An ultrafast BODIPY single molecular sensor for multi-analytes (acid/base/Cu2+/Bi3+) with different sensing mechanism. (June 2019)

• Record Type: Journal Article
• Authors: Chen, Yuting; Pan, Houhe; Wang, Fang; Zhao, Yunying; Yin, Haoyan; Chen, Yuxiang; Zhang, Junlong; Jiang, Jianzhuang
• Is Part Of: Dyes and pigments. Volume 165(2019)
• Page Start: 279
• Page End: 286
• Publication Date: 2019-06
• Subjects: BODIPY -- Single molecular sensor -- Ultrafast-detecting -- Multi-analytes -- Lysosome; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2019.02.034
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Towards future practical applications, it is necessary to develop the fluorescent sensors with only single fluorophore and single receptor for multiple-analytes detection. In the present work, a novel molecular sensor containing single receptor (the naphthol-azomethine-phenol framework) and single fluorophore (BODIPY), NAP-BODIPY, has been designed and synthesize. Single crystal X-ray diffraction analysis reveals the keto-enamine rather than the enol-imine constitution of the ortho-hydroxy naphthalene azomethine moiety in NAP-BODIPY. As a consequence, along with the conversion between acid and basic conditions in the mixed DMSO/H2 O, the enol-keto tautomerization occurs in the ortho-hydroxy naphthalene azomethine moiety of NAP-BODIPY, resulting in a diverse change over the electronic absorption and fluorescence emission spectra. Moreover, addition of Cu 2+ into NAP-BODIPY solution leads to an obvious red-shift in the maximum absorption and the naked-eye observed change from pale-orange to magenta turbid due to the metal-induced aggregation interaction. Nevertheless, adding Bi 3+ into NAP-BODIPY solution induces a remarkable enhancement over the weak fluorescence emission owing to the inhibition of photo-induced electron transfer process. Subsequent addition of Cu 2+ into the NAP-BODIPY-Bi 3+ (1:10) system triggers a triple-signal change associated with the metal displacement. This, in combination with the fast responsive time of NAP-BODIPY to acid/base/Cu 2+ /Bi 3+ (within several seconds), endows NAP-BODIPY an ultrafast-detecting sensor nature for multi-analytes. In particular, NAP-BODIPY can selectively stain lysosomes and therefore detect the pH change in live cells upon lysosomal acidification, revealing its great application potential for multiple-analytes. Graphical abstract: The naphthol-azomethine-phenol-modified BODIPY molecular sensor consisting only single fluorophore and single receptor exhibits ultrafast-detection for multi-analytes (Acid/Base/Cu 2+ /Bi 3+ ) and acts as good detector for lysosome upon pH change in live Hela cells. Image 1 Highlights: The new BODIPY single molecular sensor displays multi-sensing to Acid/Base/Cu 2+ /Bi 3+ . This BODIPY sensor shows fast-response to multi-analytes based on different mechanisms. This BODIPY sensor can act as a good lysosome acidification detector in live HeLa cells.