Keto-benzo[h]-Coumarin-Based Near-Infrared Dyes with Large Stokes Shifts for Bioimaging Applications

Guangle Niu; Weimin Liu; Hongyan Xiao; Hongyan Zhang; Jianhong Chen; Qing Dai; Jiechao Ge; Jiasheng Wu; Pengfei Wang

doi:10.1002/asia.201501026

Keto-benzo[h]-Coumarin-Based Near-Infrared Dyes with Large Stokes Shifts for Bioimaging Applications

Guangle Niu, Weimin Liu^*, Hongyan Xiao, Hongyan Zhang, Jianhong Chen, Qing Dai, Jiechao Ge, Jiasheng Wu, Pengfei Wang

^*Corresponding author for this work

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

37 Citations (Scopus)

Abstract

Fluorescence imaging is a promising tool for the visualization of biomolecules in living systems and there is great demand for new fluorescent dyes that absorb and emit in the near-infrared (NIR) region. Herein, we constructed three new fluorescent dyes (NBC dyes) based on keto-benzo[h]coumarin (k-BC) and benzopyrilium salts. These dyes showed large Stokes shifts (>100nm) and NIR emission (>800nm). The relationship between the structures and optical properties of these dyes was further investigated by using density functional theory calculations at the B3LYP/6-3G level of theory. Fluorescence images indicated that the fabricated dyes exhibited good photostability and low cytotoxicity and, thus, have potential applications as imaging agents in living cells and animals.

Original language	English
Pages (from-to)	498-504
Number of pages	7
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	4
DOIs	https://doi.org/10.1002/asia.201501026
Publication status	Published - 18 Feb 2016
Externally published	Yes

Keywords

benzo[h]coumarin
dyes/pigments
fluorescence
imaging agents
near-infrared

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10.1002/asia.201501026

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@article{2b4affc6fe244ab18596f384ad02ec18,

title = "Keto-benzo[h]-Coumarin-Based Near-Infrared Dyes with Large Stokes Shifts for Bioimaging Applications",

abstract = "Fluorescence imaging is a promising tool for the visualization of biomolecules in living systems and there is great demand for new fluorescent dyes that absorb and emit in the near-infrared (NIR) region. Herein, we constructed three new fluorescent dyes (NBC dyes) based on keto-benzo[h]coumarin (k-BC) and benzopyrilium salts. These dyes showed large Stokes shifts (>100nm) and NIR emission (>800nm). The relationship between the structures and optical properties of these dyes was further investigated by using density functional theory calculations at the B3LYP/6-3G level of theory. Fluorescence images indicated that the fabricated dyes exhibited good photostability and low cytotoxicity and, thus, have potential applications as imaging agents in living cells and animals.",

keywords = "benzo[h]coumarin, dyes/pigments, fluorescence, imaging agents, near-infrared",

author = "Guangle Niu and Weimin Liu and Hongyan Xiao and Hongyan Zhang and Jianhong Chen and Qing Dai and Jiechao Ge and Jiasheng Wu and Pengfei Wang",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

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doi = "10.1002/asia.201501026",

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AU - Niu, Guangle

AU - Liu, Weimin

AU - Xiao, Hongyan

AU - Zhang, Hongyan

AU - Chen, Jianhong

AU - Dai, Qing

AU - Ge, Jiechao

AU - Wu, Jiasheng

AU - Wang, Pengfei

PY - 2016/2/18

Y1 - 2016/2/18

N2 - Fluorescence imaging is a promising tool for the visualization of biomolecules in living systems and there is great demand for new fluorescent dyes that absorb and emit in the near-infrared (NIR) region. Herein, we constructed three new fluorescent dyes (NBC dyes) based on keto-benzo[h]coumarin (k-BC) and benzopyrilium salts. These dyes showed large Stokes shifts (>100nm) and NIR emission (>800nm). The relationship between the structures and optical properties of these dyes was further investigated by using density functional theory calculations at the B3LYP/6-3G level of theory. Fluorescence images indicated that the fabricated dyes exhibited good photostability and low cytotoxicity and, thus, have potential applications as imaging agents in living cells and animals.

AB - Fluorescence imaging is a promising tool for the visualization of biomolecules in living systems and there is great demand for new fluorescent dyes that absorb and emit in the near-infrared (NIR) region. Herein, we constructed three new fluorescent dyes (NBC dyes) based on keto-benzo[h]coumarin (k-BC) and benzopyrilium salts. These dyes showed large Stokes shifts (>100nm) and NIR emission (>800nm). The relationship between the structures and optical properties of these dyes was further investigated by using density functional theory calculations at the B3LYP/6-3G level of theory. Fluorescence images indicated that the fabricated dyes exhibited good photostability and low cytotoxicity and, thus, have potential applications as imaging agents in living cells and animals.

KW - benzo[h]coumarin

KW - dyes/pigments

KW - fluorescence

KW - imaging agents

KW - near-infrared

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SN - 1861-4728

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SP - 498

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

Keto-benzo[h]-Coumarin-Based Near-Infrared Dyes with Large Stokes Shifts for Bioimaging Applications

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Keywords

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