Novel fluorescent ESIPT probe based on flavone for nitroxyl in aqueous solution and serum

Xiaodong Jin; Xiaoli Sun; Xiaoyu Di; Xueqiong Zhang; Hai Huang; Jingning Liu; Pengwei Ji; Hongjun Zhu

doi:10.1016/j.snb.2015.09.072

Novel fluorescent ESIPT probe based on flavone for nitroxyl in aqueous solution and serum

Xiaodong Jin, Xiaoli Sun, Xiaoyu Di, Xueqiong Zhang, Hai Huang, Jingning Liu, Pengwei Ji, Hongjun Zhu

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

47 Scopus citations

Abstract

A excited-state intramolecular proton transfer (ESIPT) fluorescent turn-on probe (FLA-1) for the detection of nitroxyl (HNO) is designed and synthesized. It consists of a flavone derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group as a recognition receptor, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent flavone derivative. In addition, the results showed that FLA-1 exhibited a selective response to HNO over other biological reductants and can quantitatively detect HNO in the range of 0-20 μM with the detection limit of 1.28 × 10^-7 M in aqueous solution. Importantly, FLA-1 was successfully applied to detect HNO in the range of 2-20 μM with the detection limit of 3.96 × 10^-7 M in complex biological samples (serum) demonstrating its value in practical application.

Original language	English
Pages (from-to)	209-216
Number of pages	8
Journal	Sensors and Actuators B: Chemical
Volume	224
DOIs	https://doi.org/10.1016/j.snb.2015.09.072
State	Published - 1 Mar 2016

Keywords

Bovine serum
ESIPT
Flavone
Nitroxyl

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10.1016/j.snb.2015.09.072

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title = "Novel fluorescent ESIPT probe based on flavone for nitroxyl in aqueous solution and serum",

abstract = "A excited-state intramolecular proton transfer (ESIPT) fluorescent turn-on probe (FLA-1) for the detection of nitroxyl (HNO) is designed and synthesized. It consists of a flavone derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group as a recognition receptor, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent flavone derivative. In addition, the results showed that FLA-1 exhibited a selective response to HNO over other biological reductants and can quantitatively detect HNO in the range of 0-20 μM with the detection limit of 1.28 × 10-7 M in aqueous solution. Importantly, FLA-1 was successfully applied to detect HNO in the range of 2-20 μM with the detection limit of 3.96 × 10-7 M in complex biological samples (serum) demonstrating its value in practical application.",

keywords = "Bovine serum, ESIPT, Flavone, Nitroxyl",

author = "Xiaodong Jin and Xiaoli Sun and Xiaoyu Di and Xueqiong Zhang and Hai Huang and Jingning Liu and Pengwei Ji and Hongjun Zhu",

year = "2016",

month = mar,

day = "1",

doi = "10.1016/j.snb.2015.09.072",

language = "英语",

volume = "224",

pages = "209--216",

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TY - JOUR

T1 - Novel fluorescent ESIPT probe based on flavone for nitroxyl in aqueous solution and serum

AU - Jin, Xiaodong

AU - Sun, Xiaoli

AU - Di, Xiaoyu

AU - Zhang, Xueqiong

AU - Huang, Hai

AU - Liu, Jingning

AU - Ji, Pengwei

AU - Zhu, Hongjun

PY - 2016/3/1

Y1 - 2016/3/1

N2 - A excited-state intramolecular proton transfer (ESIPT) fluorescent turn-on probe (FLA-1) for the detection of nitroxyl (HNO) is designed and synthesized. It consists of a flavone derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group as a recognition receptor, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent flavone derivative. In addition, the results showed that FLA-1 exhibited a selective response to HNO over other biological reductants and can quantitatively detect HNO in the range of 0-20 μM with the detection limit of 1.28 × 10-7 M in aqueous solution. Importantly, FLA-1 was successfully applied to detect HNO in the range of 2-20 μM with the detection limit of 3.96 × 10-7 M in complex biological samples (serum) demonstrating its value in practical application.

AB - A excited-state intramolecular proton transfer (ESIPT) fluorescent turn-on probe (FLA-1) for the detection of nitroxyl (HNO) is designed and synthesized. It consists of a flavone derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group as a recognition receptor, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent flavone derivative. In addition, the results showed that FLA-1 exhibited a selective response to HNO over other biological reductants and can quantitatively detect HNO in the range of 0-20 μM with the detection limit of 1.28 × 10-7 M in aqueous solution. Importantly, FLA-1 was successfully applied to detect HNO in the range of 2-20 μM with the detection limit of 3.96 × 10-7 M in complex biological samples (serum) demonstrating its value in practical application.

KW - Bovine serum

KW - ESIPT

KW - Flavone

KW - Nitroxyl

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U2 - 10.1016/j.snb.2015.09.072

DO - 10.1016/j.snb.2015.09.072

M3 - 文章

AN - SCOPUS:84946113058

SN - 0925-4005

VL - 224

SP - 209

EP - 216

JO - Sensors and Actuators B: Chemical

JF - Sensors and Actuators B: Chemical

ER -

Novel fluorescent ESIPT probe based on flavone for nitroxyl in aqueous solution and serum

Abstract

Keywords

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