C11-BODIPY581/591, an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)spectroscopic characterization and validation of methodology
Abstract
C11-BODIPY(581/591) is a fluorescent radio-probe for indexing lipid peroxidation and antioxidant efficacy in model membrane systems and living cells, with excellent characteristics: (i) emission in the visible range of the electromagnetic spectrum, with good spectral separation of the nonoxidized (595 nm) and oxidized (520 nm) forms; (ii) has a high quantum yield and because of this, low labeling concentrations can be used, ensuring minimal perturbation of the membrane whilst retaining favorable signal to noise ratios; (iii) has a good photo-stability and displays very few fluorescence artifacts; (iv) is virtually insensitive to environmental changes, i.e., pH or solvent polarity; (v) is lipophilic and as such easily enters membranes; (vi) once oxidized, C11-BODIPY(581/591) remains lipophilic and does not spontaneously leave the lipid bilayer; (vii) C11-BODIPY(581/591) localizes in two distinct pools within the lipid bilayer, a shallow pool at 18 A and a deep pool at < 7.5 A from the center of the bilayer; (viii) is not cytotoxic to rat-1 fibroblasts up to 50 microM; (ix) is sensitive to a variety of oxy-radicals and peroxynitrite, but not to superoxide, nitric oxide, transition metal ions, and hydroperoxides per se; (x) its sensitivity to oxidation is comparable to that of endogenous fatty acyl moieties.
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The ratio of green to red BODIPY C11 fluorescence acts as a readout of lipid peroxidation in cell membranes.
“BODIPY C11 shifts its fluorescence emission wavelength from red to green when oxidized in the presence of lipid peroxides, and the ratio of green to red BODIPY C11 fluorescence acts as a readout of lipid peroxidation in cell membranes.”
From APOE traffics to astrocyte lipid droplets and modulates triglyceride saturation and droplet size (2024) · cites this paper as Drummen et al., 2002
BODIPY C11 shifts its fluorescence emission wavelength from red to green when oxidized in the presence of lipid peroxides.
“BODIPY C11 shifts its fluorescence emission wavelength from red to green when oxidized in the presence of lipid peroxides, and the ratio of green to red BODIPY C11 fluorescence acts as a readout of lipid peroxidation in cell membranes.”
From APOE traffics to astrocyte lipid droplets and modulates triglyceride saturation and droplet size (2024) · cites this paper as Drummen et al., 2002
BODIPY C11 contains an 11-carbon fatty acid moiety that allows it to incorporate into lipid membranes.
“BODIPY C11 contains an 11-carbon fatty acid moiety that allows it to incorporate into lipid membranes (Drummen et al., 2002).”
From APOE traffics to astrocyte lipid droplets and modulates triglyceride saturation and droplet size (2024) · cites this paper as Drummen et al., 2002
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- Authors
- Drummen, G. P. C., van Liebergen, L. C. M., Op den Kamp, J. A. F., & Post, J. A.
- Affiliations
- Utrecht University (NL)
- Corresponding author
- Post, Jan A
- ORCID
- Drummen, Gregor P.C
- Venue
- Free Radical Biology and Medicine
- Publisher
- Elsevier BV
- Published
- 2002-08
- Volume
- 33
- Issue
- 4
- Pages
- 473-490
- ISSN
- 0891-5849 (ISSN-L)
- OpenAlex
- W2007396482
- Cited by
- 594
- References
- 1
- Citations by year
- 2026: 65 · 2025: 54 · 2024: 67 · 2023: 51 · 2022: 44 · 2021: 28 · 2020: 37 · 2019: 29 · 2018: 14 · 2017: 16 · 2016: 17 · 2015: 26 · 2014: 9 · 2013: 23 · 2012: 21
- FWCI
- 3.02
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Free Radical Biology and Medicine (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
- Keywords
- lipid peroxidation, antioxidant efficacy, membrane localization, lipid bilayers, peroxynitrite, reactive oxygen species, photostability, cytotoxicity, Rat-1 fibroblasts
- MeSH terms
- Animals, Antioxidants, Aza Compounds, Carbon Radioisotopes, Cations, Cell Division, Cell Line, Cell Membrane, Fatty Acids, Fibroblasts, Fluorescent Dyes, Free Radicals, Hydrogen Peroxide, Image Processing, Computer-Assisted, Lipid Bilayers, Lipids, Membrane Lipids, Microscopy, Fluorescence, Nitric Oxide, Oxidation-Reduction, Sensitivity and Specificity, Spectrometry, Fluorescence, Superoxides, Reproducibility of Results, Lipid Peroxidation, Artifacts, Reactive Oxygen Species, Microscopy, Confocal, Peroxynitrous Acid, Rats
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