Synthesis of a novel thiazolidinedione and evaluation of its modulatory effect on IFN- γ, IL-6, IL-17A, and IL-22 production in PBMCs from rheumatoid arthritis patients

BioMed Research International

Volumn 2013, Issue , 2013, Pages

  Da Rocha Junior, Laurindo Ferreira ^a,b   De Melo Rêgo, Moacyr Jesus Barreto ^b   Cavalcanti, Mariana Brayner ^b   Pereira, Michelly Cristiny ^b   Pitta, Marina Galdino Da Rocha ^b,c   De Oliveira, Priscilla Stela Santana ^b   Gonçalves, Sayonara Maria Calado ^b   Duarte, Angela Luzia Branco Pinto ^a   De Lima, Maria Do Carmo Alves ^c   Pitta, Ivan Da Rocha ^b,c   Pitta, Maira Galdino Da Rocha ^b,c  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^b Laboratório de Imunomodulação e Novas Abordagens Terapêuticas Núcleo de Pesquisa Em Inovação Terapêutica Suely Galdino   (Brazil)

^c Cidade Universitária   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 THIAZOLIDINEDIONE DERIVATIVE; 5 (5 BROMO 2 METHOXY BENZYLIDENE) 3 (2 NITRO BENZYL)THIAZOLIDINE 2,4 DIONE; ANTIRHEUMATIC AGENT; GAMMA INTERFERON; INTERLEUKIN 17; INTERLEUKIN 22; INTERLEUKIN 6; MESSENGER RNA; METHYLPREDNISOLONE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA AGONIST; RHEUMATOID FACTOR; ROSIGLITAZONE; TM 17; UNCLASSIFIED DRUG; 2,4 THIAZOLIDINEDIONE; 2,4-THIAZOLIDINEDIONE; AUTACOID; CYTOKINE; INTERLEUKIN DERIVATIVE; INTERLEUKIN-22;

ADULT; AGED; ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL VIABILITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; CYTOTOXICITY; DISEASE ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IMMUNOMODULATION; MACROPHAGE; MACROPHAGE MIGRATION; MALE; MOUSE; NONHUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PROTEIN EXPRESSION; REMISSION; RHEUMATOID ARTHRITIS; SPLEEN CELL; ANIMAL; BAGG ALBINO MOUSE; BIOSYNTHESIS; CASE CONTROL STUDY; CHEMISTRY; DEMOGRAPHY; DRUG EFFECT; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; MIDDLE AGED; MONONUCLEAR CELL; PATHOLOGY; SYNTHESIS; VERY ELDERLY; DRUG EFFECTS;

ADULT; AGED; AGED, 80 AND OVER; ANIMALS; ARTHRITIS, RHEUMATOID; CASE-CONTROL STUDIES; CYTOKINES; DEMOGRAPHY; GENE EXPRESSION REGULATION; HUMANS; INFLAMMATION MEDIATORS; INTERFERON-GAMMA; INTERLEUKIN-17; INTERLEUKIN-6; INTERLEUKINS; LEUKOCYTES, MONONUCLEAR; MALE; MICE; MICE, INBRED BALB C; MIDDLE AGED; PPAR GAMMA; RNA, MESSENGER; THIAZOLIDINEDIONES;

EID: 84884867019     PISSN: 23146133     EISSN: 23146141     Source Type: Journal    
DOI: 10.1155/2013/926060     Document Type: Article

References (29)

