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  1. Home
  3. Single-benzene-based Clickable Fluorophores For In Vitro And In Vivo Bioimaging.
  1. Home
  3. Single-benzene-based Clickable Fluorophores For In Vitro And In Vivo Bioimaging.

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Single-Benzene-Based Clickable Fluorophores for In Vitro and In Vivo Bioimaging.

Raja Mohanrao1,2, Clyde S Pinto1, Andrejus Suchenko1

  • 1Centre for Mechanochemical Cell Biology and Warwick Medical School, Division of Biomedical Science, University of Warwick, CoventryCV4 7AL, UK.

Chemistryselect
|June 24, 2025

View abstract on PubMed

Summary
This summary is machine-generated.

New single-benzene fluorophores offer enhanced photophysical properties for bioimaging. These clickable molecules, derived from tetrafluoroterephthalonitrile, show promise in both in vitro and in vivo applications.

Keywords:
BioconjugatesBioimagingChromophoresFluorescent probesSingle-benzene fluorophores

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Area of Science:

  • Organic chemistry
  • Photophysics
  • Biomedical imaging

Background:

  • Development of novel fluorophores is crucial for advancing bioimaging techniques.
  • Miniaturized, single-benzene-based fluorophores offer potential advantages in terms of synthesis and application.
  • Tetrafluoroterephthalonitrile serves as a versatile precursor for synthesizing functional organic molecules.

Purpose of the Study:

  • To report a series of miniaturized, clickable single-benzene-based fluorophores.
  • To investigate the structure-property relationships of these fluorophores, focusing on photophysical characteristics.
  • To demonstrate the utility of these novel fluorophores in bioimaging applications.

Main Methods:

  • Synthesis of fluorophores derived from tetrafluoroterephthalonitrile.
  • Characterization of photophysical properties, including absorption and emission spectra.
  • Protein conjugation of the synthesized fluorophores.
  • Evaluation of fluorophore performance in in vitro and in vivo bioimaging models.

    • Main Results:

    • A series of miniaturized, clickable single-benzene-based fluorophores were successfully synthesized.
    • Fluorophores featuring a tetrahydroquinoxaline skeleton displayed improved photophysical properties compared to those with a dihydro[1,4]thiazine skeleton.
    • Enhanced electron delocalization in the tetrahydroquinoxaline derivatives contributed to their superior performance.
    • The synthesized clickable fluorophores were effectively applied in both in vitro and in vivo bioimaging after protein conjugation.

    Conclusions:

    • Miniaturized, single-benzene-based fluorophores derived from tetrafluoroterephthalonitrile represent a promising class of imaging agents.
    • The tetrahydroquinoxaline scaffold offers a viable strategy for enhancing fluorophore photophysical properties.
    • These easily synthesized and clickable fluorophores are suitable for protein-based bioimaging, facilitating diverse biological studies.