Analytica chimica acta · 2026
Stereospecific recognition of S-fluoxetine enabled by HOF-101-based multimodal probe.
СтатьяПоддержка исследования: вне правительства СШАНазвание и аннотация: Перевод в очереди
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Chen Yiqi, Zhang Yuxin, Jiang Fuyang, Zhang Lianming, Li Jianping
Аннотация
BACKGROUND: Given the distinct pharmacological activities and toxicological profiles of fluoxetine enantiomers, highly selective analytical tools are essential to ensure medication safety and advance the accuracy of chiral recognition. The hydrogen-bonded organic framework HOF-101 possesses well defined porous channels, abundant directional hydrogen-bonding sites, and intrinsic fluorescence, and can achieve chiral recognition through differential cavity confinement and stereospecific hydrogen-bonding interactions. Based on this, we have developed a multimodal chiral fluorescent probe based on HOF-101 to identify the enantiomers of fluoxetine.
RESULTS: By leveraging the ordered porous structure and abundant active sites of HOF-101, we effectively identified the enantiomers of fluoxetine using a combination of colorimetric, fluorescent, and electrochemical detection methods. We investigated the probe's performance across three orthogonal detection modalities: visual colorimetry response, fluorescence turn-on (λem blue-shift from 550.0 nm to 450.0 nm; PLQY increase from 7.38% to 87.77%), and electrochemistry response. The limits of detection (LODs) were 0.464 nM (fluorescence) and 0.0303 nM (electrochemistry), respectively, the probe achieved sub-nanomolar sensitivity. The selective recognition mechanism involves competitive hydrogen bonding, wherein S-FLX enters the cavity of HOF-101, inducing a structural collapse that elicits pronounced photophysical and electrochemical responses. In contrast, the R-enantiomer is excluded due to steric incompatibility, resulting in negligible signal changes.
SIGNIFICANCE AND NOVELTY: These results highlight that cross validation across all three modes confirms result reproducibility and eliminates modality specific artifacts. This study provides a new technical solution for the rapid recognition and high sensitivity detection of chiral drugs.
RESULTS: By leveraging the ordered porous structure and abundant active sites of HOF-101, we effectively identified the enantiomers of fluoxetine using a combination of colorimetric, fluorescent, and electrochemical detection methods. We investigated the probe's performance across three orthogonal detection modalities: visual colorimetry response, fluorescence turn-on (λem blue-shift from 550.0 nm to 450.0 nm; PLQY increase from 7.38% to 87.77%), and electrochemistry response. The limits of detection (LODs) were 0.464 nM (fluorescence) and 0.0303 nM (electrochemistry), respectively, the probe achieved sub-nanomolar sensitivity. The selective recognition mechanism involves competitive hydrogen bonding, wherein S-FLX enters the cavity of HOF-101, inducing a structural collapse that elicits pronounced photophysical and electrochemical responses. In contrast, the R-enantiomer is excluded due to steric incompatibility, resulting in negligible signal changes.
SIGNIFICANCE AND NOVELTY: These results highlight that cross validation across all three modes confirms result reproducibility and eliminates modality specific artifacts. This study provides a new technical solution for the rapid recognition and high sensitivity detection of chiral drugs.