Modification of cysteine residues by cyclopentenone prostaglandins: Interplay with redox regulation of protein function

Mass Spectrometry Reviews

Volumn 33, Issue 2, 2014, Pages 110-125

  Oeste, Clara L ^a   Pérez Sala, Dolores ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

Author keywords

cyclopentenone prostaglandins; electrophilic lipids; palmitoylation; Ras proteins; redox regulation

Indexed keywords

ANTI-OXIDANT RESPONSE; COVALENT MODIFICATIONS; CYCLOPENTENONES; ELECTROPHILIC LIPIDS; ELECTROPHILIC NATURES; PALMITOYLATION; REDOX REGULATION; SIGNALING MECHANISMS;

ADDITION REACTIONS; AMINO ACIDS; CELL PROLIFERATION; CELL SIGNALING; LIPIDS; MOLECULAR BIOLOGY; PATHOLOGY;

PROTEINS;

CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; CYSTEINE; PROSTAGLANDIN; PROTEIN; RAS PROTEIN;

ANIMAL; CHEMISTRY; CYCLOPENTENONE PROSTAGLANDINS; ELECTROPHILIC LIPIDS; HUMAN; LIPOYLATION; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; OXIDATION REDUCTION REACTION; PALMITOYLATION; PROTEOMICS; REDOX REGULATION; REVIEW; SIGNAL TRANSDUCTION;

CYCLOPENTENONE PROSTAGLANDINS; ELECTROPHILIC LIPIDS; PALMITOYLATION; RAS PROTEINS; REDOX REGULATION;

ANIMALS; CYCLOPENTANES; CYSTEINE; HUMANS; LIPOYLATION; MASS SPECTROMETRY; OXIDATION-REDUCTION; PROSTAGLANDINS; PROTEINS; PROTEOMICS; RAS PROTEINS; SIGNAL TRANSDUCTION;

EID: 84893766780     PISSN: 02777037     EISSN: 10982787     Source Type: Journal    
DOI: 10.1002/mas.21383     Document Type: Review

References (131)

