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

R M Claramunt; L Bouissane; M P Cabildo; M P Cornago; J Elguero; A Radziwon; C Medina

doi:10.1016/j.bmc.2008.12.029

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

Bioorg Med Chem. 2009 Feb 1;17(3):1290-6. doi: 10.1016/j.bmc.2008.12.029. Epub 2009 Jan 6.

Authors

R M Claramunt¹, L Bouissane, M P Cabildo, M P Cornago, J Elguero, A Radziwon, C Medina

Affiliation

¹ Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain. rclaramunt@ccia.uned.es

PMID: 19128977
DOI: 10.1016/j.bmc.2008.12.029

Abstract

Seven N-unsubstituted curcuminoid pyrazoles have been synthesized from the corresponding beta-diketones (including curcumin). We evaluated the possibility of curcuminoid pyrazoles regulating the activity of matrix metalloproteinases (MMPs) by human intestinal epithelial cells in vitro. Zymographic analysis revealed that three compounds significantly down-regulated MMP-9 activity on inflammation-induced intestinal epithelial cells, making them original candidates for the treatment of inflammatory bowel disease (IBD).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Caco-2 Cells
Curcumin / chemical synthesis
Curcumin / chemistry
Curcumin / pharmacology*
Gelatinases / metabolism
Humans
Inflammatory Bowel Diseases / drug therapy
Inflammatory Bowel Diseases / enzymology*
Interleukin-1beta / metabolism
Matrix Metalloproteinase Inhibitors*
Pyrazoles / chemical synthesis
Pyrazoles / chemistry
Pyrazoles / pharmacology*
Tumor Necrosis Factor-alpha / metabolism

Substances

Interleukin-1beta
Matrix Metalloproteinase Inhibitors
Pyrazoles
Tumor Necrosis Factor-alpha
Gelatinases
Curcumin