3-Phenylcoumarin derivatives selectively modulate different steps of reactive oxygen species production by immune complex-stimulated human neutrophils

International Immunopharmacology

Volumn 15, Issue 2, 2013, Pages 387-394

  Andrade, Micássio F ^a   Kabeya, Luciana M ^a   Azzolini, Ana Elisa C S ^a   Santos, Everton O L ^a   Figueiredo Rinhel, Andréa S G ^a   Paris, Márcio R P ^a   Emery, Flávio S ^a   Pupo, Mônica T ^a   Lucisano Valim, Yara M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

3 Phenylcoumarin; Immune complex; Myeloperoxidase; NADPH oxidase; Neutrophil; Reactive oxygen species

Indexed keywords

3 PHENYLCOUMARIN DERIVATIVE; 6,7 DIHYDROXY 3 [3',4' DIHYDROXYPHENYL] COUMARIN; 6,7 DIHYDROXY 3 [3',4' METHYLENEDIOXYPHENYL] COUMARIN; COUMARIN DERIVATIVE; HYPOCHLOROUS ACID; LUCIGENIN; MYELOPEROXIDASE; QUERCETIN; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CELL STIMULATION; CELL VIABILITY; CHEMOLUMINESCENCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; NEUTROPHIL; NORMAL HUMAN; PRIORITY JOURNAL;

ANTIGEN-ANTIBODY COMPLEX; CELLS, CULTURED; COUMARINS; DRUG DISCOVERY; FREE RADICAL SCAVENGERS; HUMANS; IMMUNE COMPLEX DISEASES; IMMUNOMODULATION; LUMINESCENT MEASUREMENTS; MOLECULAR TARGETED THERAPY; NEUTROPHILS; OXIDATION-REDUCTION; PEROXIDASE; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84873034372     PISSN: 15675769     EISSN: 18781705     Source Type: Journal    
DOI: 10.1016/j.intimp.2013.01.001     Document Type: Article

References (52)

