Nitroarachidonic acid, a novel peroxidase inhibitor of prostaglandin endoperoxide H synthases 1 and 2
Open accessAbstract
Prostaglandin endoperoxide H synthase (PGHS) catalyzes the oxidation of arachidonate to prostaglandin H(2). We have previously synthesized and chemically characterized nitroarachidonic acid (AANO(2)), a novel anti-inflammatory signaling mediator. Herein, the interaction of AANO(2) with PGHS was analyzed. AANO(2) inhibited oxygenase activity of PGHS-1 but not PGHS-2. AANO(2) exhibited time- and concentration-dependent inhibition of peroxidase activity in both PGHS-1 and -2. The plot of k(obs) versus AANO(2) concentrations showed a hyperbolic function with k(inact) = 0.045 s(-1) and K(i)(*app) = 0.019 μM for PGHS-1 and k(inact) = 0.057 s(-1) and K(i)(*app) = 0.020 μM for PGHS-2. Kinetic analysis suggests that inactivation of PGHS by AANO(2) involves two sequential steps: an initial reversible binding event (described by K(i)) followed by a practically irreversible event (K(i)(*app)) leading to an inactivated enzyme. Inactivation was associated with irreversible disruption of heme binding to the protein. The inhibitory effects of AANO(2) were selective because other nitro-fatty acids tested, such as nitrooleic acid and nitrolinoleic acid, were unable to inhibit enzyme activity. In activated human platelets, AANO(2) significantly decreased PGHS-1-dependent thromboxane B(2) formation in parallel with a decrease in platelet aggregation, thus confirming the biological relevance of this novel inhibitory pathway.
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Nitroalkylation directly inhibits the catalytic activity of enzymes including xanthine oxidoreductase, cyclooxygenase and soluble epoxide hydrolase, reactions that result in significant beneficial physiological responses.
“Nitroalkylation also directly inhibits the catalytic activity of enzymes including xanthine oxidoreductase [33], cyclooxygenase [37] and soluble epoxide hydrolase (Cys521) [34], reactions that result in significant beneficial physiological responses.”
From Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes (2015) · cites this paper as [37]
Electrophilic nitroalkenes exert signaling actions via the modulation of the expression and activity of both anti-inflammatory and pro-inflammatory enzymes.
“Electrophilic nitroalkenes exert signaling actions via the modulation of the expression and activity of both anti-inflammatory [32] and pro-inflammatory enzymes [23].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [23]
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Cites
Cyclooxygenases: Structural, cellular, and molecular biology
Smith, W. L., DeWitt, D. L., & Garavito, R. M. (2000) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.69.1.145 · Cited by 2,925 · see citing works
n−3 Polyunsaturated fatty acids, inflammation, and inflammatory diseases
Calder, P. C. (2006) · The American Journal of Clinical Nutrition · doi:10.1093/ajcn/83.6.1505s · Cited by 2,525 · see citing works
Prostaglandin Endoperoxide H Synthases (Cyclooxygenases)-1 and −2
Smith, W. L., Garavito, R. M., & DeWitt, D. L. (1996) · Journal of Biological Chemistry · doi:10.1074/jbc.271.52.33157 · Cited by 1,973 · see citing works
Esters of Methanesulfonic Acid as Irreversible Inhibitors of Acetylcholinesterase
Kitz, R. J., & Wilson, I. B. (1962) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)50153-8 · Cited by 1,523 · see citing works
Simultaneous determination of hemes a, b, and c from pyridine hemochrome spectra
Berry, E. A., & Trumpower, B. L. (1987) · Analytical Biochemistry · doi:10.1016/0003-2697(87)90643-9 · Cited by 918 · see citing works
