Dyes and Pigments, volume 176, pages 108209

Highly photostable ketopyrrolyl-BODIPYs with red aggregation-induced emission characteristics for ultrafast wash-free mitochondria-targeted bioimaging

Wu Hao ¹

Guo Xing ¹

Yu Changjiang ^{2, 3, 4}

Wong Wai-yeung ²

Hao Erhong ¹

Jiao Lijuan ¹

Hide authors affiliations Show authors affiliations: 4 affiliations

The Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, School of Chemistry and Materials Science, Anhui Normal University , Wuhu 241000, China. |

Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, China |

State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China |

⁴

Publication type: Journal Article

Publication date: 2020-05-01

Elsevier

Journal: Dyes and Pigments

Quartile SCImago

Quartile WOS

Impact factor: 4.5

ISSN: 01437208, 18733743

DOI: 10.1016/j.dyepig.2020.108209

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General Chemical Engineering

Process Chemistry and Technology

Abstract

Subcellular organelle-specific probes, including mitochondria-targeted fluorescent probes, have attracted enormous research interests because they can monitor or visualize the morphology or biological activities of specific organelles and play an indispensable role in disease diagnosis. To follow the process, highly specific and photostable fluorescent probes are in demand. However, commercially available mitochondria probes normally suffer from poor photostability under laser irradiation and aggregation caused quenching (ACQ) in the aggregate state. In this work, two simple aggregation-induced emission(AIE)-active meso-2-ketopyrrolyl BODIPYs were developed via a convenient one-pot synthetic procedure from 2-methylpyrrole and corresponding pyrrolyldiketone in the presence of BF3·OEt2. The two AIE luminogens (AIEgens) both show very weak fluorescence (maximum emission peaks at 545 and 559 nm, respectively) in DMSO and strong near-infrared solid-state emission. The fluorescence was dramatically intensified and redshifted to 635 and 643 nm, respectively, when water fraction was increased up to above 95% in the DMSO/water mixtures. Both AIEgens were found to specifically “light up” the cell mitochondria with high biocompatibility. Interestingly, the staining process can be shortened for less than a minute after the addition of the AIEgens and without the involvement of a washing procedure, indicating an ultrafast and easy-to-operate staining protocol. Furthermore, their fluorescent images in deep tissue penetration were captured with a satisfied signal-to-noise ratio at a depth of 20 and 30 μm along the direction of the z-axis. Importantly, both AIEgens exhibit high photostability under harsh continuous laser irradiation, demonstrating their potential application as in visualizing and tracking specific mitochondria-associated dynamic changes.

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Dyes and Pigments	Dyes and Pigments, 5, 27.78% Dyes and Pigments 5 publications, 27.78%
Chemistry - A European Journal	Chemistry - A European Journal, 2, 11.11% Chemistry - A European Journal 2 publications, 11.11%
Colloids and Surfaces A: Physicochemical and Engineering Aspects	Colloids and Surfaces A: Physicochemical and Engineering Aspects, 1, 5.56% Colloids and Surfaces A: Physicochemical and Engineering Aspects 1 publication, 5.56%
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 1, 5.56% Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 1 publication, 5.56%
Sensors and Actuators, B: Chemical	Sensors and Actuators, B: Chemical, 1, 5.56% Sensors and Actuators, B: Chemical 1 publication, 5.56%
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Biomaterials Science	Biomaterials Science, 1, 5.56% Biomaterials Science 1 publication, 5.56%
Journal of Materials Chemistry C	Journal of Materials Chemistry C, 1, 5.56% Journal of Materials Chemistry C 1 publication, 5.56%
Chemical Communications	Chemical Communications, 1, 5.56% Chemical Communications 1 publication, 5.56%
Coordination Chemistry Reviews	Coordination Chemistry Reviews, 1, 5.56% Coordination Chemistry Reviews 1 publication, 5.56%
Applied Surface Science	Applied Surface Science, 1, 5.56% Applied Surface Science 1 publication, 5.56%
Chemical Reviews	Chemical Reviews, 1, 5.56% Chemical Reviews 1 publication, 5.56%
Chemical Society Reviews	Chemical Society Reviews, 1, 5.56% Chemical Society Reviews 1 publication, 5.56%
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Citations by publishers

	2 4 6 8 10
Elsevier	Elsevier, 10, 55.56% Elsevier 10 publications, 55.56%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 4, 22.22% Royal Society of Chemistry (RSC) 4 publications, 22.22%
Wiley	Wiley, 3, 16.67% Wiley 3 publications, 16.67%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 5.56% American Chemical Society (ACS) 1 publication, 5.56%
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Wu H. et al. Highly photostable ketopyrrolyl-BODIPYs with red aggregation-induced emission characteristics for ultrafast wash-free mitochondria-targeted bioimaging // Dyes and Pigments. 2020. Vol. 176. p. 108209.

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Wu H., Guo X., Yu C., Wong W., Hao E., Jiao L. Highly photostable ketopyrrolyl-BODIPYs with red aggregation-induced emission characteristics for ultrafast wash-free mitochondria-targeted bioimaging // Dyes and Pigments. 2020. Vol. 176. p. 108209.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.dyepig.2020.108209

UR - https://doi.org/10.1016%2Fj.dyepig.2020.108209

TI - Highly photostable ketopyrrolyl-BODIPYs with red aggregation-induced emission characteristics for ultrafast wash-free mitochondria-targeted bioimaging

T2 - Dyes and Pigments

AU - Wu, Hao

AU - Guo, Xing

AU - Yu, Changjiang

AU - Wong, Wai-yeung

AU - Hao, Erhong

AU - Jiao, Lijuan

PY - 2020

DA - 2020/05/01 00:00:00

PB - Elsevier

SP - 108209

VL - 176

SN - 0143-7208

SN - 1873-3743

ER -

BibTex

Cite this

BibTex Copy

@article{2020_Wu,

author = {Hao Wu and Xing Guo and Changjiang Yu and Wai-yeung Wong and Erhong Hao and Lijuan Jiao},

title = {Highly photostable ketopyrrolyl-BODIPYs with red aggregation-induced emission characteristics for ultrafast wash-free mitochondria-targeted bioimaging},

journal = {Dyes and Pigments},

year = {2020},

volume = {176},

publisher = {Elsevier},

month = {may},

url = {https://doi.org/10.1016%2Fj.dyepig.2020.108209},

pages = {108209},

doi = {10.1016/j.dyepig.2020.108209}

}

Found error?

Publisher

Elsevier

Journal

Dyes and Pigments

Quartile SCImago

Quartile WOS

Impact factor

4.5

ISSN

01437208 (Print)
18733743 (Electronic)