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.
“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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Preconditioning with ischemia: a delay of lethal cell injury in ischemic myocardium.
Murry, C. E., Jennings, R. B., & Reimer, K. A. (1986) · Circulation · doi:10.1161/01.cir.74.5.1124 · Cited by 7,813 · see citing works
Resolving inflammation: dual anti-inflammatory and pro-resolution lipid mediators
Serhan, C. N., Chiang, N., & Van Dyke, T. E. (2008) · Nature Reviews Immunology · doi:10.1038/nri2294 · Cited by 2,932 · see citing works
Modern physical organic chemistry
(2006) · Choice Reviews Online · doi:10.5860/choice.43-3398 · Cited by 2,312 · see citing works
Inducible cyclooxygenase may have anti-inflammatory properties
Gilroy, D. W., Colville‐Nash, P., Willis, D., Chivers, J. E., Paul‐Clark, M. J., & Willoughby, D. A. (1999) · Nature Medicine · doi:10.1038/9550 · Cited by 1,243 · see citing works
15-Deoxy-Δ 12,14 -prostaglandin J 2 inhibits multiple steps in the NF-κB signaling pathway
Straus, D. S., Pascual, G., Li, M., Welch, J. S., Ricote, M., Hsiang, C., Sengchanthalangsy, L. L., Ghosh, G., & Glass, C. K. (2000) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.97.9.4844 · Cited by 1,004 · see citing works
Mechanism and Theory in Organic Chemistry
Lowry, T. H., & Richardson, K. S. (1976) · Andalas University Repository (Andalas University) · Cited by 842 · see citing works
Marnett, L. J., Riggins, J. N., & West, J. D. (2003) · Journal of Clinical Investigation · doi:10.1172/jci200318022 · Cited by 476 · see citing works
Protein Adducts Generated from Products of Lipid Oxidation: Focus on HNE and ONE
Sayre, L. M., Lin, D., Yuan, Q., Zhu, X., & Tang, X. (2006) · Drug Metabolism Reviews · doi:10.1080/03602530600959508 · Cited by 364 · see citing works
Fatty Acid Transduction of Nitric Oxide Signaling
Baker, P. R. S., Lin, Y., Schopfer, F. J., Woodcock, S. R., Groeger, A. L., Batthyany, C., Sweeney, S., Long, M. H., Iles, K. E., Baker, L. M. S., et al. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m504212200 · Cited by 358 · see citing works
Self-citationNitrated Fatty Acids: Endogenous Anti-inflammatory Signaling Mediators
Cui, T., Schopfer, F. J., Zhang, J., Chen, K., Ichikawa, T., Baker Paul, R. S., Batthyany, C., Chacko, B. K., Feng, X., Patel, R. P., et al. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m603357200 · Cited by 351 · see citing works
Self-citationBiosynthesis of 15-deoxy-Δ12,14-PGJ2 and the ligation of PPARγ
Bell, L. C., Ide, T., Lawson, J. A., McNamara, P., Reilly, M. P., & FitzGerald, G. A. (2003) · Journal of Clinical Investigation · doi:10.1172/jci18012 · Cited by 341 · see citing works
Biosynthesis of 15-deoxy-Δ12,14-PGJ2 and the ligation of PPARγ
Bell-Parikh, L. C., Ide, T., Lawson, J. A., et al. (2003) · Journal of Clinical Investigation · doi:10.1172/jci200318012 · Cited by 302 · see citing works
Cernuda‐Morollón, E., Pineda‐Molina, E., Cañada, F. J., & Pérez‐Sala, D. (2001) · Journal of Biological Chemistry · doi:10.1074/jbc.m104518200 · Cited by 292 · see citing works
Reversible Post-translational Modification of Proteins by Nitrated Fatty Acids in Vivo
Batthyany, C., Schopfer, F. J., Baker, P. R. S., Durán, R., Baker, L. M. S., Huang, Y., Cerveñansky, C., Branchaud, B. P., & Freeman, B. A. (2006) · Journal of Biological Chemistry · doi:10.1074/jbc.m602814200 · Cited by 285 · see citing works
