Electrophilic nitro-fatty acids activate NRF2 by a KEAP1 cysteine 151-independent mechanism
Open accessAbstract
Nitro-fatty acids (NO(2)-FAs) are electrophilic signaling mediators formed in vivo via nitric oxide (NO)- and nitrite (NO(2)(-))-dependent reactions. Nitro-fatty acids modulate signaling cascades via reversible covalent post-translational modification of nucleophilic amino acids in regulatory proteins and enzymes, thus altering downstream signaling events, such as Keap1-Nrf2-antioxidant response element (ARE)-regulated gene expression. In this study, we investigate the molecular mechanisms by which 9- and 10-nitro-octadec-9-enoic acid (OA-NO(2)) activate the transcription factor Nrf2, focusing on the post-translational modifications of cysteines in the Nrf2 inhibitor Keap1 by nitroalkylation and its downstream responses. Of the two regioisomers, 9-nitro-octadec-9-enoic acid was a more potent ARE inducer than 10-nitro-octadec-9-enoic acid. The most OA-NO(2)-reactive Cys residues in Keap1 were Cys(38), Cys(226), Cys(257), Cys(273), Cys(288), and Cys(489). Of these, Cys(273) and Cys(288) accounted for ∼50% of OA-NO(2) reactions in a cellular milieu. Notably, Cys(151) was among the least OA-NO(2)-reactive of the Keap1 Cys residues, with mutation of Cys(151) having no effect on net OA-NO(2) reaction with Keap1 or on ARE activation. Unlike many other Nrf2-activating electrophiles, OA-NO(2) enhanced rather than diminished the binding between Keap1 and the Cul3 subunit of the E3 ligase for Nrf2. OA-NO(2) can therefore be categorized as a Cys(151)-independent Nrf2 activator, which in turn can influence the pattern of gene expression and therapeutic actions of nitroalkenes.
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
NO2-FAs exert pleiotropic post-translational, anti-oxidant and anti-inflammatory effects that include inhibition of vascular smooth muscle proliferation and neointima formation after injury, cardioprotection, improved endothelial function, and activation of downstream NO signaling pathways.
“NO2-FAs exert pleiotropic post-translational, anti-oxidant and anti-inflammatory effects[105,321,385] that include inhibition of vascular smooth muscle proliferation and neointima formation after injury, cardioprotection, improved endothelial function[94,386–390], and activation of downstream NO signaling pathways[385,389,391–394].”
From Enterosalivary nitrate metabolism and the microbiome: Intersection of microbial metabolism, nitric oxide and diet in cardiac and pulmonary vascular health (2017) · cites this paper as [389]
This post-translational modification of functionally-significant hyperreactive thiols induces pleiotropic responses that include the cGMP-independent activation of transcriptional programs regulated by Nrf2 and nuclear lipid receptors, as well as inhibition of pro-inflammatory signaling by NF-kβ.
“This post-translational modification of functionally-significant hyperreactive thiols induces pleiotropic responses that include the cGMP-independent activation of transcriptional programs regulated by nuclear factor (erythroid-derived-2)-like 2 (Nrf2) and nuclear lipid receptors, as well as inhibition of pro-inflammatory signaling by nuclear factor kappa-β (NF-kβ) [12–15].”
From Nitrite and nitrate-dependent generation of anti-inflammatory fatty acid nitroalkenes (2015) · cites this paper as [13]
NO2-CLA mediates signaling actions analogous to those reported for NO2-LA and NO2-OA.
“To further confirm that NO 2 -CLA mediates signaling actions analogous to those reported for NO 2 -LA and NO 2 -OA (2, 15), HO-1 expression in RAW 264.7 macrophages was evaluated.”
From Conjugated linoleic acid is a preferential substrate for fatty acid nitration (2012) · cites this paper as [15]
Nitroalkene derivatives of fatty acids (NO2-FA) activate Nrf2-dependent antioxidant gene expression by adduction of critical thiols in the Nrf2 regulatory protein Keap1.
“Via this mechanism, NO2-FA activate Nrf2-dependent antioxidant gene expression by adduction of critical thiols in the Nrf2 regulatory protein Keap1 [17].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [17]
Nitroalkene derivatives of fatty acids (NO2-FA) instigate adaptive anti-inflammatory gene expression and metabolic responses.
“Since NO2-FA instigate adaptive anti-inflammatory gene expression and metabolic responses, these redox-derived metabolites may contribute to the cardiovascular benefits associated with the Mediterranean diet.”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [17]
NO2-FA activate Nrf2-regulated anti-inflammatory gene expression and heat shock factor-regulated heat shock protein expression.