The Behavior and Significance of Slow‐Binding Enzyme Inhibitors
Morrison, J. F., & Walsh, C. T. (1988) · Advances in enzymology and related areas of molecular biology/Advances in enzymology and related subjects · doi:10.1002/9780470123072.ch5 · Cited by 843 · see citing works
Structural and Functional Basis of Cyclooxygenase Inhibition
Blobaum, A. L., & Marnett, L. J. (2007) · Journal of Medicinal Chemistry · doi:10.1021/jm0613166 · Cited by 552 · see citing works
Self-citationArachidonic Acid Oxygenation by COX-1 and COX-2
Marnett, L. J., Rowlinson, S. W., Goodwin, D. C., Kalgutkar, A. S. S., & Lanzo, C. A. (1999) · Journal of Biological Chemistry · doi:10.1074/jbc.274.33.22903 · Cited by 524 · see citing works
Self-citationLandino, L. M., Crews, B. C., Timmons, M. D., Morrow, J. D., & Marnett, L. J. (1996) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.93.26.15069 · Cited by 423 · see citing works
Self-citationFatty 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
Prütz, W. A., Mönig, H., Butler, J., & Land, E. J. (1985) · Archives of Biochemistry and Biophysics · doi:10.1016/0003-9861(85)90780-5 · Cited by 338 · see citing works
The Productive Conformation of Arachidonic Acid Bound to Prostaglandin Synthase
Malkowski, M. G., Ginell, S. L., Smith, W. L., & Garavito, R. M. (2000) · Science · doi:10.1126/science.289.5486.1933 · Cited by 309 · 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
Mechanism of Free Radical Oxygenation of Polyunsaturated Fatty Acids by Cyclooxygenases
Rouzer, C. A., & Marnett, L. J. (2003) · Chemical Reviews · doi:10.1021/cr000068x · Cited by 266 · 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
Fatty Acid Transduction of Nitric Oxide Signaling
Schopfer, F. J., Baker, P. R. S., Giles, G. I., Chumley, P., Batthyány, C., Crawford, J. H., Patel, R. P., Hogg, N., Branchaud, B. P., Lancaster, J. R., et al. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m414689200 · Cited by 171 · see citing works
Goodwin, D. C., Landino, L. M., & Marnett, L. J. (1999) · The FASEB Journal · doi:10.1096/fasebj.13.10.1121 · Cited by 168 · see citing works
Self-citationSalvemini, D., Currie, M. G., & Mollace, V. (1996) · Journal of Clinical Investigation · doi:10.1172/jci118704 · Cited by 165 · see citing works
The Cyclooxygenase Reaction Mechanism
van der Donk, W. A., Tsai, A.-L., & Kulmacz, R. J. (2002) · Biochemistry · doi:10.1021/bi026938h · Cited by 165 · see citing works
Activated Platelets and Monocytes Generate Four Hydroxyphosphatidylethanolamines via Lipoxygenase
Maskrey, B. H., Bermúdez-Fajardo, A., Morgan, A. H., Stewart-Jones, E., Dioszeghy, V., Taylor, G. W., Baker, P. R. S., Coles, B., Coffey, M. J., Kühn, H., et al. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m611776200 · Cited by 139 · see citing works
Self-citationInteraction between nitric oxide and cyclooxygenase pathways
Rosa, M. D., Ialenti, A., Ianaro, A., & Sautebin, L. (1996) · Prostaglandins Leukotrienes and Essential Fatty Acids · doi:10.1016/s0952-3278(96)90053-8 · Cited by 131 · see citing works
Goodwin, D. C., Gunther, M. R., Hsi, L. C., Crews, B. C., Eling, T. E., Mason, R. P., & Marnett, L. J. (1998) · Journal of Biological Chemistry · doi:10.1074/jbc.273.15.8903 · Cited by 125 · see citing works
Self-citationKulmacz, R. J., Pendleton, R. B., & Lands, W. E. M. (1994) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)37493-8 · Cited by 120 · 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
Activated platelets and monocytes generate four hydroxyphosphatidylethanolamines via lipoxygenase.
