Chemical synthesis, docking studies and biological effects of a pan peroxisome proliferator-activated receptor agonist and cyclooxygenase inhibitor

European Journal of Pharmaceutical Sciences

Volumn 48, Issue 4-5, 2013, Pages 689-697

  Santin, José Roberto ^a   Uchôa, Flávia D T ^b   Lima, Maria Do Carmo A ^b   Rabello, Marcelo M ^b   MacHado, Isabel Daufenback ^a   Hernandes, Marcelo Z ^b   Amato, Angelica A ^c   Milton, Flora Aparecida ^c,d   Webb, Paul ^d   Neves, Francisco De Assis Rocha ^c   Galdino, Suely L ^b   Pitta, Ivan Rocha ^b   Farsky, Sandra H P ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^c UNIVERSITY OF BRASILIA   (Brazil)

^d HOUSTON METHODIST RESEARCH INSTITUTE   (United States)

Author keywords

Air pouch; GW9962; Inflammation; Interleukin 1 ; Mice; Neutrophils

Indexed keywords

CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; ESCHERICHIA COLI LIPOPOLYSACCHARIDE; INTERLEUKIN 1BETA; NITRIC OXIDE; PARTIAL AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR DELTA AGONIST; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; PROSTAGLANDIN SYNTHASE INHIBITOR;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; COMPUTER MODEL; ENZYME ACTIVITY; ENZYME INHIBITION; IN VIVO STUDY; MALE; MOUSE; NEUTROPHIL; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; REPORTER GENE; SECRETION (PROCESS);

ANIMALS; ANTI-INFLAMMATORY AGENTS; CARRAGEENAN; CELL MOVEMENT; CYCLOOXYGENASE INHIBITORS; HELA CELLS; HUMANS; INDOLES; INFLAMMATION; LEUKOCYTES; MALE; MICE; MODELS, MOLECULAR; PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS; THIAZOLIDINEDIONES;

EID: 84873469982     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.12.029     Document Type: Article

References (61)

