Dehydroxymethylepoxyquinomicin inhibits expression and production of inflammatory mediators in interleukin-1β-induced human chondrocytes

Cellular Physiology and Biochemistry

Volumn 25, Issue 4-5, 2010, Pages 543-550

  Cardile, Venera ^a   Frasca, Giuseppina ^a   Libra, Massimo ^a   Caggia, Silvia ^a   Umezawa, Kazuo ^b   Panico, Annamaria ^a   Malaponte, Grazia ^a  

^a UNIVERSITY OF CATANIA   (Italy)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Anti inflammatory effects; Cartilage; Chemokines; Cyclooxygenase; DHMEQ; Nitric oxide

Indexed keywords

CHEMOKINE; CYCLOOXYGENASE 2; DEHYDROXYMETHYLEPOXYQUINOMICIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERCELLULAR ADHESION MOLECULE 1; INTERLEUKIN 1BETA; INTERLEUKIN 8; MONOCYTE CHEMOTACTIC PROTEIN 1; NITRITE; RANTES;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARTILAGE CELL; CARTILAGE DEGENERATION; CARTILAGINOUS TISSUE; CONTROLLED STUDY; DRUG EFFECT; HUMAN; HUMAN CELL; INFLAMMATION; JOINT DEGENERATION; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN EXPRESSION;

EID: 77949920496     PISSN: 10158987     EISSN: None     Source Type: Journal    
DOI: 10.1159/000303058     Document Type: Article

References (45)

