Bioorganic & Medicinal Chemistry 2013-01-15

Cytotoxic betulin-derived hydroxypropargylamines trigger apoptosis.

René Csuk, Ronny Sczepek, Bianka Siewert, Christoph Nitsche

Index: Bioorg. Med. Chem. 21(2) , 425-35, (2013)

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Abstract

Several novel betulin derivatives were prepared and evaluated for their antitumor activity. Among others, 3-O-acetylbetulinic aldehyde served as an ideal starting material for the synthesis of 28-acetylenic derivatives that were further transformed into Mannich bases. These hydroxypropargylamines were screened for their antitumor activity in a panel of nine human cancer cell lines in a sulforhodamine B (SRB) assay. Several compounds showed a noteworthy antitumor activity. The results from acridine orange/propidium iodide staining and annexinV-FITC assays as well as DNA laddering experiments provided evidence for an apoptotic cell death.Copyright © 2012 Elsevier Ltd. All rights reserved.


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