Molecules 2013, 18(4), 4526-4543; doi:10.3390/molecules18044526
Synthesis, Structure and Cytotoxic Activity of New Acetylenic Derivatives of Betulin
1
Department of Organic Chemistry, Medical University of Silesia, 4 Jagiellonska Str., 41-200 Sosnowiec, Poland
2
Department of Experimental Oncology, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 R. Weigla Str., 53-114 Wrocław, Poland
3
Department of Solid State Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
4
Department of Physics of Crystals, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
*
Author to whom correspondence should be addressed.
Received: 21 March 2013 / Revised: 8 April 2013 / Accepted: 11 April 2013 / Published: 17 April 2013
(This article belongs to the Section Medicinal Chemistry)
Abstract
A new series of betulin derivatives containing one or two pharmacophores bearing an acetylenic and carbonyl function at the C-3 and/or C-28 positions has been synthesized and characterized by 1H- and 13C-NMR, IR, MS and elemental analyses. The crystal structure of 28-O-propynoylbetulin was determined by X-ray structural analysis. All new compounds, as well as betulin, were tested in vitro for their antiproliferative activity against human SW707 colorectal, CCRF/CEM leukemia, T47D breast cancer, and against murine P388 leukemia and Balb3T3 normal fibroblasts cell lines. Most of the compounds showed better cytotoxicity than betulin and cisplatin used as reference agent. 28-O-Propynoylbetulin was the most potent derivative, being over 500 times more potent than betulin and about 100 times more cytotoxic than cisplatin against the human leukemia (CCRF/CEM) cell line, with an ID50 value of 0.02 μg/mL. View Full-TextKeywords:
acetylenic betulins; synthesis; crystal structure; cytotoxic activity
▼
Figures
Figure 1
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
Share & Cite This Article
MDPI and ACS Style
Boryczka, S.; Bębenek, E.; Wietrzyk, J.; Kempińska, K.; Jastrzębska, M.; Kusz, J.; Nowak, M. Synthesis, Structure and Cytotoxic Activity of New Acetylenic Derivatives of Betulin. Molecules 2013, 18, 4526-4543.
Related Articles
Article Metrics
Comments
[Return to top]
Molecules
EISSN 1420-3049
Published by MDPI AG, Basel, Switzerland
RSS
E-Mail Table of Contents Alert