1. Novotny NM, Markel TA, Crisostomo PR, Meldrum DR: Differential IL-6 and VEGF secretion in adult and neonatal mesenchymal stem cells: role of NFkB. Cytokine 2008;43:215-219.
2. Sun XF, Zhang H: NFkB and NFkBI polymorphisms in relation to susceptibility of tumor and other diseases. Histol Histopathol 2007;22:1387-1398.
3. Suna S, Sakata Y, Sato H, Mizuno H, Nakatani D, Shimizu M, Usami M, Takashima S, Takeda H, Hori M.: Up-regulation of cell adhesion molecule genes in human endothelial cells stimulated by lymphotoxin alpha: DNA microarray analysis. J Atheroscler Thromb 2008;15:160-165.
4. van der Kraan PM, van den Berg, WB: Anabolic and destructive mediators in osteoarthritis. Curr Opinion Clin Nutr Metabolic Care 2000;3:205-211.
5. Geng Y, Valbracht J, Lotz M: Selective activation of mitogen-activated protein kinase subgroups c-Jun NH2 terminal kinase and p38 by IL-1 and TNF in human articular chondrocytes. J Clin Inv 1996;98:2425-2430.
6. Eder J: Tumor necrosis factor and interleukin 1 signalling: do MAPKK kinases connect it all? Trends Pharm Sci 1997;18:319-322.
7. Amin AR, Abramson SB: The role of nitric oxide in articular cartilage breakdown in osteoarthritis. Curr Opinion Rheumatol 1998;10:263-268.
8. Nedelec E, Abid A, Cipolletta C, Presle N, Terlain B, Netter P, Jouzeau J: Stimulation of cyclooxygenase-2-activity by nitric oxide-derived species in rat chondrocytes: lack of contribution to loss of cartilage anabolism. Biochem Pharmacol 2001;61:965-978.
9. Lopez-Collazo E, Hortelano S, Rojas A, Bosca L: Triggering of peritoneal macrophages with IFN-alpha/beta attenuates the expression of inducible nitric oxide synthase through a decrease in NF-kB activation. J Immunol 1998;60:2889-2895.
10. Vera M, Taylor B, Wang Q, Shapiro RA, Billiarb TR, Geller DA: Dexamethasone suppresses iNOS gene expression by upregulating I-kBa and inhibiting NF-kB. Am J Physiol 1997;273:G1290-1296.
11. Newton R, Kuitert LM, Bergmann M, Adcock IM, Barnes PJ: Evidence for involvement of NF-kB in the transcrip-tional control of COX-2 gene expression by IL-1β. Biochem Biophys Res Commun 1997;237:28-32.
12. Ana MB, Mara P, Soraya L: Ethanol-induced iNOS and COX-2 expression in cultured astrocytes via NF-kB. Neuroreport 2004;15:681-683.
13. Matsumoto N, Ariga A, To-e S Nakamura H, Agata N, Hirano S, Inoue J, Umezawa K: Synthesis of NF-kappaB activation inhibitors derived from epoxyquinomicin C. Bioorg Med Chem Lett 2000;10:865-869.
14. Ariga A, Namekawa J, Matsumoto N, Inoue J, Umezawa K: Inhibition of tumor necrosis factor-alpha-induced nuclear translocation and activation of NF-kappaB by dehydroxymethylepoxy-quinomicin. J Biol Chem 2002;277:24625-24630.
15. Liang MC, Bardhan S, Pace EA, Rosman D, Beutler JA, Porco JA, Gilmore TD: Inhibition of transcription factor NF-kB signaling proteins IKKâ and p65 through specific cysteine residues by epoxyqui-none A monomer: Correlation with its anti-cancer cell growth activity. Biochem Pharm 2006;71:634-645.
16. Miyajima A, Kosaka T, Seta K, Asno T, Umezawa K, Hayakawa M: Novel nuclear factor kappa B activation inhibitor prevents inflammatory injury in unilateral ureteral obstruction. J Urol 2003;169:1559-1563.
17. Kikuchi E, Horiguchi Y, Nakashima J, Kuroda K, Oya M, Ohigashi T, Takahashi N, Shima Y, Umezawa K, Murai M: Suppression of hormone-refractory prostate cancer by a novel nuclear kappaB inhibitor in nude mice. Cancer Res 2003;63:107-110.
18. Horiguchi Y, Kuroda K, Nakashima J, Murai M, Umezawa K: Antitumor effect of a novel nuclear factor-kappaB activation inhibitor in bladder cancer cells. Expert Rev Anticancer Ther 2003;3:793-798.
19. Panico AM, Cardile V, Garufi, F, Puglia C, Bonina F, Ronsisvalle G: Effect of hyaluronic acid and polysaccharides from Opuntia ficus indica (L.) cladodes on the metabolism of human chondrocyte cultures. J Ethnopharmacol 2007;111:315-321.
20. Adolphe M, Benoit B: Cultere de chondrocyte articulaires humains. Interet en pharmacotoxicologie. Ann Pharmaceutiques Francaises 1994;52:177-183.
21. Green LC, Wagner DA, Glogowski J, Reis DJ: Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal Biochem 1982;126:131-138.
22. Brazel D, Nakanishi S, Oster W: Interleukin-1, characterization of the molecule, functional activity, and clinical implications. Biotech Ther 1991;2:241-267.
