Synthesis and biological evaluation of curcuminoid pyrazoles as new therapeutic agents in inflammatory bowel disease: Effect on matrix metalloproteinases

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 3, 2009, Pages 1290-1296

  Claramunt, R M ^a   Bouissane, L ^a   Cabildo, M P ^a   Cornago, M P ^a   Elguero, J ^b   Radziwon, A ^c   Medina, C ^c  

^a UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^c TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Caco 2 cells; Crohn's disease; Curcumin; Gelatinases; Inflammatory bowel disease; Matrix metalloproteinases; Pyrazole; Ulcerative colitis

Indexed keywords

3(5)[BETA (4 HYDROXY 3 METHOXYPHENYL)ETHENYL] 4,5(3) DIMETHYL 1H PYRAZOLE; 3(5)[BETA (4 HYDROXY 3 METHOXYPHENYL)ETHENYL] 5(3) METHYL 1H PYRAZOLE; 3,5 BIS[BETA (4 HYDROXY 3 METHOXYPHENYL)ETHENYL] 1H PYRAZOLE; CURCUMIN; GELATINASE B; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DOWN REGULATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENTERITIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; INTESTINE EPITHELIUM CELL; REACTION ANALYSIS; STRUCTURE ANALYSIS;

CACO-2 CELLS; CURCUMIN; GELATINASES; HUMANS; INFLAMMATORY BOWEL DISEASES; INTERLEUKIN-1BETA; MATRIX METALLOPROTEINASE 9; MATRIX METALLOPROTEINASES; PYRAZOLES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 58949100279     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.12.029     Document Type: Article

References (51)