Maskrey, B. H., Bermúdez-Fajardo, A., Morgan, A. H., Stewart-Jones, E., Dioszeghy, V., Taylor, G. W., Baker, P. R. S., Coles, B., Coffey, M. J., Kühn, H., et al. (2009) · Journal of Biological Chemistry · doi:10.1074/jbc.a611776200 · Cited by 115 · see citing works
Self-citationSchopfer, 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., et al. (2009) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2008.12.025 · Cited by 104 · see citing works
Marnett, L. J., Siedlik, P. H., Ochs, R. C., Pagels, W. R., Das, M., Honn, K. V., Warnock, R., Tainer, B., & Eling, T. E. (1984) · Molecular Pharmacology · doi:10.1016/s0026-895x(25)15092-x · Cited by 100 · see citing works
Self-citationColes, B., Bloodsworth, A., Eiserich, J. P., Coffey, M. J., McLoughlin, R. M., Giddings, J. C., Lewis, M. J., Haslam, R. J., Freeman, B. A., & O'Donnell, V. B. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m105209200 · Cited by 98 · see citing works
Self-citationSynthesis, 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
Self-citationNitro-oleic Acid, a Novel and Irreversible Inhibitor of Xanthine Oxidoreductase
Kelley, E. E., Batthyany, C. I., Hundley, N. J., Woodcock, S. R., Bonacci, G., Del Rio, J. M., Schopfer, F. J., Lancaster, J. R., Freeman, B. A., & Tarpey, M. M. (2008) · Journal of Biological Chemistry · doi:10.1074/jbc.m802402200 · Cited by 81 · see citing works
Control of Prostaglandin Stereochemistry at the 15-Carbon by Cyclooxygenases-1 and -2
Schneider, C. G., Boeglin, W. E., Prusakiewicz, J. J., Rowlinson, S. W., Marnett, L. J., Samel, N., & BRASH, A. R. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m107471200 · Cited by 79 · see citing works
Self-citationBalazy, M., Iesaki, T., Park, J. L., Jiang, H., Kaminski, P. M., & Wolin, M. S. (2001) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)29269-7 · Cited by 73 · see citing works
EPR study of ferric native prostaglandin H synthase and its ferrous NO derivative
Karthein, R., Nastainczyk, W., & Ruf, H. H. (1987) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1987.tb13499.x · Cited by 73 · see citing works
Catalytic Consumption of Nitric Oxide by Prostaglandin H Synthase-1 Regulates Platelet Function
O’Donnell, V. B., Coles, B., LEWIS, M. J., Crews, B. C., Marnett, L. J., & Freeman, B. Α. (2000) · Journal of Biological Chemistry · doi:10.1074/jbc.m001802200 · Cited by 66 · see citing works
Self-citationBiological Nitration of Arachidonic Acid
Balazy, M., & Poff, C. (2004) · Current Vascular Pharmacology · doi:10.2174/1570161043476465 · Cited by 59 · see citing works
Prostaglandin G2 levels during reaction of prostaglandin H synthase with arachidonic acid
Kulmacz, R. J. (1987) · Prostaglandins · doi:10.1016/0090-6980(87)90246-2 · Cited by 54 · see citing works
Trostchansky, A., O’Donnell, V. B., Goodwin, D. C., Landino, L. M., Marnett, L. J., Radí, R., & Rubbo, H. (2007) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2007.01.009 · Cited by 45 · see citing works
Self-citationSong, I., Ball, T., & Smith, W. L. (2001) · Biochemical and Biophysical Research Communications · doi:10.1006/bbrc.2001.6071 · Cited by 43 · see citing works
Kalgutkar, A. S. S., Crews, B. C., & Marnett, L. J. (1996) · Biochemistry · doi:10.1021/bi9605752 · Cited by 39 · see citing works
Self-citationTsai, A., Wei, C., Baek, H. K., Kulmacz, R. J., & Wart, H. E. V. (1997) · Journal of Biological Chemistry · doi:10.1074/jbc.272.14.8885 · Cited by 38 · see citing works
[52] Preparation and proteolytic cleavage of apoprostaglandin endoperoxide synthase
Odenwaller, R., Chen, Y. P., & Marnett, L. J. (1990) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/0076-6879(90)87054-7 · Cited by 33 · see citing works
Self-citationRecent developments in cyclooxygenase inhibition
Marnett, L. J. (2002) · Prostaglandins & Other Lipid Mediators · doi:10.1016/s0090-6980(02)00027-8 · Cited by 32 · see citing works
Self-citationWu, G., Vuletich, J. L., Kulmacz, R. J., Osawa, Y., & Tsai, A.-L. (2001) · Journal of Biological Chemistry · doi:10.1074/jbc.m100628200 · Cited by 31 · see citing works
MICHIBAYASHI, T. (2005) · Journal of Atherosclerosis and Thrombosis · doi:10.5551/jat.12.154 · Cited by 11 · see citing works
Platelet aggregation in platelet suspensions from Mongolian gerbils (Meriones unguiculatus).