23. Nouri AM, Panayi GS, Goodman SM: Cytokines and the chronic inflammation of rheumatic disease. II. The presence of interleukin-2 in synovial fluids. Clin Exp Immunol 1984;55:295-302.
24. Wood DD, Ihrie EJ, Dinarello CA, Cohen P: Isolation of an interleukin-1-like factor from human joint effusions. Arthritis Rheum 1983;26:975-983.
25. Chaicharoenpong C, Kato K, Umezawa K: Synthesis and structure-activity relationship of dehydroxymethylepoxyquinomicin analogues as inhibitors of NF-kappaB functions. Bioorg Med Chem 2002;10:3933-3939.
26. Taskiran D, Stefanovic-Racic M, Georgescu H, Evans CH: Nitric oxide mediates suppression of cartilage proteoglycan synthesis by interleukin-1. Biochem Biophys Res Commun 1994;200:142-148.
27. Santos LL, Morand EF, Yang Y, Hutchinson P, Holdsworth SR: Suppression of adjuvant arthritis and synovial macrophage inducible nitric oxide by N-iminoethyl-L-ornithine, a nitric oxide synthase inhibitor. Inflammation 1997;21:299-311.
28. Stefanovic-Racic M, Meyers K, Meschter C, Coffey JW, Hoffman RA, Evans CH: N-monomethyl-L-arginine, an inhibitor of NOS, suppresses the development of adjuvant arthritis in rats. Arthritis Rheum 1994;37:1062-1069.
29. Linn SC, Morelli PJ, Edry I, Cottongim SE, Szabo C, Salzman AL: Transcripti-onal regulation of human inducible nitric oxide synthase gene in an intestinal epithelial cell line. Am J Physiol 1997;272:G1499-1508.
30. Spitsin, S V, Koprowski H, Michaels FH: Characterization and functional analysis of the human inducible nitric oxide synthase gene promoter. Mol Med 1996;2:226-235.
31. Diaz-Guerra MJM, Velasco M, Martin-Sanz P, Bosca L: Evidence for common mechanisms in the transcriptional control of type II nitric oxide synthase in isolated hepatocytes. Requirement of NF-kappaB activation after stimulation with bacterial cell wall products and phorbol esters. J Biol Chem 1996;271:30114-30120.
32. Forstermann U, Kleinert H: Nitric oxide synthase: Expression and expressional control of the three isoforms. Naunyn-Schmiedeberg's Arch Pharmacol 1995;352:351-364.
33. Xie QW, Kashiwabara Y, Nathan C: Role of transcription factor NF-kB/Rel in induction of nitric oxide synthase. J Biol Chem 1994;269:4705-4708.
34. Park JY, Pillinger MH, Abramson SB: Prostaglandin E2 synthesis and secretion: the role of PGE2 synthases. Clin Immunol 2006;119:229-240.
35. Martel-Pelletier J, Pelletier J P, Fahmi H: Cyclooxygenase-2 and prostaglandins in articular tissues. Semin Arthritis Rheum 2003;33:155-167.
36. Largo R, Alvarez-Soria MA, Diez-Ortego I, Calvo E, Sanchez-Pernaute O, Egido J, Herrero-Beaumont G: Glucosamine inhibits IL-1beta-induced NFkappaB activation in human osteoarthritic chondrocytes, Osteoarthritis Cartilage 2003;11:290-298.
37. Suzuki E, Sugiyama C, Umezawa K: Inhibition of inflammatory mediator secretion by (-)-DHMEQ in mouse bone marrow-derived macrophages. Biomed Pharmacother 2009;63:351-358.
38. Jobin C, Holt L, Bradham CA, Streetz K, Brenner DA, Sartor RB: TNF receptor-associated factor-2 is involved in both IL-1 beta and TNF-alpha signaling cascades leading to NF-kappa B activation and IL-8 expression in human intestinal epithelial cells. J Immunol 1999;162:4447-4454.
39. Jobin C, Hellerbrand C, Licato LL, Brenner DA, Sartor RB: Mediation by NF-kappa B of cytokine induced expression of intercellular adhesion molecule 1 (ICAM-1) in an intestinal epithelial cell line, a process blocked by proteasome inhibitors. Gut 1998;42:779-787.
40. Chandrasekharam N, Nagineni R, Krishnan K, Detrick B, Hooks JJ: Inflammatory cytokines induce intercellular adhesion molecule-1 (ICAM-1) mRNA synthesis and protein secretion by human retinal pigment epithelial cell cultures. Cytokine 1996;8:622-630.
41. Dijkgraaf LC, de Bont LG, Boering G, Liem RS: The structure, biochemistry, and metabolism of osteoarthritic cartilage: a review of the literature. J Oral Maxillofacial Surg 1995;53:1182-1192.
42. Elford PR, Cooper PH: Induction of neutrophil-mediated cartilage degradation by IL-8 Arthritis Rheum 1991;34:325-331.
43. Kumar R, Yoneda J, Bucana CD, Fildler IJ: Regulation of distinct steps of angiogenesis by different angiogenic molecules. Int J Oncol 1998;12:749-757.
44. Baggiolini M: Chemokines and leukocyte traffic. Nature 1998;392:565-568.
45. Alaaeddine N, Olee T, Hashimoto S, Creighton-Achermann L, Lotz M: Production of the chemokine RANTES by articular chondrocytes and role incartilage degradation. Arthritis Rheum 2001;44:1633-1643.