Routes to 4-Hydroxynonenal: Fundamental Issues in the Mechanisms of Lipid Peroxidation
Schneider, C. G., Porter, N. A., & BRASH, A. R. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.r800001200 · Cited by 275 · see citing works
Nitro-fatty acid formation and signaling
Freeman, B. A., Baker, P. R. S., Schopfer, F. J., Woodcock, S. R., Napolitano, A., & d'Ischia, M. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.r800004200 · Cited by 265 · see citing works
Self-citationProtein Damage by Reactive Electrophiles: Targets and Consequences
Liebler, D. C. (2007) · Chemical Research in Toxicology · doi:10.1021/tx700235t · Cited by 235 · see citing works
Trott, A. E., West, J. D., Klaić, L., Westerheide, S. D., Silverman, R. B., Morimoto, R. I., & Morano, K. A. (2008) · Molecular Biology of the Cell · doi:10.1091/mbc.e07-10-1004 · Cited by 223 · see citing works
(E)-4-Hydroxy-2-Nonenal May be Involved in the Pathogenesis of Parkinson’s Disease
Selley, M. L. (1998) · Free Radical Biology and Medicine · doi:10.1016/s0891-5849(98)00021-5 · Cited by 215 · see citing works
Vunta, H., Davis, F. B., Palempalli, U. M. D., Bhat, D., Arner, R. J., Thompson, J. T., Peterson, D. G., Reddy, C. C., & Prabhu, K. S. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m703075200 · Cited by 211 · see citing works
Human Biochemistry of the Isoprostane Pathway
Milne, G. L., Yin, H., & Morrow, J. D. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.r700047200 · Cited by 209 · see citing works
The monoclonal antibody specific for the 4‐hydroxy‐2‐nonenal histidine adduct
Toyokuni, S., Miyake, N., Hiai, H., Hagiwara, M., Kawakishi, S., Osawa, T., & Uchida, K. (1995) · FEBS Letters · doi:10.1016/0014-5793(95)00033-6 · Cited by 207 · see citing works
Cline, D. J., Redding, S. E., Brohawn, S. G., Psathas, J. N., Schneider, J. P., & Thorpe, C. (2004) · Biochemistry · doi:10.1021/bi048329a · Cited by 203 · see citing works
Baker, P. R. S., Schopfer, F. J., Sweeney, S., & Freeman, B. A. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0402587101 · Cited by 201 · see citing works
Self-citationNitro-fatty Acid Reaction with Glutathione and Cysteine
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. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m704085200 · Cited by 200 · see citing works
Self-citationVila, A., Tallman, K. A., Jacobs, A. T., Liebler, D. C., Porter, N. A., & Marnett, L. J. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700347w · Cited by 192 · see citing works
Glyceraldehyde-3-Phosphate Dehydrogenase Inactivation by Peroxynitrite
Souza, J. M., & Radí, R. (1998) · Archives of Biochemistry and Biophysics · doi:10.1006/abbi.1998.0932 · Cited by 179 · see citing works
Redox regulation of neuronal survival mediated by electrophilic compounds
Satoh, T., & Lipton, S. A. (2006) · Trends in Neurosciences · doi:10.1016/j.tins.2006.11.004 · Cited by 154 · see citing works
15-Deoxy-Δ12,14-prostaglandin J2: An Electrophilic Trigger of Cellular Responses
Uchida, K., & Shibata, T. (2007) · Chemical Research in Toxicology · doi:10.1021/tx700177j · Cited by 139 · see citing works
Musiek, E. S., Brooks, J. D., Joo, M., Brunoldi, E. M., Porta, A., Zanoni, G., Vidari, G., Blackwell, T. S., Montine, T. J., Milne, G. L., et al. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m803625200 · Cited by 139 · see citing works