Agwu, D. E., Holub, B. J., Johnstone, I. B., & Crane, S. (1983) · Europe PMC (PubMed Central) · Cited by 4 · see citing works
Flagged first, then by citations
Research works printed but not linked: 3
- [24]O'Donnell V. B. Coles B. Lewis M. J. Crews B. C. Marnett L. J. Freeman B. A. (2000) J. Biol. Chem. 275, 38239– 38244 10993875
- [26]Copeland R. A. (2000) Enzymes, 2nd Ed., pp. 305– 317, John Wiley & Sons, Inc., New York
- [42]Agwu D. E. Holub B. J. Johnstone I. B. Crane S. (1983) Can. J. Comp. Med. 47, 203– 206 6883186 PMC1235918
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Dennis, E. A., & Norris, P. C. (2015) · Nature Reviews Immunology · doi:10.1038/nri3859 · Cited by 1,517 · see citing works
Arachidonic Acid Metabolites in Cardiovascular and Metabolic Diseases
Sonnweber, T., Pizzini, A., Nairz, M., Weiß, G., & Tancevski, I. (2018) · International Journal of Molecular Sciences · doi:10.3390/ijms19113285 · Cited by 439 · see citing works
Self-regulation of the inflammatory response by peroxisome proliferator-activated receptors
Korbecki, J., Bobiński, R., & Dutka, M. (2019) · Inflammation Research · doi:10.1007/s00011-019-01231-1 · Cited by 415 · see citing works
Lipoxidation adducts with peptides and proteins: Deleterious modifications or signaling mechanisms?
Domingues, R. M., Domingues, P. M., Melo, T., Pérez‐Sala, D., Reis, A., & Spickett, C. M. (2013) · Journal of Proteomics · doi:10.1016/j.jprot.2013.06.004 · Cited by 165 · see citing works
Olives and olive oil are sources of electrophilic fatty acid nitroalkenes
Fazzari, M., Trostchansky, A., Schopfer, F. J., Salvatore, S. R., Sánchez-Calvo, B., Vitturi, D., Valderrama, R., Barroso, J. B., Radi, R., Freeman, B. A., et al. (2014) · PLoS ONE · doi:10.1371/journal.pone.0084884 · Cited by 114 · see citing works
Self-citationRedox-Dependent Anti-Inflammatory Signaling Actions of Unsaturated Fatty Acids
Delmastro-Greenwood, M. M., Freeman, B. Α., & Wendell, S. G. (2013) · Annual Review of Physiology · doi:10.1146/annurev-physiol-021113-170341 · Cited by 114 · see citing works
Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes
Delmastro-Greenwood, M., Hughan, K. S., Vitturi, D. A., Salvatore, S. R., Grimes, G., Potti, G., Shiva, S., Schopfer, F. J., Gladwin, M. T., Freeman, B. A., et al. (2015) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2015.07.149 · Cited by 97 · see citing works
Characterization and quantification of endogenous fatty acid nitroalkene metabolites in human urine
Salvatore, S. R., Vitturi, D. A., Baker, P. R. S., Bonacci, G., Koenitzer, J. R., Woodcock, S. R., Freeman, B. A., & Schopfer, F. J. (2013) · Journal of Lipid Research · doi:10.1194/jlr.m037804 · Cited by 82 · see citing works
Modulation of Nitro-fatty Acid Signaling
Vitturi, D. A., Chen, C.-S., Woodcock, S. R., Salvatore, S. R., Bonacci, G., Koenitzer, J. R., Stewart, N. A., Wakabayashi, N., Kensler, T. W., Freeman, B. Α., et al. (2013) · Journal of Biological Chemistry · doi:10.1074/jbc.m113.486282 · Cited by 75 · see citing works
Khoo, N. K. H., Li, L., Salvatore, S. R., Schopfer, F. J., & Freeman, B. Α. (2018) · Scientific Reports · doi:10.1038/s41598-018-20460-8 · Cited by 63 · see citing works
Nitro-Fatty Acids: Formation, Redox Signaling, and Therapeutic Potential
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Self-citationMouse Models of Oxidative Stress Indicate a Role for Modulating Healthy Aging
Hamilton, R. T. (2012) · Journal of Clinical & Experimental Pathology · doi:10.4172/2161-0681.s4-005 · Cited by 52 · see citing works
