Development of Facile and Selective Fluorescent Probe for Physiological Phosphates based on Aggregation-induced Emission

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ORIGINAL ARTICLE

Development of Facile and Selective Fluorescent Probe for Physiological Phosphates based on Aggregation-induced Emission Zhe Jiao 1,2

&

Xiaojuan Long 3 & Yingfang Lu 3 & Zongning Guo 4 & Xuelin Huang 4 & Chao Song 5,6

Received: 16 March 2020 / Accepted: 16 July 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020

Abstract In this work, two new fluorescence chemosensors 2-(4-(1,2,2-triphenylvinyl)phenoxy) acetic acid (TPE-COOH) and 2,2’-(((1,2diphenylethane-1,2-diyl)bis(4,1-phenylene))bis(oxy))diacetic acid (TPE-(COOH)2) were synthesized and applied for the facile detection of physiological phosphates. Due to the aggregation-induced emission (AIE) character, the emission can be turned on after label free interaction with polyethyleneimine (PEI). When the physiological phosphates were introduced to the system, the AIEgens/PEI complex was dissociated due to stronger electrostatic interaction between PEI and phosphates, which resulted in the significant fluorescence quenching of AIEgens. As the four kinds of phosphates cytidine-5’-diphosphate disodium salt (CDP), adenosine-5 (ADP), sodium pyrophosphate (PPi) and guanosine-5’-diphosphate disodium salt (GDP) had different interaction with PEI, also the TPE-COOH and TPE-(COOH)2 had different interaction with PEI, the fluorescence quenching effect was distinct for four phosphates. The unique pattern of fluorescence variations was differentiated by chemometric methods including principal component analysis and linear discriminant analysis. The robustness of the sensor array was proved by discrimination of four kinds of phosphates in serum samples with different concentrations, and the discrimination capacity was not influenced in complicated samples Keywords AIEgens . Physiological phosphates . Sensor array . Fluorescence . PEI

Introduction Physiological phosphates play fundamental roles in biological events such as genetic information transfer, DNA replication, metabolism, and bioenergetics, etc. [1]. Adenosine-5 (ADP) plays a central role as the product of many metabolic reactions. ADP and Pyrophosphate (PPi) are phosphorylated

product. of ATP hydrolysis under cellular conditions. Although the single phosphate-containing biomolecule probe has been developed, it cannot reflect the exact biological significance of phosphates [2]. It is necessary to develop analytical method for sensing the concentration of nucleotides phosphates simultaneously, which is very important for studying the diseases diagnosis and metabolic processes.

Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10895-020-02587-y) contains supplementary material, which is available to authorized users. * Zhe Jiao [email protected] * Xuelin Huang [email protected] * Chao Song [email protected] 1

2

School of Environment and Civil Engineering, Dongguan University of Technology, Dongguan 523808, China Dongguan thonebio. Co. Ltd, Dongguan 523003, China

3

Dongguan Environmental Monitoring Centre, 523009 Dongguan, China

4

Inte