“Additionally, NO2-FA activate Nrf2-regulated anti-inflammatory gene expression and heat shock factor-regulated heat shock protein expression [17], [46], [55].”
From Olives and olive oil are sources of electrophilic fatty acid nitroalkenes (2014) · cites this paper as [17]
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Cites
Cell Survival Responses to Environmental Stresses Via the Keap1-Nrf2-ARE Pathway
Kensler, T. W., Wakabayashi, N., & Biswal, S. (2007) · Annual Review of Pharmacology and Toxicology · doi:10.1146/annurev.pharmtox.46.120604.141046 · Cited by 3,630 · see citing works
Kobayashi, A., Kang, M.-I., Okawa, H., Ohtsuji, M., Zenke, Y., Chiba, T., Igarashi, K., & Yamamoto, M. (2004) · Molecular and Cellular Biology · doi:10.1128/mcb.24.16.7130-7139.2004 · Cited by 2,224 · see citing works
Dinkova-Kostova, A. T., Holtzclaw, W. D., Cole, R. N., Itoh, K., Wakabayashi, N., Katoh, Y., Yamamoto, M., & Talalay, P. (2002) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.172398899 · Cited by 1,947 · see citing works
Self-citationZhang, D. D., & Hannink, M. (2003) · Molecular and Cellular Biology · doi:10.1128/mcb.23.22.8137-8151.2003 · Cited by 1,480 · see citing works
Keap1 Is a Redox-Regulated Substrate Adaptor Protein for a Cul3-Dependent Ubiquitin Ligase Complex
Zhang, D. D., Lo, S., Cross, J. V., Templeton, D. J., & Hannink, M. (2004) · Molecular and Cellular Biology · doi:10.1128/mcb.24.24.10941-10953.2004 · Cited by 1,262 · see citing works
Wakabayashi, N., Dinkova-Kostova, A. T., Holtzclaw, W. D., Kang, M.-I., Kobayashi, A., Yamamoto, M., Kensler, T. W., & Talalay, P. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0307301101 · Cited by 986 · see citing works
Cullinan, S. B., Gordan, J. D., Jin, J., Harper, J. W., & Diehl, J. A. (2004) · Molecular and Cellular Biology · doi:10.1128/mcb.24.19.8477-8486.2004 · Cited by 986 · see citing works
Kobayashi, A., Kang, M.-I., Watai, Y., Tong, K. I., Shibata, T., Uchida, K., & Yamamoto, M. P. (2005) · Molecular and Cellular Biology · doi:10.1128/mcb.26.1.221-229.2006 · Cited by 933 · see citing works
Self-citationTong, K. I., Katoh, Y., Kusunoki, H., Itoh, K., Tanaka, T., & Yamamoto, M. (2006) · Molecular and Cellular Biology · doi:10.1128/mcb.26.8.2887-2900.2006 · Cited by 759 · see citing works
Self-citationKobayashi, M., Li, L., Iwamoto, N., Nakajima‐Takagi, Y., Kaneko, H., Nakayama, Y., Eguchi, M., Wada, Y., Kumagai, Y., & Yamamoto, M. P. (2008) · Molecular and Cellular Biology · doi:10.1128/mcb.01080-08 · Cited by 641 · see citing works
Self-citationRegulation of γ-Glutamylcysteine Synthetase Subunit Gene Expression by the Transcription Factor Nrf2
Wild, A. C., Moinova, H., & Mulcahy, R. (1999) · Journal of Biological Chemistry · doi:10.1074/jbc.274.47.33627 · Cited by 595 · see citing works
Levonen, A., Landar, A. L., Ramachandran, A., CEASER, E. K., Dickinson, D. A., Zanoni, G., Morrow, J. D., & Darley-Usmar, V. M. (2004) · Biochemical Journal · doi:10.1042/bj20031049 · Cited by 559 · see citing works
Self-citationPhysiological Significance of Reactive Cysteine Residues of Keap1 in Determining Nrf2 Activity
Yamamoto, T., Suzuki, T., Kobayashi, A., Wakabayashi, J., Maher, J. M., Motohashi, H., & Yamamoto, M. P. (2008) · Molecular and Cellular Biology · doi:10.1128/mcb.01704-07 · Cited by 515 · see citing works
Self-citationEggler, A. L., Liu, G., Pezzuto, J. M., van Breemen, R. B., & Mesecar, A. D. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0502402102 · Cited by 459 · see citing works
Tong, K. I., Padmanabhan, B., Kobayashi, A., Shang, C., Hirotsu, Y., Yokoyama, S., & Yamamoto, M. P. (2007) · Molecular and Cellular Biology · doi:10.1128/mcb.00753-07 · Cited by 447 · see citing works
Self-citationMcMahon, M. J., Lamont, D. J., Beattie, K. A., & Hayes, J. D. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1007387107 · Cited by 445 · see citing works
