Design, synthesis, and biological evaluation of curcumin analogues as multifunctional agents for the treatment of Alzheimer's disease

被引：96

作者：

Chen, Shang-Ying ^{[1
]}

Chen, Yuan ^{[1
]}

Li, Yan-Ping ^{[1
]}

Chen, Shu-Han ^{[1
]}

Tan, Jia-Heng ^{[1
]}

Ou, Tian-Miao ^{[1
]}

Gu, Lian-Quan ^{[1
]}

Huang, Zhi-Shu ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2011年 / 19卷 / 18期

关键词：

Curcumin analogue; Anti-Alzheimer agent; A beta aggregation; Oxidative stress; Metal chelating; BETA FIBRIL FORMATION; OXIDATIVE STRESS HYPOTHESIS; TARGETING A-BETA; AGGREGATION INHIBITORS; HYDROGEN-PEROXIDE; AMYLOID FIBRILS; IN-VITRO; PEPTIDE; DERIVATIVES; TOXICITY;

D O I：

10.1016/j.bmc.2011.07.033

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

A series of novel curcumin analogues were designed, synthesized, and evaluated as potential multifunctional agents for the treatment of AD. The in vitro studies showed that these compounds had better inhibitory properties against A beta aggregation than curcumin. Superior anti-oxidant properties (better than the reference compound Trolox) of these compounds were observed by the oxygen radical absorbance capacity (ORAC) method and a cell-based assay using DCFH-DA as a probe. In addition they were able to chelate metals such as iron and copper and decrease metal-induced A beta aggregation. The structure-activity relationships were discussed. The results suggested that our curcumin analogues could be selected as multifunctional agents for further investigation of AD treatment. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5596 / 5604

页数：9

共 42 条

[1]

Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents [J].

Adams, BK ;

Ferstl, EM ;

Davis, MC ;

Herold, M ;

Kurtkaya, S ;

Camalier, RF ;

Hollingshead, MG ;

Kaur, G ;

Sausville, EA ;

Rickles, FR ;

Snyder, JP ;

Liotta, DC ;

Shoji, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (14) :3871-3883

[2]

Baum L, 2004, J ALZHEIMERS DIS, V6, P367

[3]

Multi-target-directed drug design strategy: From a dual binding site acetylcholinesterase inhibitor to a trifunctional compound against Alzheimer's disease [J].

Bolognesi, Maria Laura ;

Cavalli, Andrea ;

Valgimigli, Luca ;

Bartolini, Manuela ;

Rosini, Michela ;

Andrisano, Vincenza ;

Recanatini, Maurizio ;

Melchiorre, Carlo .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (26) :6446-6449

[4]

Novel class of quinone-bearing polyamines as multi-target-directed ligands to combat Alzheimer's disease [J].

Bolognesi, Maria Laura ;

Banzi, Rita ;

Bartolini, Manuela ;

Cavalli, Andrea ;

Tarozzi, Andrea ;

Andrisano, Vincenza ;

Minarini, Anna ;

Rosini, Michela ;

Tumiatti, Vincenzo ;

Bergamini, Christian ;

Fato, Romana ;

Lenaz, Giorgio ;

Hrelia, Patrizia ;

Cattaneo, Antonino ;

Recanatini, Maurizio ;

Melchiorre, Carlo .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (20) :4882-4897

[5]

Poly-N-methylated Amyloid β-Peptide (Aβ) C-Terminal Fragments Reduce Aβ Toxicity in Vitro and in Drosophila melanogaster [J].

Bose, Partha Pratim ;

Chatterjee, Urmimala ;

Nerelius, Charlotte ;

Govender, Thavendran ;

Norstrom, Thomas ;

Gogoll, Adolf ;

Sandegren, Anna ;

Gothelid, Emmanuelle ;

Johansson, Jan ;

Arvidsson, Per I. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (24) :8002-8009

[6]

Bis-styrylpyridine and bis-styrylbenzene derivatives as inhibitors for Aβ fibril formation [J].

Byeon, Seong Rim ;

Lee, Ji Hoon ;

Sohn, Ji-Hoon ;

Kim, Dong Chan ;

Shin, Kye Jung ;

Yoo, Kyung Ho ;

Mook-Jung, Inhee ;

Lee, Won Koo ;

Kim, Dong Jin .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (05) :1466-1470

[7]

Aminostyrylbenzofuran derivatives as potent inhibitors for Aβ fibril formation [J].

Byun, Ji Hun ;

Kim, HyeYun ;

Kim, YoungSoo ;

Mook-Jung, Inhee ;

Kim, Dong Jin ;

Lee, Won Koo ;

Yoo, Kyung Ho .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (20) :5591-5593

[8]

Design of small molecules that target metal-Aβ species and regulate metal-induced Aβ aggregation and neurotoxicity [J].

Choi, Jung-Suk ;

Braymer, Joseph J. ;

Nanga, Ravi P. R. ;

Ramamoorthy, Ayyalusamy ;

Lim, Mi Hee .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (51) :21990-21995

[9]

Drug therapy - Alzheimer's disease [J].

Cummings, JL .

NEW ENGLAND JOURNAL OF MEDICINE, 2004, 351 (01) :56-67

[10]

Preliminary studies of a novel bifunctional metal chelator targeting Alzheimer's amyloidogenesis [J].

Dedeoglu, A ;

Cormier, K ;

Payton, S ;

Tseitlin, KA ;

Kremsky, JN ;

Lai, L ;

Li, XH ;

Moir, RD ;

Tanzi, RE ;

Bush, AI ;

Kowall, NW ;

Rogers, JT ;

Huang, XD .

EXPERIMENTAL GERONTOLOGY, 2004, 39 (11-12) :1641-1649

← 1 2 3 4 5 →