1. Aldini G, Carini M, Vistoli G, Shibata T, Kusano Y, Gamberoni L, Dalle-Donne I, Milzani A, Uchida K,. 2007. Identification of actin as a 15-Deoxy-Delta(12,14)-prostaglandin J(2) target in neuroblastoma cells: Mass spectrometric, computational, and functional approaches to investigate the effect on cytoskeletal derangement. Biochemistry 46: 2707-2718. (Pubitemid 46417911)
2. Amici C, Sistonen L, Santoro MG, Morimoto RI,. 1992. Antiproliferative prostaglandins activate heat shock transcription factor. Proc Natl Acad Sci USA 89: 6227-6231.
3. Atsmon J, Sweetman BJ, Baertschi SW, Harris TM, Jackson L, Roberts I,. 1990. Formation of thiol conjugates of 9-deoxy-D9,D12(E)-prostaglandin D2 and D12(E)-prostaglandin D2. Biochemistry 29: 3760-3765.
4. Batthyany C, Schopfer FJ, Baker PR, Duran R, Baker LM, Huang Y, Cervenansky C, Branchaud BP, Freeman BA,. 2006. Reversible post-translational modification of proteins by nitrated fatty acids in vivo. J Biol Chem 281: 20450-20463. (Pubitemid 44065818)
5. Bickley JF, Ciucci A, Evans P, Roberts SM, Ross N, Santoro GM,. 2004. Reactions of some cyclopentenones with selected cysteine derivatives and biological activities of the product thioethers. Bioorg Med Chem 12: 3221-3227. (Pubitemid 38680711)
6. Burgoyne JR, Haeussler DJ, Kumar V, Ji Y, Pimental DR, Zee RS, Costello CE, Lin C, McComb ME, Cohen RA, Bachschmid MM,. 2012. Oxidation of HRas cysteine thiols by metabolic stress prevents palmitoylation in vivo and contributes to endothelial cell apoptosis. FASEB J 26: 832-841.
7. Byrns MC, Duan L, Lee SH, Blair IA, Penning TM,. 2010. Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer. J Steroid Biochem Mol Biol 118: 177-187.
8. Ceaser EK, Moellering DR, Shiva S, Ramachandran A, Landar A, Venkartraman A, Crawford J, Patel R, Dickinson DA, Ulasova E, Ji S, Darley-Usmar VM,. 2004. Mechanisms of signal transduction mediated by oxidized lipids: The role of the electrophile-responsive proteome. Biochem Soc Trans 32: 151-155. (Pubitemid 38283038)
9. 2 inhibition of NF-κB DNA binding through covalent modification of the p50 subunit. J Biol Chem 276: 35530-35536.
10. Charles RL, Burgoyne JR, Mayr M, Weldon SM, Hubner N, Dong H, Morisseau C, Hammock BD, Landar A, Eaton P,. 2011. Redox regulation of soluble epoxide hydrolase by 15-deoxy-delta-prostaglandin J2 controls coronary hypoxic vasodilation. Circ Res 108: 324-334.
11. Chatterjee PK, Patel NS, Cuzzocrea S, Brown PA, Stewart KN, Mota-Filipe H, Britti D, Eberhardt W, Pfeilschifter J, Thiemermann C,. 2004. The cyclopentenone prostaglandin 15-deoxy-Delta(12,14)-prostaglandin J(2) ameliorates ischemic acute renal failure. Cardiovasc Res 61: 630-643. (Pubitemid 38210168)
12. Chavez J, Chung WG, Miranda CL, Singhal M, Stevens JF, Maier CS,. 2010. Site-specific protein adducts of 4-hydroxy-2(E)-nonenal in human THP-1 monocytic cells: Protein carbonylation is diminished by ascorbic acid. Chem Res Toxicol 23: 37-47.
13. Chavez JD, Wu J, Bisson W, Maier CS,. 2011. Site-specific proteomic analysis of lipoxidation adducts in cardiac mitochondria reveals chemical diversity of 2-alkenal adduction. J Proteomics 74: 2417-2429.
14. Clavreul N, Adachi T, Pimental DR, Ido Y, Schoneich C, Cohen RA,. 2006a. S-glutathiolation by peroxynitrite of p21ras at cysteine-118 mediates its direct activation and downstream signaling in endothelial cells. FASEB J 20: 518-520. (Pubitemid 46671235)
15. Clavreul N, Bachschmid MM, Hou X, Shi C, Idrizovic A, Ido Y, Pimentel D, Cohen RA,. 2006b. S-glutathiolation of p21ras by peroxynitrite mediates endothelial insulin resistance caused by oxidized low-density lipoprotein. Arterioscler Thromb Vasc Biol 26: 2454-2461. (Pubitemid 44607465)
16. Cocca C, Dorado J, Calvo E, Lopez JA, Santos A, Perez-Castillo A,. 2009. 15-Deoxi-Delta(12,14)-prostaglandin J2 is a tubulin-binding agent that destabilizes microtubules and induces mitotic arrest. Biochem Pharmacol 78: 1330-1339.
17. Combs CK, Johnson DE, Karlo JC, Cannady SB, Landreth GE,. 2000. Inflammatory mechanisms in Alzheimer's disease: Inhibition of beta-amyloid-stimulated proinflammatory responses and neurotoxicity by PPARgamma agonists. J Neurosci 20: 558-567. (Pubitemid 30225558)
