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
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Christoph Reiter
- Aysun Capci Karagoez
- Tony Froehlich
- Volker Klein
- Maen Zeino
- Katrin Viertel
- Jana Held
- Benjamin Mordmueller
- Safiye Emirdag Ozturk
- Huseyin Anil
- Thomas Efferth
- Svetlana B Tsogoeva
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000333775600039&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1016/j.ejmech.2014.01.043
- eISSN
- 1768-3254
- Externe Identifier
- Clarivate Analytics Document Solution ID: AE2AL
- PubMed Identifier: 24561670
- ISSN
- 0223-5234
- Zeitschrift
- EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
- Schlüsselwörter
- Artemisinin
- Egonol
- Hybrid
- Cancer
- Malaria
- Ferrocene
- Paginierung
- 403 - 412
- Datum der Veröffentlichung
- 2014
- Status
- Published
- Titel
- Synthesis and study of cytotoxic activity of 1,2,4-trioxane- and egonol-derived hybrid molecules against <i>Plasmodium falciparum</i> and multidrug-resistant human leukemia cells
- Sub types
- Article
- Ausgabe der Zeitschrift
- 75
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Christoph Reiter
- Aysun Çapcı Karagöz
- Tony Fröhlich
- Volker Klein
- Maen Zeino
- Katrin Viertel
- Jana Held
- Benjamin Mordmüller
- Safiye Emirdağ Öztürk
- Hüseyin Anıl
- Thomas Efferth
- Svetlana B Tsogoeva
- DOI
- 10.1016/j.ejmech.2014.01.043
- ISSN
- 0223-5234
- Zeitschrift
- European Journal of Medicinal Chemistry
- Sprache
- en
- Paginierung
- 403 - 412
- Datum der Veröffentlichung
- 2014
- Status
- Published
- Herausgeber
- Elsevier BV
- Herausgeber URL
- http://dx.doi.org/10.1016/j.ejmech.2014.01.043
- Datum der Datenerfassung
- 2020
- Titel
- 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
- Ausgabe der Zeitschrift
- 75
Data source: Crossref
- Abstract
- Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that possess improved properties compared to their parent compounds, a series of novel 1,2,4-trioxane-based hybrids incorporating egonol and/or ferrocene fragments were synthesized and tested in vitro against P. falciparum strains, CCRF-CEM cells and the multidrug-resistant P-glycoprotein-over-expressing CEM/ADR5000 cells. The most active compounds against P. falciparum strains were artesunic acid homodimers 12 and 13 (IC50 of 0.32 and 0.30 nM, respectively), whereas novel hybrids 7 (1,2,4-trioxane-ferrocene-egonol), 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol) showed a remarkable cytotoxicity toward CCRF-CEM cells (IC50 of 0.07, 0.25 and 0.18 μM, respectively). A cooperative and synergistic effect of the three moieties 1,2,4-trioxane, ferrocene and egonol in hybrid molecule 7 is significant and is obviously stronger than in hybrids 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol), which comprises of only two of the three considered parent compounds. Interestingly, hybrid 9 containing a 1,2,4-trioxane and a ferrocene fragment has shown to be the most effective among the studied hybrids against the tested multidrug-resistant leukemia CEM/ADR5000 cells (IC50 of 0.57 μM) and possesses a degree of cross-resistance of 2.34.
- Addresses
- Institute of Organic Chemistry I, University of Erlangen-Nuremberg, Henkestrasse 42, 91054 Erlangen, Germany.
- Autoren
- Christoph Reiter
- Aysun Capcı Karagöz
- Tony Fröhlich
- Volker Klein
- Maen Zeino
- Katrin Viertel
- Jana Held
- Benjamin Mordmüller
- Safiye Emirdağ Öztürk
- Hüseyin Anıl
- Thomas Efferth
- Thomas Efferth
- Svetlana B Tsogoeva
- DOI
- 10.1016/j.ejmech.2014.01.043
- eISSN
- 1768-3254
- Externe Identifier
- PubMed Identifier: 24561670
- Open access
- false
- ISSN
- 0223-5234
- Zeitschrift
- European journal of medicinal chemistry
- Schlüsselwörter
- Humans
- Plasmodium falciparum
- Malaria, Falciparum
- Leukemia
- Ferrous Compounds
- Heterocyclic Compounds
- Benzofurans
- Antineoplastic Agents
- Antimalarials
- Drug Resistance, Multiple
- Cell Lineage
- Drug Resistance, Neoplasm
- Metallocenes
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2014
- Paginierung
- 403 - 412
- Datum der Veröffentlichung
- 2014
- Status
- Published
- Datum der Datenerfassung
- 2014
- Titel
- 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.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 75
Data source: Europe PubMed Central
- Abstract
- Malaria and cancer cause the death of millions of people every year. To combat these two diseases, it is important that new pharmaceutically active compounds have the ability to overcome multidrug resistance in cancer and Plasmodium falciparum strains. In search of effective anti-cancer and anti-malaria hybrids that possess improved properties compared to their parent compounds, a series of novel 1,2,4-trioxane-based hybrids incorporating egonol and/or ferrocene fragments were synthesized and tested in vitro against P. falciparum strains, CCRF-CEM cells and the multidrug-resistant P-glycoprotein-over-expressing CEM/ADR5000 cells. The most active compounds against P. falciparum strains were artesunic acid homodimers 12 and 13 (IC50 of 0.32 and 0.30 nM, respectively), whereas novel hybrids 7 (1,2,4-trioxane-ferrocene-egonol), 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol) showed a remarkable cytotoxicity toward CCRF-CEM cells (IC50 of 0.07, 0.25 and 0.18 μM, respectively). A cooperative and synergistic effect of the three moieties 1,2,4-trioxane, ferrocene and egonol in hybrid molecule 7 is significant and is obviously stronger than in hybrids 9 (1,2,4-trioxane-ferrocene) and 11 (artesunic acid-egonol), which comprises of only two of the three considered parent compounds. Interestingly, hybrid 9 containing a 1,2,4-trioxane and a ferrocene fragment has shown to be the most effective among the studied hybrids against the tested multidrug-resistant leukemia CEM/ADR5000 cells (IC50 of 0.57 μM) and possesses a degree of cross-resistance of 2.34.
- Date of acceptance
- 2014
- Autoren
- Christoph Reiter
- Aysun Capcı Karagöz
- Tony Fröhlich
- Volker Klein
- Maen Zeino
- Katrin Viertel
- Jana Held
- Benjamin Mordmüller
- Safiye Emirdağ Öztürk
- Hüseyin Anıl
- Thomas Efferth
- Svetlana B Tsogoeva
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/24561670
- DOI
- 10.1016/j.ejmech.2014.01.043
- eISSN
- 1768-3254
- Zeitschrift
- Eur J Med Chem
- Schlüsselwörter
- Artemisinin
- Cancer
- Egonol
- Ferrocene
- Hybrid
- Malaria
- Antimalarials
- Antineoplastic Agents
- Benzofurans
- Cell Lineage
- Drug Resistance, Multiple
- Drug Resistance, Neoplasm
- Ferrous Compounds
- Heterocyclic Compounds
- Humans
- Leukemia
- Malaria, Falciparum
- Metallocenes
- Plasmodium falciparum
- Sprache
- eng
- Country
- France
- Paginierung
- 403 - 412
- PII
- S0223-5234(14)00089-0
- Datum der Veröffentlichung
- 2014
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2014
- Titel
- 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.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 75
Data source: PubMed
- Beziehungen:
- Property of