A Cu2+ fluorescent chemosensor suitable for quantitative detection of tyrosinase in potatoes over a wide pH range

Anal Sci. 2024 Jun;40(6):1167-1175. doi: 10.1007/s44211-024-00546-2. Epub 2024 Mar 24.

Abstract

Cu2+ as an important trace element plays an essential role in various biologic processes due to the unique redox active nature. For this reason, much effort has been made to develop effective methods for Cu2+ detection. In this study, a novel structure fluorescent chemosensor, 1-(6-(((5-(5, 5-difluoro-1, 3, 7, 9-tetramethyl-5H-4λ4, 5λ4-dipyrrolo[1, 2-c:2', 1'-f][1, 3, 2] diazaborinin-10-yl)quinolin-8-yl)oxy)methyl)pyridin-2-yl)-N, N-bis(pyridin-2-ylmethyl)methanamine (1), was synthesized and characterized by 1H and 13C nuclear magnetic resonance spectroscopy, and electrospray ionization mass spectrometry. Sensor 1 showed an obviously "on-off" fluorescence response to Cu2+ with a 1:1 binding stoichiometry by UV-vis and fluorescence spectrophotometry. The detection limit of sensor 1 to Cu2+ was determined to be 1.9 µM, and the stable pH range for Cu2+ detection was from 3 to 13. Sensor 1 can be used for recognition and detection of tyrosinase in potatoes.

Keywords: 8-hydroxyquinoline; BODIPY; Cu2+; Fluorescent chemosensors; Tyrosinase.

MeSH terms

  • Copper* / chemistry
  • Fluorescent Dyes* / chemical synthesis
  • Fluorescent Dyes* / chemistry
  • Hydrogen-Ion Concentration
  • Limit of Detection
  • Monophenol Monooxygenase* / chemistry
  • Monophenol Monooxygenase* / metabolism
  • Solanum tuberosum* / chemistry
  • Spectrometry, Fluorescence*

Substances

  • Copper
  • Fluorescent Dyes
  • Monophenol Monooxygenase