18. Cummins TD, Higdon AN, Kramer PA, Chacko BK, Riggs DW, Salabei JK, Dell'italia LJ, Zhang J, Darley-Usmar VM, Hill BG,. 2013. Utilization of fluorescent probes for the quantification and identification of subcellular proteomes and biological processes regulated by lipid peroxidation products. Free Radic Biol Med 59: 56-68.
19. Cuzzocrea S, Ianaro A, Wayman NS, Mazzon E, Pisano B, Dugo L, Serraino I, Di Paola R, Chatterjee PK, Di Rosa M, Caputi AP, Thiemermann C,. 2003. The cyclopentenone prostaglandin 15-deoxy-delta(12,14)-PGJ2 attenuates the development of colon injury caused by dinitrobenzene sulphonic acid in the rat. Br J Pharmacol 138: 678-688. (Pubitemid 36315316)
20. Del Corso A, Dal Monte M, Vilardo PG, Cecconi I, Moschini R, Banditelli S, Cappiello M, Tsai L, Mura U,. 1998. Site-specific inactivation of aldose reductase by 4-hydroxynonenal. Arch Biochem Biophys 350: 245-248. (Pubitemid 28368650)
21. Diab A, Deng C, Smith JD, Hussain RZ, Phanavanh B, Lovett-Racke AE, Drew PD, Racke MK,. 2002. Peroxisome proliferator-activated receptor-gamma agonist 15-deoxy-Delta(12,14)-prostaglandin J(2) ameliorates experimental autoimmune encephalomyelitis. J Immunol 168: 2508-2515. (Pubitemid 34171857)
22. Diers AR, Higdon AN, Ricart KC, Johnson MS, Agarwal A, Kalyanaraman B, Landar A, Darley-Usmar VM,. 2010. Mitochondrial targeting of the electrophilic lipid 15-deoxy-Delta12,14-Prostaglandin J2 increases apoptotic efficacy via redox cell signaling mechanisms. Biochem J 426: 31-41.
23. Díez-Dacal B, Pérez-Sala D,. 2010. Anti-inflammatory prostanoids: Focus on the interactions between electrophile signalling and resolution of inflammation. The Scientific World Journal 10: 655-675.
24. Díez-Dacal B, Pérez-Sala D,. 2012. A-class prostaglandins: Early findings and new perspectives for overcoming tumor chemoresistance. Cancer Lett 320: 150-157.
25. Díez-Dacal B, Gayarre J, Gharbi S, Timms JF, Coderch C, Gago F, Pérez-Sala D,. 2011. Identification of aldo-keto reductase AKR1B10 as a selective target for modification and inhibition by PGA1: implications for anti-tumoral activity. Cancer Res 71: 4161-4171.
26. Dugo L, Collin M, Cuzzocrea S, Thiemermann C,. 2004. 15d-prostaglandin J2 reduces multiple organ failure caused by wall-fragment of Gram-positive and Gram-negative bacteria. Eur J Pharmacol 498: 295-301. (Pubitemid 39208092)
27. Funk CD,. 2001. Prostaglandins and leukotrienes: Advances in eicosanoid biology. Science 294: 1871-1875. (Pubitemid 33101574)
28. Gao L, Zackert WE, Hasford JJ, Danekis ME, Milne GL, Remmert C, Reese J, Yin H, Tai HH, Dey SK, Porter NA, Morrow JD,. 2003. Formation of prostaglandins E2 and D2 via the isoprostane pathway: A mechanism for the generation of bioactive prostaglandins independent of cyclooxygenase. J Biol Chem 278: 28479-28489. (Pubitemid 36935750)
29. 1 allows assessment of PPAR-independent effects and identification of novel cellular targets for covalent modification. Chem Biol Interact 183: 212-221.
30. Garzõn B, Oeste CL, Díez-Dacal B, Pérez-Sala D,. 2011. Proteomic studies on protein modification by cyclopentenone prostaglandins: Expanding our view on electrophile actions. J Proteomics 74: 2243-2263.
31. 2: Role of glutathione. FEBS Lett 579: 5803-5808. (Pubitemid 41455667)
32. Gazi L, Gyles S, Rose J, Lees S, Allan C, Xue L, Jassal R, Speight G, Gamble V, Pettipher R,. 2005. Delta12-prostaglandin D2 is a potent and selective CRTH2 receptor agonist and causes activation of human eosinophils and Th2 lymphocytes. Prostaglandins Other Lipid Mediat 75: 153-167. (Pubitemid 40248385)
33. 1: Focus on vimentin. J Mass Spectrom 42: 1474-1484. (Pubitemid 350113465)
34. Gilroy DW, Colville-Nash PR, Willis D, Chivers J, Paul-Clark MJ, Willoughby DA,. 1999. Inducible cyclooxygenase may have anti-inflammatory properties. Nat Med 5: 698-701. (Pubitemid 29289435)
35. Gilroy DW, Lawrence T, Perretti M, Rossi AG,. 2004. Inflammatory resolution: New opportunities for drug discovery. Nat Rev Drug Discov 3: 401-416. (Pubitemid 38618123)
36. Hancock JF, Magee AI, Childs JE, Marshall CJ,. 1989. All ras proteins are polyisoprenylated but only some are palmitoylated. Cell 57: 1167-1177. (Pubitemid 19169813)
37. Hayes JD, McMahon M, Chowdhry S, Dinkova-Kostova AT,. 2010. Cancer chemoprevention mechanisms mediated through the Keap1-Nrf2 pathway. Antioxid Redox Signal 13: 1713-1748.
