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Detection and quantification of protein adduction by electrophilic fatty acids: mitochondrial generation of fatty acid nitroalkene derivatives
Open accessAbstract
Nitroalkene fatty acid derivatives manifest a strong electrophilic nature, are clinically detectable, and induce multiple transcriptionally regulated anti-inflammatory responses. At present, the characterization and quantification of endogenous electrophilic lipids are compromised by their Michael addition with protein and small-molecule nucleophilic targets. Herein, we report a trans-nitroalkylation reaction of nitro-fatty acids with beta-mercaptoethanol (BME) and apply this reaction to the unbiased identification and quantification of reaction with nucleophilic targets. Trans-nitroalkylation yields are maximal at pH 7 to 8 and occur with physiological concentrations of target nucleophiles. This reaction is also amenable to sensitive mass spectrometry-based quantification of electrophilic fatty acid-protein adducts upon electrophoretic resolution of proteins. In-gel trans-nitroalkylation reactions also permit the identification of protein targets without the bias and lack of sensitivity of current proteomic approaches. Using this approach, it was observed that fatty acid nitroalkenes are rapidly metabolized in vivo by a nitroalkene reductase activity and mitochondrial beta-oxidation, yielding a variety of electrophilic and nonelectrophilic products that could be structurally characterized upon BME-based trans-nitroalkylation reaction. This strategy was applied to the detection and quantification of fatty acid nitration in mitochondria in response to oxidative inflammatory conditions induced by myocardial ischemia-reoxygenation.
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“The electrophilic character of NO2-FA in EVOO was confirmed by HPLC-MS/MS detection of Michael reaction products in fresh olives (Figure 4) [38].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [38]
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Metadata
- Authors
- Schopfer, F. J., Batthyany, C., Baker, P. R. S., Bonacci, G., Cole, M. P., Rudolph, V., Groeger, A. L., Rudolph, T. K., Nadtochiy, S., Brookes, P. S., & Freeman, B. A.
- Affiliations
- University of Pittsburgh (US)
- Universität Hamburg (DE)
- University of Rochester Medicine (US)
- Venue
- Free Radical Biology and Medicine
- Publisher
- Elsevier BV
- Published
- 2009-05
- Volume
- 46
- Issue
- 9
- Pages
- 1250-1259
- ISSN
- 0891-5849 (ISSN-L)
- PMC
- PMC3144282
- OpenAlex
- W1990185204
- Cited by
- 104
- References
- 46
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 6 · 2023: 2 · 2022: 1 · 2021: 3 · 2020: 5 · 2019: 9 · 2018: 14 · 2017: 5 · 2016: 5 · 2015: 7 · 2014: 5 · 2013: 9 · 2012: 6
- FWCI
- 3.75
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Free Radical Biology and Medicine (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institutes of Health (5p30dk046204-15)
- National Heart, Lung, and Blood Institute (HL 64937, R01HL064937, HL 58115, R37HL058115, R01HL058115)
- National Institute of Diabetes and Digestive and Kidney Diseases (P30 DK 046204-15, T32DK007052)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Health Sciences › Nursing › Nutrition and Dietetics › Fatty Acid Research and Health
- Keywords
- protein adducts, 2-mercaptoethanol, mitochondrial fatty acid metabolism, fatty acid beta-oxidation
- MeSH terms
- Alkenes, Animals, Biochemistry, Fatty Acids, Male, Mercaptoethanol, Mice, Inbred C57BL, Mitochondria, Heart, Nitro Compounds, Oxidation-Reduction, Oxidoreductases, Sensitivity and Specificity, Myocardial Ischemia, Oxidative Stress, Dimerization, Mice, Rats, Tandem Mass Spectrometry
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