1. A.A.M. Abdel-Aziz, M.A. Al-Omar, A.S. El-Azab, and T. Kunieda Conformational preferences of sterically congested 2-imidazolidinone using X-ray analysis and computational studies. Part 1: Trans-1-acetyl-4,5-di-tert-butyl-2- imidazolidinone J. Mol. Struct. 969 2010 145 154
2. A.A. Amato, and F.A. Neves Idealized PPARgamma-Based Therapies: Lessons from Bench and Bedside PPAR Res. 2012 2012 978687
3. A.A. Amato, S. Rajagopalan, J.Z. Lin, B.M. Carvalho, A.C. Figueira, J. Lu, D. Ayers, M. Mottin, R.L. Silveira, P.C. Souza, R.H. Mourão, M.J. Saad, M. Togashi, L.A. Simeoni, D.S. Abdalla, M.S. Skaf, I. Polikparpov, M.C. Lima, S.L. Galdino, R.G. Brennan, J.D. Baxter, I.R. Pitta, P. Webb, K.J. Phillips, and F.A. Neves GQ-16, a novel peroxisome proliferator-activated receptor γ (PPARγ) ligand, promotes insulin sensitization without weight gain J. Biol. Chem. 287 2012 28169 28179
4. M.T. Bility, B. Zhu, B.H. Kang, F.J. Gonzalez, and J.M. Peters Ligand Activation of Peroxisome Proliferator-Activated Receptor-{beta}/{delta} (PPAR{beta}/{delta}) and Inhibition of Cyclooxygenase 2 (COX2) Enhances Inhibition of Skin Tumorigenesis Toxicol. Sci. 113 2010 27 36
5. D.M. Cavalcanti, C.M. Lotufo, P. Borelli, Z.S. Ferreira, R.P. Markus, and S.H. Farsky Endogenous glucocorticoids control neutrophil mobilization from bone marrow to blood and tissues in non-inflammatory conditions Br. J. Pharmacol. 152 2007 1291 1300
6. D.M. Cavalcanti, C.M. Lotufo, P. Borelli, A.M. Tavassi, A.L. Pereira, R.P. Markus, and S.H. Farsky Adrenal deficiency alters mechanisms of neutrophil mobilization Mol. Cell Endocrinol. 249 2006 32 39
7. B.K. Chacko, D.W. Scott, R.T. Chandler, and R.P. Patel Endothelial surface N-glycansmediate monocyte adhesion and are targets for anti-inflammatory effects ofperoxisome proliferator-activated receptor γ ligands J. Biol. Chem. 286 2011 38738 38747
8. J.H. Choi, A.S. Banks, J.L. Estall, S. Kajimura, P. Boström, D. Laznik, J.L. Ruas, M.J. Chalmers, T.M. Kamenecka, M. Blüher, P.R. Griffin, and B.M. Spiegelman Anti-diabetic drugs inhibit obesity-linked phosphorylation of PPARgamma by Cdk5 Nature 466 2010 451 456
9. J.H. Choi, A.S. Banks, T.M. Kamenecka, S.A. Busby, M.J. Chalmers, N. Kumar, D.S. Kuruvilla, Y. Shin, Y. He, J.B. Bruning, D.P. Marciano, M.D. Cameron, D. Laznik, M.J. Jurczak, S.C. Schürer, D. Vidović, G.I. Shulman, B.M. Spiegelman, and P.R. Griffin Antidiabetic actions of a non-agonist PPARγ ligand blocking Cdk5-mediated phosphorylation Nature 477 2011 477 481
10. T.A. Cock, S.M. Houten, and J. Auwerx Peroxisome proliferator-activated receptor-γ: too much of a good thing causes harm EMBO Rep. 5 2004 142 147
11. M. Collino, N.S. Patel, and C.C. Thiemermann PPARs as new therapeutic targets for the treatment of cerebral ischemia/reperfusion injury Ther. Adv. Cardiovasc. Dis. 2 2008 179 197
12. P. Colville-Nash, D. Willis, J. Papworth, C. Freemantle, C. Lam, G. Andrews, and D. Willoughby The peroxisome proliferator-activated receptor alpha activator, Wy14,643, is anti-inflammatory in vivo Inflammopharmacology 12 2005 493 504
13. C. Delayre-Orthez, J. Becker, I. Guenon, V. Lagente, J. Auwerx, N. Frossard, and F. Pons PPARalpha downregulates airway inflammation induced by lipopolysaccharide in the mouse Respir. Res. 9 2005 6 91
14. C. Delayre-Orthez, J. Becker, J. Auwerx, N. Frossard, and F. Pons Suppression of allergen-induced airway inflammation and immune response by the peroxisome proliferator-activated receptor-alpha agonist fenofibrate Eur. J. Pharmacol. 581 2008 177 184
