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

Stefanie Libnow; Karen Methling; Martin Hein; Dirk Michalik; Manuela Harms; Kristian Wende; Anke Flemming; Martin Köckerling; Helmut Reinke; Patrick J Bednarski; Michael Lalk; Peter Langer

doi:10.1016/j.bmc.2008.04.003

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

Bioorg Med Chem. 2008 May 15;16(10):5570-83. doi: 10.1016/j.bmc.2008.04.003. Epub 2008 Apr 6.

Authors

Stefanie Libnow¹, Karen Methling, Martin Hein, Dirk Michalik, Manuela Harms, Kristian Wende, Anke Flemming, Martin Köckerling, Helmut Reinke, Patrick J Bednarski, Michael Lalk, Peter Langer

Affiliation

¹ Institut für Chemie der Universität Rostock, Germany.

PMID: 18434163
DOI: 10.1016/j.bmc.2008.04.003

Abstract

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.

Publication types

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

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Crystallography, X-Ray
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Glycosides / chemical synthesis*
Glycosides / chemistry
Glycosides / pharmacology*
Humans
Indoles / chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism
Structure-Activity Relationship

Substances

Antineoplastic Agents
Glycosides
Indoles
indirubin