Nadtochiy, S. M., Baker, P. R. S., Freeman, B. A., & Brookes, P. S. (2009) · Cardiovascular Research · doi:10.1093/cvr/cvn323 · Cited by 131 · see citing works
Cuzzocrea, S., Wayman, N. S., Mazzon, E., Dugo, L., Paola, R. D., Serraino, I., Britti, D., Chatterjee, P. K., Caputi, A. P., & Thiemermann, C. (2002) · Molecular Pharmacology · doi:10.1124/mol.61.5.997 · Cited by 122 · see citing works
Alterations in Gene Expression Induced by the Lipid Peroxidation Product, 4-Hydroxy-2-nonenal
West, J. D., & Marnett, L. J. (2005) · Chemical Research in Toxicology · doi:10.1021/tx050211n · Cited by 121 · see citing works
Nitro-fatty Acid Metabolome: Saturation, Desaturation, β-Oxidation, and Protein Adduction
Rudolph, V., Schopfer, F. J., Khoo, N. K. H., Rudolph, T. K., Cole, M. P., Woodcock, S. R., Bonacci, G., Groeger, A. L., Golin-Bisello, F., Chen, C.-S., et al. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m802298200 · Cited by 115 · see citing works
Self-citationOh, J. Y., Giles, N. M., Landar, A. L., & Darley-Usmar, V. M. (2008) · Biochemical Journal · doi:10.1042/bj20071189 · Cited by 106 · see citing works
Heat Shock Factor 1 Attenuates 4-Hydroxynonenal-mediated Apoptosis
Jacobs, A. T., & Marnett, L. J. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m706799200 · Cited by 104 · see citing works
Characterization of linoleic acid nitration in human blood plasma by mass spectrometry
Lima, É. S., Di Mascio, P., Rubbo, H., & Abdalla, D. S. P. (2002) · Biochemistry · doi:10.1021/bi025504j · Cited by 103 · see citing works
Cyclooxygenase-2-mediated DNA Damage
Lee, S. H., Williams, M. V., DuBois, R. N., & Blair, I. A. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m504178200 · Cited by 102 · see citing works
Satoh, K., Yamada, S., Koike, Y., Igarashi, Y., Toyokuni, S., Kumano, T., Takahata, T., Hayakari, M., Tsuchida, S., & Uchida, K. (1999) · Analytical Biochemistry · doi:10.1006/abio.1999.4073 · Cited by 88 · see citing works
Synthesis, Isomer Characterization, and Anti-Inflammatory Properties of Nitroarachidonate
Trostchansky, A., Souza, J. M., Ferreira, A. M., Ferrari, M., Blanco, F., Trujillo, M., Castro, D., Cerecetto, H., Baker, P. R. S., O’Donnell, V. B., et al. (2007) · Biochemistry · doi:10.1021/bi602652j · Cited by 83 · see citing works
Brooks, J. D., Milne, G. L., Yin, H., Sanchez, S. C., Porter, N. A., & Morrow, J. D. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m800122200 · Cited by 82 · see citing works
Macrophage activation induces formation of the anti-inflammatory lipid cholesteryl-nitrolinoleate
Ferreira, A. M., Ferrari, M. I., Trostchansky, A., Batthyany, C., Souza, J. M., Alvarez, M. N., López, G. V., Baker, P. R. S., Schopfer, F. J., O'Donnell, V., et al. (2009) · Biochemical Journal · doi:10.1042/bj20080701 · Cited by 78 · see citing works
Self-citationCholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins
Lima, É. S., Mascio, P. D., & Abdalla, D. S. P. (2003) · Journal of Lipid Research · doi:10.1194/jlr.m200467-jlr200 · Cited by 72 · see citing works
Fahey, J. W., & Kensler, T. W. (2007) · Chemical Research in Toxicology · doi:10.1021/tx7000459 · Cited by 61 · see citing works
Biological Nitration of Arachidonic Acid
Balazy, M., & Poff, C. (2004) · Current Vascular Pharmacology · doi:10.2174/1570161043476465 · Cited by 59 · see citing works
A quantitative solid-phase enzymeimmunoassay for 13,14-dihydro-15-keto-prostaglandin F2α in plasma