15. C.A. De Simone, J. Zukerman-Schpector, M.A. Pereira, C. Luu-Duc, I.R. Pitta, S.L. Galdino, and E.L.C. Amorim 3-(4-Bromobenzyl)-5-(4-fluorobenzylidene) -imidazolidine-2,4-dione Acta Cryst. C51 1995 2620 2621
16. R. Di Paola, E. Esposito, E. Mazzon, I. Paterniti, M. Galuppo, and S. Cuzzocrea GW0742, a selective PPAR-beta/delta agonist, contributes to the resolution of inflammation after gut ischemia/reperfusion injury J. Leukoc. Biol. 88 2010 291 301
17. C.A. Dinarello Anti-inflammatory agents: present and future Cell 140 2010 935 950
18. N. Dufton, and M. Perretti Therapeutic anti-inflammatory potential of formyl-peptide receptor agonists Pharmacol. Ther. 127 2010 175 188
19. J.D. Durrant, and J.A. Mccammon BINANA: a novel algorithm for ligand-binding characterization J. Mol. Graph. Model. 29 2011 888 893
20. Durrenberger, P.F., Grünblatt, E., Fernando, F.S., Monoranu, C.M., Evans, J., Riederer, P., Reynolds, R., Dexter, D.T., 2012. Inflammatory Pathways in Parkinson's Disease; A BNEMicroarray Study. Parkinsons Dis. 2012-214714.
21. Eikelenboom, P., Hoozemans, J.J., Veerhuis, R., van Exel, E., Rozemuller, A.J., van Gool, Whether, W.A., 2012. when and how chronic inflammation increases the risk of developinglate-onset Alzheimer's disease. Alzheimers Res. Ther. 4, 15.
22. L. Fajas, M.B. Debril, and J. Auwerx PPAR gamma: an essential role in metabolic control Nutr. Metab. Cardiovasc. 11 2001 64 69
23. S.H. Farsky, P. Borelli, R.A. Fock, S.Z. Proto, J.M. Ferreira, and S.B. Mello Chronic blockade of nitric oxide biosynthesis in rats: effect on leukocyte endothelial interaction and on leukocyte recruitment Inflamm. Res. 53 2004 442 452
24. A.L. Franks, and J.E. Slansky Multiple associations between a broad spectrum ofautoimmune diseases, chronic inflammatory diseases and cancer Anticancer Res. 32 2012 1119 1136
25. A.J.S. Goes, M.C.A. Lima, S.L. Galdino, I.R. Pitta, and C. Luu-Duc Synthesis and antifungal activity of chlorobenzyl (benzylidene) thiazolidinediones and imidazolidinediones Ann. Pharm. Fr. 49 1991 92 98
26. J. Handzlik, E. Szymańska, R. Wójcik, A. Dela, M. Jastrzȩbska-Wiȩsek, J. Karolak-Wojciechowska, A. Fruziński, A. Siwek, B. Filipek, and K. Kieć-Kononowicz Synthesis and SAR-study for novel arylpiperazine derivatives of 5-arylidenehydantoin with α1-adrenoceptor antagonistic properties Bioorg. Med. Chem. 20 2012 4245 4247
27. S. Hazra, K.A. Peebles, S. Sharma, J.T. Mao, and S.M. Dubinett The Role of PPARgamma in the Cyclooxygenase Pathway in Lung Cancer PPAR Res. 2008 2008 790568
28. C.B. Hebeda, S.A. Teixeira, E.K. Tamura, M.N. Muscará, S.B. de Mello, R.P. Markus, and S.H. Farsky Nitric oxide modulates lipopolysaccharide- induced endothelial platelet endothelial cell adhesion molecule expression via interleukin-10 Clin. Exp. Immunol. 165 2011 172 179
29. M.T. Heneka, G.E. Landreth, and M. Hüll Drug insight: effects mediated by peroxisomeproliferator-activated receptor-gamma in CNS disorders Nat. Clin. Pract. Neurol. 9 2007 496 504
30. A.N. Jain Surflex-Dock 2.1: robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search J. Comput. Aided. Mol. Des. 21 2007 281 306
31. R.R. Ji, Z.Z. Xu, G. Strichartz, and C.N. Serhan Emerging roles of resolvins in the resolution of inflammation and pain Trends Neurosci. 34 2011 599 609
