An efficient fluorescent probe for rapid sensing of different concentration ranges of cysteine with two-stage ratiometric signals. (October 2018)

• Record Type: Journal Article
• Authors: Wang, Lingyun; Zhuo, Shaochun; Tang, Hao; Cao, Derong
• Is Part Of: Dyes and pigments. Volume 157(2018)
• Page Start: 284
• Page End: 289
• Publication Date: 2018-10
• Subjects: α, β-unsaturated ketone -- Diketopyrrolopyrrole -- Acrylate -- Fluorescent probe -- Biological thiols; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2018.05.004
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: A diketopyrrolopyrrole-based fluorescent probe (DPP-AC ) for rapid sensing of different concentration ranges of cysteine (Cys) has been designed and synthesized, where acrylate group and α, β-unsaturated ketone moiety onDPP-AC are employed as the high and low sensitivity sites, respectively. On the basis of proposed strategy, probeDPP-AC showed ratiometric fluorescent change from 605 nm to 578 nm in presence of low concentration of Cys because of the conjugate addition-cyclization-elimination sequence reaction of acrylate group ofDPP-AC with Cys. The addition of excess Cys caused second stage of ratiometric fluorescent change from 578 nm to 560 nm, which due to the Michael addition reaction between α, β-unsaturated ketone ofDPP-AC and Cys. Moreover, different concentration ranges of cysteine detection can be completed in 6 min at room temperature. The limit of detection (LOD) was found to be 0.18 μM and 2.9 μM in less and excess Cys ranges, respectively. Furthermore, probeDPP-AC possessed highly selective property to differentiate Cys over glutathione and homocysteine.DPP-AC was also successfully used in cell imaging. Graphical abstract: Highlights: A diketopyrrolopyrrole (DPP)-based fluorescent probe was synthesized. Two distinct ratiometric fluorescent signals were achieved in presence of less and excess Cys. Probe can rapidly distinguish Cys from Hcy and GSH.