Vecchio, R. P. D., Maxey, K. M., & Lewis, G. S. (1992) · Prostaglandins · doi:10.1016/0090-6980(92)90032-o · Cited by 28 · see citing works
Bittner, B., Thelly, T., Isel, H., & Mountfield, R. J. (2000) · International Journal of Pharmaceutics · doi:10.1016/s0378-5173(00)00481-6 · Cited by 23 · see citing works
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Formation and signaling actions of electrophilic lipids
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Self-citationCyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids
Groeger, A. L., Cipollina, C., Cole, M. P., Woodcock, S. R., Bonacci, G., Rudolph, T. K., Rudolph, V., Freeman, B. A., & Schopfer, F. J. (2010) · Nature Chemical Biology · doi:10.1038/nchembio.367 · Cited by 295 · see citing works
Self-citationElectrophilic nitro-fatty acids activate NRF2 by a KEAP1 cysteine 151-independent mechanism
Kansanen, E., Bonacci, G., Schopfer, F. J., Kuosmanen, S. M., Tong, K. I., Leinonen, H., Woodcock, S. R., Yamamoto, M., Carlberg, C., Ylä-Herttuala, S., et al. (2011) · Journal of Biological Chemistry · doi:10.1074/jbc.m110.190710 · Cited by 208 · see citing works
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Rudolph, T. K., & Freeman, B. Α. (2009) · Science Signaling · doi:10.1126/scisignal.290re7 · Cited by 200 · see citing works
Rudolph, V., Rudolph, T. K., Schopfer, F. J., Bonacci, G., Woodcock, S. R., Cole, M. P., Baker, P. R. S., Ramani, R., & Freeman, B. A. (2010) · Cardiovascular Research · doi:10.1093/cvr/cvp275 · Cited by 188 · see citing works
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Schopfer, F. J., Cole, M. P., Groeger, A. L., Chen, C.-S., Khoo, N. K. H., Woodcock, S. R., Golin-Bisello, F., Motanya, U. N., Li, Y., Zhang, J., et al. (2010) · Journal of Biological Chemistry · doi:10.1074/jbc.m109.091512 · Cited by 171 · see citing works
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Self-citationMata-Pérez, C., Sánchez-Calvo, B., Padilla, M. N., Begara-Morales, J. C., Luque, F., Melguizo, M., Jiménez‐Ruiz, J., Fierro-Risco, J., Peñas, A., Valderrama, R., et al. (2015) · PLANT PHYSIOLOGY · doi:10.1104/pp.15.01671 · Cited by 126 · see citing works
Ježek, P., Holendová, B., Garlid, K., & Jabůrek, M. (2018) · Antioxidants and Redox Signaling · doi:10.1089/ars.2017.7225 · Cited by 126 · see citing works
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Villacorta, L., Chang, L., Salvatore, S. R., Ichikawa, T., Zhang, J., Petrovic-Djergovic, D., Jia, L., Carlsen, H., Schopfer, F. J., Freeman, B. A., et al. (2013) · Cardiovascular Research · doi:10.1093/cvr/cvt002 · Cited by 116 · see citing works
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Self-citationTsikas, D., Zoerner, A. A., Mitschke, A., & Gutzki, F. (2009) · Lipids · doi:10.1007/s11745-009-3332-4 · Cited by 82 · see citing works
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Nitro-fatty acids in cardiovascular regulation and diseases characteristics and molecular mechanisms
Villacorta, L. (2015) · Frontiers in bioscience · doi:10.2741/4425 · Cited by 50 · see citing works
Regulation of arachidonic acid oxidation and metabolism by lipid electrophiles
Trostchansky, A., Wood, I., & Rubbo, H. (2020) · Prostaglandins & Other Lipid Mediators · doi:10.1016/j.prostaglandins.2020.106482 · Cited by 49 · see citing works
Tsikas, D., Zoerner, A. A., & Jordan, J. (2011) · Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids · doi:10.1016/j.bbalip.2011.06.015 · Cited by 47 · see citing works
