A highly selective ESIPT-based fluorescent probe with a large Stokes shift for the turn-on detection of cysteine and its application in living cells

Huace Sheng; Yonghong Hu; Yi Zhou; Shimin Fan; Yang Cao; Xinxin Zhao; Wenge Yang

doi:10.1016/j.dyepig.2018.07.036

A highly selective ESIPT-based fluorescent probe with a large Stokes shift for the turn-on detection of cysteine and its application in living cells

Huace Sheng, Yonghong Hu, Yi Zhou, Shimin Fan, Yang Cao, Xinxin Zhao, Wenge Yang

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82 Scopus citations

Abstract

A new imidazo [1,5-a]pyridine-based fluorescent probe, named MZC-AC, is developed for the detection of cysteine (Cys) based on an excited state intramolecular proton transfer (ESIPT) mechanism. The probe MZC-AC uses an acrylate moiety as the ESIPT blocking group as well as the recognition site. Upon the treatment with Cys, MZC-AC exhibits a dramatic fluorescence enhancement (85-fold) and a large Stokes shift (166 nm). The limit of detection obtained from fluorescent titration was as low as 0.07 μM. MZC-AC displays highly sensitive and selective response to Cys over homocysteine (Hcy) and glutathione (GSH). Significantly, MZC-AC could be used to detect Cys in living cells.

Original language	English
Pages (from-to)	48-57
Number of pages	10
Journal	Dyes and Pigments
Volume	160
DOIs	https://doi.org/10.1016/j.dyepig.2018.07.036
State	Published - Jan 2019

Keywords

Cell imaging
Cysteine
Fluorescent probe
Imidazo[1,5-a]pyridine
Michael addition

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10.1016/j.dyepig.2018.07.036

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title = "A highly selective ESIPT-based fluorescent probe with a large Stokes shift for the turn-on detection of cysteine and its application in living cells",

abstract = "A new imidazo [1,5-a]pyridine-based fluorescent probe, named MZC-AC, is developed for the detection of cysteine (Cys) based on an excited state intramolecular proton transfer (ESIPT) mechanism. The probe MZC-AC uses an acrylate moiety as the ESIPT blocking group as well as the recognition site. Upon the treatment with Cys, MZC-AC exhibits a dramatic fluorescence enhancement (85-fold) and a large Stokes shift (166 nm). The limit of detection obtained from fluorescent titration was as low as 0.07 μM. MZC-AC displays highly sensitive and selective response to Cys over homocysteine (Hcy) and glutathione (GSH). Significantly, MZC-AC could be used to detect Cys in living cells.",

keywords = "Cell imaging, Cysteine, Fluorescent probe, Imidazo[1,5-a]pyridine, Michael addition",

author = "Huace Sheng and Yonghong Hu and Yi Zhou and Shimin Fan and Yang Cao and Xinxin Zhao and Wenge Yang",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2019",

month = jan,

doi = "10.1016/j.dyepig.2018.07.036",

language = "英语",

volume = "160",

pages = "48--57",

journal = "Dyes and Pigments",

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TY - JOUR

T1 - A highly selective ESIPT-based fluorescent probe with a large Stokes shift for the turn-on detection of cysteine and its application in living cells

AU - Sheng, Huace

AU - Hu, Yonghong

AU - Zhou, Yi

AU - Fan, Shimin

AU - Cao, Yang

AU - Zhao, Xinxin

AU - Yang, Wenge

PY - 2019/1

Y1 - 2019/1

N2 - A new imidazo [1,5-a]pyridine-based fluorescent probe, named MZC-AC, is developed for the detection of cysteine (Cys) based on an excited state intramolecular proton transfer (ESIPT) mechanism. The probe MZC-AC uses an acrylate moiety as the ESIPT blocking group as well as the recognition site. Upon the treatment with Cys, MZC-AC exhibits a dramatic fluorescence enhancement (85-fold) and a large Stokes shift (166 nm). The limit of detection obtained from fluorescent titration was as low as 0.07 μM. MZC-AC displays highly sensitive and selective response to Cys over homocysteine (Hcy) and glutathione (GSH). Significantly, MZC-AC could be used to detect Cys in living cells.

AB - A new imidazo [1,5-a]pyridine-based fluorescent probe, named MZC-AC, is developed for the detection of cysteine (Cys) based on an excited state intramolecular proton transfer (ESIPT) mechanism. The probe MZC-AC uses an acrylate moiety as the ESIPT blocking group as well as the recognition site. Upon the treatment with Cys, MZC-AC exhibits a dramatic fluorescence enhancement (85-fold) and a large Stokes shift (166 nm). The limit of detection obtained from fluorescent titration was as low as 0.07 μM. MZC-AC displays highly sensitive and selective response to Cys over homocysteine (Hcy) and glutathione (GSH). Significantly, MZC-AC could be used to detect Cys in living cells.

KW - Cell imaging

KW - Cysteine

KW - Fluorescent probe

KW - Imidazo[1,5-a]pyridine

KW - Michael addition

UR - http://www.scopus.com/inward/record.url?scp=85050867600&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2018.07.036

DO - 10.1016/j.dyepig.2018.07.036

M3 - 文章

AN - SCOPUS:85050867600

SN - 0143-7208

VL - 160

SP - 48

EP - 57

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

A highly selective ESIPT-based fluorescent probe with a large Stokes shift for the turn-on detection of cysteine and its application in living cells

Abstract

Keywords

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