Flavanone-Based Fluorophores with Aggregation-Induced Emission Enhancement Characteristics for Mitochondria-Imaging and Zebrafish-Imaging.

Abstract

Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction of o-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (φF), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.

• Authors: Na Li, Liyan Liu, Huiqing Luo, Huaqiao Wang, Depo Yang, Feng He
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 25 Issue 14 (Jul 21 2020) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 32708080 (Publication Type: Journal Article)

Chemical References

• Biocompatible Materials
• Flavanones
• Fluorescent Dyes

Topics

• A549 Cells
• Animals
• Biocompatible Materials (chemistry)
• Biomedical Enhancement
• Cell Membrane Permeability
• Cell Survival
• Flavanones (chemical synthesis)
• Fluorescent Dyes (chemical synthesis)
• Humans
• Mitochondria (ultrastructure)
• Molecular Structure
• Optical Imaging (methods)
• Zebrafish