Nitrated fatty acids: Synthesis and measurement

Free Radical Biology and Medicine

Volumn 59, Issue , 2013, Pages 14-26

  Woodcock, Steven R ^a   Bonacci, Gustavo ^a   Gelhaus, Stacy L ^a   Schopfer, Francisco J ^a  

^a UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

Author keywords

Free radicals; Mass spectrometry; Nitrated fatty acid; Nitration; Organic synthesis; Quantification

Indexed keywords

CARBON 13; NITRATED FATTY ACID; NITROGEN DIOXIDE; PROTON; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID; FATTY ACID; NITRIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; FATTY ACID SYNTHESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MERCURIATION; NITRATION; PRIORITY JOURNAL; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; SELENATION;

FATTY ACIDS; NITRATES;

EID: 84876499189     PISSN: 08915849     EISSN: 18734596     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2012.11.015     Document Type: Short Survey

References (34)

1. H.A. Brown, and L.J. Marnett Introduction to lipid biochemistry, metabolism, and signaling Chem. Rev. 111 2011 5817 5820
2. A.L. Groeger, C. Cipollina, M.P. Cole, S.R. Woodcock, G. Bonacci, T.K. Rudolph, V. Rudolph, B.A. Freeman, and F.J. Schopfer Cyclooxygenase-2 generates anti-inflammatory mediators from omega-3 fatty acids Nat. Chem. Biol. 6 2010 433 441
3. F.J. Schopfer, C. Cipollina, and B.A. Freeman Formation and signaling actions of electrophilic lipids Chem. Rev. 111 2011 5997 6021
4. C.N. Serhan, S. Krishnamoorthy, A. Recchiuti, and N. Chiang Novel anti-inflammatory-pro-resolving mediators and their receptors Curr. Top. Med. Chem. 11 2011 629 647
5. F.J. Schopfer, P.R.S. Baker, and B.A. Freeman NO-dependent protein nitration: a cell signaling event or an oxidative inflammatory response? Trends Biochem. Sci. 28 2003 646 654
6. T. Sawa, M.H. Zaki, T. Okamoto, T. Akuta, Y. Tokutomi, S. Kim-Mitsuyama, H. Ihara, A. Kobayashi, M. Yamamoto, S. Fujii, H. Arimoto, and T. Akaike Protein S-guanylation by the biological signal 8-nitroguanosine 3′,5′- cyclic monophosphate Nat. Chem. Biol. 3 2007 727 735
7. P.R.S. Baker, F.J. Schopfer, S. Sweeney, and B.A. Freeman Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation Proc. Natl. Acad. Sci. USA 101 2004 11577 11582
8. C. Batthyany, F.J. Schopfer, P.R.S. Baker, R. Durán, L.M.S. Baker, Y. Huang, C. Cerveñansky, B.P. Branchaud, and B.A. Freeman Reversible post-translational modification of proteins by nitrated fatty acids in vivo J. Biol. Chem. 281 2006 20450 20463
9. V.B. O'Donnell, J.P. Eiserich, P.H. Chumley, M.J. Jablonsky, N.R. Krishna, M. Kirk, S. Barnes, V.M. Darley-Usmar, and B.A. Freeman Nitration of unsaturated fatty acids by nitric oxide-derived reactive nitrogen species peroxynitrite, nitrous acid, nitrogen dioxide, and nitronium ion Chem. Res. Toxicol. 12 1999 83 92
10. H. Yin, L. Xu, and N.A. Porter Free radical lipid peroxidation: mechanisms and analysis Chem. Rev. 111 2011 5944 5972
11. M. d'Ischia, A. Napolitano, P. Manini, and L. Panzella Secondary targets of nitrite-derived reactive nitrogen species: nitrosation/nitration pathways, antioxidant defense mechanisms and toxicological implications Chem. Res. Toxicol. 24 2011 2071 2092
12. G. Bonacci, E.K. Asciutto, S.R. Woodcock, S.R. Salvatore, B.A. Freeman, and F.J. Schopfer Gas-phase fragmentation analysis of nitro-fatty acids J. Am. Soc. Mass Spectrom 22 2011 1534 1551
13. E.J. Corey, and H. Estreicher New synthesis of conjugated nitro cyclo olefins, unusually versatile synthetic intermediates J. Am. Chem. Soc. 100 1978 6294 6295
14. T. Hayama, S. Tomoda, Y. Takeuchi, and Y. Nomura Synthesis of conjugated nitroalkenes via nitroselenenylation of alkenes Tetrahedron Lett. 23 1982 4733 4734
15. R.L. Alexander, D.J.P. Bates, M.W. Wright, S.B. King, and C.S. Morrow Modulation of nitrated lipid signaling by multidrug resistance protein 1 (MRP1): glutathione conjugation and MRP1-mediated efflux inhibit nitrolinoleic acid-induced, PPAR gamma-dependent transcription activation Biochemistry 45 2006 7889 7896