32. A. Jungbauer, and S. Medjakovic Anti-inflammatory properties of culinary herbs andspices that ameliorate the effects of metabolic syndrome Maturitas 71 2012 227 239
33. R.G. Kalaitzidis, P.A. Sarafidis, and G.I. Bakris Effects of thiazolidinediones beyond glycaemic control Curr. Pharm. Des. 15 2009 529 536
34. K.P. Karalis, P. Giannogonas, E. Kodela, Y. Koutmani, M. Zoumakis, and T. Teli Mechanisms of obesity and related pathology: linking immune responses tometabolic stress FEBS J. 276 2009 5747 5754
35. J. Karolak-Wojciechowska, E. Szymanska, A. Mrozek, and K. Kiec-Kononowicz Crystallographic and spectroscopic studies of 5-arylidene-2-amino-imidazol-4- ones J. Mol. Struct. 930 2009 126 134
36. S.D. Kobayashi, and F.R. DeLeo Role of neutrophils in innate immunity: a systemsbiology-level approach Wiley Interdiscip. Rev. Syst. Biol. Med. 1 2009 309 333
37. S. Lahiri, T. Sen, and G. Palit Involvement of glucocorticoid receptor and peroxisome proliferator activated receptor-gamma in pioglitazone mediated chronic gastric ulcer healing in rats Eur. J. Pharmacol. 609 2009 118 125
38. J.M. Lehmann, J.M. Lenhard, B.B. Oliver, G.M. Ringold, and S.A. Kliewer Peroxisome proliferator-activated receptors α and are Activated by Indomethacin and other non-steroidal anti-inflammatory drugs J. Biol. Chem. 272 1997 3406 3410
39. L.F.C.C. Leite, R.H.V. Mourão, M.C.A. Lima, S.L. Galdino, M.Z. Hernandes, F.A.R. Neves, S. Vidal, J. Barbe, and I.R. Pitta Synthesis, biological evaluation and molecular modeling studies of arylidene- thiazolidinediones with potential hypoglycemic and hypolipidemic activities Eur. J. Med. Chem. 42 2007 1263 1271
40. H.A. Lim, E.K. Lee, J.M. Kim, M.H. Park, D.H. Kim, Y.J. Choi, Y.M. Ha, J.H. Yoon, J.S. Choi, B.P. Yu, and H.Y. Chung PPARγ activation by baicalin suppresses NF-κB-mediated inflammationin aged rat kidney Biogerontology 13 2012 133 145
41. H.L. Martin, R.B. Mounsey, S. Mustafa, K. Sathe, and P. Teismann Pharmacological manipulation of peroxisome proliferator-activated receptor γ (PPARγ) reveals a role for anti-oxidant protection in a model of Parkinson's disease Exp. Neurol. 235 2012 528 538
42. P.L. McCormack Celecoxib: a review of its use for symptomatic relief in thetreatment of osteoarthritis, rheumatoid arthritis and ankylosing spondylitis Drugs 71 2011 2457 2489
43. Meyer, S., Vogt, T., Landthaler, M., Berand, A., Reichle, A., Bataille, F., Marx, A.H., Menz, A., Hartmann, A., Kunz-Schughart, L.A., Wild, P.J., 2009. Cyclooxygenase 2 (COX2) and Peroxisome Proliferator-Activated Receptor Gamma (PPARG) Are Stage-Dependent Prognostic Markers of Malignant Melanoma. PPAR Res. 848645.
44. R.H. Mourão, T.G. Silva, A.L.M. Soares, E.S. Vieira, J.N. Santos, M.C.A. Lima, V.L.M. Lima, S.L. Galdino, J. Barbe, and I.R. Pitta Synthesis and biological activity of novel acridinylidene and benzylidene thiazolidinediones Eur. J. Med. Chem. 40 2005 1129 1133
45. Y. Naito, and T. Yoshikawa PPARgamma as a new therapeutic target in inflammatory diseases Nihon Rinsho 68 2010 341 349
46. M. Pancione, N. Forte, L. Sabatino, E. Tomaselli, D. Parente, A. Febbraro, and V. Colantuoni Reduced beta-catenin and peroxisome proliferator-activated receptor-gamma expression levels are associated with colorectal cancer metastatic progression: correlation with tumor-associated macrophages, cyclooxygenase 2, and patient outcome Hum. Pathol. 40 2009 714 725