Nitrolinoleic acid. An endogenous peroxisome proliferator-activated receptor γ ligand
Schopfer, F. J., Lin, Y., Baker, P. R. S., Cui, T., Garcia-Barrio, M., Zhang, J., Chen, K., Chen, Y. E., & Freeman, B. A. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0408384102 · Cited by 428 · see citing works
Self-citationThe Keap1 BTB/POZ dimerization function is required to sequester Nrf2 in cytoplasm
Zipper, L. M., & Mulcahy, R. T. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m206530200 · Cited by 366 · 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-citationNitro-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
Ogura, T., Tong, K. I., Mio, K., Maruyama, Y., Kurokawa, H., Sato, C., & Yamamoto, M. P. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0914036107 · Cited by 232 · see citing works
Self-citationDinkova‐Kostova, A. T., Holtzclaw, W. D., & Wakabayashi, N. (2005) · Biochemistry · doi:10.1021/bi047434h · Cited by 220 · see citing works
Rachakonda, G., Xiong, Y., Sekhar, K. R., Stamer, S. L., Liebler, D. C., & Freeman, M. L. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700302s · Cited by 210 · see citing works
Transduction of Redox Signaling by Electrophile-Protein Reactions
Rudolph, T. K., & Freeman, B. Α. (2009) · Science Signaling · doi:10.1126/scisignal.290re7 · Cited by 200 · see citing works
Self-citationRudolph, 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
Self-citationEggler, A. L., Small, E., Hannink, M., & Mesecar, A. D. (2009) · Biochemical Journal · doi:10.1042/bj20090471 · Cited by 178 · see citing works
Covalent Peroxisome Proliferator-activated Receptor γ Adduction by Nitro-fatty Acids
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
Self-citationElectrophilic tuning of the chemoprotective natural product sulforaphane
Ahn, Y., Hwang, Y., Liu, H., Wang, X. J., Zhang, Y., Stephenson, K. K., Boronina, T. N., Cole, R. N., Dinkova‐Kostova, A. T., Talalay, P., et al. (2010) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1004104107 · Cited by 170 · see citing works
Nrf2-dependent and -independent Responses to Nitro-fatty Acids in Human Endothelial Cells
Kansanen, E., Jyrkkänen, H.-K., Volger, O. L., Leinonen, H., Kivelä, A. M., Häkkinen, S.-K., Woodcock, S. R., Schopfer, F. J., Horrevoets, A. J., Ylä-Herttuala, S., et al. (2009) · Journal of Biological Chemistry · doi:10.1074/jbc.m109.064873 · Cited by 165 · see citing works
Self-citationJyrkkänen, H.-K., Kansanen, E., Inkala, M., Kivelä, A. M., Hurttila, H., Heinonen, S. E., Goldsteins, G., Jauhiainen, S., Tiainen, S., Makkonen, H., et al. (2008) · Circulation Research · doi:10.1161/circresaha.108.176883 · Cited by 154 · see citing works
Self-citationRegulation of Nrf2-dependent gene expression by 15-deoxy-Δ12,14-prostaglandin J2
Kansanen, E., Kivelä, A. M., & Levonen, A. (2009) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2009.06.030 · Cited by 150 · see citing works
Self-citationVillacorta, L., Zhang, J., Garcia-Barrio, M. T., Chen, X.-L., Freeman, B. A., Chen, Y. E., & Cui, T. (2007) · American Journal of Physiology-Heart and Circulatory Physiology · doi:10.1152/ajpheart.00261.2007 · Cited by 144 · see citing works
Self-citationLevonen, A., Dickinson, D. A., Moellering, D. R., Mulcahy, R., Forman, H. J., & Darley-Usmar, V. M. (2001) · Arteriosclerosis Thrombosis and Vascular Biology · doi:10.1161/hq1101.098488 · Cited by 141 · see citing works
Self-citationWang, X.-J., Sun, Z., Chen, W., Li, Y., Villeneuve, N. F., & Zhang, D. D. (2008) · Toxicology and Applied Pharmacology · doi:10.1016/j.taap.2008.03.003 · Cited by 135 · see citing works
The hepatotoxic metabolite of acetaminophen directly activates the Keap1‐Nrf2 cell defense system†
Copple, I. M., Goldring, C. E., Jenkins, R. E., Chia, A. J. L., Randle, L. E., Hayes, J. D., Kitteringham, N. R., & Park, B. K. (2008) · Hepatology · doi:10.1002/hep.22472 · Cited by 133 · see citing works
