Hydroxycinnamyl Derived BODIPY as a Lipophilic Fluorescence Probe for Peroxyl Radicals
Herein, we describe the synthesis of a fluorescent probe <b>NB-2</b> 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, dipyrro...
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| Main Authors: | , , , |
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| Format: | Book |
| Published: |
MDPI AG,
2020-01-01T00:00:00Z.
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| Online Access: | Connect to this object online. |
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| Summary: | Herein, we describe the synthesis of a fluorescent probe <b>NB-2</b> 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 <b>NB-2</b> confirmed its ability to trap lipid peroxyl radicals with the rate constant <i>k</i><sub>inh</sub> = 1000 M<sup>−1</sup>·s<sup>−1</sup>, which is ten-fold smaller than for pentamethylchromanol (an analog of α-tocopherol). The reaction of <b>NB-2</b> 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 <b>NB-2</b> 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 <b>NB-2</b> 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. |
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| Item Description: | 2076-3921 10.3390/antiox9010088 |