Nitro-fatty Acid Reaction with Glutathione and Cysteine
Open accessAbstract
Fatty acid nitration by nitric oxide-derived species yields electrophilic products that adduct protein thiols, inducing changes in protein function and distribution. Nitro-fatty acid adducts of protein and reduced glutathione (GSH) are detected in healthy human blood. Kinetic and mass spectrometric analyses reveal that nitroalkene derivatives of oleic acid (OA-NO2) and linoleic acid (LNO2) rapidly react with GSH and Cys via Michael addition reaction. Rates of OA-NO2 and LNO2 reaction with GSH, determined via stopped flow spectrophotometry, displayed second-order rate constants of 183 M(-1)S(-1) and 355 M(-1)S(-1), respectively, at pH 7.4 and 37 degrees C. These reaction rates are significantly greater than those for GSH reaction with hydrogen peroxide and non-nitrated electrophilic fatty acids including 8-iso-prostaglandin A2 and 15-deoxy-Delta(12,14)-prostaglandin J2. Increasing reaction pH from 7.4 to 8.9 enhanced apparent second-order rate constants for the thiol reaction with OA-NO2 and LNO2, showing dependence on the thiolate anion of GSH for reactivity. Rates of nitroalkene reaction with thiols decreased as the pKa of target thiols increased. Increasing concentrations of the detergent octyl-beta-d-glucopyranoside decreased rates of nitroalkene reaction with GSH, indicating that the organization of nitro-fatty acids into micellar or membrane structures can limit Michael reactivity with more polar nucleophilic targets. In aggregate, these results reveal that the reversible adduction of thiols by nitro-fatty acids is a mechanism for reversible post-translational regulation of protein function by nitro-fatty acids.
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Primary mechanisms of nitrated fatty acid signaling include activation of PPARγ and Michael addition to thiol-containing proteins in a number of signaling pathways.
“Primary mechanisms of nitrated fatty acid signaling include activation of PPARγ (55, 583) and Michael addition to thiol-containing proteins in a number of signaling pathways (53, 955).”
From Sources of Vascular Nitric Oxide and Reactive Oxygen Species and Their Regulation (2019) · cites this paper as [53]
Nitroalkene derivatives of fatty acids (NO2-FA) are electrophilic if the nitro group is adducted to alkenyl carbons.
“Biochemical studies and cell models revealed that NO2-FA are electrophilic, if the nitro group is adducted to alkenyl carbons.”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [16]
Nitroalkene derivatives of fatty acids (NO2-FA) rapidly react via Michael addition with thiols and to a lesser extent primary and secondary amines.
“These species rapidly react via Michael addition with thiols and to a lesser extent primary and secondary amines [16].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [16]
The facile and reversible Michael addition of NO2-FA with susceptible thiols of specific protein targets explains why only low concentrations and rates of generation of electrophilic lipids are needed to accumulate target protein adduction and instigate downstream signaling responses.
“This is explained by the facile and reversible Michael addition of NO2-FA with susceptible thiols of specific protein targets, thus requiring only low concentrations and rates of generation of electrophilic lipids to result in the accumulation of target protein adduction and instigation of downstream signaling responses [16], [54].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [16]
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Ferreira, A. M., Minarrieta, L., Lamas Bervejillo, M., & Rubbo, H. (2012) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2012.08.572 · Cited by 16 · see citing works
- Authors
- Baker, L. M. S., Baker, P. R. S., Golin-Bisello, F., Schopfer, F. J., Fink, M., Woodcock, S. R., Branchaud, B. P., Radi, R., & Freeman, B. A.
- Affiliations
- University of Pittsburgh (US)
- University of Oregon (US)
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2007-10
- Volume
- 282
- Issue
- 42
- Pages
- 31085-31093
- ISSN
- 0021-9258 (ISSN-L)
- PMC
- PMC2169496
- OpenAlex
- W2016532893
- Cited by
- 200
- References
- 63
- Citations by year
- 2026: 6 · 2025: 10 · 2024: 9 · 2023: 7 · 2022: 7 · 2021: 11 · 2020: 13 · 2019: 11 · 2018: 16 · 2017: 11 · 2016: 10 · 2015: 7 · 2014: 8 · 2013: 12 · 2012: 11
- FWCI
- 5.43
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Heart, Lung, and Blood Institute (HL 64937, R01HL064937, HL 58115, R37HL058115, R01HL058115)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Glutathione Transferases and Polymorphisms
- Keywords
- nitro-fatty acids, nitric oxide, glutathione, cysteine, Michael addition, oleic acid, linoleic acid, reaction kinetics, thiolate anion, post-translational regulation, electrophilic metabolites, octyl-β-D-glucopyranoside, micellar structure
- MeSH terms
- Cysteine, Fatty Acids, Unsaturated, Glutathione, Kinetics, Nitric Oxide, Nitro Compounds, Oxidation-Reduction, Sulfhydryl Compounds
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