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Molecules 2018, 23(9), 2290; https://doi.org/10.3390/molecules23092290

Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging

1
School of Pharmaceutical Science, Sun Yat-sen University, Guangzhou 510006, China
2
School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
3
Department of Anatomy and Neurobiology, Zhongshan School of Medicine, Sun Yat-sen University, Guangzhou 510080, China
*
Author to whom correspondence should be addressed.
Received: 16 August 2018 / Revised: 3 September 2018 / Accepted: 5 September 2018 / Published: 7 September 2018
(This article belongs to the Section Chemical Biology)
Full-Text   |   PDF [5735 KB, uploaded 7 September 2018]   |  

Abstract

Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (ФF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging. View Full-Text
Keywords: AIEE; multicolor; flavone; fluorophores; mitochondria AIEE; multicolor; flavone; fluorophores; mitochondria
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Liu, L.; Lei, Y.; Zhang, J.; Li, N.; Zhang, F.; Wang, H.; He, F. Rational Design for Multicolor Flavone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics and Applications in Mitochondria-Imaging. Molecules 2018, 23, 2290.

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