38. Heo J, Prutzman KC, Mocanu V, Campbell SL,. 2005. Mechanism of free radical nitric oxide-mediated Ras guanine nucleotide dissociation. J Mol Biol 346: 1423-1440. (Pubitemid 40248839)
39. Heo J, Raines KW, Mocanu V, Campbell SL,. 2006. Redox regulation of RhoA. Biochemistry 45: 14481-14489. (Pubitemid 44865203)
40. Hilliard M, Frohnert C, Spillner C, Marcone S, Nath A, Lampe T, Fitzgerald D, Kehlenbach RH,. 2010. The anti-inflammatory prostaglandin 15-Deoxy-{Delta}12,14 PGJ2 inhibits CRM1-dependent nuclear protein export. J Biol Chem 285: 22202-22210.
41. Homem de Bittencourt PI Jr, Lagranha DJ, Maslinkiewicz A, Senna SM, Tavares AM, Baldissera LP, Janner DR, Peralta JS, Bock PM, Gutierrez LL, Scola G, Heck TG, Krause MS, Cruz LA, Abdalla DS, Lagranha CJ, Lima T, Curi R,. 2007. LipoCardium: Endothelium-directed cyclopentenone prostaglandin-based liposome formulation that completely reverses atherosclerotic lesions. Atherosclerosis 193: 245-258. (Pubitemid 47064399)
42. Ianaro A, Ialenti A, Maffia P, Di Meglio P, Di Rosa M, Santoro MG,. 2003. Anti-inflammatory activity of 15-deoxy-delta12,14-PGJ2 and 2-cyclopenten-1-one: Role of the heat shock response. Mol Pharmacol 64: 85-93. (Pubitemid 36759821)
43. Ishii T, Uchida K,. 2004. Induction of reversible cysteine-targeted protein oxidation by an endogenous electrophile 15-deoxy-delta(12,14)- prostaglandin J2. Chem Res Toxicol 17: 1313-1322. (Pubitemid 39391208)
44. Ishii T, Sakurai T, Usami H, Uchida K,. 2005. Oxidative modification of proteasome: Identification of an oxidation-sensitive subunit in 26 S proteasome. Biochemistry 44: 13893-13901. (Pubitemid 41507469)
45. Itoh K, Mochizuki M, Ishii Y, Ishii T, Shibata T, Kawamoto Y, Kelly V, Sekizawa K, Uchida K, Yamamoto M,. 2004. Transcription factor Nrf2 regulates inflammation by mediating the effect of 15-Deoxy-Delta(12,14)-prostaglandin J(2). Mol Cell Biol 24: 36-45. (Pubitemid 38010033)
46. Kalantari P, Narayan V, Henderson AJ, Prabhu KS,. 2009. 15-Deoxy-Delta12,14-prostaglandin J2 inhibits HIV-1 transactivating protein, Tat, through covalent modification. FASEB J 23: 2366-2373.
47. Kamagata C, Tsuji N, Moriai M, Kobayashi D, Watanabe N,. 2007. 15-Deoxy-Delta(12,14)-prostaglandin J2 inhibits G2-M phase progression in human breast cancer cells via the down-regulation of cyclin B1 and survivin expression. Breast Cancer Res Treat 102: 263-273. (Pubitemid 46474841)
48. Kansanen E, Kivela AM, Levonen AL,. 2009. Regulation of Nrf2-dependent gene expression by 15-deoxy-Delta12,14-prostaglandin J2. Free Radic Biol Med 47: 1310-1317.
49. Kato T, Fukushima M, Kurozumi S, Noyori R,. 1986. Antitumor activity of delta 7-prostaglandin A1 and delta 12-prostaglandin J2 in vitro and in vivo. Cancer Res 46: 3538-3542. (Pubitemid 16096904)
50. Kim EH, Surh YJ,. 2006. 15-Deoxy-Delta12,14-prostaglandin J2 as a potential endogenous regulator of redox-sensitive transcription factors. Biochem Pharmacol 72: 1516-1528.
51. Kim EH, Surh YJ,. 2008. The role of 15-deoxy-delta(12,14)-prostaglandin J(2), an endogenous ligand of peroxisome proliferator-activated receptor gamma, in tumor angiogenesis. Biochem Pharmacol 76: 1544-1553.
52. Kim IK, Lee JH, Sohn HW, Kim HS, Kim SH,. 1993. Prostaglandin A2 and delta 12-prostaglandin J2 induce apoptosis in L1210 cells. FEBS Lett 321: 209-214.
53. Kim HJ, Kim JY, Meng Z, Wang LH, Liu F, Conrads TP, Burke TR, Veenstra TD, Farrar WL,. 2007. 15-Deoxy-Delta12,14-prostaglandin J2 inhibits transcriptional activity of estrogen receptor-alpha via covalent modification of DNA-binding domain. Cancer Res 67: 2595-2602. (Pubitemid 46548945)
54. Kim DH, Kim EH, Na HK, Sun Y, Surh YJ,. 2010. 15-Deoxy-Delta(12,14)- prostaglandin J(2) stabilizes, but functionally inactivates p53 by binding to the cysteine 277 residue. Oncogene 29: 2560-2576.
55. Kobayashi M, Li L, Iwamoto N, Nakajima-Takagi Y, Kaneko H, Nakayama Y, Eguchi M, Wada Y, Kumagai Y, Yamamoto M,. 2009. The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds. Mol Cell Biol 29: 493-502.
56. Koenitzer JR, Freeman BA,. 2010. Redox signaling in inflammation: Interactions of endogenous electrophiles and mitochondria in cardiovascular disease. Ann NY Acad Sci 1203: 45-52.
57. Kondo M, Oya-Ito T, Kumagai T, Osawa T, Uchida K,. 2001. Cyclopentenone prostaglandins as potential inducers of intracellular oxidative stress. J Biol Chem 276: 12076-12083.
