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一种用于比色和荧光 pH 传感的两亲性吡啶酰腙探针。

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

机构信息

Department of Agriculture, University of Napoli Federico II, via Università 100, 80055 Portici NA, Italy.

Department of Chemical Sciences, University of Napoli Federico II, via Cintia, 80126 Napoli, Italy.

出版信息

Molecules. 2019 Oct 24;24(21):3833. doi: 10.3390/molecules24213833.

DOI:10.3390/molecules24213833
PMID:31652986
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6864485/
Abstract

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.

摘要

基于具有柔性侧链和末端三甲铵基团的取代芳酰腙（PHA）设计并合成了一种新型 pH 传感器。末端季铵保证了在水中的优异溶解性。同时，探针在疏水环境中也非常可溶。吡啶甲酰腙部分作为 pH 敏感的荧光团/生色团探针。已经对溴化物盐 PHABr 进行了广泛的物理化学特性研究。基于单晶 X 射线数据的 DFT 计算允许对光学行为进行合理化解释。分子动力学模拟允许阐明与脂质膜的相互作用模式。已经研究了探针在不同 pH 值和不同极性介质中响应颜色和荧光变化的能力。PHABr 在吸收和荧光光谱中均表现出显著的 pH 依赖性行为，在中性 pH 值下具有高灵敏度和强开-关开关效应，即使肉眼也能察觉到。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/c0539ae876a3/molecules-24-03833-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/507bed66eb4a/molecules-24-03833-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/0ec8929e34b5/molecules-24-03833-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/0def13d702bd/molecules-24-03833-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/2e8b49314699/molecules-24-03833-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/e30ca89b6763/molecules-24-03833-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/6e21699a4a04/molecules-24-03833-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/6862b01a71df/molecules-24-03833-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/4d88ec0d8754/molecules-24-03833-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/42ca314e42fe/molecules-24-03833-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/71c62591bfcf/molecules-24-03833-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/64ef6d880fd1/molecules-24-03833-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/75662c6c0518/molecules-24-03833-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/8a074df2c425/molecules-24-03833-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/c0539ae876a3/molecules-24-03833-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/507bed66eb4a/molecules-24-03833-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/0ec8929e34b5/molecules-24-03833-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/0def13d702bd/molecules-24-03833-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/2e8b49314699/molecules-24-03833-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/e30ca89b6763/molecules-24-03833-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/6e21699a4a04/molecules-24-03833-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/6862b01a71df/molecules-24-03833-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/4d88ec0d8754/molecules-24-03833-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/42ca314e42fe/molecules-24-03833-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/71c62591bfcf/molecules-24-03833-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/64ef6d880fd1/molecules-24-03833-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/75662c6c0518/molecules-24-03833-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/8a074df2c425/molecules-24-03833-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ba8a/6864485/c0539ae876a3/molecules-24-03833-g013.jpg

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