5-Arylidene-4-thiazolidinone derivatives active as antidegenerative agents on human chondrocyte cultures

Medicinal Chemistry

Volumn 9, Issue 1, 2013, Pages 84-90

  Panico, Annamaria ^a   MacCari, Rosanna ^b   Cardile, Venera ^a   Crascí, Lucia ^a   Ronsisvalle, Simone ^a   Ottanà, Rosaria ^b  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

5 Arylidene 2 phenylimino 4 thiazolidinones; 5 Arylidene 4 thiazolidinones; Anti inflammatory activity; Antidegenerative activity; Glycosaminoglycans; Human chondrocytes; Matrix metalloproteinase 13; Nitric oxide

Indexed keywords

4 THIAZOLIDINONE DERIVATIVE; ANTIINFLAMMATORY AGENT; COLLAGENASE 3; INTERLEUKIN 1BETA; NITRIC OXIDE;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CARTILAGE CELL; CARTILAGE DEGENERATION; CONTROLLED STUDY; DRUG SCREENING; ENZYME INHIBITION; HUMAN; HUMAN CELL; OSTEOARTHRITIS; PRIORITY JOURNAL;

EID: 84874037212     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340613804488378     Document Type: Article

References (22)

1. Flugge, L.A.; Miller-Deist, L.A.; Petillo, P.A. Towards a molecular understanding of arthritis. Chemistry & Biology, 1999, 6, 157-166.
2. Moulton, P.J. Inflammatory joint disease: the role of cytokines, cyclooxygenases and reactive oxygen species. British J. Biomed. Sci., 1996, 5, 3317-324.
3. Cipolletta, C.; Jouzeau, J.Y.; Gegout-Pottie, P.; Presle, N.; Bordji, K.; Netter, P.; Terlain, B. Modulation of IL-1-induced cartilage injury by NO synthase inhibitors: a comparative study with rat chondrocytes and cartilage entities. British J. Pharm., 1998, 124, 1719-1727.
4. Srivastava, S.K., Yadav, U.C.S.; Reddy, A.B.M.; Saxena, A.; Tammali, R.; Shoeb, M.; Ansari, N.H.; Bhatnagar, A.; Petrash, M.J.; Srivastava, S.; Ramana, K.V. Aldose reductase inhibitor suppresses oxidative stress-induced inflammatory disorders. Chem.-Biol. Interact., 2011, 191, 330-338.
5. Srivastava, S.K.,; Ramana, K.V. Focus on molecules: nuclear factor-kappaB. Exp. Eye Res., 2009, 88, 2-3.
6. Mclnnes, I.B.; Leung, B.E.; Field, M.; Wei, X.Q.; Huang, F.P.; Sturrock, R.D.; Kinninmonthfl, A.; Weidner, J.; Mumford, R.; Liew, F.Y. Production of nitric oxide in the synovial membrane of rheumatoid and osteoarthritis patients. J. Exp. Med., 1996, 184, 1519-1524.
7. Iannone, F.; Lapadula, G. The pathophysiology of osteoarthritis. Aging Clin. Exp. Res., 2003, 15, 364-372.
8. Pelletier, J.P.; Fernandes, J.C.; Jovanovic, D.V.; Reboul, P.; Martel-Pelletier, J. Chondrocyte death in experimental osteoarthritis is mediated by MEK 1/2 and p38 pathways: role of cyclooxygenase-2 and inducible nitric oxide synthase. J. Rheumatol., 2001, 28, 2509-2519.
9. Forsyth, C.B.; Cole, A.; Murphy, G.; Bienias, J.L.; Loeser, R.F. Increased matrix metalloproteinase-13 production with aging by human articular chondrocytes in response to catabolic stimuli. J. Gerontol. A Biol. Sci. Med. Sci., 2005, 60, 1118-1124.
