Modulation of nitrated lipid signaling by multidrug resistance protein 1 (MRP1): Glutathione conjugation and MRP1-mediated efflux inhibit nitrolinoleic acid-induced, PPARγ-dependent transcription activation

Biochemistry

Volumn 45, Issue 25, 2006, Pages 7889-7896

  Alexander, Richard L ^a   Bates, Darcy J P ^a   Wright, Marcus W ^b   King, S Bruce ^b   Morrow, Charles S ^a  

^a WAKE FOREST SCHOOL OF MEDICINE   (United States)

^b WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; ISOMERS; LIPIDS; PROTEINS; SYNTHESIS (CHEMICAL);

ANTIPLATELET; NITROLINOLEIC ACID; REGIOISOMERS; TRANSCRIPTION;

BIOCHEMISTRY;

ADENOSINE TRIPHOSPHATE; GLUTATHIONE; LINOLEIC ACID; MULTIDRUG RESISTANCE PROTEIN 1; NITROLINOLEIC ACID; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CONJUGATION; CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; GLUTATHIONE METABOLISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MICHAEL ADDITION; NITRATION; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REPORTER GENE; STEREOCHEMISTRY; TRANSCRIPTION INITIATION; TRANSCRIPTION REGULATION;

CELL MEMBRANE; GLUTATHIONE; HUMANS; LINOLEIC ACIDS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NITRO COMPOUNDS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PPAR GAMMA; SIGNAL TRANSDUCTION; TRANS-ACTIVATION (GENETICS); TUMOR CELLS, CULTURED;

EID: 33746882132     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi0605639     Document Type: Article

References (29)

