluorescent probes (S)-/(R)-1 featuring a 2-methylthiophenimide unit were designed and synthesized. The fluorescent response to enantiomer pairs of amino acids revealed that (S)- and (R)-enantimer of the probe had chiral bias to L- and d-amino acids, respectively. The compound (S)-1 showed outstanding enantioselective fluorescence enhancement toward 10 amino acids (Asn, Glu, Val, Leu, Met, Ser, Gln, Arg, Phe and Ala) in both solvents of EtOH/H₂O and DMSO/H₂O at the condition of pH 7.5. Extremely high enantiomeric fluorescence enhancement ratio (ef, [I_L-I₀]/[I_D-I₀]) were obtained for Asn (646.2), Glu (318.9), Val (255.6), Leu (252.4), Thr (223.9) in EtOH/H₂O, and the ef values to Val, Ala, Ser, Glu, Arg, Gln were all larger than 20 in DMSO/H₂O. Chiral fluorescent imaging of the four amino acids (Ser, Val, Arg and Gln) were obtained in both living cells and zebrafishes via the probe (R)-1, which provides a new concept for the diagnosis and treatment of diseases associated with amino acid racemization. Results of ¹H NMR and HRMS revealed the enantioselective fluorescence enhancement mechanism.

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.