1. S. Jancar, and M.S. Crespo Immune complex-mediated tissue injury: a multistep paradigm Trends Immunol 26 2005 48 55
2. T.N. Mayadas, G.C. Tsokos, and N. Tsuboi Mechanisms of immune complex-mediated neutrophil recruitment and tissue injury Circulation 120 2009 2012 2024
3. Z.Y. Huang, S. Hunter, P. Chien, M.K. Kim, T.H. Han-Kim, and Z.K. Indik Interaction of two phagocytic host defense systems: Fcγ receptors and complement receptor 3 J Biol Chem 286 2011 160 168
4. B. Amulic, C. Cazalet, G.L. Hayes, K.D. Metzler, and A. Zychlinsky Neutrophil function: from mechanisms to disease Annu Rev Immunol 30 2012 459 489
5. M. Hultqvist, L.M. Olsson, K.A. Gelderman, and R. Holmdahl The protective role of ROS in autoimmune disease Trends Immunol 30 2009 201 208
6. V. Kumar, and A. Sharma Neutrophils: Cinderella of innate immune system Int Immunopharmacol 10 2010 1325 1334
7. A. Mantovani, M.A. Cassatella, C. Costantini, and S. Jaillon Neutrophils in the activation and regulation of innate and adaptive immunity Nat Rev Immunol 11 2011 519 531
8. L.I. Filippin, R. Vercelino, N.P. Marroni, and R.M. Xavier Redox signaling and the inflammatory response in rheumatoid arthritis Clin Exp Immunol 152 2008 415 422
9. M. Dhiman, and N.J. Garg NADPH oxidase inhibition ameliorates Trypanosoma cruzi-induced myocarditis during Chagas disease J Pathol 225 2011 583 596
10. A. Kanashiro, L.M. Kabeya, A.C.M. Polizello, N.P. Lopes, J.L.C. Lopes, and Y.M. Lucisano-Valim Inhibitory activity of flavonoids from Lychnophora sp. on generation of reactive oxygen species by neutrophils upon stimulation by immune complexes Phytother Res 81 2004 61 65
11. A. Kanashiro, J.G. Souza, L.M. Kabeya, A.E.C.S. Azzolini, and Y.M. Lucisano-Valim Elastase release by stimulated neutrophils inhibited by flavonoids: importance of the catechol group Z Naturforsch C 62 2007 357 361
12. M.R. Moreira, A. Kanashiro, L.M. Kabeya, A.C.M. Polizello, A.E.C.S. Azzolini, and C. Curti Neutrophil effector functions triggered by Fc-gamma and/or complement receptors are dependent on B-ring hydroxylation pattern and physicochemical properties of flavonols Life Sci 81 2007 317 326
13. L.M. Kabeya, A. Kanashiro, A.E.C.S. Azzolini, F.M. Soriani, J.L.C. Lopes, and Y.M. Lucisano-Valim Inhibitory effect of eight simple coumarins on the lucigenin enhanced chemiluminescence of rabbit neutrophils Res Commun Mol Pathol Pharmacol 111 2002 103 114
14. L.M. Kabeya, A.A. Marchi, A. Kanashiro, N.P. Lopes, C.H.T.P. Silva, and M.T. Pupo Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: synthesis and structure-activity relationships Bioorg Med Chem 15 2007 1516 1524
15. L.M. Kabeya, C.H.T.P. Silva, A. Kanashiro, J.M. Campos, A.E.C.S. Azzolini, and A.C.M. Polizello Inhibition of immune complex-mediated neutrophil oxidative metabolism: a pharmacophore model for 3-phenylcoumarin derivatives using GRIND-based 3D-QSAR and 2D-QSAR procedures Eur J Med Chem 43 2008 996 1007
16. A. Kanashiro, L.M. Kabeya, C.F.F. Grael, C.O. Jordão, A.E.C.S. Azzolini, and J.L.C. Lopes Sesquiterpene lactones from Lychnophora pohlii: neutrophil chemiluminescence inhibition and free radical scavenger activity J Pharm Pharmacol 58 2006 853 858
17. J.R.S. Hoult, and M. Payá Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential Gen Pharmacol 27 1996 713 722
18. L. Wu, X. Wang, W. Xu, F. Farzaneh, and R. Xu The structure and pharmacological functions of coumarins and their derivatives Curr Med Chem 16 2009 4236 4260
19. M. Ghate, and R.A. Kusanur Synthesis and in vivo analgesic and anti-inflammatory activity of some bi heterocyclic coumarin derivatives Eur J Med Chem 40 2005 882 887
20. C.A. Kontogiorgis, and D.J. Hadjipavlou-Litina Synthesis and anti-inflammatory activity of coumarin derivatives J Med Chem 48 2005 6400 6408
21. C.A. Kontogiorgis, K. Savvoglou, and D.J. Hadjipavlou-Litina Anti-inflammatory and antioxidant evaluation of novel coumarin derivatives J Enzyme Inhib Med Chem 21 2006 21 29
22. C.A. Kontogiorgis, Y. Xu, D. Hadjipavlou-Litina, and Y. Luo Coumarin derivatives protection against ROS production in cellular models of Ab toxicities Free Radic Res 41 2007 1168 1180
23. M. Khoobi, S. Emami, G. Dehghan, A. Foroumadi, A. Ramazani, and A. Shafiee Synthesis and free radical scavenging activity of coumarin derivatives containing a 2-methylbenzothiazoline motif Arch Pharm (Weinheim) 344 2011 588 594
24. M. Roussaki, C.A. Kontogiorgis, D. Hadjipavlou-Litina, S. Hamilakis, and A. Detsi A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity Bioorg Med Chem Lett 20 2010 3889 3892
25. C.M.O. Simões, E.P. Schenkel, G. Gosmann, J.C.P. Mello, L.A. Mentz, and P.R. Petrovick Farmacognosia: da planta ao medicamento 2007 Editora da UFRGS Porto Alegre
26. A.E. Nkengfack, A.K. Waffo, G.A. Azebaze, Z.T. Fomum, M. Meyer, and B. Bodo A new 3-phenylcoumarin from root bark of Erythrina indica J Nat Prod 63 2000 855 856
