Structural Effect on the Cellular Selectivity of an NIR-Emitting Cyanine Probe: From Lysosome to Simultaneous Nucleus and Mitochondria Selectivity with Potential for Monitoring Mitochondria Dysfunction in Cells

Chathura S. Abeywickrama, Keti A. Bertman, Caroline B. Plescia, Robert V. Stahelin, Yi Pang

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Bright red to NIR emitting cyanine probes 2-3 were synthesized in very good yields. Probes 2-3 exhibited excellent fluorescent quantum yields (φfl ≈ 0.1-0.4) and large Stokes shift (Î"λ > 150 nm) due to efficient intramolecular charge transfer (ICT) in the conjugated πsystem. Organelle specificity of these probes was investigated by live cell fluorescence confocal microscopy studies. Probe 3 exhibited the ability to visualize the cell nucleus and mitochondria simultaneously in live cell samples during imaging experiments. However, in structurally modified probe 2 with different substituents (i.e., benzothiazolium vs benzothiazole), the selectivity of the probe switched entirely toward cellular lysosomes. Spectrometric DNA titration experiments were conducted to confirm the DNA/nucleus selectivity of probe 3. The study further evaluates the role of the substituent toward DNA selectivity. Probe 3 was identified as a valuable fluorescent marker to visually identify and study mitochondrial dysfunction in live cells via fluorescent confocal microscopy.

Original languageEnglish (US)
JournalACS Applied Bio Materials
DOIs
StatePublished - 2019
Externally publishedYes

Keywords

  • fluorescence confocal microscopy
  • fluorescent probes
  • mitochondria dysfunction
  • nucleus staining
  • organelle selectivity

ASJC Scopus subject areas

  • Biomaterials
  • Chemistry(all)
  • Biomedical Engineering
  • Biochemistry, medical

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