58. Kondo M, Shibata T, Kumagai T, Osawa T, Shibata N, Kobayashi M, Sasaki S, Iwata M, Noguchi N, Uchida K,. 2002. 15-Deoxy-Delta 12,14-prostaglandin J2: The endogenous electrophile that induces neuronal apoptosis. Proc Natl Acad Sci USA 99: 7367-7372. (Pubitemid 34568697)
59. Landar A, Oh JY, Giles NM, Isom A, Kirk M, Barnes S, Darley-Usmar VM,. 2006a. A sensitive method for the quantitative measurement of protein thiol modification in response to oxidative stress. Free Radic Biol Med 40: 459-468. (Pubitemid 43139681)
60. Landar A, Shiva S, Levonen AL, Oh JY, Zaragoza C, Johnson MS, Darley-Usmar VM,. 2006b. Induction of the permeability transition and cytochrome c release by 15-deoxy prostaglandin J2 in mitochondria. Biochem J 394: 185-195. (Pubitemid 43259668)
61. Landar A, Zmijewski JW, Dickinson DA, Legoffe C, Johnson M, Milne G, Zanoni G, Vidari G, Morrow J, Darley-Usmar VM,. 2006c. The interaction of electrophilic lipid oxidation products with mitochondria in endothelial cells and the formation of reactive oxygen species. Am J Physiol Heart Circ Physiol 290: H1777-H1787.
62. Lander HM, Hajjar DP, Hempstead BL, Mirza UA, Chait BT, Campbell S, Quilliam LA,. 1997. A molecular redox switch on p21ras. Structural basis for the nitric oxide-p21ras interaction. J Biol Chem 272: 4323-4326. (Pubitemid 27078505)
63. Levin G, Duffin KL, Obukowicz MG, Hummert SL, Fujiwara H, Needleman P, Raz A,. 2002. Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: Implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem J 365: 489-496. (Pubitemid 36135320)
64. Levonen AL, Dickinson DA, Moellering DR, Mulcahy RT, Forman HJ, Darley-Usmar VM,. 2001. Biphasic effects of 15-deoxy-delta(12,14)-prostaglandin J(2) on glutathione induction and apoptosis in human endothelial cells. Arterioscler Thromb Vasc Biol 21: 1846-1851. (Pubitemid 34219791)
65. Levonen AL, Landar A, Ramachandran A, Ceaser EK, Dickinson DA, Zanoni G, Morrow JD, Darley-Usmar VM,. 2004. Cellular mechanisms of redox cell signaling: The role of cysteine modification in controlling antioxidant defenses in response to electrophilic lipid oxidation products. Biochem J 378: 373-382. (Pubitemid 38367228)
66. Lin YC, Huang GD, Hsieh CW, Wung BS,. 2012. The glutathionylation of p65 modulates NF-kappaB activity in 15-deoxy-Delta(1)(2),(1)(4)-prostaglandin J(2)-treated endothelial cells. Free Radic Biol Med 52: 1844-1853.
67. Liu SQ, Bhatnagar A, Ansari NH, Srivastava SK,. 1993. Identification of the reactive cysteine residue in human placenta aldose reductase. Biochim Biophys Acta 1164: 268-272. (Pubitemid 23234577)
68. Liu H, Li W, Ahmad M, Miller TM, Rose ME, Poloyac SM, Uechi G, Balasubramani M, Hickey RW, Graham SH,. 2011. Modification of ubiquitin-C-terminal hydrolase-L1 by cyclopentenone prostaglandins exacerbates hypoxic injury. Neurobiol Dis 41: 318-328.
69. Mallis RJ, Buss JE, Thomas JA,. 2001. Oxidative modification of H-ras: S-thiolation and S-nitrosylation of reactive cysteines. Biochem J 355: 145-153. (Pubitemid 32304245)
70. Martinez B, Perez-Castillo A, Santos A,. 2005. The mitochondrial respiratory complex I is a target for 15-deoxy-delta12,14-prostaglandin J2 action. J Lipid Res 46: 736-743. (Pubitemid 43073283)
71. 2 exerts pro- and anti-inflammatory effects in mesangial cells in a concentration-dependent manner. Inflamm Allergy Drug Targets 11: 58-65.
72. 2 in a model of skin carcinogenesis. Carcinogenesis 27: 328-336. (Pubitemid 43159887)
73. Monneret G, Li H, Vasilescu J, Rokach J, Powell WS,. 2002. 15-Deoxy-delta 12,14-prostaglandins D2 and J2 are potent activators of human eosinophils. J Immunol 168: 3563-3569. (Pubitemid 34250426)
74. Morimoto RI, Santoro MG,. 1998. Stress-inducible responses and heat shock proteins: New pharmacologic targets for cytoprotection. Nat Biotechnol 16: 833-838. (Pubitemid 28405852)
75. Mossner E, Iwai H, Glockshuber R,. 2000. Influence of the pK(a) value of the buried, active-site cysteine on the redox properties of thioredoxin-like oxidoreductases. FEBS Lett 477: 21-26. (Pubitemid 30438851)
76. Narumiya S, Fukushima M,. 1985. delta 12-Prostaglandin J2, an ultimate metabolite of prostaglandin D2 exerting cell growth inhibition. Biochem Biophys Res Commun 127: 739-745. (Pubitemid 15037590)
