Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Abstract

Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted increasing interest in recent years. On the basis of our previous research, we successfully designed and synthesized eleven chalcones. Through an optical performance experiment, we confirmed that compounds 1–6 had obvious AIEE properties. As these AIEE molecules had excellent fluorescence properties and a large Stokes shift, we studied their application in living cell imaging, and the results showed that these compounds had low cytotoxicity and good biocompatibility at the experimental concentrations. More importantly, they could specifically label mitochondria. Subsequently, we selected zebrafish as experimental animals to explore the possibilities of these compounds in animal imaging. The fluorescence imaging of zebrafish showed that these AIEE molecules can enter the embryo and can be targeted to aggregate in the digestive tract, which provides a strong foundation for their practical application in the field of biological imaging. Compared with traditional fluorophores, these AIEE molecules have the advantages of possessing a small molecular weight and high flexibility. Therefore, they have excellent application prospects in the field of biological imaging. In addition, the findings of this study have very positive practical significance for the discovery of more AIEE molecules.

AIEE-Active Flavones as a Promising Tool for the Real-Time Tracking of Uptake and Distribution in Live Zebrafish

“…This indicates that with the gradual Increase in the water content in the mixed solution, new aggregates were formed in the solution, which led to the gradual enhancement of the fluorescence emission of the compounds. This is consistent with our previous study [ 33 ].…”

“…In our previous study, we found that RIR is supposed to be the main reason for the AIEE properties of the flavonoids, flavones, and chalcones we investigated [ 32 , 33 ]. The same experimental approaches were used to explore the cause of the AIEE phenomenon of compounds 1 – 3 .…”

“…In recent years, flavonoids have attracted the attention of many researchers due to their remarkable array of biological and pharmacological effects as antioxidant, anti-inflammatory, antimicrobial, anticancer, antilipoperoxidant, anti-ischemic, and so on [ 25 , 26 , 27 , 28 , 29 , 30 ]. In our previous studies, we synthesized a series of flavonoids and flavanones and found that several of them had significant AIEE properties [ 31 , 32 , 33 ].…”

Discriminative ‘Turn-on’ Detection of Al3+ and Ga3+ Ions as Well as Aspartic Acid by Two Fluorescent Chemosensors

“…At f w = 95%, the emission bands were distributed equally at both wavelengths. We believe as the hydrophobic anthracene rings repel water, they minimize their contact with water and thus rupture the aggregates beyond a water percentage of 70% [ 62 , 63 ]. Figure 1 b displays changes at various percentages of water varying from 10% to 95% in a MeOH-H 2 O system under UV light.…”

Naturally Occurring Chalcones with Aggregation-Induced Emission Enhancement Characteristics

“…Organic luminophores with high quantum efficiencies have attracted attention due to their widespread applications in organic optoelectronics [1][2][3], laser displays [4,5], lightemitting diodes (OLEDs) [6], fluorescent sensors and biological imaging [7][8][9][10]. However, many traditional fluorophores usually show strong fluorescence only in dilute solutions.…”