Activation of Peroxisome Proliferator-Activated Receptor γ (PPARγ) by nitroalkene fatty acids: Importance of nitration position and degree of unsaturation

Journal of Medicinal Chemistry

Volumn 52, Issue 15, 2009, Pages 4631-4639

  Gorczynski, Michael J ^b   Smitherman, Pamela K ^a   Akiyama, Taro E ^c   Wood, Harold B ^c   Berger, Joel P ^c   King, S Bruce ^b   Morrow, Charles S ^a  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

^b WAKE FOREST UNIVERSITY   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBON; FATTY ACID; LINOLEIC ACID; NITRO DERIVATIVE; OLEIC ACID; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; ROSIGLITAZONE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; DOSE RESPONSE; FATTY ACID ANALYSIS; ISOMER; LIGAND BINDING; NITRATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ALKENES; CELL LINE, TUMOR; FATTY ACIDS; HUMANS; PPAR GAMMA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 68549140147     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900326c     Document Type: Article

References (27)

1. 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.; Branchaud, B. P.; Chen, Y. E.; Freeman, B. A. 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. 2005, 280, 42464-42475.
2. Cui, T.; Schopfer, F. J.; Zhang, J.; Chen, K.; Ichikawa, T.; Baker, P. R. S.; Batthyany, C.; Chacko, B. K.; Feng, X.; Patel, R. P.; Agarwal, A.; Freeman, B. A.; Chen, Y. E. Nitrated fatty acids: endogenous anti-inflammatory signaling mediators. J. Biol. Chem. 2006, 281, 35686-35698.
3. Schopfer, F. J.; Lin, Y.; Baker, P. R. S.; Cui, T.; Garcia-Barrio, M.; Zhang, J.; Chen, K.; Chen, Y. E.; Freeman, B. A. Nitrolinoleic acid: an endogenous peroxisome proliferator-activated receptor {gamma} ligand. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 2340-2345.
4. Villacorta, L.; Zhang, J.; Garcia-Barrio, M. T.; Chen, X.-l.; Freeman, B. A.; Chen, Y. E.; Cui, T. Nitro-linoleic acid inhibits vascular smooth muscle cell proliferation via the Keap1/Nrf2 signaling pathway. Am. J. Physiol.: Heart Circ. Physiol. 2007, 293, H770-H776.
5. Freeman, B. A.; Baker, P. R. S.; Schopfer, F. J.; Woodcock, S. R.; Napolitano, A.; d'Ischia, M. Nitro-fatty acid formation and signaling. J. Biol. Chem. 2008, 283, 15515-15519.
6. Lima, E. S.; Bonini, M. G.; Augusto, O.; Barbeiro, H. V.; Souza, H. P.; Abdalla, D. S. Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation. Free Radical Biol. Med. 2005, 39, 532-539.
7. Alexander, R.; Wright, M.; Gorczynski, M.; Smitherman, P.; Akiyama, T.; Wood, H.; Berger, J.; King, S.; Morrow, C. Differential potencies of naturally occurring regioisomers of nitrolinoleic acid in PPARgamma activation. Biochemistry 2009, 48, 492-498.
8. Baker, P. R. S.; Schopfer, F. J.; Sweeney, S.; Freeman, B. A. Red cell membrane and plasma linoleic acid nitration products: synthesis, clinical identification, and quantitation. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11577-11582.
9. Li, Y.; Zhang, J.; Schopfer, F. J.; Martynowski, D.; Garcia-Barrio, M. T.; Kovach, A.; Suino-Powell, K.; Baker, P. R.; Freeman, B. A.; Chen, Y. E.; Xu, H. E. Molecular recognition of nitrated fatty acids by PPAR gamma. Nat. Struct. Mol. Biol. 2008, 15, 865-867.
10. Gorczynski, M.; Huang, J.; King, S. Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10- nitrooctadec-9-enoic acids. Org. Lett. 2006, 8, 2305-2308.
11. Denmark, S. E.; Kesler, B. S.; Moon, Y. C. Intermolecular and intramolecular [4 + 2] cycloadditions of nitroalkenes with olefins. 2-Nitrostyrenes. J. Org. Chem. 1992, 57, 4912-4924.