77. Narumiya S, Ohno K, Fukushima M, Fujiwara M,. 1987. Site and mechanism of growth inhibition by prostaglandins. III. Distribution and binding of prostaglandin A2 and delta 12-prostaglandin J2 in nuclei. J Pharmacol Exp Ther 242: 306-311. (Pubitemid 17112295)
78. Nencioni A, Lauber K, Grunebach F, Van Parijs L, Denzlinger C, Wesselborg S, Brossart P,. 2003. Cyclopentenone prostaglandins induce lymphocyte apoptosis by activating the mitochondrial apoptosis pathway independent of external death receptor signaling. J. Immunol 171: 5148-5156. (Pubitemid 37432798)
79. Nishida M, Sawa T, Kitajima N, Ono K, Inoue H, Ihara H, Motohashi H, Yamamoto M, Suematsu M, Kurose H, van der Vliet A, Freeman BA, Shibata T, Uchida K, Kumagai Y, Akaike T,. 2012. Hydrogen sulfide anion regulates redox signaling via electrophile sulfhydration. Nat Chem Biol 8: 714-724.
80. Oeste CL, Díez-Dacal B, Bray F, García de Lacoba M, de la Torre BG, Andreu D, Ruiz-Sánchez AJ, Pérez-Inestrosa E, García-Domínguez CA, Rojas JM, Pérez-Sala D,. 2011. The C-terminus of H-Ras as a target for the covalent binding of reactive compounds modulating Ras-dependent pathways. PLoS ONE 6: e15866.
81. Oh JY, Giles N, Landar A, Darley-Usmar V,. 2008. Accumulation of 15-deoxy-delta(12,14)-prostaglandin J2 adduct formation with Keap1 over time: Effects on potency for intracellular antioxidant defence induction. Biochem J 411: 297-306. (Pubitemid 351580182)
82. Ohno K, Fujiwara M, Fukushima M, Narumiya S,. 1986. Metabolic dehydration of prostaglandin E2 and cellular uptake of the dehydration product: Correlation with prostaglandin E2-induced growth inhibition. Biochem Biophys Res Commun 139: 808-815. (Pubitemid 16002496)
83. 2 binds to and activates H-Ras. Proc Natl Acad Sci USA 100: 4772-4777. (Pubitemid 36469241)
84. Parker J,. 1995. Prostaglandin A2 protein interactions and inhibition of cellular proliferation. Prostaglandins 50: 359-375. (Pubitemid 26082607)
85. Paumi CM, Wright M, Townsend AJ, Morrow CS,. 2003. Multidrug resistance protein (MRP) 1 and MRP3 attenuate cytotoxic and transactivating effects of the cyclopentenone prostaglandin, 15-deoxy-Delta(12,14)prostaglandin J2 in MCF7 breast cancer cells. Biochemistry 42: 5429-5437. (Pubitemid 36560440)
86. Paumi CM, Smitherman PK, Townsend AJ, Morrow CS,. 2004. Glutathione S-transferases (GSTs) inhibit transcriptional activation by the peroxisomal proliferator-activated receptor g (PPARg) ligand, 15-deoxy-D12,14prostaglandin J2 (15-d-PGJ2). Biochemistry 43: 2345-2352. (Pubitemid 38279980)
87. Pérez-Sala D,. 2007. Protein isoprenylation in biology and disease: General overview and perspectives from studies with genetically engineered animals. Front Biosci 12: 4456-4472.
88. 2. J Biol Chem 278: 51251-51260. (Pubitemid 38020362)
89. Pierre SR, Lemmens MA, Figueiredo-Pereira ME,. 2009. Subchronic infusion of the product of inflammation prostaglandin J2 models sporadic Parkinson's disease in mice. J Neuroinflamm 6: 18.
90. Pineda-Molina E, Klatt P, Vázquez J, Marina A, de Lacoba MG, Pérez-Sala D, Lamas S,. 2001. Glutathionylation of the p50 subunit of NF-κB: A mechanism for redox-induced inhibition of DNA-binding. Biochemistry 40: 14134-14142. (Pubitemid 33081616)
91. Prage EB, Morgenstern R, Jakobsson PJ, Stec DF, Voehler MW, Armstrong RN,. 2012. Observation of two modes of inhibition of human microsomal prostaglandin E synthase 1 by the cyclopentenone 15-deoxy-Delta(12,14)- prostaglandin J(2). Biochemistry 51: 2348-2356.
92. Qin ZH, Wang Y, Chen RW, Wang X, Ren M, Chuang DM, Chase TN,. 2001. Prostaglandin A(1) protects striatal neurons against excitotoxic injury in rat striatum. J Pharmacol Exp Ther 297: 78-87. (Pubitemid 32242565)
93. Rajakariar R, Hilliard M, Lawrence T, Trivedi S, Colville-Nash P, Bellingan G, Fitzgerald D, Yaqoob MM, Gilroy DW,. 2007. Hematopoietic prostaglandin D2 synthase controls the onset and resolution of acute inflammation through PGD2 and 15-deoxyDelta12 14 PGJ2. Proc Natl Acad Sci USA 104: 20979-20984.
94. Renedo M, Gayarre J, García-Domínguez CA, Pérez-Rodríguez A, Prieto A, Cañada FJ, Rojas JM, Pérez-Sala D,. 2007. Modification and activation of Ras proteins by electrophilic prostanoids with different structure are site-selective. Biochemistry 46: 6607-6616. (Pubitemid 46870126)
95. Rocks O, Peyker A, Kahms M, Verveer PJ, Koerner C, Lumbierres M, Kuhlmann J, Waldmann H, Wittinghofer A, Bastiaens PI,. 2005. An acylation cycle regulates localization and activity of palmitoylated Ras isoforms. Science 307: 1746-1752. (Pubitemid 40388611)