16. S.R. Woodcock, A.J.V. Marwitz, P. Bruno, and B.P. Branchaud Synthesis of nitrolipids: all four possible diastereomers of nitrooleic acids: (E)- and (Z)-, 9- and 10-nitro-octadec-9-enoic acids Org. Lett. 8 2006 3931 3934
17. M.J. Gorczynski, J.M. Huang, and S.B. King Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10-nitrooctadec-9- enoic acids Org. Lett 8 2006 2305 2308
18. E. Dunny, and P. Evans Stereocontrolled synthesis of the PPAR-gamma agonist 10-nitrolinoleic acid J. Org. Chem. 75 2010 5334 5336
19. G. Zanoni, M.V.L Bendjeddou, A. Porta, P. Bruno, and G. Vidari Improved synthesis of (E)-12-nitrooctadec-12-enoic acid, a potent PPAR gamma activator: development of a "buffer-free" enzymatic method for hydrolysis of methyl esters J. Org. Chem. 75 2010 8311 8314
20. N. Kornblum, and H.E. Ungnade 1-Nitroöctane Org. Synth. 4 1963 724
21. V. Rudolph, F.J. Schopfer, N.K.H. Khoo, T.K. Rudolph, M.P. Cole, S.R. Woodcock, G. Bonacci, A.L. Groeger, F. Golin-Bisello, C.S. Chen, P.R.S. Baker, and B.A. Freeman Nitro-fatty acid metabolome: saturation, desaturation, β-oxidation, and protein adduction J. Biol. Chem. 284 2009 1461 1473
22. Vogel, A. I.; Furniss, B. S., Eds. Vogel's Textbook of Practical Organic Chemistry. 1989.
23. D.L. Pavia, G.M. Lampman, G.S. Kriz, and R.G. Engel Brooks/Cole Laboratory Series for Organic Chemistry 2010 Brooks Cole Pacific Grove, CA
24. W.C. Still, M. Kahn, and A. Mitra Rapid chromatographic technique for preparative separations with moderate resolution J. Org. Chem. 43 1978 2923 2925
25. H. Waldmann, and H. Kunz The allyl group as mildly and selectively removable carboxy-protecting group for the synthesis of labile 0-glycopeptides Liebigs Ann. Chem 10 1983 1712 1725
26. N. Ono, and K. Maruyama Preparation of pyrroles having long alkyl chains from nitroalkenes B Chem. Soc. Jpn 61 1988 4470 4472
27. R.G. Soengas, J.C. Estevez, and R.J. Estevez Transformation of D-glucose into 1D-3-deoxy-3-hydroxymethyl-myo-inositol by stereocontrolled intramolecular Henry reaction Org. Lett. 5 2003 4457 4459
28. A.G. Myers, J.K. Barbay, and B.Y. Zhong Asymmetric synthesis of chiral organofluorine compounds: use of nonracemic fluoroiodoacetic acid as a practical electrophile and its application to the synthesis of monofluoro hydroxyethylene dipeptide isosteres within a novel series of HIV protease inhibitors J. Am. Chem. Soc 123 2001 7207 7219
29. H. Hey, and H.J. Arpe Removal of allyl groups by formic-acid catalyzed by (triphenylphosphane)palladium Angew. Chem. Int. Ed. 12 1973 928 929
30. R. Radi Nitric oxide, oxidants, and protein tyrosine nitration Proc. Natl. Acad. Sci. USA 101 2004 4003 4008
31. S.E. Farias, M. Basselin, L. Chang, K.A. Heidenreich, S.I. Rapoport, and R.C. Murphy Formation of eicosanoids, E-2/D-2 isoprostanes, and docosanoids following decapitation-induced ischemia, measured in high-energy-microwaved rat brain J. Lipid Res. 49 2008 1990 2000
32. L. Yuan, D. Zhang, M. Jemal, and A.F. Aubry Systematic evaluation of the root cause of non-linearity in liquid chromatography/tandem mass spectrometry bioanalytical assays and strategy to predict and extend the linear standard curve range Rapid Commun. Mass Spectrom 26 2012 1465 1474
33. F.F. Hsu, and J. Turk Elucidation of the double-bond position of long-chain unsaturated fatty acids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization J. Am. Soc. Mass Spectrom 19 2008 1673 1680
34. P.R.S. Baker, Y. Lin, F.J. Schopfer, S.R. Woodcock, A.L. Groeger, C. Batthyany, S. Sweeney, M.H. Long, K.E. Iles, L.M.S. Baker, B.P. Branchaud, Y.E. Chen, and B.A. Freeman Fatty acid transduction of nitric oxide signaling: multiple nitrated unsaturated fatty acid derivatives exist in human blood and urine and serve as endogenous peroxisome proliferator-activated receptor ligands J. Biol. Chem. 280 2005 42464 42475