Nitroalkylation — A redox sensitive signaling pathway
Geisler, A. C., & Rudolph, T. K. (2011) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2011.06.014 · Cited by 44 · see citing works
Cardiovascular Consequences When Nitric Oxide and Lipid Signaling Converge
Rudolph, V., & Freeman, B. Α. (2009) · Circulation Research · doi:10.1161/circresaha.109.202077 · Cited by 43 · see citing works
Nitro-fatty acids: novel anti-inflammatory lipid mediators
Rubbo, H. (2013) · Brazilian Journal of Medical and Biological Research · doi:10.1590/1414-431x20133202 · Cited by 45 · see citing works
Melo, T., Montero‐Bullón, J., Domingues, P. M., & Domingues, M. R. (2019) · Redox Biology · doi:10.1016/j.redox.2019.101106 · Cited by 44 · see citing works
González-Perilli, L., Álvarez, M. N., Prolo, C., Radí, R., Rubbo, H., & Trostchansky, A. (2013) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2012.12.020 · Cited by 41 · see citing works
Fazzari, M., Vitturi, D. A., Woodcock, S. R., Salvatore, S. R., Freeman, B. Α., & Schopfer, F. J. (2018) · Journal of Lipid Research · doi:10.1194/jlr.m088815 · Cited by 39 · see citing works
Self-citationEndogenous Generation and Signaling Actions of Omega-3 Fatty Acid Electrophilic Derivatives
Cipollina, C. (2015) · BioMed Research International · doi:10.1155/2015/501792 · Cited by 38 · see citing works
Wendell, S. G., Golin-Bisello, F., Wenzel, S. E., Sobol, R. W., Holguín, F., & Freeman, B. Α. (2015) · Journal of Biological Chemistry · doi:10.1074/jbc.m114.635151 · Cited by 36 · see citing works
Koenitzer, J. R., Bonacci, G., Woodcock, S. R., Chen, C.-S., Cantú‐Medellín, N., Kelley, E. E., & Schopfer, F. J. (2015) · Redox Biology · doi:10.1016/j.redox.2015.11.002 · Cited by 35 · see citing works
Self-citationGeneration and esterification of electrophilic fatty acid nitroalkenes in triacylglycerides
Fazzari, M., Khoo, N. K. H., Woodcock, S. R., Li, L., Freeman, B. Α., & Schopfer, F. J. (2015) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2015.05.033 · Cited by 34 · see citing works
Self-citationGil, M., Graña, M., Schopfer, F. J., Wagner, T., Denicola, A., Freeman, B. Α., Alzari, P. M., Batthyány, C., & Durán, R. (2013) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2013.06.021 · Cited by 33 · see citing works
Self-citationDetection of electrophile-sensitive proteins
Wall, S. B., Smith, M. R., Ricart, K. C., Zhou, F., Vayalil, P. K., Oh, J., & Landar, A. L. (2013) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2013.09.003 · Cited by 31 · see citing works
Fatty Acid Transduction of Nitric Oxide Signaling
Cole, M. P., & Freeman, B. Α. (2010) · Elsevier eBooks · doi:10.1016/b978-0-12-373866-0.00011-3 · Cited by 29 · see citing works
Regulation of protein kinase C by nitroarachidonic acid: Impact on human platelet activation
Bonilla, L., O’Donnell, V. B., Clark, S., Rubbo, H., & Trostchansky, A. (2013) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2013.03.001 · Cited by 28 · see citing works
Regulation of stress signaling pathways by nitro-fatty acids
Deen, A. J., Sihvola, V., Härkönen, J., Patinen, T., Adinolfi, S., & Levonen, A. (2018) · Nitric Oxide · doi:10.1016/j.niox.2018.03.012 · Cited by 27 · see citing works
New Insights into the Anti‐Inflammatory and Antioxidant Properties of Nitrated Phospholipids