1. Wolfe F., Mitchell D. M., Sibley J. T., Fries J. F., Bloch D. A., Williams C. A., Spitz P. W., Haga M., Kleinheksel S. M., Cathey M. A., The mortality of rheumatoid arthritis. Arthritis and Rheumatism 1994 37 4 481 494 2-s2.0-0028328810 (Pubitemid 24115934)
2. Brasington D. R. Jr., Hochberg M. C., Smolen J. S., Weinblatt M. E., Weisman M. H., Clinical features of rheumatoid arthritis. Rheumatology 2011 1 5th Philadelphia, Pa, USA Elsevier 829 837
3. McInnes I. B., Schett G., The pathogenesis of rheumatoid arthritis. The New England Journal of Medicine 2011 365 23 2205 2219 2-s2.0-84855172814
4. McInnes I. B., Schett G., Cytokines in the pathogenesis of rheumatoid arthritis. Nature Reviews Immunology 2007 7 6 429 442 2-s2.0-34249720998 10.1038/nri2094 (Pubitemid 46834849)
5. Chabaud M., Fossiez F., Taupin J., Miossec P., Enhancing effect of IL-17 on IL-1-induced IL-6 and leukemia inhibitory factor production by rheumatoid arthritis synoviocytes and its regulation by Th2 cytokines. Journal of Immunology 1998 161 1 409 414 2-s2.0-0031802932 (Pubitemid 28285549)
6. Miossec P., Korn T., Kuchroo V. K., Interleukin-17 and type 17 helper T cells. The New England Journal of Medicine 2009 361 9 848 898 2-s2.0-69349093225 10.1056/NEJMra0707449
7. Giaginis C., Giagini A., Theocharis S., Peroxisome proliferator-activated receptor- γ (PPAR- γ) ligands as potential therapeutic agents to treat arthritis. Pharmacological Research 2009 60 3 160 169 2-s2.0-67651089911 10.1016/j.phrs.2009.02.005
8. Palma A., Sainaghi P. P., Amoruso A., Peroxisome proliferator-activated receptor-gamma expression in monocytes/macrophages from rheumatoid arthritis patients: relation to disease activity and therapy efficacy-a pilot study. Rheumatology 2012 51 11 1942 1952
9. Schmidt M. V., Brüne B., von Knethen A., The nuclear hormone receptor PPAR γ as a therapeutic target in major diseases. The Scientific World Journal 2010 10 2181 2197 2-s2.0-78650286735 10.1100/tsw.2010.213
10. Pascual G., Glass C. K., Nuclear receptors versus inflammation: mechanisms of transrepression. Trends in Endocrinology and Metabolism 2006 17 8 321 327 2-s2.0-33748702268 10.1016/j.tem.2006.08.005 (Pubitemid 44397567)
11. Straus D. S., Glass C. K., Anti-inflammatory actions of PPAR ligands: new insights on cellular and molecular mechanisms. Trends in Immunology 2007 28 12 551 558 2-s2.0-36049034344 10.1016/j.it.2007.09.003 (Pubitemid 350101420)
12. Farmer S. R., Transcriptional control of adipocyte formation. Cell Metabolism 2006 4 4 263 273 2-s2.0-33748942837 10.1016/j.cmet.2006.07.001 (Pubitemid 44430910)
13. Willson T. M., Lambert M. H., Kliewer S. A., Peroxisome proliferator-activated receptor γ and metabolic disease. Annual Review of Biochemistry 2001 70 341 367 2-s2.0-0034923501 10.1146/annurev.biochem.70.1.341 (Pubitemid 32662214)
14. Lehrke M., Lazar M. A., The many faces of PPAR γ Cell 2005 123 6 993 999 2-s2.0-28944446431 10.1016/j.cell.2005.11.026 (Pubitemid 41785415)
15. Széles L., Töröcsik D., Nagy L., PPAR γ in immunity and inflammation: cell types and diseases. Biochimica et Biophysica Acta 2007 1771 8 1014 1030 2-s2.0-34547627893 10.1016/j.bbalip.2007.02.005 (Pubitemid 47202035)
16. Choi J., Bothwell A. L. M., The nuclear receptor PPARs as important regulators of T-cell functions and autoimmune diseases. Molecules and Cells 2012 33 3 217 222 2-s2.0-84857492034 10.1007/s10059-012-2297-y
17. Cariou B., Charbonnel B., Staels B., Thiazolidinediones and PPAR γ agonists: time for a reassessment. Trends in Endocrinology and Metabolism 2012 23 5 205 215 2-s2.0-84860375795 10.1016/j.tem.2012.03.001
18. Desreumaux P., Dubuquoy L., Nutten S., Peuchmaur M., Englaro W., Schoonjans K., Derijard B., Desvergne B., Wahli W., Chambon P., Leibowitz M. D., Colombel J., Auwerx J., Attenuation of colon inflammation through activators of the retinoid X receptor (RXR)/peroxisome proliferator-activated receptor γ (PPAR γ) heterodimer: a basis for new therapeutic strategies. Journal of Experimental Medicine 2001 193 7 827 838 2-s2.0-0035794293 10.1084/jem.193.7.827 (Pubitemid 32524532)