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Self-citationPiesche, M., Roos, J., Kuhn, B. R., Fettel, J., Hellmuth, N., Brat, C., Maucher, I. V., Awad, O., Matrone, C., Comerma-Steffensen, S., et al. (2020) · Frontiers in Pharmacology · doi:10.3389/fphar.2020.01297 · Cited by 44 · see citing works
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Self-citationMelo, 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
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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
Self-citationTrostchansky, A., Mastrogiovanni, M., Miquel, E., Rodríguez-Bottero, S., Palma, L. M., Cassina, P., & Rubbo, H. (2018) · Frontiers in Molecular Neuroscience · doi:10.3389/fnmol.2018.00131 · Cited by 41 · see citing works
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Self-citationDíaz‐Amarilla, P., Miquel, E., Trostchansky, A., Trías, E., Ferreira, A. M., Freeman, B. Α., Cassina, P., Barbeito, L., Vargas, M. R., & Rubbo, H. (2016) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2016.03.013 · Cited by 31 · see citing works
Self-citationWood, I., Trostchansky, A., & Rubbo, H. (2020) · Biochimie · doi:10.1016/j.biochi.2020.09.021 · Cited by 29 · see citing works
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Self-citationSánchez-Calvo, B., Cassina, A., Ríos, N., Peluffo, G., Boggia, J. G., Radí, R., Rubbo, H., & Trostchansky, A. (2016) · PLoS ONE · doi:10.1371/journal.pone.0150459 · Cited by 15 · see citing works
Self-citationWood, 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
Self-citationFatty acid nitroalkenes – Multi-target agents for the treatment of sickle cell disease
Chowdhury, F. A., Colussi, N., Sharma, M., Wood, K. C., Xu, J. Z., Freeman, B. Α., Schopfer, F. J., & Straub, A. C. (2023) · Redox Biology · doi:10.1016/j.redox.2023.102941 · Cited by 12 · 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
Koudelka, A., Buchan, G. J., Cechova, V., O’Brien, J. P., Stevenson, E. R., Uvalle, C. E., Liu, H., Woodcock, S. R., Mullett, S. J., Zhang, C., et al. (2024) · Journal of Lipid Research · doi:10.1016/j.jlr.2024.100705 · Cited by 13 · see citing works
Hellmuth, N., Brat, C., Awad, O., George, S., Kahnt, A. S., Bauer, T., Phuoc, H. P. H., Steinhilber, D., Angioni, C., Hassan, M. E., et al. (2021) · Frontiers in Pharmacology · doi:10.3389/fphar.2021.715076 · Cited by 11 · see citing works
(Poly)phenols and nitrolipids: Relevant participants in nitric oxide metabolism
Fraga, C. G., Trostchansky, A., Rocha, B. S., Laranjinha, J. A. N., Rubbo, H., & Galleano, M. (2022) · Molecular Aspects of Medicine · doi:10.1016/j.mam.2022.101158 · Cited by 11 · see citing works
Self-citation5-LOX inhibition by natural products
Rubbo, H., & Wood, I. (2020) · Nature Chemical Biology · doi:10.1038/s41589-020-0568-z · Cited by 10 · see citing works
Self-citationTomato 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
Self-citationFreeman, 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
Self-citationChaki, M., Aranda‐Caño, L., Begara-Morales, J. C., Sánchez-Calvo, B., López-Jaramillo, J., Padilla, M. N., Valderrama, R., Pedrajas, J. R., & Barroso, J. B. (2025) · Protein Science · doi:10.1002/pro.70076 · Cited by 5 · see citing works
Fatty acid nitration in human low-density lipoprotein
Mastrogiovanni, M., Trostchansky, A., & Rubbo, H. (2019) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2019.108190 · Cited by 5 · see citing works