Melo, T., Marques, S. S., Ferreira, I., Cruz, M. T., Domingues, P. M., Segundo, M. A., & Domingues, M. R. M. (2018) · Lipids · doi:10.1002/lipd.12007 · Cited by 27 · see citing works
Sánchez-Calvo, B., Cassina, A., Mastrogiovanni, M., Santos, M., Trías, E., Kelley, E. E., Rubbo, H., & Trostchansky, A. (2021) · The Journal of Nutritional Biochemistry · doi:10.1016/j.jnutbio.2021.108646 · Cited by 28 · see citing works
Nitric oxide release from nitro-fatty acids in Arabidopsis roots
Mata-Pérez, C., Sánchez-Calvo, B., Begara-Morales, J. C., Padilla, M. N., Valderrama, R., Corpas, F. J., & Barroso, J. B. (2016) · Plant Signaling & Behavior · doi:10.1080/15592324.2016.1154255 · Cited by 27 · see citing works
Dapueto, R., Rodriguez‐Duarte, J., Galliussi, G., Kamaid, A., Bresque, M., Batthyány, C., López, G. V., & Escande, C. (2020) · Redox Biology · doi:10.1016/j.redox.2020.101833 · Cited by 25 · see citing works
González-Perilli, L., Mastrogiovanni, M., Fernandes, D. C., Rubbo, H., Laurindo, F. R. M., & Trostchansky, A. (2017) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2017.02.013 · Cited by 25 · see citing works
Mass spectrometry-based study defines the human urine nitrolipidome
Salvatore, S. R., Rowart, P., & Schopfer, F. J. (2020) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2020.10.305 · Cited by 23 · see citing works
Self-citationKuhn, B. R., Brat, C., Fettel, J., Hellmuth, N., Maucher, I. V., Bulut, U., Hock, K. J., Grimmer, J., Manolikakes, G., Rühl, M., et al. (2018) · Biochemical Pharmacology · doi:10.1016/j.bcp.2018.06.014 · Cited by 24 · see citing works
Redox properties and human serum albumin binding of nitro-oleic acid
Zatloukalová, M., Mojović, M., Pavićević, A. A., Kabeláč, M., Freeman, B. Α., Pekarová, M., & Vacek, J. (2019) · Redox Biology · doi:10.1016/j.redox.2019.101213 · Cited by 23 · see citing works
The chemical foundations of nitroalkene fatty acid signaling through addition reactions with thiols
Turell, L., Steglich, M., & Álvarez, B. (2018) · Nitric Oxide · doi:10.1016/j.niox.2018.03.014 · Cited by 22 · see citing works
Arachidonic Acid and Nitroarachidonic: Effects on NADPH Oxidase Activity
González-Perilli, L., Prolo, C., & Álvarez, M. N. (2019) · Advances in experimental medicine and biology · doi:10.1007/978-3-030-11488-6_6 · Cited by 22 · see citing works
Begara-Morales, J. C., Mata-Pérez, C., Padilla, M. N., Chaki, M., Valderrama, R., Aranda‐Caño, L., & Barroso, J. B. (2020) · Journal of Experimental Botany · doi:10.1093/jxb/eraa517 · Cited by 21 · see citing works
In vitro nitro-fatty acid release from Cys-NO2-fatty acid adducts under nitro-oxidative conditions
Padilla, M. N., Mata-Pérez, C., Melguizo, M., & Barroso, J. B. (2016) · Nitric Oxide · doi:10.1016/j.niox.2016.12.009 · Cited by 21 · see citing works
Gas-Phase Fragmentation Analysis of Nitro-Fatty Acids
Bonacci, G., Asciutto, E. K., Woodcock, S. R., Salvatore, S. R., Freeman, B. Α., & Schopfer, F. J. (2011) · Journal of the American Society for Mass Spectrometry · doi:10.1007/s13361-011-0185-x · Cited by 20 · see citing works
Self-citationBiological properties of nitro-fatty acids in plants
Mata-Pérez, C., Padilla, M. N., Sánchez-Calvo, B., Begara-Morales, J. C., Valderrama, R., Chaki, M., & Barroso, J. B. (2018) · Nitric Oxide · doi:10.1016/j.niox.2018.03.011 · Cited by 19 · see citing works
Unraveling the Transport Properties of RONS across Nitro-Oxidized Membranes
