1. In vitro anticancer studies of alpha- and beta-D-glucopyranose betulin anomers.
- Author
-
Kommera H, Kaluderović GN, Bette M, Kalbitz J, Fuchs P, Fulda S, Mier W, and Paschke R
- Subjects
- Antineoplastic Agents chemical synthesis, Apoptosis physiology, Caspase 3 metabolism, Cell Cycle drug effects, Cell Cycle physiology, Cell Line, Tumor, DNA Fragmentation drug effects, Drug Screening Assays, Antitumor, Glucose chemical synthesis, Glucose chemistry, HCT116 Cells, Humans, Isomerism, Magnetic Resonance Spectroscopy, Mass Spectrometry, Pentacyclic Triterpenes, Time Factors, Triterpenes chemical synthesis, Triterpenes pharmacology, X-Ray Diffraction, Betulinic Acid, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Apoptosis drug effects, Glucose analogs & derivatives, Glucose pharmacology, Triterpenes chemistry
- Abstract
Four derivatives of betulin containing a D-glucopyranosyl moiety at C3 position were synthesized and characterized by (1)H and (13)C NMR spectroscopy as well as mass spectrometry. The crystal structure of 28-O-acetylbetulin-3-yl-beta-D-(2',3',4',6'-tetra-O-acetyl)glucopyranoside was determined. The compounds were tested against fifteen tumor cell lines of different histogenic origins. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside, exerted a dose dependent antiproliferative action towards the tumor cell lines. Treatment of HCT-116 cells for 24h induced apoptosis, which was confirmed by the appearance of a typical ladder pattern in the DNA fragmentation assay and cell cycle analysis. The alpha- and beta-anomers of 28-O-acetylbetulin-3-yl-D-glucopyranoside seem to induce apoptosis by activation of different upstream caspases on colon cancer HCT-116 cell line., (2010 Elsevier Ireland Ltd. All rights reserved.)
- Published
- 2010
- Full Text
- View/download PDF