96. Sánchez-Gõmez FJ, Gayarre J, Avellano MI, Pérez-Sala D,. 2007. Direct evidence for the covalent modification of glutathione-S- transferase P1-1 by electrophilic prostaglandins: Implications for enzyme inactivation and cell survival. Arch Biochem Biophys 457: 150-159. (Pubitemid 46048697)
97. Sánchez-Gõmez FJ, Díez-Dacal B, Pajares MA, Llorca O, Pérez-Sala D,. 2010. Cyclopentenone prostaglandins with dienone structure promote cross-linking of the chemoresistance-inducing enzyme glutathione transferase P1-1. Mol Pharmacol 78: 723-733.
98. Sandig H, Pease JE, Sabroe I,. 2007. Contrary prostaglandins: The opposing roles of PGD2 and its metabolites in leukocyte function. J Leukoc Biol 81: 372-382. (Pubitemid 46198387)
99. Santoro MG,. 1997. Antiviral activity of cyclopentenone prostanoids. Trends Microbiol 5: 276-281. (Pubitemid 27314516)
100. Sasaki H, Niimi S, Akiyama M, Tanaka T, Hazato A, Kurozumi S, Fukushima S, Fukushima M,. 1999. Antitumor activity of 13,14-dihydro-15-deoxy-delta7- prostaglandin-A1-methyl ester integrated into lipid microspheres against human ovarian carcinoma cells resistant to cisplatin in vivo. Cancer Res 59: 3919-3922. (Pubitemid 29393553)
101. Sawyer N, Cauchon E, Chateauneuf A, Cruz RP, Nicholson DW, Metters KM, O'Neill GP, Gervais FG,. 2002. Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2. Br J Pharmacol 137: 1163-1172. (Pubitemid 36071733)
102. Schopfer FJ, Cipollina C, Freeman BA,. 2011. Formation and signaling actions of electrophilic lipids. Chem Rev 111: 5997-6021.
103. Sethuraman M, Clavreul N, Huang H, McComb ME, Costello CE, Cohen RA,. 2007. Quantification of oxidative posttranslational modifications of cysteine thiols of p21ras associated with redox modulation of activity using isotope-coded affinity tags and mass spectrometry. Free Radic Biol Med 42: 823-829. (Pubitemid 46274168)
104. Shen Y, Zhong L, Johnson S, Cao D,. 2011. Human aldo-keto reductases 1B1 and 1B10: A comparative study on their enzyme activity toward electrophilic carbonyl compounds. Chem Biol Interact 191: 192-198.
105. Shibata T, Kondo M, Osawa T, Shibata N, Kobayashi M, Uchida K,. 2002. 15-Deoxy-Delta 12,14-prostaglandin J2. A prostaglandin D2 metabolite generated during inflammatory processes. J Biol Chem 277: 10459-10466. (Pubitemid 34968167)
106. Shibata T, Yamada T, Ishii T, Kumazawa S, Nakamura H, Masutani H, Yodoi J, Uchida K,. 2003. Thioredoxin as a molecular target of cyclopentenone prostaglandins. J Biol Chem 278: 26046-26054. (Pubitemid 36835372)
107. Shin SW, Seo CY, Han H, Han JY, Jeong JS, Kwak JY, Park JI,. 2009. 15d-PGJ2 induces apoptosis by reactive oxygen species-mediated inactivation of Akt in leukemia and colorectal cancer cells and shows in vivo antitumor activity. Clin Cancer Res 15: 5414-5425.
108. Shiraki T, Kamiya N, Shiki S, Kodama TS, Kakizuka A, Jingami H,. 2005. α,β-Unsaturated ketone is a core moiety of natural ligands for covalent binding to peroxisome proliferator-activated receptor. J Biol Chem 280: 14145-14153. (Pubitemid 40517317)
109. Song NY, Kim DH, Kim EH, Na HK, Kim NJ, Suh YG, Surh YJ,. 2011. Multidrug resistance-associated protein 1 mediates 15-deoxy-Delta(12,14)-prostaglandin J2-induced expression of glutamate cysteine ligase expression via Nrf2 signaling in human breast cancer cells. Chem Res Toxicol 24: 1231-1241.
110. Srivastava SK, Ramana KV, Chandra D, Srivastava S, Bhatnagar A,. 2003. Regulation of aldose reductase and the polyol pathway activity by nitric oxide. Chem Biol Interact 143-144: 333-340. (Pubitemid 36246450)
111. Stamatakis K, Sánchez-Gõmez FJ, Pérez-Sala D,. 2004. Protein modification by cyclopentenone prostaglandin addition: Biological actions and therapeutic implications. Gene Ther Mol Biol 8: 241-258.
112. 2 in mesangial cells reveals multiple interactions with the cytoskeleton. J Am Soc Nephrol 17: 89-98.
113. Straus DS, Glass CK,. 2001. Cyclopentenone prostaglandins: New insights on biological activities and cellular targets. Med Res Rev 21: 185-210. (Pubitemid 32303994)
114. Straus DS, Pascual G, Li M, Welch JS, Ricote M, Hsiang CH, Sengchanthalangsy LL, Ghosh G, Glass CK,. 2000. 15-Deoxy-delta 12,14-prostaglandin J2 inhibits multiple steps in the NF-kappa B signaling pathway. Proc Natl Acad Sci USA 97: 4844-4849. (Pubitemid 30238645)
