Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells

Reiter, Christoph; Karagöz, Aysun Çapcı; Fröhlich, Tony; Klein, Volker; Zeino, Maen; Viertel, Katrin; Held, Jana; Mordmüller, Benjamin; Öztürk, Safiye Emirdağ; Anıl, Hüseyın; Efferth, Thomas; Tsogoeva, Svetlana B.

doi:10.1016/j.ejmech.2014.01.043

Cited by 77 publications

(42 citation statements)

References 103 publications

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“…The authors observed significant activities (IC 50 \ 10 lg/mL) of EG against C6 and Hep-2 cells and of HE against C6 and HeLa cells when compared to the positive control streptonigrin after 24 h of treatment. Reiter et al (2014), evaluating the cytotoxicity of EG and derivatives against a wild-type human T cell lymphoblastlike cell line (CCRF-CEM) and a human leukemia cell line (CEM/ADR5000), observed considerable cytotoxicity of EG (IC 50 = 1.88 ± 0.41 lM). Li et al (2005) evaluated the cytotoxicity of fractions of an EtOH extract of S. perkinsiae and isolated compounds in two breast cancer cell lines (MCF-7 and MDA-MB-231) after 48 h of treatment using a colorimetric chemosensitivity assay with sulforhodamine B and demonstrated the cytotoxic activity of EG at high concentrations (IC 50 [ 100 lg/mL).…”

Section: Discussionmentioning

confidence: 99%

Study of the cytotoxic activity of Styrax camporum extract and its chemical markers, egonol and homoegonol

et al. 2015

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The benzofuran lignans egonol and homoegonol are found in all species of the genus Styrax. Since natural products are important sources of new anticancer drugs, this study evaluated the cytotoxic activity of a hydroalcoholic extract of the stems of S. camporum (SCHE) and their chemical markers, egonol (EG) and homoegonol (HE), against different tumor cell lines (B16F10, MCF-7, HeLa, HepG2, and MO59J). A normal human cell line (GM07492A) was included. Cytotoxic activity was evaluated at different treatment times (24, 48 and 72 h) using the XTT assay. More effective results were observed after 72 h of treatment. The lowest IC 50 values were found for the HepG2 cell line, ranging from 11.2 to 55.0 lg/mL. The combination of EG and HE exerted higher cytotoxic activity than SCHE or treatment with either lignan alone, with the lowest IC 50 (13.31 lg/mL) being observed for the MCF-7 line. Furthermore, treatment with these lignans was significantly more cytotoxic for some tumor cell lines compared to the normal cell line, GM07492A, indicating selectivity. These results suggest that these lignans may be used to treat cancer without affecting normal cells.

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Section: Discussionmentioning

confidence: 99%

Study of the cytotoxic activity of Styrax camporum extract and its chemical markers, egonol and homoegonol

et al. 2015

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“…The natural sesquiterpene peroxide artemisinin (qinghaosu), used since centuries in Chinese folk medicine as a plant extract, has initiated and stimulated this field of research [50]. The enormous potency of the natural product that involves also anti-cancer drug activity just recently emerged [51,52]. At the same time, however, reports appeared that describe the appearance of malaria-producing plasmodium species resistant against artemisinin and artemisinin-derivatives [53,54].…”

Section: Combinations Of Natural Product Motifs For Singlet Oxygenationmentioning

confidence: 99%

Singlet oxygen and natural substrates: functional polyunsaturated models for the photooxidative degradation of carotenoids

Griesbeck

Kleczka

Kiff

et al. 2015

Pure and Applied Chemistry

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The primary chemical reactions of singlet molecular oxygen with polyunsaturated carotenoids are the focus of this research report. Model compounds that exhibit electronic properties and substituent pattern similar to natural carotenes, xanthophylls or apocarotenoids, respectively, were investigated with regard to photooxygenation reactivity. For dienes and trienes as substrates, high tandem reactivity was observed and hydroperoxy-endoperoxides were isolated as the secondary products of singlet oxygen reaction. The electronic gem-effect on the regioselectivity of the ene reaction is conserved also in vinylogous positions and thus appears to originate from a radical-stabilizing effect. In an attempt to combine different peroxide groups derived from natural products as a tool for new pharmaceutically active products, a dyade synthesis of an artemisinine-safranol with subsequent singlet oxygen addition was realized.

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“…Dimer 4 is known from literature, [37] but was prepared only by degradation of artesunic acid (3) and up to now not investigated for its potential against cancer cells and HCMV. The two artesunic acid dimers 8 and 9, previously reported by our group [38,39] were investigated for their antiviral potential in the present work.…”

Section: Introductionmentioning

confidence: 99%

Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities

Reiter

Fröhlich

Gruber

et al. 2015

Bioorganic & Medicinal Chemistry

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Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against Plasmodium falciparum and multidrug-resistant human leukemia cells

Cited by 77 publications

References 103 publications

Study of the cytotoxic activity of Styrax camporum extract and its chemical markers, egonol and homoegonol

Study of the cytotoxic activity of Styrax camporum extract and its chemical markers, egonol and homoegonol

Singlet oxygen and natural substrates: functional polyunsaturated models for the photooxidative degradation of carotenoids

Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities

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