A naphthol hydrazone Schiff base bearing benzothiadiazole unit for fluorescent detection of Fe3+ in PC3 cells

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Mar 15:289:122242. doi: 10.1016/j.saa.2022.122242. Epub 2022 Dec 15.

Abstract

Naphthol hydrazone derivatives are recognized as efficient chelating agents for both qualitative and quantitative detection of metal ions. Here we design a naphthol hydrazine-based chemosensor with covalently linking a strong electron-withdrawing benzothiadiazole group to modulate the molecular electronic structure, nominated as NtHzBtd. The fluorescent probe performs excellent selectivity and sensitivity towards Fe3+ with 1:1 binding stoichiometry, while exhibiting a quick response at 55 s with a relatively low limit of detection of 0.036 µM. A series of spectroscopic measurements in tandem with theoretical calculations suggest that the probe undergoes both intramolecular charge transfer (ICT) and chelation enhanced quenching (CHEQ) processes. Successful color rendering of paper strips and bioimaging in PC3 cells demonstrate the promising applicability of NtHzBtd for portable Fe3+ detection in real samples and biosystems.

Keywords: Benzothiadiazole; Chemosensor; Ferric ion; Naphthol hydrazone; PC3 cells.

MeSH terms

  • Fluorescent Dyes / chemistry
  • Humans
  • Hydrazones
  • Naphthols* / chemistry
  • PC-3 Cells
  • Schiff Bases* / chemistry

Substances

  • Naphthols
  • benzo-1,2,3-thiadiazole
  • Schiff Bases
  • Hydrazones
  • Fluorescent Dyes