Self-citationГрубер, Ф. (2016) · Springer eBooks · doi:10.1007/978-3-319-43157-4_1 · 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
Self-citationLescano, C. H., de Lima, F. F., Catelan, T. B. S., Guimarães, V. H. D., Pereira, U. A., Aguilar, C. M., Cardoso, C. A. L., Santos, S. H. S., Borges, A., & de Oliveira, I. P. (2023) · Food Bioscience · doi:10.1016/j.fbio.2023.102955 · Cited by 3 · see citing works
Nitro-arachidonic Acid: Downstream Signaling and Therapeutics
Rubbo, H., González-Perilli, L., Mastrogiovanni, M., Sánchez-Calvo, B., & Trostchansky, A. (2016) · Springer eBooks · doi:10.1007/978-3-319-45865-6_6 · Cited by 2 · see citing works
Self-citationMethods for the Analysis of Arachidonic Acid-Derived Metabolites in Platelets
Mastrogiovanni, M., Eduardo Fuentes, Q., Wehinger, S., Méndez, D., Palomo, I. F., & Trostchansky, A. (2023) · Interdisciplinary biotechnological advances · doi:10.1007/978-981-19-8342-9_3 · Cited by 1 · see citing works
Self-citationNitro-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
Self-citationProtective Effects on the Cardiovascular System
Chang, Z., Gu, J., & Li, X. (2025) · Springer eBooks · doi:10.1007/978-981-95-2824-0_7
Rodríguez, L., Fernandez-Rojas, M., Morales-Malvarez, L., Eduardo Fuentes, Q., & Trostchansky, A. (2025) · Food Bioscience · doi:10.1016/j.fbio.2025.108175
Self-citationEnhanced Antiplatelet Activity of Nitrated Fatty Acid Extracts from Phaseolus vulgaris L.
Rodríguez, L., Montecino-Garrido, H. L., Lagos, F., Carrasco, B., Palomo, I. F., Ormazabal, P., Trostchansky, A., & Eduardo Fuentes, Q. (2026) · Molecules · doi:10.3390/molecules31030488
Self-citationWood, I., Grosso, F., Bonilla, L., Radí, R., Goodman, M., Marnett, L. J., Trostchansky, A., & Rubbo, H. (2026) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2026.111002
Self-citation
- Authors
- Trostchansky, A., Bonilla, L., Thomas, C. P., O'Donnell, V. B., Marnett, L. J., Radi, R., & Rubbo, H.
- Affiliations
- Universidad de la República de Uruguay (UY)
- Cardiff University (GB)
- Vanderbilt University (US)
- Corresponding author
- Rubbo, Homero
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2011-04
- Volume
- 286
- Issue
- 15
- Pages
- 12891-12900
- ISSN
- 0021-9258 (ISSN-L)
- PMC
- PMC3075636
- OpenAlex
- W2039023342
- Cited by
- 58
- References
- 45
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 4 · 2023: 4 · 2022: 1 · 2021: 2 · 2020: 5 · 2019: 8 · 2018: 6 · 2017: 3 · 2016: 6 · 2015: 4 · 2014: 1 · 2013: 7 · 2012: 2
- FWCI
- 2.34
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion, cc-by-nc)
- PubMed Central (publishedVersion, cc-by-nc)
- PubMed (publishedVersion)
- ORCA Online Research @Cardiff (Cardiff University) (submittedVersion)
- Funders
- Howard Hughes Medical Institute
- Wellcome Trust
- National Institute of General Medical Sciences (GM 15431, P50GM015431, P01GM015431)
- Topics
- Health Sciences › Medicine › Pharmacology › Inflammatory mediators and NSAID effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Eicosanoids and Hypertension Pharmacology
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Keywords
- PGHS-1, prostaglandin H synthase-2, peroxidase inhibition, enzyme inactivation, heme binding, nitro-fatty acids, thromboxane B2, platelet aggregation, anti-inflammatory signaling
- MeSH terms
- Arachidonic Acids, Blood Platelets, Dose-Response Relationship, Drug, Kinetics, Peroxidase, Platelet Aggregation, Protein Binding, Thromboxane B2, Cyclooxygenase 1, Cyclooxygenase 2, Cyclooxygenase 2 Inhibitors
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