RESUMEN
BACKGROUND: The selective recognition of drugs and its metabolism or decomposition products is significant to drug development and drug resistance research. Fluorescence-based techniques provide satisfying sensitivity by target-triggered chemical reaction. However, the interference from the matrix or additives usually restricts the specific detection. It is highly desirable to explore specific chemical reactions for achieving selective perception of these species. RESULTS: We report a specific m-aminophenol (MAP)-dopamine (DA) reaction, which generates highly fluorescent azamonardine-like products. Based on this reaction, fluorometric and indirect detection of p-aminosalicylic acid (typical antituberculosis drug, PAS) can be realized using the DA-based probe with high sensitivity. The acid induces the decarboxylation of PAS and produces MAP, which reacts with DA and generates fluorescent azamonardine-like products. The practical application of the proposed method is validated by the accurate PAS analysis in urine samples and Pasinazid tablets. Interestingly, none of additives in the Pasinazid tablets contribute comparable fluorescence variation. SIGNIFICANCE: This work discovers a new MAP-DA reaction for the first time, it not only explores sensitive PAS drug detection probe, but also demonstrates the feasibility of the development of novel drug analysis platform by recognizing decomposition product with specific reaction. Thus, new avenues for the exploration of simple and rapid spectrophotometric probes toward various drug analytes with high specify and sensitivity based on this tactic might be possible in analytical and drug-related fields.
Asunto(s)
Ácido Aminosalicílico , Dopamina , Espectrofotometría , Fluorometría , Bioensayo , ColorantesRESUMEN
A novel fluorescent probe based on azamonardine (Aza) fluorophore was designed and synthesized for the highly selective detection of cysteine (Cys) in vivo and in vitro. After reacting with acryloyl chloride, the fluorescence of Aza is effectively quenched, resulting in the formation of the Aza-acryl probe. Upon the addition of Cys, the ester bond of Aza-acryl is cleaved, releasing a new compound (Compound 1) with strong fluorescence, thereby achieving fluorescence turn-on detection of Cys. The structure of Aza-acryl was characterized using X-ray crystallography and NMR spectroscopy. Additionally, density functional theory was employed to elucidate the quenching mechanism of the acyl group on the Aza. Aza-acryl exhibits high selectivity towards Cys and distinguishes it from other biothiols such as homocysteine (Hcy) and glutathione (GSH). The mechanism of Aza-acryl for detecting Cys was investigated through HPLC, NMR spectroscopy, high-resolution mass spectrometry, and reaction kinetics experiments. Aza-acryl demonstrates excellent imaging capabilities for Cys in cells and zebrafish, providing a reliable and selectable tool for the detection and imaging of Cys in biological systems.
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Cisteína , Pez Cebra , Animales , Colorantes Fluorescentes , Cromatografía Líquida de Alta Presión , Cristalografía por Rayos X , GlutatiónRESUMEN
The sensitive and selective perception of dopamine (DA, a typical neurotransmitter) is important to evaluate the biological environment. In this study, a catechin-functionalized gold nanocluster (C-Au NC) nanoprobe has been explored for the ratiometric DA sensing. The detection mechanism is based on the formation of azamonardine via selective DA-catechin chemical reaction and subsequent enhanced fluorescence emission. Using Au NC emission as the internal reference, ratiometric fluorescence variation is realized, which allows sensitive DA analysis with a limit of detection of 1.0 nM (S/N = 3) and linear response concentration range from 0 to 500 nM. The characteristic chemical reaction between catechin and DA affords favorable selectivity over other amino acids, metal ions and small molecules. In addition, the practical application of the proposed nanoprobe is validated by the accurate detection of DA content in urea and cell lysate samples.
Asunto(s)
Catequina , Nanopartículas del Metal , Dopamina/análisis , Colorantes Fluorescentes/química , Oro/química , Límite de Detección , Nanopartículas del Metal/química , Espectrometría de FluorescenciaRESUMEN
We propose a sensitive, selective, and rapid fluorescent assay for detecting resorcinol (RC) based on its specific chemical reaction with dopamine. Under alkaline condition, RC would react with dopamine to yield fluorescent azamonardine, which emits strong blue fluorescence and has a superior excitation wavelength at 416 nm and an emission wavelength at 461 nm. The azamonardine with a molecular weight of 258.1 confirmed by ICP-MS has a quantum yield of 71.3%. The reaction is completed within 1 min showing great potential for point-of-care testing. This assay showed high sensitivity and had a good relationship between fluorescent intensity at 461 nm and RC concentration (I461 = 106.4 + 93.6*CRC; R2 = 0.9904) over the range of 0-40 µM. More importantly, the assay showed a prominent anti-interference from various substances and even can distinguish RC from its isomers, o-dihydroxybenzene and p-dihydroxybenzene. Finally, our assay successfully quantified RC contents in wheat powder and hair dyes with high accuracy.
Asunto(s)
Compuestos Aza/química , Dopamina/química , Colorantes Fluorescentes/química , Resorcinoles/análisis , Tinturas para el Cabello/química , Polvos/química , Triticum/químicaRESUMEN
A simple, fast and low-cost method for dopamine (DA) detection based on turn-on fluorescence using resorcinol is developed. The rapid reaction between resorcinol and DA allows the detection to be performed within 5 min, and the reaction product (azamonardine) with high quantum yield generates strong fluorescence signal for sensitive optical detection. The detection exhibits a high sensitivity to DA with a wide linear range of 10 nM-20 µM and the limit of detection is estimated to be 1.8 nM (S/N = 3). This approach has been successfully applied to determine DA concentrations in human urine samples with satisfactory quantitative recovery of 97.84%-103.50%, which shows great potential in clinical diagnosis.