A novel Schiff base derivative: Synthesis, two-photon absorption properties and application for bioimaging

Spectrochim Acta A Mol Biomol Spectrosc. 2018 Jun 5:198:304-308. doi: 10.1016/j.saa.2018.03.039. Epub 2018 Mar 13.

Abstract

A novel donor-π-acceptor-π-donor type (D-π-A-π-D') Schiff base derivative (L) has been designed and synthesized. The structure of L is confirmed by single-crystal X-ray diffraction analysis as well. The photophysical properties of compound L were comprehensively investigated by using both experimental and theoretical methods. The results indicate that L exhibits large Stokes shift and moderate two-photon action (2PA) cross-section in the near infrared (NIR) region. Furthermore, the confocal microscopy imaging study demonstrates that compound L could penetrate into cells and target the cellular mitochondria compartment. Due to its low cytotoxicity, compound L provides a promising tool for directly lighting up the mitochondria compartment in living HepG2 cells.

Keywords: Bioimaging; Crystal structure; Mitochondria; Schiff base derivative; Two-photon absorption.

MeSH terms

  • Crystallography, X-Ray
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacokinetics
  • Hep G2 Cells
  • Humans
  • Microscopy, Confocal
  • Mitochondria / drug effects
  • Mitochondria / metabolism
  • Molecular Imaging / methods*
  • Molecular Structure
  • Photons
  • Schiff Bases / chemistry*
  • Spectrometry, Fluorescence / methods
  • Spectrophotometry, Ultraviolet

Substances

  • Fluorescent Dyes
  • Schiff Bases