10. Ottanà, R.; Maccari, R.; Barreca, M.L.; Bruno, G.; Rotondo, A.; Rossi, A.; Chiricosta, G.; Di Paola, R.; Sautebin, L.; Cuzzocrea, S.; Vigorita, M.G. 5-Arylidene-2-imino-4-thiazolidinones: design and synthesis of novel anti-inflammatory agents. Bioorg. Med. Chem., 2005, 13, 4243-4252.
11. Ottanà, R.; Maccari, R.; Ciurleo, C.; Vigorita, M.G.; Panico, A.M.; Cardile, V.; Garufi, F.; Ronsisvalle, S. Synthesis and in vitro evaluation of 5-arylidene-3-hydroxyalkyl-2-phenylimino-4-thiazolidinones with antidegenerative activity on human chondrocyte cultures. Bioorg. Med. Chem., 2007, 15, 7618-7625.
12. Maccari, R.; Paoli, P.; Ottanà, R.; Jacomelli, M.; Ciurleo, R.; Manao, G.; Steindl, T.; Langer, T.; Vigorita, M.G.; Camici, G. 5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases. Bioorg. Med. Chem., 2007, 15, 5137-5149.
13. Ottanà, R.; Maccari, R.; Ciurleo, R.; Paoli, P.; Jacomelli, M.; Manao, G.; Camici, G.; Laggner, C.; Langer, T. 5-Arylidene-2-phenylimino-4- thiazolidinones as PTP1B and LMW-PTP inhibitors. Bioorg. Med. Chem., 2009, 17, 1928-1937.
14. Bruno, G.; Costantino, L.; Curinga, C.; Maccari, R.; Monforte, F.; Nicolò, F.; Ottanà, R.; Vigorita, M.G. Synthesis and aldose reductase inhibitory activity of 5-arylidene-2,4-thiazolidinediones. Bioorg. Med. Chem., 2002, 10, 1077-1084.
15. Maccari, R.; Ottanà, R.; Curinga, C.; Vigorita, M.G.; Rakowitz, D.; Steindl, T.; Langer, T. Structure-activity relationships and molecular modelling of 5-arylidene-2,4-thiazolidinediones active as aldose reductase inhibitors. Bioorg. Med. Chem., 2005, 13, 2809-2823.
16. Li, J.J.; Nahra, J.; Johnson, A.R.; Bunker, A.; O'Brien, P.; Yue, W.S.; Ortwine, D.F.; Man, C.F.; Baragi, V.; Kilgore, K.; Dyer, R.D.; Han, H.K. Quinazolinones and pyrido[3,4-d]pyrimidin-4-ones as orally active and specific matrix metalloproteinase-13 inhibitors for the treatment of osteoarthritis. J. Med. Chem., 2008, 51, 835-841.
17. Verma, R.P.; Hansch, C. Matrix metalloproteinases (MMPs): chemical-biological functions and (Q)SARs. Bioorg. Med. Chem., 2007, 15, 2223-2268.
18. Bursavich, M.G.; Gilbert, A.M.; Lombardi, S.; Georgiadis, K.E.; Reifenberg, E.; Flannery, C.R.; Morris, E.A. Synthesis and evaluation of aryl thioxothiazolidinone inhibitors of ADAMTS-5 (Aggrecanase-2). Bioorg. Med. Chem. Lett., 2007, 17, 1185-1188.
19. Bertini, I.; Calderone, V.; Fragai, M.; Giachetti, A.; Loconte, M.; Luchinat, C.; Maletta, M.; Nativi, C.; Yeo, K.J. Exploring the subtleties of drug-receptor interactions: the case of matrix metalloproteinases. J. Am. Chem. Soc., 2007, 129, 2466-2475.
20. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods., 1983, 65, 55-63.
21. Green, L.C.; Wagner, D.A.; Glogowski, J.; Skipper, P.L.; Wishnok, J.S.; Tannenbaum, S.R. Analysis of nitrate, nitrite, and [15N]nitrate in biological fluids. Anal. Biochem., 1982, 126, 131-138.
22. Farndale, R.W.; Sayers, C.A.; Barrett, A.J. A Direct spectrophotometric microassay for sulfated glycosaminoglycans in cartilage cultures. Connect. Tissue Res., 1982, 9, 247-248.