Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
A new “off–on” fluorescent probe for Al3+ in aqueous solution based on rhodamine B and its application to bioimaging
Graphical abstract
Introduction
Aluminum is the most abundant metal element in the earth’s crust that has been widely used in cooking utensils, aluminum-based pharmaceuticals and food additives [1], [2]. However, aluminum is a known neurotoxic element which involved many neurodegenerative diseases such as Parkinson’s disease and Alzheimer’s disease [3], [4], [5]. Thus, it is of great importance to develop efficient methods for the detection of Al3+ in environmental and biological samples. At present, various methods have been employed for the treatment of aluminum, including electrochemical detection [6], HPLC-coupled atomic spectra [7] and mass spectrometry [8]. Although these methods have the characteristics of the fast measurement and good sensitivity, they require complicated sample-pretreatment procedures [9]. Compared with these methods, colorimetric and fluorimetric methods have not only the advantages of operational simplicity, high selectivity, sensitivity and rapidity, but also nondestructive. In the past decades, some chemists and environmentalists has been drawn to study selective and sensitive fluorescent sensors for biological and environmental applications, especially in molecular biology [10]. Up to now, a lot of scientific and technological achievements have been made in the preparation and characterization of fluorescent probes to detect metal ions in environmental samples and imaging of them in living cells [11], [12], [13], [14], [15], [16], [17], [18]. Despite these discoveries, there are comparatively few compounds that target Al3+ with high affinity and specificity.
As we all know, rhodamine is an ideal platforms for development of fluorescent probe owing to its excellent photophysical properties [19], [20]. Specifically, it is based on spirolactam (nonfluorescent) to ring-opened amide (fluorescent) process utilized for the detection of metal ions [21]. Based on this mechanism, our ambition was to design and synthesize a new fluorescent probe for detection of Al3+in aqueous media.
Herein, we introduce a novel and simple method to prepare rhodamine B-based chemosensor by one step reaction. The sensor RBP showed “off–on” type fluorogenic and chromogenic behavior toward Al3+ over other interfering metal ions. Furthermore, the sensor RBP was successfully applied in detection of Al3+ in tap water, lake water and imaging of Al3+ in living cells.
Section snippets
Apparatus
A Hitachi F-7000 FL spectrofluorometer was used for fluorescence measurements. The absorption spectra were recorded with a U-4100 Spectrophotometer. An Olympus Zeiss 710 laser scanning confocal microscopy was used for fluorescence image of cells. 1H and 13C NMR spectra were measured on a Bruker DMX-300 spectrometer at 400 MHz in CDCl3 and DMSO-d6, respectively. The MS spectra were performed on Bruker ESQUIRE HPLC-MS AB 4000Q.
Reagents
Rhodamine B was purchased from Beijing chemical plant, Hydrazine
Absorption and fluorescence response of RBP to different metal ions
The UV/vis titration absorption spectra of RBP (10 μM) were first explored in Tris–HCl (pH 7.2) aqueous buffer solution in the presence of 2 equivalent of different metal ions and the results were depicted in Fig. 1. A solution of RBP in Tris–HCl (pH 7.2) aqueous buffer solution is colorless. The sensor RBP exhibited very weak absorption in the visible range. Upon binding of metal ions (Ag+, Pb2+, Na+, K+, Hg2+, Cd2+, Ba2+, Zn2+, Mg2+, Cu2+, Ni2+, Ca2+, Al3+, Pd2+, Cr3+, Fe3+ and Pt2+), it was
Conclusion
In summary, our present contribution reports a successful “off–on” type fluorescent probe RBP for Al3+ with color changes from colorless to pink in aqueous media. The fluorescent probe was easily synthesized from rhodamine B hydrazide and pyridoxal hydrochloride which showed a high sensitivity and excellent selectivity for determination of Al3+ ion in aqueous media. It has also been successfully applied in detection of Al3+ in tap water, lake water and imaging of Al3+ in living cells.
Acknowledgements
The authors are grateful for the base and cutting-edge technology research project of Henan Province (142300410369), the Natural Science Research project of Henan Province education department (2014A610013).
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