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Photoluminescence: Applications

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Updated: Jul 15, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Styrylpyridinium Derivatives for Fluorescent Cell Imaging.

Reinis Putralis^1,2, Ksenija Korotkaja³, Martins Kaukulis^1,4

¹Latvian Institute of Organic Synthesis, LV-1006 Riga, Latvia.

Pharmaceuticals (Basel, Switzerland)

|September 28, 2023

Summary

New styrylpyridinium (SP) compounds exhibit intense near-infrared fluorescence and potential for cell labeling. These novel fluorescent probes show promising biocompatibility for biomedical applications.

Keywords:

cell labelling julolidine macrophages near-infrared fluorescent dye self-assembly styrylpyridines

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Published on: July 6, 2016

Area of Science:

Organic Chemistry
Materials Science
Biomedical Imaging

Background:

Styrylpyridinium (SP) compounds are explored for their spectroscopic and cell labeling properties.
Designing SP compounds with varied electron-donating groups, linkers, and electron-withdrawing parts is crucial for tuning their optical characteristics.

Purpose of the Study:

To synthesize and characterize novel styrylpyridinium (SP) compounds.
To investigate their spectroscopic properties, including fluorescence and Stokes' shifts.
To evaluate their potential as near-infrared fluorescent probes for biomedical applications.

Main Methods:

Synthesis of various SP compounds, including geminal bis-SP derivatives.
Spectroscopic analysis to determine fluorescence, Stokes' shifts, and photoluminescence quantum yield (PLQY).
Cytotoxicity assays on cancerous (HT-1080, MH-22A) and normal (NIH3T3) cell lines.
Cell staining experiments and liposome formation studies.

Main Results:

Compounds with divinyl linkers and julolidine donors showed intense near-infrared fluorescence (~760 nm).
SP compound 6e demonstrated high cytotoxicity to cancer cells (IC50 ~0.4-1.0 µg/mL) with moderate basal toxicity (LD50 = 477 mg/kg).
Large Stokes' shifts were observed (up to 352 nm), with highest PLQY for compounds 6a,b (15.1%, 12.2%).
Compound 6e localized in the cytoplasm, not nuclei, and formed 118 nm liposomes, indicating self-assembly.

Conclusions:

Novel SP compounds possess strong near-infrared fluorescence and large Stokes' shifts.
Compound 6e shows potential as a cytoplasm-specific fluorescent probe with self-assembly capabilities.
These findings support the development of new biocompatible dyes for advanced biomedical imaging.