Synthesis of indirubin-N′-glycosides and their anti-proliferative activity against human cancer cell lines

被引：52

作者：

Libnow, Stefanie ^{[1
]}

Methling, Karen ^{[2
]}

Hein, Martin ^{[1
]}

Michalik, Dirk ^{[3
]}

Harms, Manuela ^{[2
]}

Wende, Kristian ^{[2
]}

Flemming, Anke ^{[1
]}

Koeckerling, Martin ^{[1
]}

Reinke, Helmut ^{[1
]}

Bednarski, Patrick J. ^{[2
]}

Lalk, Michael ^{[2
]}

Langer, Peter ^{[1
,3
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Ernst Moritz Arndt Univ Greifswald, Inst Pharm, D-17487 Greifswald, Germany

[3] Univ Rostock, Leibniz Inst Katalyse eVan, D-18059 Rostock, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2008年 / 16卷 / 10期

关键词：

anti-proliferative activity; carbohydrates; N-heterocycles; indirubin;

D O I：

10.1016/j.bmc.2008.04.003

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

The first indirubin-N'-glycosides were prepared based on reactions of isatin-N'-glycosides with indoxyls. The products show a significant anti-proliferative activity against various human cancer cell lines. Good results were observed for an indirubin-N'- mannoside which was shown to have medium to high anti-proliferative activity against all investigated cell lines. The highest activities and selectivities against the MCF-7 breast cancer cell line were observed for indirubin-N'-rhamnosides. (C) 2008 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5570 / 5583

页数：14

相关论文

共 33 条

[1]

Indirubin and indigo are potent aryl hydrocarbon receptor ligands present in human urine [J].

Adachi, J ;

Mori, Y ;

Matsui, S ;

Takigami, H ;

Fujino, J ;

Kitagawa, H ;

Miller, CA ;

Kato, T ;

Saeki, K ;

Matsuda, T .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (34) :31475-31478

[2]

Synthesis of novel 5-substituted indirubins as protein kinases inhibitors [J].

Beauchard, Anne ;

Ferandin, Yoan ;

Frere, Stephane ;

Lozach, Olivier ;

Blairvacq, Melina ;

Meijer, Laurent ;

Thiery, Valerie ;

Besson, Thierry .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (18) :6434-6443

[3]

Correlations between the activities of 19 anti-tumor agents and the intracellular glutathione concentrations in a panel of 14 human cancer cell lines:: comparisons with the National Cancer Institute data [J].

Bracht, K ;

Boubakari ;

Grünert, R ;

Bednarski, PJ .

ANTI-CANCER DRUGS, 2006, 17 (01) :41-51

[4]

NMR-STUDIES OF D-RIBOSYLAMINES IN SOLUTION - DERIVATIVES OF PRIMARY AMINES .1. [J].

CHAVIS, C ;

DEGOURCY, C ;

DUMONT, F ;

IMBACH, JL .

CARBOHYDRATE RESEARCH, 1983, 113 (01) :1-20

[5]

Anti-mitotic properties of indirubin-3'-monoxime, a CDK/GSK-3 inhibitor: induction of endoreplication following prophase arrest [J].

Damiens, E ;

Baratte, B ;

Marie, D ;

Eisenbrand, G ;

Meijer, L .

ONCOGENE, 2001, 20 (29) :3786-3797

[6]

Inhibitor binding to active and inactive CDK2: The crystal structure of CDK2-cyclin A/indirubin-5-sulphonate [J].

Davies, TG ;

Tunnah, P ;

Meijer, L ;

Marko, D ;

Eisenbrand, G ;

Endicott, JA ;

Noble, MEM .

STRUCTURE, 2001, 9 (05) :389-397

[7]

Inhibition of cyclin-dependent kinases by purine analogues - Crystal structure of human cdk2 complexed with roscovitine [J].

DeAzevedo, WF ;

Leclerc, S ;

Meijer, L ;

Havlicek, L ;

Strnad, M ;

Kim, SH .

EUROPEAN JOURNAL OF BIOCHEMISTRY, 1997, 243 (1-2) :518-526

[8]

Plasmodium falciparum glycogen synthase kinase-3:: molecular model, expression, intracellular localisation and selective inhibitors [J].

Droucheau, E ;

Primot, A ;

Thomas, V ;

Mattei, D ;

Knockaert, M ;

Richardson, C ;

Sallicandro, P ;

Alano, P ;

Jafarshad, A ;

Baratte, B ;

Kunick, C ;

Parzy, D ;

Pearl, L ;

Doerig, C ;

Meijer, L .

BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS, 2004, 1697 (1-2) :181-196

[9]

Cyclin-dependent kinase inhibitor indirubin-3′-oxime selectively inhibits human papillomavirus type 16 E7-induced numerical centrosome anomalies [J].

Duensing, S ;

Duensing, A ;

Lee, DC ;

Edwards, KM ;

Piboonniyom, SO ;

Manuel, E ;

Skaltsounis, L ;

Meijer, L ;

Münger, K .

ONCOGENE, 2004, 23 (50) :8206-8215

[10]

Grese TA, 1996, ANNU REP MED CHEM, V31, P181

← 1 2 3 4 →