Inhibition of NF-κB and metalloproteinase-9 expression and secretion by parthenolide derivatives

被引:27
作者
Dell'Agli, Mario [1 ]
Galli, Germana V. [1 ]
Bosisio, Enrica [1 ]
D'Ambrosio, Michele [2 ]
机构
[1] Univ Milan, Dept Pharmacol Sci, I-20122 Milan, Italy
[2] Univ Trent, Chim Bioorgan Lab, I-38100 Trento, Italy
关键词
Metalloproteinase-9; Gene expression; Parthenolide; Sesquiterpenes; Parthenolide derivatives; NF-kappa B driven transcription; SESQUITERPENE LACTONES; MATRIX METALLOPROTEINASES; ACTIVATION; MATRIX-METALLOPROTEINASE-9; P65/NF-KAPPA-B; FEVERFEW; PATHWAY; ALPHA;
D O I
10.1016/j.bmcl.2009.02.080
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Semisynthetic derivatives of parthenolide (1) were tested on NF-kappa B driven transcription and metalloproteinase-9 (MMP-9) expression and secretion. The four membered ring compounds 5 and 6, obtained by acidic treatment of 1, exhibited a higher activity with respect to 1 in all the biological assays. Then an increased ability of the 5 and 6 to inhibit NF-kappa B driven transcription may lead to a down-regulation of MMP-9 expression and secretion. This work provides new details about the structural requisites for NF-kappa B inhibition. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1858 / 1860
页数:3
相关论文
共 23 条
[1]   Suppression of the nuclear factor-κB activation pathway by spice-derived phytochemicals -: Reasoning for seasoning [J].
Aggarwal, BB ;
Shishodia, S .
SIGNAL TRANSDUCTION PATHWAYS, CHROMATIN STRUCTURE, AND GENE EXPRESSION MECHANISMS AS THERAPEUTIC TARGETS, 2004, 1030 :434-441
[2]   Matrix metalloproteinases, inflammation and atherosclerosis: therapeutic perspectives [J].
Beaudeux, JL ;
Giral, P ;
Bruckert, E ;
Foglietti, MJ ;
Chapman, MJ .
CLINICAL CHEMISTRY AND LABORATORY MEDICINE, 2004, 42 (02) :121-131
[3]   Phase I dose escalation trial of feverfew with standardized doses of parthenolide in patients with cancer [J].
Curry, EA ;
Murry, DJ ;
Yoder, C ;
Fife, K ;
Armstrong, V ;
Nakshatri, H ;
O'Connell, M ;
Sweeney, CJ .
INVESTIGATIONAL NEW DRUGS, 2004, 22 (03) :299-305
[4]   A structure-activity study for the inhibition of metalloproteinase-9 activity and gene expression by analogues of gallocatechin-3-gallate [J].
Dell'Agli, M ;
Bellosta, S ;
Rizzi, L ;
Galli, G ;
Canavesi, M ;
Rota, F ;
Parente, R ;
Bosisio, E ;
Romeo, S .
CELLULAR AND MOLECULAR LIFE SCIENCES, 2005, 62 (23) :2896-2903
[5]   RAPID COLORIMETRIC ASSAY FOR CELL-GROWTH AND SURVIVAL - MODIFICATIONS TO THE TETRAZOLIUM DYE PROCEDURE GIVING IMPROVED SENSITIVITY AND RELIABILITY [J].
DENIZOT, F ;
LANG, R .
JOURNAL OF IMMUNOLOGICAL METHODS, 1986, 89 (02) :271-277
[6]   STIMULATION OF WITCHWEED GERMINATION BY SESQUITERPENE LACTONES - A STRUCTURE ACTIVITY STUDY [J].
FISCHER, NH ;
WEIDENHAMER, JD ;
RIOPEL, JL ;
QUIJANO, L ;
MENELAOU, MA .
PHYTOCHEMISTRY, 1990, 29 (08) :2479-2483
[7]   Antimycobacterial evaluation of germacranolides [J].
Fischer, NH ;
Lu, TS ;
Cantrell, CL ;
Castañeda-Acosta, J ;
Quijano, L ;
Franzblau, SG .
PHYTOCHEMISTRY, 1998, 49 (02) :559-564
[8]   Role of cysteine residues of p65/NF-κB on the inhibition by the sesquiterpene lactone parthenolide and-N-ethyl maleimide, and on its transactivating potential [J].
Garcia-Piñeres, AJ ;
Lindenmeyer, MT ;
Merfort, I .
LIFE SCIENCES, 2004, 75 (07) :841-856
[9]   Cysteine 38 in p65/NF-κB plays a crucial role in DNA binding inhibition by sesquiterpene lactones [J].
García-Piñeres, AJ ;
Castro, V ;
Mora, G ;
Schmidt, TJ ;
Strunck, E ;
Pahl, HL ;
Merfort, I .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (43) :39713-39720
[10]   Sesquiterpene lactones specifically inhibit activation of NF-κB by preventing the degradation of IκB-α and IκB-β [J].
Hehner, SP ;
Heinrich, M ;
Bork, PM ;
Vogt, M ;
Ratter, F ;
Lehmann, V ;
Schulze-Osthoff, K ;
Dröge, W ;
Schmitz, ML .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (03) :1288-1297