47. Y.S. Park, E.P. Lillehoj, K. Kato, C.S. Park, and K.C. Kim PPARγ inhibits airway epithelial cell inflammatory response through a MUC1-dependent mechanism Am. J. Physiol. Lung Cell Mol. Physiol. 302 2012 679 687
48. M. Perretti, and F. D'Acquisto Annexin A1 and glucocorticoids as effectors of the resolution of inflammation Nat. Rev. Immunol. 9 2009 62 70
49. R.C. Reddy, V.R. Narala, V.G. Keshamouni, J.E. Milam, M.W. Newstead, and T.J. Standiford Sepsis-induced inhibition of neutrophil chemotaxis is mediated by activation of peroxisome proliferator-activated receptor-{gamma} Blood 112 2008 4250 4258
50. G.B. Rocha, R.O. Freire, A.M. Simas, and J.J. Stewart RM1: a reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I J. Comput. Chem. 27 2006 1101 1111
51. L.C. Santos, F.T. Uchôa, A.R.P.A. Cañas, I.A. Sousa, R.O. Moura, M.C.A. Lima, S.L. Galdino, I.R. Pitta, and J. Barbe Synthesis and antiinflamatory activity of new 4-thioxothiazolidinones and 2- thioxoimidazolidinones Heterocycl. Commun. 11 2005 121 128
52. M. Sastre, I. Dewachter, S. Rossner, N. Bogdanovic, E. Rosen, P. Borghgraef, B.O. Evert, L. Dumitrescu-Ozimek, D.R. Thal, G. Landreth, J. Walter, T. Klockgether, F. van Leuven, and M.T. Heneka Nonsteroidal anti-inflammatory drugs repress beta-secretase genepromoter activity by the activation of PPARgamma Proc. Natl. Acad. Sci. USA 103 2006 443 448
53. G.B. Segel, M.W. Halterman, and M.A. Lichtman The paradox of the neutrophil's role intissue injury J. Leukoc. Biol. 89 2011 359 372
54. C. Sostres, C.J. Gargallo, M.T. Arroyo, and A. Lanas Adverse effects of non-steroidal anti-inflammatorydrugs (NSAIDs, aspirin and coxibs) on upper gastrointestinal tract Best. Pract. Res. Clin. Gastroenterol. 24 2010 121 132
55. M. Spite, and C.N. Serhan Novel lipid mediators promote resolution of acute inflammation: impact of aspirin and statins Circ. Res. 107 2010 1170 1184
56. W.H. Sun, G.S. Chen, X.L. Ou, Y. Yang, C. Luo, Y. Zhang, Y. Shao, H.C. Xu, B. Xiao, Y.P. Xue, S.M. Zhou, Q.S. Zhao, and G.X. Ding Inhibition of COX-2 and activation of peroxisome proliferator-activated receptor gamma synergistically inhibits proliferation and induces apoptosis of human pancreatic carcinoma cells Cancer Lett. 275 2009 247 255
57. T. Takagi, Y. Naito, H. Ichikawa, N. Tomatsuri, K. Katada, Y. Isozaki, M. Kuroda, S. Kokura, N. Yoshida, and T. Yoshikawa A PPAR-gamma ligand,15-deoxy-Delta12,14-prostaglandin J(2), inhibited gastric mucosal injury induced by ischemia-reperfusion in rats Redox Rep. 9 2004 376 981
58. F. Tan, K.P. Ang, and Y.F. Fong (Z)- and (E)-5-arylmethylenehydantoins: spectroscopic properties and configuration assignment J. Chem. Soc. Perkin Trans. II 12 1986 1941 1944
59. F.T. Uchôa, T.G. Silva, M.C.A. Lima, S.L. Galdino, I.R. Pitta, and T.D. Costa Preclinical pharmacokinetic and pharmacodynamic evaluation of thiazolidinone PG15: an anti-inflammatory candidate J. Pharm. Pharmacol. 61 2009 339 345
60. A. Yamauchi, I. Takahashi, S. Takasawa, K. Nata, N. Noguchi, T. Ikeda, T. Yoshikawa, N.J. Shervani, I. Suzuki, A. Uruno, M. Unno, H. Okamoto, and A. Sugawara Thiazolidinediones inhibit REG alpha gene transcription in gastrointestinal cancer cells Biochem. Biophys. Res. Commun. 379 2009 743 748
61. F. Zhang, Y. Lu, and S. Zheng Peroxisome proliferator-activated receptor-γ cross-regulation of signaling events implicated in liver fibrogenesis Cell Signal 24 2012 596 605