Nitro-oleic acid inhibits angiotensin II-induced hypertension
Zhang, J., Villacorta, L., Chang, L., Fan, Z., Hamblin, M., Zhu, T., Chen, C. S., Cole, M. P., Schopfer, F. J., Deng, C. X., et al. (2010) · Circulation Research · doi:10.1161/circresaha.110.218404 · Cited by 121 · see citing works
Self-citationLi, L., Kobayashi, M., Kaneko, H., Nakajima‐Takagi, Y., Nakayama, Y., & Yamamoto, M. P. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m708702200 · Cited by 111 · 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
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
Self-citationOxidative stress-inducible lentiviral vectors for gene therapy
Hurttila, H., Koponen, J., Kansanen, E., Jyrkkänen, H.-K., Kivelä, A. M., Kylätie, R., Ylä‐Herttuala, S., & Levonen, A. (2008) · Gene Therapy · doi:10.1038/gt.2008.75 · Cited by 56 · see citing works
Self-citationWoodcock, S. R., Marwitz, A. J. V., Bruno, P., & Branchaud, B. P. (2006) · Organic Letters · doi:10.1021/ol0613463 · Cited by 51 · see citing works
Self-citationGorczynski, M. J., Smitherman, P. K., Akiyama, T. E., Wood, H. B., Berger, J. P., King, S. B., & Morrow, C. S. (2009) · Journal of Medicinal Chemistry · doi:10.1021/jm900326c · Cited by 33 · see citing works
Flagged first, then by citations
Research works printed but not linked: 7
- Dinkova-Kostova, A. T., Holtzclaw, W. D., Cole, R. N., Itoh, K., Waka- bayashi, N., Katoh, Y., Yamamoto, M., and Talalay, P. (2002) Proc. Natl. Acad. Sci. U.S.A. 99, 11908 -11913
- Wakabayashi, N., Dinkova-Kostova, A. T., Holtzclaw, W. D., Kang, M. I., Kobayashi, A., Yamamoto, M., Kensler, T. W., and Talalay, P. (2004) Proc. Natl. Acad. Sci. U.S.A. 101, 2040 -2045
- Schopfer, F. J., Lin, Y., Baker, P. R., Cui, T., Garcia-Barrio, M., Zhang, J., Chen, K., Chen, Y. E., and Freeman, B. A. (2005) Proc. Natl. Acad. Sci.
- Ogura, T., Tong, K. I., Mio, K., Maruyama, Y., Kurokawa, H., Sato, C., and Yamamoto, M. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 2842-2847
- Ahn, Y. H., Hwang, Y., Liu, H., Wang, X. J., Zhang, Y., Stephenson, K. K., Boronina, T. N., Cole, R. N., Dinkova-Kostova, A. T., Talalay, P., and Cole, P. A. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 9590 -9595
- Eggler, A. L., Liu, G., Pezzuto, J. M., van Breemen, R. B., and Mesecar, A. D. (2005) Proc. Natl. Acad. Sci. U.S.A. 102, 10070 -10075
- McMahon, M., Lamont, D. J., Beattie, K. A., and Hayes, J. D. (2010) Proc. Natl. Acad. Sci. U.S.A. 107, 18838 -18843
Cited by
Sorted by citations
NRF2 and the Hallmarks of Cancer
Rojo de la Vega, M., Chapman, E., & Zhang, D. D. (2018) · Cancer Cell · doi:10.1016/j.ccell.2018.03.022 · Cited by 1,672 · see citing works
Magesh, S., Chen, Y., & Hu, L. (2012) · Medicinal Research Reviews · doi:10.1002/med.21257 · Cited by 760 · see citing works
Molecular Basis of Electrophilic and Oxidative Defense: Promises and Perils of Nrf2
Ma, Q., & He, X. (2012) · Pharmacological Reviews · doi:10.1124/pr.110.004333 · Cited by 317 · see citing works
Formation and signaling actions of electrophilic lipids
Schopfer, F. J., Cipollina, C., & Freeman, B. A. (2011) · Chemical Reviews · doi:10.1021/cr200131e · Cited by 299 · see citing works
Self-citationCharacterizations of Three Major Cysteine Sensors of Keap1 in Stress Response
Saito, R., Suzuki, T., Hiramoto, K., Asami, S., Naganuma, E., Suda, H., Iso, T., Yamamoto, H., Morita, M., Baird, L., et al. (2016) · Molecular and Cellular Biology · doi:10.1128/mcb.00868-15 · Cited by 294 · see citing works
Self-citationKoch, C. D., Gladwin, M. T., Freeman, B. A., Lundberg, J. O., Weitzberg, E., & Morris, A. (2017) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2016.12.015 · Cited by 186 · see citing works
Self-citationPhenotypic modulation of macrophages in response to plaque lipids