115. Suzuki M, Mori M, Niwa T, Hirata R, Furuta K, Ishikawa T, Noyori R,. 1997. Chemical implications for antitumor and antiviral prostaglandins: Reaction of D7-prostaglandin A1 and prostaglandin A1 methyl esters with thiols. J Am Chem Soc 119: 2376-2385. (Pubitemid 27167854)
116. Syeda PK, Hossain MS, Chowdhury AA, Rahman MS, Khan F, Nishimura K, Jisaka M, Nagaya T, Shono F, Yokota K,. 2012a. A monoclonal antibody specific for delta(12)-prostaglandin j(2) and its utilization in the immunological assay in cell culture system of adipocytes. Hybridoma (Larchmt) 31: 364-371.
117. Syeda PK, Hossain MS, Chowdhury AA, Rahman MS, Nishimura K, Jisaka M, Nagaya T, Shono F, Yokota K,. 2012b. Generation of monoclonal antibody for 15-deoxy-Delta(1)(2),(1)(4)-prostaglandin J(2) and development of enzyme-linked immunosorbent assay for its quantification in culture medium of adipocytes. Appl Biochem Biotechnol 167: 1107-1118.
118. Takaya K, Suzuki T, Motohashi H, Onodera K, Satomi S, Kensler TW, Yamamoto M,. 2012. Validation of the multiple sensor mechanism of the Keap1-Nrf2 system. Free Radic Biol Med 53: 817-827.
119. Tsikas D, Zoerner AA, Mitschke A, Gutzki FM,. 2009. Nitro-fatty acids occur in human plasma in the picomolar range: A targeted nitro-lipidomics GC-MS/MS study. Lipids 44: 855-865.
120. Vunta H, Davis F, Palempalli UD, Bhat D, Arner RJ, Thompson JT, Peterson DG, Reddy CC, Prabhu KS,. 2007. The anti-inflammatory effects of selenium are mediated through 15-deoxy-Delta12,14-prostaglandin J2 in macrophages. J Biol Chem 282: 17964-17973. (Pubitemid 47100228)
121. Waku T, Shiraki T, Oyama T, Fujimoto Y, Maebara K, Kamiya N, Jingami H, Morikawa K,. 2009. Structural insight into PPARgamma activation through covalent modification with endogenous fatty acids. J Mol Biol 385: 188-199.
122. Westerheide SD, Morimoto RI,. 2005. Heat shock response modulators as therapeutic tools for diseases of protein conformation. J Biol Chem 280: 33097-33100. (Pubitemid 41397104)
123. Yamaguchi S, Aldini G, Ito S, Morishita N, Shibata T, Vistoli G, Carini M, Uchida K,. 2010. Delta(12)-prostaglandin J(2) as a product and ligand of human serum albumin: formation of an unusual covalent adduct at His146. J Am Chem Soc 132: 824-832.
124. Yan XD, Kumar B, Nahreini P, Hanson AJ, Prasad JE, Prasad KN,. 2005. Prostaglandin-induced neurodegeneration is associated with increased levels of oxidative markers and reduced by a mixture of antioxidants. J Neurosci Res 81: 85-90. (Pubitemid 41139113)
125. Zhang DD,. 2010. The Nrf2-Keap1-ARE signaling pathway: The regulation and dual function of Nrf2 in cancer. Antioxid Redox Signal 13: 1623-1626.
126. Zhang HL, Gu ZL, Savitz SI, Han F, Fukunaga K, Qin ZH,. 2008. Neuroprotective effects of prostaglandin A(1) in rat models of permanent focal cerebral ischemia are associated with nuclear factor-kappaB inhibition and peroxisome proliferator-activated receptor-gamma up-regulation. J Neurosci Res 86: 1132-1141. (Pubitemid 351441311)
127. Zhang HX, Tanji K, Yoshida H, Hayakari M, Shibata T, Mori F, Uchida K, Wakabayashi K,. 2010. Alteration of biochemical and pathological properties of TDP-43 protein by a lipid mediator, 15-deoxy-Delta(12,14)-prostaglandin J(2). Exp Neurol 222: 296-303.
128. Zhang Y, Ahn YH, Benjamin IJ, Honda T, Hicks RJ, Calabrese V, Cole PA, Dinkova-Kostova AT,. 2011. HSF1-dependent upregulation of Hsp70 by sulfhydryl-reactive inducers of the KEAP1/NRF2/ARE pathway. Chem Biol 18: 1355-1361.
129. Ziboh VA, Miller CC, Cho Y,. 2000. Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: Generation of antiinflammatory and antiproliferative metabolites. Am J Clin Nutr 71: 361S-366S. (Pubitemid 30046143)
130. Zingarelli B, Sheehan M, Hake PW, O'Connor M, Denenberg A, Cook A,. 2003. Peroxisome proliferator activator receptor-gamma ligands, 15-deoxy-delta(12,14) -prostaglandin J2 and ciglitazone, reduce systemic inflammation in polymicrobial sepsis by modulation of signal transduction pathways. J Immunol 171: 6827-6837. (Pubitemid 37532118)
131. Zorrilla S, Garzõn B, Pérez-Sala D,. 2010. Selective binding of the fluorescent dye 8-anilinonaphthalene-1-sulfonic acid to PPARγ allows ligand identification and characterization. Anal Biochem 399: 84-92.