1. Fiocchi C. Am. J. Physiol. Gastrointest. Liver Physiol. 273 (1997) G769
2. Podolsky D.K. N. Engl. J. Med. 34 (2002) 417
3. Baugh M.D., Perry M.J., Hollander A.P., Davies D.R., Cross S.S., Lobo A.J., Taylor C.J., and Evans G.S. Gastroenterology 117 (1999) 814
4. Heuschkel R.B., MacDonald T.T., Monteleone G., Bajaj-Elliott M., Smith J.A.W., and Pender S.L. Gut 47 (2000) 57
5. Kirkegaard T., Hansen A., Bruun E., and Brynskov J. Gut 53 (2004) 701
6. Medina C., and Radomski M.W. J. Pharmacol. Exp. Ther. 318 (2006) 933
7. Von Lampe B., Barthel B., Coupland S.E., Riecken E.O., and Rosewicz S. Gut 47 (2000) 63
8. Di Sebastiano P., di Mola F.F., Artese L., Rossi C., Mascetta G., Pernthaler H., and Innocenti P. Digestion 63 (2001) 234
9. Medina C., Santana A., Llopis M., Paz-Cabrera M.C., Antolin M., Mourelle M., Guarner F., Vilaseca J., Gonzalez C., Salas A., Quintero E., and Malagelada J.-R. Inflamm. Bowel Dis. 11 (2005) 99
10. Medina C., Santana A., Paz M.C., Diaz F., Farre E., Salas A., Radomski M.W., and Quintero E. J. Leukocyte Biol. 79 (2006) 954
11. Medina C., Videla S., Radomski A., Radomski M., Antolin M., Guarner F., Vilaseca J., Salas A., and Malagelada J.-R. Scand. J. Gastroenterol. 36 (2001) 1314
12. Medina C., Videla S., Radomski A., Radomski M.W., Antolin M., Guarner F., Vilaseca J., Salas A., and Malagelada J.-R. Am. J. Physiol. Gastrointest. Liver Physiol. 284 (2003) G116
13. Jovanovic S.V., Steenken S., Boone C.W., and Simic M.G. J. Am. Chem. Soc. 121 (1999) 9677
14. Masuda T., Hidaka K., Shinohara A., Maekawa T., Takeda Y., and Yamaguchi H. J. Agric. Food Chem. 47 (1999) 71
15. Weber W.M., Hunsaker L.A., Abcouwer S.F., Deck L.M., and Vander Jagt D.L. Bioorg. Med. Chem. 13 (2005) 3811
16. Brouet I., and Ohshima H. Biochem. Biophys. Res. Commun. 206 (1995) 533
17. Arbiser J.L., Klauber N., Rohan R., van Leeuwen R., Huang M.T., Fisher C., Flynn E., and Byers H. Mol. Med. 4 (1998) 376
18. Jacob A., Wu R., Zhou M., and Wang P. PPAR Res. (2007) 89369
19. Sharma R.A., Ireson C.R., Verschoyle R.D., Hill K.A., Williams M.L., Leuratti C., Manson M.M., Marnett L.J., Steward W.P., and Gescher A. Clin. Cancer Res. 7 (2001) 1452
20. Füllbeck M., Huang X., Dumdey R., Frommel C., Dubiel W., and Preissner R. BMC Cancer 5 (2005) 97
21. Siwak D.R., Shishodia S., Aggarwal B.B., and Kurzrock R. Cancer 104 (2005) 879
22. Egan M.E., Pearson M., Weiner S.A., Rajendran V., Rubin D., Glockner-Pagel J., Canny S., Du K., Lukacs G.L., and Caplan M.J. Science 304 (2004) 600
23. Sundaryono A., Nourmamode A., Gardrat C., Fritsch A., and Castellan A. J. Mol. Struct. 649 (2003) 177
24. Zsila F., Bikadi Z., and Simonyi M. Org. Biomol. Chem. 2 (2004) 2902
25. Kong L., Priyadarsini I., and Zhang H.-Y. J. Mol. Struct. (TheoChem) 684 (2004) 111
26. Kim G.-Y., Kim K.-H., Lee S.-H., Yoon M.-S., Lee H.-J., Moon D.-O., Lee C.-M., Ahn S.-C., Park Y.C., and Park Y.-M. J. Immunol. 174 (2005) 8116
27. Aggarwal B.B., Kumar A., Aggarwal M.S., and Shishodia S. In: Bagchi D., and Preuss H.G. (Eds). Phytochemicals in Cancer Chemoprevention (2005), CRC Press, Boca Raton 349
28. Maheshwari R.K., Singh A.K., Gaddipati J., and Srimal R.C. Life Sci. 78 (2006) 2081
29. In: Aggarwal B.B., Shishodia S., and Surh Y.-J. (Eds). The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease (2007), Springer Publishers, New York
30. Wright J.S. J. Mol. Struct. (TheoChem) 591 (2002) 207
31. Jayaprakasha G.K., Jaganmohan Rao L., and Sakariah K.K. Food Chem. 98 (2006) 720
32. Flynn D.L., Belliotti T.R., Boctor A.M., Connor D.T., Kostlan C.R., Nies D.E., Ortwine D.F., Schrier D.J., and Sircar J.C. J. Med. Chem. 34 (1991) 518
33. Shim J.S., Kim D.H., Jung H.J., Kim J.H., Lim D., Lee S.-K., Kim K.-W., Ahn J.W., Yoo J.-S., Rho J.-R., Shin J., and Kwon H.J. Bioorg. Med. Chem. 10 (2002) 2439
34. Ishida J., Ohtsu H., Tachibana Y., Nakanishi Y., Bastow K.F., Nagai M., Wang H.-K., Itokawa H., and Lee K.-H. Bioorg. Med. Chem. 10 (2002) 3481
35. Ohtsu H., Xiao Z., Ishida J., Nagai M., Wang H.K., Itokawa H., Su C.Y., Shih C., Chiang T., Chang E., Lee Y.F., Tsai M.Y., Chang C., and Lee K.H. J. Med. Chem. 45 (2002) 5037
36. Selvam C., Jachak S.M., Thilagavathi R., and Chakraborti A.K. Bioorg. Med. Chem. Lett. 15 (2005) 1793
37. Narlawar R., Baumann K., and Schubenel R. Neurodegener Dis. 4 (2007) 88
38. Narlawar R., Pickhardt M., Leuchtenberger S., Baumann K., Krause S., Dyrks T., Weggen S., Mandelkow E., and Schmidt E. ChemMedChem 3 (2008) 65
39. Levin J.I., Gu Y., Nelson F.C., Zask A., DiJoseph J.F., Sharr M.A., Sung A., Jin G., Cowling R., Chanda P., Cosmi S., Hsiao C.-L., Edris W., Wilhelm J., Killar L.M., and Skotnicki J.S. Bioorg. Med. Chem. Lett. 11 (2001) 239
40. Shishodia S., Koul D., and Aggarwal B.B. J. Immunol. (2004) 2011
41. Donnini S., Monti M., Castagnini C., Solito R., Botta M., Schenone S., Giachetti A., and Ziche M. Int. J. Cancer 120 (2007) 995
42. Cornago M.P., Cabildo M.P., Claramunt R.M., Bouissane L., Pinilla E., Torres M.R., and Elguero J. New J. Chem. 33 (2009) 125
43. Castaneda F.E., Walia B., Vijay-Kumar M., Patel N.R., Roser S., Kolachala V.L., Rojas M., Wang L., Oprea G., Garg P., Gewirtz A.T., Roman J., Merlin D., and Sitaraman S.V. Gastroenterology 129 (2005) 1991
44. Santana A., Medina C., Paz-Cabrera M., Díaz-Gonzalez F., Farre E., Salas A., Radomski M.W., and Quintero E. World J. Gastroenterol. 12 (2006) 6464
45. Gan X., Wong B., Wright S.D., and Cai T.-Q. J. Interferon Cytokine Res. 21 (2001) 93
46. Huhtala P., Tuuttila A., Chow L.T., Lohi J., Keski-Oja J., and Tryggvason K. J. Biol. Chem. 266 (1991) 16485
47. Huhtala P., Eddy R.L., Fan Y.S., Byers M.G., Shows T.B., and Tryggvason K. Genomics 6 (1990) 554
48. Shakibaei M., John T., Schulze-Tanzil G., Lehmann I., and Mobasheri A. Biochem. Pharmacol. 73 (2007) 1434
49. Saja K., Babu M.S., Karunagaran D., and Sudhakaran P.R. Int. Immunopharmacol. 7 (2007) 1659
50. Berger S., and Braun S. In 200 More NMR Experiments: A Practical Course (2004), J Wiley & Sons, New York
51. Payton F., Sandusky P., and Alworth W.L. J. Nat. Prod. 70 (2007) 143