A dual-selective fluorescent probe for GSH and Cys detection: Emission and pH dependent selectivity.
Anal Chim Acta
; 993: 87-95, 2017 Nov 15.
Article
em En
| MEDLINE
| ID: mdl-29078959
ABSTRACT
A novel fluorescent probe 1 based on acridine orange was developed for the selective detection and bioimaging of biothiols. The probe exhibits higher selectivity and turn-on fluorescence response to cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) than to other amino acids. Importantly, the probe responds to GSH and Cys/Hcy with distinct fluorescence emissions in PBS buffer at pH of 7.4. The Cys/Hcy-triggered tandem SNAr-rearrangement reaction and GSH-induced SNAr reaction with the probe led to the corresponding amino-acridinium and thio-acridinium dyes, respectively, which can discriminate GSH from Cys/Hcy through different emission channels. Interestingly, Cys finishes the tandem reaction with the probe and subsequently forms amino-acridinium and Hcy/GSH induces SNAr reaction with the probe to form thio-acridiniums at weakly acidic conditions (pH 6.0), enabling Cys to be discriminated from Hcy/GSH at different emissions. Finally, we demonstrated that probe 1 can selectively probe GSH over Cys and Hcy or Cys over GSH and Hcy in HeLa cells through multicolor imaging.
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Base de dados:
MEDLINE
Assunto principal:
Cisteína
/
Corantes Fluorescentes
/
Glutationa
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article