19. Arnett F. C., Edworthy S. M., Bloch D. A., McShane D. J., Fries J. F., Cooper N. S., Healey L. A., Kaplan S. R., Liang M. H., Luthra H. S., Medsger T. A. Jr., Mitchell D. M., Neustadt D. H., Pinals R. S., Schaller J. G., Sharp J. T., Wilder R. L., Hunder G. G., The American Rheumatism Association 1987 revised criteria for the classification of rheumatoid arthritis. Arthritis and Rheumatism 1988 31 3 315 324 2-s2.0-0023945481 (Pubitemid 18091653)
20. Barros C. D., Amato A. A., Oliveira T. B. D., Iannini K. B. R., Silva A. L. D., Silva T. G. D., Leite E. S., Hernandes M. Z., Lima M. D. C. A. D., Galdino S. L., Neves F. D. A. R., Pitta I. D. R., Synthesis and anti-inflammatory activity of new arylidene-thiazolidine-2,4-diones as PPAR γ ligands. Bioorganic and Medicinal Chemistry 2010 18 11 3805 3811 2-s2.0-77953326342 10.1016/j.bmc.2010.04.045
21. Tan S. F., Ang K. P., Fong Y. F., (2)- and ()-5-arylmethylenehydantoins: spectroscopic properties and configuration assignment. Journal of the Chemical Society, Perkin Transactions 1986 2 1941
22. Albuquerque J. F. C., Albuquerque A., Azevedo C. C., Thomasson F., Galdino L. S., Chantegrel J., Catanho M. T. J., Pitta I. R., Luu-Duc C., Substituted thiazolidinediones and thio-imidazolidinones: synthesis, structural study and pharmacological activity. Pharmazie 1995 50 6 387 389 2-s2.0-0029003612
23. Guarda V. L. M., Pereira M. A., De Simone C. A., Albuquerque J. F. C., Galdino S. L., Chantegrel J., Perrissin M., Beney C., Thomasson F., Pitta I. R., Luu-duc C., Synthesis and structural study of arylidene thiazolidine and benzothiazine compounds. Sulfur Letters 2003 26 1 17 27 2-s2.0-0037870719 10.1080/0278611021000048712
24. Hirota K., Duarte J. H., Veldhoen M., Hornsby E., Li Y., Cua D. J., Ahlfors H., Wilhelm C., Tolaini M., Menzel U., Garefalaki A., Potocnik A. J., Stockinger B., Fate mapping of IL-17-producing T cells in inflammatory responses. Nature Immunology 2011 12 3 255 263 2-s2.0-79951677394 10.1038/ni.1993
25. Schroder K., Hertzog P. J., Ravasi T., Hume D. A., Interferon- γ: an overview of signals, mechanisms and functions. Journal of Leukocyte Biology 2004 75 2 163 189 2-s2.0-0842266786 10.1189/jlb.0603252 (Pubitemid 38174573)
26. Heinrich P. C., Behrmann I., Haan S., Hermanns H. M., Müller-Newen G., Schaper F., Principles of interleukin (IL)-6-type cytokine signalling and its regulation. Biochemical Journal 2003 374 1 1 20 2-s2.0-0041677606 10.1042/BJ20030407 (Pubitemid 37046923)
27. Ma Y., Wang X., Wu X., Wei X., Ma L., Zheng H., Qi B., Zhu W., Luo Y., Wei Y., Chen L., (Z)-5-(4-methoxybenzylidene) thiazolidine-2, 4-dione ameliorates the adjuvant-induced arthritis via inhibiting the migration of macrophage and down-regulating the cytokine mRNA expression. International Immunopharmacology 2010 10 11 1456 1462 2-s2.0-77958150988 10.1016/j.intimp. 2010.08.022
28. Faine L. A., Rudnicki M., César F. A., Heras B. L., Boscá L., Souza E. S., Hernandes M. Z., Galdino S. L., Lima M. C. A., Pitta I. R., Abdalla D. S. P., Anti-inflammatory and antioxidant properties of a new arylidene- thiazolidinedione in macrophages. Current Medicinal Chemistry 2011 18 22 3351 3360 2-s2.0-79961075382 10.2174/092986711796504600
29. Klotz L., Burgdorf S., Dani I., Saijo K., Flossdorf J., Hucke S., Alferink J., Novak N., Beyer M., Mayer G., Langhans B., Klockgether T., Waisman A., Eberl G., Schultze J., Famulok M., Kolanus W., Glass C., Kurts C., Knolle P. A., The nuclear receptor PPAR γ selectively inhibits Th17 differentiation in a T cell-intrinsic fashion and suppresses CNS autoimmunity. Journal of Experimental Medicine 2009 206 10 2079 2089 2-s2.0-70350459594 10.1084/jem.20082771