Abduvokhidov, D., Yusupov, M., Shahzad, A., Attri, P., Shiratani, M., Oliveira, M. C., & Razzokov, J. (2023) · Biomolecules · doi:10.3390/biom13071043 · Cited by 17 · see citing works
Rodriguez‐Duarte, J., Dapueto, R., Galliussi, G., Turell, L., Kamaid, A., Khoo, N. K. H., Schopfer, F. J., Freeman, B. Α., Escande, C., Batthyány, C., et al. (2018) · Scientific Reports · doi:10.1038/s41598-018-31218-7 · Cited by 17 · see citing works
Self-citationNitro-fatty acids as novel electrophilic ligands for peroxisome proliferator-activated receptors
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
Screening for natural chemoprevention agents that modify human Keap1
Hu, C., Nikolic, D. S., Eggler, A. L., Mesecar, A. D., & van Breemen, R. B. (2011) · Analytical Biochemistry · doi:10.1016/j.ab.2011.10.028 · Cited by 16 · see citing works
Melo, T., Domingues, P. M., Ribeiro‐Rodrigues, T., Girão, H., Segundo, M. A., & Domingues, M. R. (2017) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2017.02.033 · Cited by 16 · see citing works
Trostchansky, A., & Rubbo, H. (2016) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2016.10.003 · Cited by 16 · see citing works
Wood, I., Trostchansky, A., Xu, Y., Qian, S. Y., Radí, R., & Rubbo, H. (2019) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2019.03.022 · Cited by 14 · see citing works
Nitro-fatty acids: promising agents for the development of new cancer therapeutics
Roos, J., Manolikakes, G., Schlomann, U., Klinke, A., Schopfer, F. J., Neumann, C. A., & Maier, T. J. (2024) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2024.09.009 · Cited by 13 · see citing works
Self-citationReconnoitering the role of Lipid Metabolites in Ferroptosis
Raju, M. V., Chandrasekaran, M. K., Ahalliya, R. M., & Kanniappan, G. V. (2024) · Advances in Redox Research · doi:10.1016/j.arres.2024.100117 · Cited by 12 · see citing works
Neves, B., Pérez‐Sala, D., Ferreira, H. B., Guerra, I. M. S., Moreira, A. S. P., Domingues, P. M., Domingues, M. R., & Melo, T. (2022) · Progress in Lipid Research · doi:10.1016/j.plipres.2022.101176 · Cited by 11 · see citing works
Cysteamine assay for the evaluation of bioactive electrophiles
Novák, D., Vrba, J., Zatloukalová, M., Roubalová, L., Stolarczyk, K., Dorčák, V., & Vacek, J. (2021) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2021.01.007 · Cited by 10 · see citing works
Shiva, S., Castro, L., & Brookes, P. S. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-804273-1.00011-9 · Cited by 10 · see citing works
Hydrogen Peroxide (H2O2)- and Nitric Oxide (NO)-Derived Posttranslational Modifications
Valderrama, R., Begara-Morales, J. C., Chaki, M., Mata-Pérez, C., Padilla, M. N., & Barroso, J. B. (2019) · Springer eBooks · doi:10.1007/978-3-030-11129-8_3 · Cited by 8 · see citing works
Streamlined One‐Pot Synthesis of Nitro Fatty Acids
Hassan, M. E., Krieg, S., Nde, C. N., Roos, J., Maier, T. J., Rady, E. A. E., Raslan, M. A.-E., Sadek, K. U., & Manolikakes, G. (2021) · European Journal of Organic Chemistry · doi:10.1002/ejoc.202100247 · Cited by 8 · see citing works
Tomato pomace-derived nitrated fatty acids: Synthesis and antiplatelet activity
Rodríguez, L., Lagos, F., Mastrogiovanni, M., Flores, A., Plaza, A., Tellería, F., Palomo, I. F., Eduardo Fuentes, Q., & Trostchansky, A. (2024) · Biomedicine & Pharmacotherapy · doi:10.1016/j.biopha.2024.117154 · Cited by 7 · see citing works
