An Amphiphilic Pyridinoyl-hydrazone Probe for Colorimetric and Fluorescence pH Sensing

A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA ) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirorn...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-10, Vol.24 (21), p.3833
Main Authors: Diana, Rosita, Panunzi, Barbara, Tuzi, Angela, Piotto, Stefano, Concilio, Simona, Caruso, Ugo
Format: Article
Language:English
Subjects:
Ammonium
Chromophores
Colorimetry
Ethanol
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
fluorophore/chromophore probe
Hydrazones
Hydrazones - chemical synthesis
Hydrazones - chemistry
Hydrogen-Ion Concentration
Hydrophobicity
Ligands
Lipids
Membranes
molecular dynamic simulation
Molecular dynamics
Molecular Dynamics Simulation
Molecular Structure
ph sensor
pH sensors
Physiology
Polarity
Quantum dots
Sensors
Single crystals
Solvents
Spectral sensitivity
Spectrometry, Fluorescence
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Summary:A new pH sensor based on a substituted aroylhydrazide with a flexible side chain and a terminal trimethyl ammonium group (PHA ) was designed and synthesized. The terminal quaternary ammonium guarantees excellent solubility in water. At the same time, the probe is very soluble in hydrophobic envirornments. The pyridinoyl-hydrazone moiety acts as the pH-sensitive fluorophore/chromophore probe. Extensive physicochemical characterization has been performed on the bromide salt PHABr. DFT calculations, based on single-crystal X-ray data, permitted to rationalize the optical behavior. Molecular dynamics simulations permitted to clarify the mode of interaction with lipid membrane. The ability of the probe to change color and fluorescence in response to different pH and media of different polarity has been investigated. PHABr shows a remarkable pH-dependent behavior in both absorption and fluorescence spectra with high sensitivity and strong on-off switch effect at neutral pH, perceptible even to the naked eye.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24213833