Pterostilbene fluorescent probes as potential tools for targeting neurodegeneration in biological applications

J Enzyme Inhib Med Chem. 2022 Dec;37(1):1812-1820. doi: 10.1080/14756366.2022.2091556.

Abstract

Several epidemiological studies suggest that a diet rich in fruit and vegetables reduces the incidence of neurodegenerative diseases. Resveratrol (Res) and its dimethylated metabolite, pterostibene (Ptb), have been largely studied for their neuroprotective action. The clinical use of Res is limited because of its rapid metabolism and its poor bioavailability. Ptb with two methoxy groups and one hydroxyl group has a good membrane permeability, metabolic stability and higher in vivo bioavailability in comparison with Res. The metabolism and pharmacokinetics of Ptb are still sparse, probably due to the lack of tools that allow following the Ptb destiny both in living cells and in vivo. In this contest, we propose two Ptb fluorescent derivatives where Ptb has been functionalised by benzofurazan and rhodamine-B-isothiocyanate, compounds 1 and 2, respectively. Here, we report the synthesis, the optical and structural characterisation of 1 and 2, and, their putative cytotoxicity in two different cell lines.

Keywords: Ptb fluorescent probes; citotoxicity; pterostilbene 7-nitrobenzofurazan (NBD) derivative; pterostilbene rhodamine-B-isothiocyanate (Rhd B-Itc) derivative; spectrophotometric.

MeSH terms

  • Biological Availability
  • Fluorescent Dyes* / pharmacology
  • Resveratrol / chemistry
  • Resveratrol / pharmacology
  • Stilbenes* / chemistry
  • Stilbenes* / pharmacology

Substances

  • Fluorescent Dyes
  • Stilbenes
  • pterostilbene
  • Resveratrol

Grants and funding

This research was supported by the PRIN 2017 grant prot. 2017SNRXH3 from the Italian Ministry of Education, University and Research (MIUR).