Synthesis and Anticancer Activity of Novel Betulinic acid and Betulin Derivatives

A series of novel betulinic acid derivatives 3–11 and betulin derivatives 12–17 were synthesized. The compounds were characterized by the means of 1H‐ and 13C‐NMR spectroscopy as well as mass spectrometry. The compounds have been tested on ten tumor cell lines of different histogenic origin. The mos...

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Bibliographic Details
Published in:Archiv der Pharmazie (Weinheim) 2010-08, Vol.343 (8), p.449-457
Main Authors: Kommera, Harish, Kaluđerović, Goran N., Kalbitz, Jutta, Paschke, Reinhard
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Apoptosis
Betulin
Betulinic acid
Cell Line, Tumor
Cell Proliferation - drug effects
Cytotoxicity
Drug Screening Assays, Antitumor
Humans
Mass Spectrometry
Structure-Activity Relationship
Thyroid Neoplasms - drug therapy
Thyroid Neoplasms - pathology
Triterpenes - chemical synthesis
Triterpenes - pharmacology
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Summary:A series of novel betulinic acid derivatives 3–11 and betulin derivatives 12–17 were synthesized. The compounds were characterized by the means of 1H‐ and 13C‐NMR spectroscopy as well as mass spectrometry. The compounds have been tested on ten tumor cell lines of different histogenic origin. The most active derivatives, containing a chloroacetyl group on C‐3 in betulinic acid 9 and C‐28 in betulin 15, were up to ten times more cytotoxic and many fold more selective towards tumor cells in comparison to normal cells (fibroblasts) than betulinic acid. Furthermore, compound 15 was found to possess cell growth inhibition even when treated for a short time on anaplastic thyroid cancer cells (SW1736). Betulinic acid and its precursor betulin are members of the class of pentacyclic triterpenes and are found to possess antitumor properties. Thus, new betulinic acid and betulin derivatives were prepared and tested in vitro on ten tumor cell lines of different histogenic origin.
ISSN:0365-6233
1521-4184
DOI:10.1002/ardp.201000011