Adamson, S., & Leitinger, N. (2011) · Current Opinion in Lipidology · doi:10.1097/mol.0b013e32834a97e4 · Cited by 154 · see citing works
Conjugated linoleic acid is a preferential substrate for fatty acid nitration
Bonacci, G., Baker, P. R. S., Salvatore, S. R., Shores, D., Khoo, N. K. H., Koenitzer, J. R., Vitturi, D. A., Woodcock, S. R., Golin-Bisello, F., Cole, M. P., et al. (2012) · Journal of Biological Chemistry · doi:10.1074/jbc.m112.401356 · Cited by 147 · see citing works
Self-citationVillacorta, 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
Self-citationOlives 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-citationCharles, R. L., Rudyk, O., Prysyazhna, O., Kamynina, A., Yang, J., Morisseau, C., Hammock, B. D., Freeman, B. A., & Eaton, P. (2014) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1402965111 · Cited by 100 · 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
Self-citationInorganic nitrite supplementation for healthy arterial aging
Sindler, A. L., DeVan, A. E., Fleenor, B. S., & Seals, D. R. (2014) · Journal of Applied Physiology · doi:10.1152/japplphysiol.01100.2013 · Cited by 68 · see citing works
The nitrated fatty acid 10-nitro-oleate attenuates allergic airway disease
Reddy, A. T., Lakshmi, S. P., Dornadula, S., Pinni, S., Rampa, D. R., & Reddy, R. C. (2013) · The Journal of Immunology · doi:10.4049/jimmunol.1300730 · Cited by 42 · see citing works
Narala, V. R., Subramani, P. A., Narasimha, V. R., Shaik, F. B., & Panati, K. (2014) · International Immunopharmacology · doi:10.1016/j.intimp.2014.09.009 · Cited by 33 · see citing works
Cuadrado, A., Cazalla, E., Bach, A., Bathish, B., Naidu, S. D., DeNicola, G. M., Dinkova-Kostova, A. T., Fernández-Ginés, R., Grochot-Przeczek, A., Hayes, J. D., et al. (2025) · Redox Biology · doi:10.1016/j.redox.2025.103569 · Cited by 28 · 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
Bates, D. J. P., Smitherman, P. K., Townsend, A. J., King, S. B., & Morrow, C. S. (2011) · Biochemistry · doi:10.1021/bi2005784 · Cited by 15 · see citing works
- Authors
- 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., Freeman, B. A., & Levonen, A.-L.
- Affiliations
- University of Eastern Finland (FI)
- University of Pittsburgh (US)
- Tohoku University (JP)
- Corresponding author
- Levonen, Anna-Liisa
- ORCID
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2011-04
- Volume
- 286
- Issue
- 16
- Pages
- 14019-14027
- ISSN
- 0021-9258 (ISSN-L)
- PMC
- PMC3077602
- OpenAlex
- W2000198750
- Cited by
- 208
- References
- 44
- Citations by year
- 2026: 7 · 2025: 13 · 2024: 11 · 2023: 10 · 2022: 8 · 2021: 14 · 2020: 18 · 2019: 16 · 2018: 19 · 2017: 11 · 2016: 15 · 2015: 13 · 2014: 17 · 2013: 17 · 2012: 12
- FWCI
- 6.89
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- American Diabetes Association
- Suomen Kulttuurirahasto
- National Institutes of Health
- Japan Society for the Promotion of Science (19GS0312)
- National Heart, Lung, and Blood Institute (HL 64937, R01HL064937, HL 58115, R37HL058115, R01HL058115, R01HL132550)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Genomics, phytochemicals, and oxidative stress
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
- Keywords
- nitro-fatty acids, Nrf2 activation, Keap1, antioxidant response element, post-translational modification, nitric oxide
- MeSH terms
- Kelch-Like ECH-Associated Protein 1, Animals, Chromatography, Liquid, Cysteine, Cytoskeletal Proteins, Fatty Acids, Gene Expression Regulation, Humans, Linoleic Acids, Mutation, Nitro Compounds, Oleic Acids, Protein Processing, Post-Translational, Mass Spectrometry, Transcription Factors, Signal Transduction, Ubiquitin-Protein Ligases, Intracellular Signaling Peptides and Proteins, Adaptor Proteins, Signal Transducing, NF-E2-Related Factor 2, Mice
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
