BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues

Peroxynitrite (ONOO<sup>−</sup>) plays an important role in many physiological and pathological processes. Excessive ONOO<sup>−</sup> in cells leads to oxidative stress and inflammation. However, precise monitoring of ONOO<sup>−</sup> levels in specific organelles...

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Main Authors: Qian Wu, Ziwei Hu, Guoyang Zhang, Yulong Jin, Zhuo Wang
Format: Article
Language:English
Published: MDPI AG 2024-12-01
Series:Biosensors
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Online Access:https://www.mdpi.com/2079-6374/14/12/638
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author Qian Wu
Ziwei Hu
Guoyang Zhang
Yulong Jin
Zhuo Wang
author_facet Qian Wu
Ziwei Hu
Guoyang Zhang
Yulong Jin
Zhuo Wang
author_sort Qian Wu
collection DOAJ
description Peroxynitrite (ONOO<sup>−</sup>) plays an important role in many physiological and pathological processes. Excessive ONOO<sup>−</sup> in cells leads to oxidative stress and inflammation. However, precise monitoring of ONOO<sup>−</sup> levels in specific organelles (e.g., mitochondria) is still lacking and urgently needed. Herein, we rationally designed a mitochondria-targeted ratiometric fluorescent probe, MOBDP-I, for imaging of ONOO<sup>−</sup> in the mitochondria of inflammatory cells and model mice. This probe, MOBDP-I, was synthesized by conjugating a BODIPY fluorophore to a mitochondria-targeting moiety–indole-salt group by a carbon–carbon double bond (C=C). In the presence of ONOO<sup>−</sup>, the C=C bond between the BODIPY backbone and the indole-salt group was oxidized and broken, leading to an 18-fold enhancement of fluorescence at 510 nm, along with a significant fluorescence decrease at 596 nm. The ratiometric response property bestowed the probe with advantages in the precise quantification of ONOO<sup>−</sup> in cells, thus allowing estimation of the extent of inflammation in living cells and mouse models of rheumatoid arthritis, peritonitis, and brain inflammation. MOBDP-I could act as an effective molecular tool to study the relationship between ONOO<sup>−</sup> and the occurrence and development of inflammatory diseases.
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spelling doaj-art-bbca8d0287434e5ab936af9f8a3280652025-08-20T02:00:51ZengMDPI AGBiosensors2079-63742024-12-01141263810.3390/bios14120638BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and TissuesQian Wu0Ziwei Hu1Guoyang Zhang2Yulong Jin3Zhuo Wang4State Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, ChinaState Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, ChinaState Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, ChinaState Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, ChinaState Key Laboratory of Chemical Resource Engineering, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, ChinaPeroxynitrite (ONOO<sup>−</sup>) plays an important role in many physiological and pathological processes. Excessive ONOO<sup>−</sup> in cells leads to oxidative stress and inflammation. However, precise monitoring of ONOO<sup>−</sup> levels in specific organelles (e.g., mitochondria) is still lacking and urgently needed. Herein, we rationally designed a mitochondria-targeted ratiometric fluorescent probe, MOBDP-I, for imaging of ONOO<sup>−</sup> in the mitochondria of inflammatory cells and model mice. This probe, MOBDP-I, was synthesized by conjugating a BODIPY fluorophore to a mitochondria-targeting moiety–indole-salt group by a carbon–carbon double bond (C=C). In the presence of ONOO<sup>−</sup>, the C=C bond between the BODIPY backbone and the indole-salt group was oxidized and broken, leading to an 18-fold enhancement of fluorescence at 510 nm, along with a significant fluorescence decrease at 596 nm. The ratiometric response property bestowed the probe with advantages in the precise quantification of ONOO<sup>−</sup> in cells, thus allowing estimation of the extent of inflammation in living cells and mouse models of rheumatoid arthritis, peritonitis, and brain inflammation. MOBDP-I could act as an effective molecular tool to study the relationship between ONOO<sup>−</sup> and the occurrence and development of inflammatory diseases.https://www.mdpi.com/2079-6374/14/12/638ratiometric probeperoxynitritefluorescence imaginginflammatory
spellingShingle Qian Wu
Ziwei Hu
Guoyang Zhang
Yulong Jin
Zhuo Wang
BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues
Biosensors
ratiometric probe
peroxynitrite
fluorescence imaging
inflammatory
title BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues
title_full BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues
title_fullStr BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues
title_full_unstemmed BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues
title_short BODIPY-Based Ratiometric Fluorescent Probe for Sensing Peroxynitrite in Inflammatory Cells and Tissues
title_sort bodipy based ratiometric fluorescent probe for sensing peroxynitrite in inflammatory cells and tissues
topic ratiometric probe
peroxynitrite
fluorescence imaging
inflammatory
url https://www.mdpi.com/2079-6374/14/12/638
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