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Benzoyl Peroxide Detection in Real Samples and Zebrafish Imaging by a Designed Near-Infrared Fluorescent Probe

Benzoyl Peroxide Detection in Real Samples and Zebrafish Imaging by a Designed Near-Infrared Fluorescent Probe

Xinwei Tian, Zhao Li, Yaxing Pang, Dongyu Li, Xingbin Yang

J Agric Food Chem. 2017 Nov 1;65(43):9553-9558.

PMID: 28994594

Abstract:

A novel near-infrared fluorescence off-on probe, (E)-3,3-dimethyl-1-propyl-2-(2-(6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3H-indolium (1), is developed and applied to benzoyl peroxide (BPO) detection in real samples and fluorescence imaging in living cells and zebrafish. When arylboronate as the recognition unit is connected to a stable hemicyanine skeleton, the probe is readily prepared, which exhibits superior analytical performance, such as near-infrared fluorescence emission over 700 nm and high sensitivity with a low detection limit of 47 nM. Upon reaction with BPO, phenylboronic acid pinacol ester is oxidized, followed by hydrolysis and 1,4-elimination of o-quinone methide to release fluorophore. In addtion, the probe displays high selectivity toward BPO over other common substances, which makes it of great potential use in quantitative and simple detection of BPO in wheat flour and antimicrobial agent. More importantly, the probe has been successfully demonstrated for monitoring BPO in living HeLa cells and zebrafish. The probe with superior properties could be of great potential use in other biosystems and in vivo studies.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP146631007	4-(Benzyloxy)phenylboronic acid	146631-00-7	Price
AP156682541	3-(Benzyloxy)phenylboronic acid	156682-54-1	Price
AP754226409	4-(Benzyloxy)phenylboronic acid pinacol ester	754226-40-9	Price
AP849062175	2,2′:5′,2″-Terthiophene-5-boronic acid pinacol ester	849062-17-5	Price
AP864754198	1-(Thiophen-2-ylmethyl)-1H-pyrazole-4-boronic acid pinacol ester	864754-19-8	Price
LS79340	2-(Benzyloxy)phenylboronic acid pinacol ester		Price
LS79341	3-(Benzyloxy)phenylboronic acid pinacol ester		Price
LS793443	3,5-Difluoro-2-methoxyphenylboronic acid, pinacol ester		Price

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