Journal
ANALYTICA CHIMICA ACTA
Volume 933, Issue -, Pages 175-181Publisher
ELSEVIER
DOI: 10.1016/j.aca.2016.05.019
Keywords
Biomarker; pH probe; Lysosome; benzo[a]phenoxazinium; Photoinduced electron transfer
Categories
Funding
- National Natural Science Foundation of China [51273136]
- Natural Science Fund of Jiangsu Province [BK20151262]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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In this paper, the design of a lysosome-targetable pH probe that has a fluorescent OFF (pH = 4) to ON (pH = 5-6) response is described to identify lysosomes in normal cells. The mechanism of photoinduced electron transfer with a fluorophore-based reaction (FBR-PET) was proposed. Benzo[a]phenoxazines with electro-donating aryl groups were selected, its (2,5-dimethoxyphenyl) imino-, (2-hydroxyphenyl) imino- and (2-hydroxy-5-methoxyphenyl)-imino-derivatives (probes 1a-c) were prepared and their optical responses towards pH were evaluated; their fluorescence pH titration experiments gave regularly changes with the increasing electro-donating abilities at the linked aryl groups, the (2-hydroxy-5-methoxyphenyl) iminobenzo[a]phenoxazine (probe 1c) exhibited a nearly OFF-ON response at 580-800 nm. All probes were reversible, and they showed excellent selectivity toward the proton over other competitive species. Fluorescence confocal images were performed with HeLa, KB cancer cells and V79 normal cells, probes 1a-c are all lysosome-targetable pH probes, and benzo[a]phenoxazine with (2-hydroxy-5-methoxyphenyl) imino-group (probe 1c) has potential applications in selective differentiation of normal cells from cancer cells. (C) 2016 Elsevier B.V. All rights reserved.
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