12. Denmark, S. E.; Gomez, L. Tandem double intramolecular [4+2]/[3+2] cycloadditions of nitroalkenes. The fused/bridged mode. J. Org. Chem. 2003, 68, 8015-8024.
13. Lucet, D.; Heyse, P.; Gissot, A.; Le Gall, T.; Mioskowski, C. Synthesis of the diastereomers of dethiobiotin using the conjugate addition of 4-phenyloxazolidin-2-one to a nitroalkene. Eur. J. Org. Chem. 2000, 3575-3579.
14. Wollenberg, R. H.; Miller, S. J. Nitroalkane synthesis. Convenient method for aldehyde reductive nitromethylation. Tetrahedron Lett. 1978, 3219-3222.
15. Alexander, R. L.; Bates, D. J.; Wright, M. W.; King, S. B.; Morrow, C. S. Modulation of nitrated lipid signaling by multidrug resistance protein 1 (MRP1): glutathione conjugation and MRP1-mediated efflux inhibit nitrolinoleic acid-induced, PPARgamma-dependent transcription activation. Biochemistry 2006, 45, 7889-7896.
16. Itoh, T.; Fairall, L.; Amin, K.; Inaba, Y.; Szanto, A.; Balint, B. L.; Nagy, L.; Yamamoto, K.; Schwabe, J. W. Structural basis for the activation of PPARgamma by oxidized fatty acids. Nat. Struct. Mol. Biol. 2008, 15, 924-931.
17. Chen, C.; Kong, A. Dietary chemopreventive compounds and ARE/EpRE signaling. Free Radical Biol. Med. 2004, 36, 1505-1516.
18. Xiao, D.; Choi, S.; Lee, Y.; Singh, S. Role of mitogen-activated protein kinases in phenethyl isothiocyanate-induced apoptosis in human prostate cancer cells. Mol. Carcinog. 2005, 43, 130-140.
19. Zhang, H.; Liu, H.; Iles, K. E.; Liu, R.-M.; Postlethwait, E. M.; Laperche, Y.; Forman, H. J. 4-Hydroxynonenal induces rat {gamma}-glutamyl transpeptidase through mitogen-activated protein kinase-mediated electrophile response element/nuclear factor erythroid 2-related factor 2 signaling. Am. J. Respir. Cell Mol. Biol. 2006, 34, 174-181.
20. Zhang, Y.; Gordon, G. B. A strategy for cancer prevention: stimulation of the Nrf2-ARE signaling pathway. Mol. Cancer Ther. 2004, 3, 885-893.
21. Enholm, E.; Joshi, A.; Wright, D. Photocurable hard and porous biomaterials from ROMP precursors cross-linked with diyl radicals. Bioorg. Med. Chem. Lett. 2005, 15, 5262-5265.
22. Ravi, S.; Padmanabhan, D.; Mamdapur, V. R. Macrocyclic musk compounds: synthetic approaches to key intermediates for exaltolide, exaltone, and dilactones. J. Indian Inst. Sci. 2001, 81, 299-312.
23. Elbrecht, A.; Chen, Y.; Adams, A.; Berger, J.; Griffin, P.; Klatt, T.; Zhang, B.; Menke, J.; Zhou, G.; Smith, R. G.; Moller, D. E. L-764406 is a partial agonist of human peroxisome proliferator-activated receptor gamma . The role of Cys313 in ligand binding. J. Biol. Chem. 1999, 274, 7913-7922.
24. Berger, J. P.; Petro, A. E.; Macnaul, K. L.; Kelly, L. J.; Zhang, B. B.; Richards, K.; Elbrecht, A.; Johnson, B. A.; Zhou, G.; Doebber, T. W.; Biswas, C.; Parikh, M.; Sharma, N.; Tanen, M. R.; Thompson, G. M.; Ventre, J.; Adams, A. D.; Mosley, R.; Surwit, R. S.; Moller, D. E. Distinct properties and advantages of a novel peroxisome proliferator-activated protein {gamma} selective modulator. Mol. Endocrinol. 2003, 17, 662-676.
25. Forman, B. M.; Tontonoz, P.; Chen, J.; Brun, R. P.; Spiegelman, B. M.; Evans, R. M. 15-Deoxy-delta 12, 14-prostaglandin J2 is a ligand for the adipocyte determination factor PPAR gamma. Cell 1995, 83, 803-812.
26. Sibhatu, M. B.; Smitherman, P. K.; Townsend, A. J.; Morrow, C. S. Expression of MRP1 and GSTP1-1 modulate the acute cellular response to treatment with the chemopreventive isothiocyanate, sulforaphane. Carcinogenesis 2008, 29, 807-815.
27. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 1990, 82, 1107-1112.