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Imaging Plasma Membrane Deformations With pTIRFM
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Thiophene-based dyes for probing membranes.

Ismael López-Duarte1, Phoom Chairatana, Yilei Wu

  • 1Department of Chemistry, Oxford University, Chemistry Research Laboratory, Oxford, UK OX1 3TA. harry.anderson@chem.ox.ac.uk.

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This summary is machine-generated.

We developed new cationic dyes for cell membrane imaging. Doubly-charged thiophene dyes show excellent performance for fluorescence and second harmonic generation (SHG) imaging in live cells with low toxicity.

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Area of Science:

  • Organic chemistry
  • Biophysics
  • Materials science

Background:

  • Fluorescent dyes are crucial for biological imaging.
  • Developing novel dyes with enhanced photophysical and photobiological properties is essential for advanced cellular studies.
  • Current membrane stains like FM4-64 have limitations in specificity and phototoxicity.

Purpose of the Study:

  • To synthesize and characterize novel cationic dipolar push–pull dyes for membrane imaging.
  • To evaluate their photophysical properties (absorption, fluorescence, hyperpolarizability).
  • To assess their photobiological characteristics including cellular uptake, localization, toxicity, and phototoxicity.

Main Methods:

  • Synthesis of four new cationic dipolar push–pull dyes with thiophene bridges and varying linker groups (vinylene/ethynylene) and charges.
  • Spectroscopic analysis (absorption, fluorescence) and hyper-Rayleigh scattering for hyperpolarizability.
  • Cellular imaging studies using HeLa, SK-OV-3, and MDA-231 cell lines.
  • Evaluation of cellular uptake, localization, toxicity, and phototoxicity.

Main Results:

  • Thiophene-based dyes showed comparable absorption, fluorescence, and hyperpolarizability to FM4-64.
  • Ethynylene-linked dyes exhibited blue-shifted spectra and reduced hyperpolarizability.
  • Doubly-charged thiophene dyes localized to plasma membranes with lower internalization than FM4-64.
  • Doubly-charged dyes demonstrated low toxicity and phototoxicity, while singly-charged dyes were phototoxic at lower concentrations.
  • Doubly-charged thiophene dyes proved more effective for live-cell SHG imaging than FM4-64.

Conclusions:

  • Novel cationic dipolar push–pull dyes were successfully synthesized and characterized.
  • Doubly-charged thiophene dyes are promising for live-cell membrane imaging via fluorescence and SHG.
  • These dyes offer advantages in terms of localization, reduced internalization, and lower phototoxicity compared to FM4-64.
  • The findings pave the way for improved bioimaging techniques using advanced fluorescent probes.