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Synthesis, Encapsulation and Antitumor Activity of New Betulin Derivatives
Author(s) -
Csuk René,
Barthel Alexander,
Sczepek Ronny,
Siewert Bianka,
Schwarz Stefan
Publication year - 2011
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201000232
Subject(s) - betulinic acid , betulin , chemistry , cytotoxicity , dna laddering , stereochemistry , apoptosis , combinatorial chemistry , organic chemistry , biochemistry , programmed cell death , dna fragmentation , in vitro , genetics , biology
Abstract Novel betulin derivatives were prepared and tested for their antitumor activity. Starting from 3‐ O ‐acetyl‐ or 3‐ O ‐methyl‐betulinic aldehyde, the synthesis of C‐28 ethynyl derivatives was performed; their subsequent transformation with several 1,3‐dipolarophiles afforded pyrazoles and 1,2,3‐triazoles. Their screening for antitumor activity was performed in a panel of 15 human cancer cell lines by a colorimetric SRB‐assay. Thereby, several compounds revealed a higher cytotoxicity than betulinic acid. In addition, the encapsulation of the lead structure 7 into liposomes was investigated. The results from a dye exclusion test and from DNA laddering experiments provided evidence for an apoptotic cell death.