27. A.K. Waffo, G.A. Azebaze, A.E. Nkengfack, S.T. Fomum, M. Meyer, and B. Bodo Indicanines D and C, two isoflavonoid derivatives from the root bark of Erythrina indica Phytochemistry 53 2000 981 985
28. D. Olmedo, R. Sancho, L.M. Bedoya, J.L. López-Pérez, E. Olmo, and E. Muñoz 3-Phenylcoumarins as inhibitors of HIV-1 replication Molecules 17 2012 9245 9257
29. K.V. Sashidhara, A. Kumar, M. Chatterjee, K.B. Rao, S. Singh, and A.K. Verma Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents Bioorg Med Chem Lett 21 2011 1937 1941
30. T. Tunali, A. Yarat, M. Bulut, and N. Emekli 6,7-Dihydroxy-3- phenylcoumarin inhibits thromboplastin induced disseminated intravascular coagulation Br J Haematol 126 2004 226 230
31. E. Quezada, G. Delogu, C. Picciau, L. Santana, G. Podda, and F. Borges Synthesis and vasorelaxant and platelet antiaggregatory activities of a new series of 6-halo-3-phenylcoumarins Molecules 15 2010 270 279
32. A.A. Marchi, M.S. Castilho, P.G.B. Nascimento, F.C. Archanjo, G. Del Ponte, and G. Oliva New 3-piperonylcoumarins as inhibitors of glycosomal glyceraldehyde-3-phosphate dehydrogenase (gGAPDH) from Trypanosoma cruzi Bioorg Med Chem 12 2004 4823 4833
33. M.J. Matos, C. Terán, Y. Pérez-Castillo, E. Uriarte, L. Santana, and D. Viña Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors J Med Chem 54 2011 7127 7137
34. M.J. Matos, L. Santana, E. Uriarte, G. Delogu, M. Corda, and M.B. Fadda New halogenated phenylcoumarins as tyrosinase inhibitors Bioorg Med Chem Lett 21 2011 3342 3345
35. K. Van Dyke, and V. Castranova Cellular chemiluminescence vol. 1 1987 CRC Press Boca Raton
36. H.G. Raj, V.S. Parmar, S.C. Jain, S. Goel, H. Poonam, and S. Malhotra Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part I: dioxygenated 4-methylcoumarins as superb antioxidant and radical scavenging agents Bioorg Med Chem 6 1998 833 839
37. Y.C. Chen, S.C. Shen, W.R. Lee, W.C. Hou, L.L. Yang, and T.J.F. Lee Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin and quercetin pentaacetate in RAW264.7 macrophages J Cell Biochem 82 2001 537 548
38. S. Kumar, B.K. Singh, N. Kalra, V. Kumar, A. Kumar, and A.K. Prasad Novel thiocoumarins as inhibitors of TNF-α induced ICAM-1 expression on human umbilical vein endothelial cells (HUVECs) and microsomal lipid peroxidation Bioorg Med Chem 13 2005 1605 1613
39. M.L. Vuotto, R. Miranda, A. Ritieni, A. Basile, L. Ricciardi, and R. Di Prisco Improvement of (+)-catechin inhibitory activity on human PMN respiratory burst by (+)-3-O-propionyl and (-)-3-O-valeryl substitution J Pharm Pharmacol 55 2003 399 405
40. 2 + in neutrophils Methods Enzymol 9 1996 591 606
41. J. El-Benna, P.M.C. Dang, and A. Perianin Peptide-based inhibitors of the phagocyte NADPH oxidase Biochem Pharmacol 80 2010 778 785
42. S.Y. Kim, K.-A. Moon, H.-Y. Jo, S. Jeong, S.-H. Seon, and E. Jung Anti-inflammatory effects of apocynin, an inhibitor of NADPH oxidase, in airway inflammation Immunol Cell Biol 90 2012 441 448
43. L.O. Regasini, J.C.R. Vellosa, D.H.S. Silva, M. Furlan, O.M.M. Oliveira, and N.M. Khalil Flavonols from Pterogyne nitens and their evaluation as myeloperoxidase inhibitors Phytochemistry 69 2008 1739 1744
44. L. Selloum, H. Djelili, L. Sebihi, and J. Arnhold Scavenger effect of flavonols on HOCl-induced luminol chemiluminescence Luminescence 19 2004 199 204
45. W. Bors, W. Heller, C. Michel, and M. Saran Flavonoids as antioxidants: determination of radical-scavenging efficiencies Methods Enzymol 186 1990 343 355
46. J.Z. Pedersen, C. Oliveira, S. Incerpi, V. Kumar, A.M. Fiore, and P. De Vito Antioxidant activity of 4-methylcoumarins J Pharm Pharmacol 59 2007 1721 1728
47. H. Opdahl, H.B. Benestad, and G. Nicolaysen Differences and similarities between human and rabbit neutrophil granulocyte responses in vitro: the effects of zymosan-activated plasma, phorbol myristate acetate and n-formyl-methionyl- leucyl-phenylalanine Acta Anaesthesiol Scand 31 1987 491 498
48. C.G. Cochrane, and D. Koffler Immune complex disease in experimental animals and man Adv Immunol 16 1973 185 264
49. Y.M. Lucisano, and B. Mantovani Lysosomal enzyme release from polymorphonuclear leukocytes induced by immune complexes of IgM and IgG J Immunol 132 1984 2015 2020
50. F.S. Paula, L.M. Kabeya, A. Kanashiro, A.S.G. Figueiredo, A.E.C.S. Azzolini, and S.A. Uyemura Modulation of human neutrophil oxidative metabolism and degranulation by extract of Tamarindus indica L. fruit pulp Food Chem Toxicol 47 2009 163 170
51. Y.M. Lucisano-Valim, L.M. Kabeya, A. Kanashiro, E.M.S. Russo-Carbolante, A.C.M. Polizello, and A.E.C.S. Azzolini A simple method to study the activity of natural compounds on the chemiluminescence of neutrophils upon stimulation by immune complex J Pharmacol Toxicol Methods 47 2002 53 58
52. J.M. Dypbukt, C. Bishop, W.M. Brooks, B. Thong, H. Eriksson, and A.J. Kettle A sensitive and selective assay for chloramines production by myeloperoxidase Free Radic Biol Med 39 2005 1468 1477