Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals

Jaroslaw Kusio, Kaja Sitkowska*, Adrian Konopko, Grzegorz Litwinienko*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

Herein, we describe the synthesis of a fluorescent probe NB-2 and its use for the detection of peroxyl radicals. This probe is composed of two receptor segments (4-hydroxycinnamyl moieties) sensitive towards peroxyl radicals that are conjugated with a fluorescent reporter, dipyrrometheneboron difluoride (BODIPY), whose emission changes depend on the oxidation state of the receptors. The measurement of the rate of peroxidation of methyl linoleate in a micellar system in the presence of 1.0 µM NB-2 confirmed its ability to trap lipid peroxyl radicals with the rate constant kinh = 1000 M−1·s−1, which is ten-fold smaller than for pentamethylchromanol (an analog of α-tocopherol). The reaction of NB-2 with peroxyl radicals was further studied via fluorescence measurements in methanol, with α,α-azobisisobutyronitrile (AIBN) used as a source of radicals generated by photolysis or thermolysis, and in the micellar system at pH 7.4, with 2,2-azobis(2-amidinopropane) (ABAP) used as a thermal source of the radicals. The reaction of NB-2 receptors with peroxyl radicals manifests itself by the strong increase of a fluorescence with a maximum at 612–616 nm, with a 14-fold enhancement of emission in methanol and a 4-fold enhancement in the micelles, as compared to the unoxidized probe. Our preliminary results indicate that NB-2 behaves as a “switch on” fluorescent probe that is suitable for sensing peroxyl radicals in an organic lipid environment and in bi-phasic dispersed lipid systems.

Original languageEnglish
Article number88
Number of pages16
JournalAntioxidants (Basel, Switzerland)
Volume9
Issue number1
DOIs
Publication statusPublished - Jan-2020

Keywords

  • antioxidant activity
  • peroxyl radicals
  • fluorescent probes
  • rate constant
  • micelles
  • REACTIVE OXYGEN
  • OXIDATIVE STRESS
  • LIPID-PEROXIDATION
  • DNA-DAMAGE
  • CELLS
  • MRI
  • ROS

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