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      Synthesis, Structure and Cytotoxic Activity of New Acetylenic Derivatives of Betulin

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          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 ID 50 value of 0.02 μg/mL.

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          Pharmacological properties of the ubiquitous natural product betulin.

          Sami Alakurtti, S Koskimies, Jari Yli-Kauhaluoma … (2006)
          Betulin (lup-20(29)-ene-3beta,28-diol) is an abundant naturally occurring triterpene and it is found predominantly in bushes and trees forming the principal extractive (up to 30% of dry weight) of the bark of birch trees. Presently, there is no significant use for this easily isolable compound, which makes it a potentially important raw material for polymers and a precursor of biologically active compounds. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs. A new mechanism of action has been confirmed for some of the most promising anti-HIV derivatives, which makes them potentially useful additives to the current anti-HIV therapy. Betulinic acid is specifically cytotoxic to several tumor cell lines by inducing apoptosis in cells. Moreover, it is non-toxic up to 500 mg/kg body weight in mice. The literature concerning derivatization of betulin for structure-activity relationship (SAR) studies and its pharmacological properties is reviewed.
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            Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis

            Harry Fong, Heebyung Chai, Ik-Soo Lee … (1995)
            Article 0 comments Cited 101 times – based on 0 reviews     Review now
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              Betulinic acid, a natural compound with potent anticancer effects.

              Harald H. Kessler, Jan Paul Medema, B Mullauer (2010)
              New therapies using novel mechanisms to induce tumor cell death are needed with plants playing a crucial role as a source for potential anticancer compounds. One highly promising class of natural compounds are the triterpenoids with betulinic acid (BetA) as the most prominent representative. In-vitro studies have identified this agent as potently effective against a wide variety of cancer cells, also those derived from therapy-resistant and refractory tumors, whereas it has been found to be relatively nontoxic for healthy cells. In-vivo preclinically applied BetA showed some remarkable anticancer effects and a complete absence of systemic toxicity in rodents. BetA also cooperated with other therapies to induce tumor cell death and several potent derivatives have been discovered. Its antitumor activity has been related to its direct effects on mitochondria where it induces Bax/Bak-independent cytochrome-c release.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 17 April 2013
                Publication date Collection: April 2013
                Volume: 18
                Issue: 4
                Pages: 4526-4543
                Affiliations
                [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 notes
                [* ]Author to whom correspondence should be addressed; E-Mail: boryczka@ 123456sum.edu.pl ; Tel.: +48-32-364-1605; Fax: +48-32-364-1600.
                Article
                Publisher ID: molecules-18-04526
                DOI: 10.3390/molecules18044526
                PMC ID: 6270304
                PubMed ID: 23595090
                SO-VID: b3b0e87d-aca2-4498-afb2-f99375d09313
                Copyright © © 2013 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 21 March 2013
                Date revision received : 08 April 2013
                Date accepted : 11 April 2013
                Categories
                Subject: Article

                Keywords: acetylenic betulins,synthesis,crystal structure,cytotoxic activity
                Data availability:
                Keywords: acetylenic betulins, synthesis, crystal structure, cytotoxic activity

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