Design, synthesis and application in biological imaging of a novel red fluorescent dye based on a rhodanine derivative

Abstract

2RDNTPA can be applied in fluorescence imaging of living cancer cells (HepG2) with red emission of 620 nm and negligible cytotoxicity with a half maximal inhibitory concentration much more than 100 μM.

Rhodanine-Based Chromophores: Fast Access to Capable Photoswitches and Application in Light-Induced Apoptosis

“…A simple one-step condensation of rhodanine and an aldehyde provides access to a large number of derivatives, which usually do not require column chromatography for purification. The thus-obtained structures are well established motifs in different areas of research such as fluorophore design, ion sensing, solar-cell dyes, − and medicinal and biological chemistry. − For example, a number of widely used kinase inhibitors such as SMI-16a , or SMI-4a , with activity against PIM (Provirus Integration site for Moloney leukemia virus) kinases − are based on this structural motif. Despite this great versatility, only the related dicyanorhodanine structure in conjunction with thiophenes , and related solar cell dye structures , were shown to undergo photoisomerization so far.…”

Polyrhodanine-based nanomaterials for biomedical applications: A review

“…Rhodanine monomer is derived from thiazolidinone, which is one of the most vital heterocyclic rings in the medical applications. Rhodanine also holds an important position in the medicinal field due to its diverse array of biological effects, including antiviral, antibacterial, and anticancer properties [ 1 , 2 ]. In addition, rhodanine is a Lewis base.…”

Design of fluorescent polymeric thermometers based on anthrapyrazolone functionalized oligo(ethylene glycol) methacrylates

“…Fluorescent dyes are generally considered for these applications for which they must have high photoluminescence quantum yield, a significant difference between excitation and emission strokes, biocompatibility, red to infrared emission for eliminating other biological environments in the background, and must be easy to synthesize. 5 Pyrazolone and its derivatives are well-established molecules due to their broad spectrum of biological activity and widerange application in designing bioactive molecules. 6 Anthrapyrazolone molecules are fused systems of a pyrazole ring with different anthraquinone derivatives.…”

“…Fluorescent dyes are generally considered for these applications for which they must have high photoluminescence quantum yield, a significant difference between excitation and emission strokes, biocompatibility, red to infrared emission for eliminating other biological environments in the background, and must be easy to synthesize. 5…”