+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on LinkedInFollow on LinkedIn

+ Translate

Dual Site-Controlled and Lysosome-Targeted Intramolecular Charge Transfer-Photoinduced Electron Transfer-Fluorescence Resonance Energy Transfer Fluorescent Probe for Monitoring pH Changes in Living Cells

Dual Site-Controlled and Lysosome-Targeted Intramolecular Charge Transfer-Photoinduced Electron Transfer-Fluorescence Resonance Energy Transfer Fluorescent Probe for Monitoring pH Changes in Living Cells

Analytical Chemistry 88(7): 4085-4091

Acidic pH is a critical physiological factor for controlling the activities and functions of lysosome. Herein, we report a novel dual site-controlled and lysosome-targeted intramolecular charge transfer-photoinduced electron transfer-Fluorescence resonance energy transfer (ICT-PET-FRET) fluorescent probe (CN-pH), which was essentially the combination of a turn-on pH probe (CN-1) and a turn-off pH probe (CN-2) by a nonconjugated linker. Coumarin and naphthalimide fluorophores were selected as donor and acceptor to construct the FRET platform. Hydroxyl group and morpholine were simultaneously employed as the two pH sensing sites and controlled the fluorescence of coumarin and naphthalimide units by ICT and PET, respectively. The sensing mechanism of CN-pH to pH was essentially an integration of ICT, PET, and FRET processes. Meanwhile, the morpholine also can serve as a lysosome-targeted group. By combining the two data analysis approaches of the ratios of the two emission intensities (R) and the reverse ratio R' (R' = 1/R), the fluorescent ratio of CN-pH can show proportional relationship to pH values in a very broad range from pH 4.0 to 8.0 with high sensitivity. The probe has been successfully applied for the fluorescence imaging of the lysosomal pH values, as well as ratiometrically visualizing chloroquine-stimulated changes of intracellular pH in living cells. These features demonstrate that the probe can afford practical application in biological systems.

(PDF emailed within 0-6 h: $19.90)

Accession: 057666455

Download citation: RISBibTeXText

PMID: 26987045

DOI: 10.1021/acs.analchem.6b00422

Related references

Ratiometric Fluorescent Probe for Vicinal Dithiol-Containing Proteins in Living Cells Designed via Modulating the Intramolecular Charge Transfer-Twisted Intramolecular Charge Transfer Conversion Process. Analytical Chemistry 88(20): 10237-10244, 2016

Implication toward a simple strategy to generate efficiency-tunable fluorescence resonance energy transfer emission: intertwining medium-polarity-sensitive intramolecular charge transfer emission to fluorescence resonance energy transfer. Journal of Physical Chemistry. A 114(20): 6097-6102, 2010

An intramolecular charge transfer process based fluorescent probe for monitoring subtle pH fluctuation in living cells. Talanta 162: 180-186, 2016

Physical mechanism of photoinduced intermolecular charge transfer enhanced by fluorescence resonance energy transfer. Physical Chemistry Chemical Physics, 2018

Triple fluorescence of acridinedione: Locally excited, photoinduced electron transfer promoted charge transfer and anion induced charge transfer states. Journal of Photochemistry and Photobiology A: Chemistry 208(2-3): 117-124, 2009

The fluorescence properties of hypocrellin B and its amino-substituted derivative: photoinduced intramolecular proton transfer and photoinduced intramolecular electron transfer. Photochemistry and Photobiology 80: 112-114, 2004

Twisted Intramolecular Charge Transfer States in 2-Arylbenzotriazoles: Fluorescence Deactivation via Intramolecular Electron Transfer Rather Than Proton Transfer. Journal of Physical Chemistry A 106(34): 7680-7689, 2002

A novel fluorophore with dual fluorescence: local excited state and photoinduced electron-transfer-promoted charge-transfer state. Chemphyschem 5(8): 1200-1209, 2004

Structural factors influencing the intramolecular charge transfer and photoinduced electron transfer in tetrapyrazinoporphyrazines. Physical Chemistry Chemical Physics 16(11): 5440-5446, 2014

DFT/TDDFT Study on the Sensing Mechanism of a Fluorescent Probe for Hydrogen Sulfide: Excited State Intramolecular Proton Transfer Coupled Twisted Intramolecular Charge Transfer. Journal of Physical Chemistry. A 121(28): 5245-5256, 2017

Influence of π-conjugation structural changes on intramolecular charge transfer and photoinduced electron transfer in donor-π-acceptor dyads. Physical Chemistry Chemical Physics 19(1): 426-435, 2016

A new fluorescence turn-on probe for biothiols based on photoinduced electron transfer and its application in living cells. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 166: 31-37, 2016

Reaction-based sensing of fluoride ions using built-in triggers for intramolecular charge transfer and photoinduced electron transfer. Organic Letters 12(7): 1400-1403, 2010

Generation of an intramolecular three-color fluorescence resonance energy transfer probe by site-specific protein labeling. Journal of Peptide Science 20(2): 115-120, 2016

In vivo monitoring of caspase activation using a fluorescence resonance energy transfer-based fluorescent probe. Methods in Enzymology 544: 299-325, 2015