Freeman, B. Α., Pekarová, M., Rubbo, H., & Trostchansky, A. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-804273-1.00016-8 · Cited by 7 · see citing works
Nitroalkylation of α-Synuclein by Nitro-Oleic Acid: Implications for Parkinson’s Disease
Chavarría, C., Trostchansky, A., Durán, R., Rubbo, H., & Souza, J. M. (2019) · Advances in experimental medicine and biology · doi:10.1007/978-3-030-11488-6_11 · Cited by 7 · see citing works
Nitric Oxide Redox Biochemistry in Lipid Environments
Trostchansky, A., Möller, M. N., Bartesaghi, S., Botti, H., Denicola, A., Radí, R., & Rubbo, H. (2010) · Elsevier eBooks · doi:10.1016/b978-0-12-373866-0.00002-2 · Cited by 6 · see citing works
Colussi, N., Chang, F., & Schopfer, F. J. (2024) · Redox Biochemistry and Chemistry · doi:10.1016/j.rbc.2024.100037 · Cited by 5 · see citing works
Self-citationMata-Pérez, C., Padilla, M. N., Sánchez-Calvo, B., Begara-Morales, J. C., Valderrama, R., Corpas, F. J., & Barroso, J. B. (2018) · Methods in molecular biology · doi:10.1007/978-1-4939-7695-9_18 · Cited by 5 · see citing works
Data of detection and characterization of nitrated conjugated-linoleic acid (NO2-cLA) in LDL
Mastrogiovanni, M., Trostchansky, A., & Rubbo, H. (2019) · Data in Brief · doi:10.1016/j.dib.2019.105037 · Cited by 5 · see citing works
Ledo, A., Rocha, B. S., & Laranjinha, J. A. N. (2019) · Advances in experimental medicine and biology · doi:10.1007/978-3-030-11488-6_10 · Cited by 4 · see citing works
Nitro-fatty acid signaling: Therapeutic potential in inflammatory diseases
Rubbo, H., & Trostchansky, A. (2024) · Redox Biochemistry and Chemistry · doi:10.1016/j.rbc.2024.100027 · Cited by 4 · see citing works
Nitro-Fatty Acids: Synthesis, Properties, and Role in Biological System
Rubbo, H., & Trostchansky, A. (2014) · Springer eBooks · doi:10.1007/978-3-319-06710-0_9 · Cited by 4 · see citing works
Palma, A. A. D., Fino, L. M. D., Salvatore, S. R., D’Ambrosio, J. M., Grozeff, G. E. G., García‐Mata, C., Schopfer, F. J., & Laxalt, A. M. (2018) · bioRxiv (Cold Spring Harbor Laboratory) · doi:10.1101/297994 · Cited by 3 · see citing works
Self-citationNitro-fatty acid signaling and intracellular biodistribution in plants
Aranda‐Caño, L., Valderrama, R., Begara-Morales, J. C., Chaki, M., Pedrajas, J. R., & Barroso, J. B. (2025) · Plant Science · doi:10.1016/j.plantsci.2025.112829 · Cited by 2 · see citing works
Redox signals and oxidative stress in the control of mitochondrial protein import
Hasberg, L., Lauterbach, V. K., Ochsenreiter, T., & Riemer, J. (2026) · Protein Science · doi:10.1002/pro.70665 · Cited by 2 · see citing works
Nitro-fatty acids as novel Virgin olive oil quality markers
Rubbo, H., Trostchansky, A., & Sánchez-Calvo, B. (2023) · Journal of Food Composition and Analysis · doi:10.1016/j.jfca.2023.105680 · Cited by 1 · see citing works
Bovine milk as a source of nitro‐conjugated linoleic acid
Barbeito, J., Mastrogiovanni, M., García-Roche, M., Mendoza, A. R., Rubbo, H., Carriquiry, M., & Trostchansky, A. (2024) · International Journal of Dairy Technology · doi:10.1111/1471-0307.13155 · Cited by 1 · see citing works
Kansanen, E. (2012) · UEF eRepo (University of Eastern Finland) · Cited by 1 · see citing works
Durand, G. (2025) · Wiley eBooks · doi:10.1002/9781119790419.ch21
- 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 › 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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