1. Chen, Y. E., Fu, M., Zhang, J., Zhu, X., Lin, Y., Akinbami, M. A., and Song, Q. (2003) Peroxisome proliferator-activated receptors and the cardiovascular system, Vitam. Horm. 66, 157-188.
2. Evans, R., Barish, G., and Wang, Y. (2004) PPARs and the complex journey to obesity. Nat. Med. 10, 355-361.
3. Kliewer, S. A., Lehmann, J., uuml, rgen, M., and Willson, T. M. (1999) Orphan Nuclear Receptors: Shifting Endocrinology into Reverse, Science 284, 757-760.
4. Fu, M. G., Zhang, J. F., Zhu, X. J., Myles, D. E., Willson, T. M., Liu, X. D., and Chen, Y. Q. E. (2001) Peroxisome proliferator-activated receptor gamma inhibits transforming growth factor β-induced connective tissue growth factor expression in human aortic smooth muscle cells by interfering with Smad3, J. Biol. Chem. 276, 45888-45894.
5. Chawla, A., Repa, J. J., Evans, R. M., and Mangelsdorf, D. J. (2001) Nuclear Receptors and Lipid Physiology: Opening the X-Files, Science 294, 1866-1870.
6. Kodera, Y., Takeyama, K.-i., Murayama, A., Suzawa, M., Masuhiro, Y., and Kato, S. (2000) Ligand type-specific Interactions of Peroxisome Proliferator-activated Receptor gamma with Transcriptional Coactivators, J. Biol. Chem. 275, 33201-33204.
7. Qi, C., Zhu, Y., and Reddy, J. K. (2000) Peroxisome proliferator- activated receptors, coactivators, and downstream targets, Cell Biochem. Biophys. 32 Spring, 187-204.
8. Lehmann, J. M., Moore, L. B., Smith-Oliver, T. A., Wilkison, W. O., Willson, T. M., and Kliewer, S. A. (1995) An Antidiabetic Thiazolidinedione Is a High Affinity Ligand for Peroxisome Proliferator-activated Receptor γ (PPARγ), J. Biol. Chem. 270, 12953-12956.
9. Forman, B. M., Tontonoz, P., Chen, J., Brun, R. P., Spiegelman, B. M., and Evans, R. M. (1995) 15-Deoxy-delta 12, 14-prostaglandin J2 is a ligand for the adipocyte determination factor PPAR gamma, Cell 83, 803-812.
10. Kliewer, S. A., Lenhard, J. M., Willson, T. M., Patel, I., Morris, D. C., and Lehmann, J. M. (1995) A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation, Cell 83, 813-819.
11. McIntyre, T. M., Pontsler, A. V., Silva, A. R., St. Hilaire, A., Xu, Y., Hinshaw, J. C., Zimmerman, G. A., Hama, K., Aoki, J., Arai, H., and Prestwich, G. D. (2003) From the Cover: Identification of an intracellular receptor for lysophosphatidic acid (LPA): LPA is a transcellular PPARgamma agonist, Proc. Natl. Acad. Sci. U.S.A. 100, 131-136.
12. Nagy, L., Tontonoz, P., Alvarez, J. G., Chen, H., and Evans, R. M. (1998) Oxidized LDL regulates macrophage gene expression through ligand activation of PPARgamma, Cell 93, 229-240.
13. Coles, B., Bloodsworth, A., Clark, S. R., Lewis, M. J., Cross, A. R., Freeman, B. A., and O'Donnell, V. B. (2002) Nitrolinoleate Inhibits Superoxide Generation, Degranulation, and Integrin Expression by Human Neutrophils: Novel Antiinflammatory Properties of Nitric Oxide-Derived Reactive Species in Vascular Cells, Circ. Res. 91, 375-381.
14. Coles, B., Bloodsworth, A., Eiserich, J. P., Coffey, M. J., McLoughlin, R. M., Giddings, J. C., Lewis, M. J., Haslam, R. J., Freeman, B. A., and O'Donnell, V. B. (2002) Nitrolinoleate Inhibits Platelet Activation by Attenuating Calcium Mobilization and Inducing Phosphorylation of Vasodilator-stimulated Phosphoprotein through Elevation of cAMP, J. Biol. Chem. 277, 5832-5840.
15. Lim, D. G., Sweeney, S., Bloodsworth, A., White, C. R., Chumley, P. H., Krishna, N. R., Schopfer, F., O'Donnell, V. B., Eiserich, J. P., and Freeman, B. A. (2002) Nitrolinoleate, a nitric oxide-derived mediator of cell function: Synthesis, characterization, and vasomotor activity, Proc. Natl. Acad. Sci. U.S.A. 99, 15941-15946.
16. Lima, E. S., Bonini, M. G., Augusto, O., Barbeiro, H. V., Souza, H. P., and Abdalla, D. S. (2005) Nitrated lipids decompose to nitric oxide and lipid radicals and cause vasorelaxation, Free Radical Biol. Med. 39, 532-539.
17. 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., and Freeman, B. A. (2005) 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, 42464-42475.
18. Schopfer, F. J., Lin, Y., Baker, P. R. S., Cui, T., Garcia-Barrio, M., Zhang, J., Chen, K., Chen, Y. E., and Freeman, B. A. (2005) Nitrolinoleic acid: An endogenous peroxisome proliferator-activated receptor γ ligand, Proc. Natl. Acad. Sci. U.S.A. 102, 2340-2345.
19. Baker, P. R. S., Schopfer, F. J., Sweeney, S., and Freeman, B. A. (2004) Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation, Proc. Natl. Acad. Sci. U.S.A. 101, 11577-11582.
20. Paumi, C., Smitherman, P., Townsend, A., and Morrow, C. (2004) Glutathione S-transferases (GSTs) inhibit transcriptional activation by the peroxisomal proliferator-activated receptor gamma (PPAR gamma) ligand, 15-deoxy-Delta(12,14)prostaglandin 3(2) (15-d-PGJ(2)), Biochemistry 43, 2345-2352.
21. Paumi, C. M., Wright, M., Townsend, A. J., and Morrow, C. S. (2003) Multidrug Resistance Protein (MRP) 1 and MRP3 Attenuate Cytotoxic and Transactivating Effects of the Cyclopentenone Prostaglandin, 15-Deoxy-Delta(12,14)Prostaglandin J(2) in MCF7 Breast Cancer Cells, Biochemistry 42, 5429-5437.
22. Smitherman, P. K., Townsend, A. J., Kute, T. E., and Morrow, C. S. (2004) Role of Multidrug Resistance Protein 2 (MRP2, ABCC2) in Alkylating Agent Detoxification: MRP2 Potentiates Glutathione S-Transferase A1-1-Mediated Resistance to Chlorambucil Cytotoxicity, J. Pharmacol Exp. Ther. 308, 260-267.
23. Paumi, C. M., Ledford, B. G., Smitherman, P. K., Townsend, A. J., and Morrow, C. S. (2001) Role of Multidrug Resistance Protein 1 (MRP1) and Glutathione S-Transferase A1-1 in Alkylating Agent Resistance. Kinetics of glutathione conjugate formation and efflux govern differential cellular sensitivity to chlorambucil versus melphalan toxicity, J. Biol. Chem. 276, 7952-7956.
24. Liu, J. M., Fujii, H., Green, S. W., Komatsu, N., Young, N., and Shimada, T. (1991) Indiscriminate activity from the B19 parvovirus P6 promoter in nonpermissive cells, Virology 182, 361-364.
25. Gurnell, M., Wentworth, J. M., Agostini, M., Adams, M., Collingwood, T. N., Provenzano, C., Browne, P. O., Rajanayagam, O., Burris, T. P., Schwabe, J. W., Lazar, M. A., and Chatterjee, V. K. K. (2000) A Dominant-negative Peroxisome Proliferator-activated Receptor gamma (PPARgamma) Mutant Is a Constitutive Repressor and Inhibits PPARgamma -mediated Adipogenesis, J. Biol. Chem. 275, 5754-5759.
26. Leier, I., Jedlitschky, G., Buchholz, U., Cole, S. P., Deeley, R. G., and Keppler, D. (1994) The MRP gene encodes an ATP-dependent export pump for leukotriene C4 and structurally related conjugates, J. Biol. Chem. 269, 27807-27810.
27. Loe, D. W., Almquist, K. C., Deeley, R. G., and Cole, S. P. C. (1996) Multidrug resistance protein (MRP)-mediated transport of leukotriene C4 and chemotherapeutic agents in membrane vesicles: demonstration of glutathione-dependent vincristine transport, J. Biol. Chem. 271, 9675-9682.
28. Wright, M. M., Schopfer, F. J., Baker, P. R. S., Vidyasagar, V., Powell, P., Chumley, P., Iles, K. E., Freeman, B. A., and Agarwal, A. (2006) Fatty acid transduction of nitric oxide signaling: Nitrolinoleic acid potently activates endothelial heme oxygenase 1 expression, Proc. Natl. Acad. Sci. U.S.A. 103, 4299-4304.
29. O'Donnell, V. B., and Freeman, B. A. (2001) Interactions Between Nitric Oxide and Lipid Oxidation Pathways: Implications for Vascular Disease, Circ. Res. 88, 12-21.