Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities
- Publication type:
- Journal article
- Metadata:
-
- Autoren
- Christoph Reiter
- Tony Froehlich
- Lisa Gruber
- Corina Hutterer
- Manfred Marschall
- Cornelia Voigtlaender
- Oliver Friedrich
- Barbara Kappes
- Thomas Efferth
- Svetlana B Tsogoeva
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000360349900021&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1016/j.bmc.2015.07.048
- eISSN
- 1464-3391
- Externe Identifier
- Clarivate Analytics Document Solution ID: CQ1IG
- PubMed Identifier: 26260339
- ISSN
- 0968-0896
- Ausgabe der Veröffentlichung
- 17
- Zeitschrift
- BIOORGANIC & MEDICINAL CHEMISTRY
- Schlüsselwörter
- Artemisinin-derived hybrids
- Artemisinin-derived dimers
- Artemisinin-derived trimers
- Antimalarial activity
- Anticancer activity
- Antiviral activity
- Paginierung
- 5452 - 5458
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Titel
- Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities
- Sub types
- Article
- Ausgabe der Zeitschrift
- 23
Data source: Web of Science (Lite)
- Other metadata sources:
-
- Autoren
- Christoph Reiter
- Tony Fröhlich
- Lisa Gruber
- Corina Hutterer
- Manfred Marschall
- Cornelia Voigtländer
- Oliver Friedrich
- Barbara Kappes
- Thomas Efferth
- Svetlana B Tsogoeva
- DOI
- 10.1016/j.bmc.2015.07.048
- ISSN
- 0968-0896
- Ausgabe der Veröffentlichung
- 17
- Zeitschrift
- Bioorganic & Medicinal Chemistry
- Sprache
- en
- Paginierung
- 5452 - 5458
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Herausgeber
- Elsevier BV
- Herausgeber URL
- http://dx.doi.org/10.1016/j.bmc.2015.07.048
- Datum der Datenerfassung
- 2018
- Titel
- Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities
- Ausgabe der Zeitschrift
- 23
Data source: Crossref
- Abstract
- New pharmaceutically active compounds can be obtained by modification of existing drugs to access more effective agents in the wake of drug resistance amongst others. To achieve this goal the concept of hybridization was established during the last decade. We employed this concept by coupling two artemisinin-derived precursors to obtain dimers or trimers with increased in vitro activity against Plasmodiumfalciparum 3D7 strain, leukemia cells (CCRF-CEM and multidrug-resistant subline CEM/ADR5000) and human cytomegalovirus (HCMV). Dimer 4 (IC50 of 2.6 nM) possess superior antimalarial activity compared with its parent compound artesunic acid(3) (IC50 of 9.0 nM). Dimer5 and trimers6 and 7 display superior potency against both leukemia cell lines (IC50 up to 0.002 μM for CCRF-CEM and IC50 up to 0.20 μM for CEM/ADR5000) and are even more active than clinically used doxorubicin (IC50 1.61 μM for CEM/ADR5000). With respect to anti-HCMV activity, trimer6 is the most efficient hybrid (IC50 0.04 μM) outperforming ganciclovir (IC50 2.6 μM), dihydroartemisinin(IC50 >10 μM) and artesunic acid (IC50 3.8 μM).
- Addresses
- Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), University of Erlangen-Nuremberg, Henkestraße 42, 91054 Erlangen, Germany.
- Autoren
- Christoph Reiter
- Tony Fröhlich
- Lisa Gruber
- Corina Hutterer
- Manfred Marschall
- Cornelia Voigtländer
- Oliver Friedrich
- Barbara Kappes
- Thomas Efferth
- Thomas Efferth
- Svetlana B Tsogoeva
- DOI
- 10.1016/j.bmc.2015.07.048
- eISSN
- 1464-3391
- Externe Identifier
- PubMed Identifier: 26260339
- Open access
- false
- ISSN
- 0968-0896
- Ausgabe der Veröffentlichung
- 17
- Zeitschrift
- Bioorganic & medicinal chemistry
- Schlüsselwörter
- Humans
- Artemisinins
- Antineoplastic Agents, Phytogenic
- Antimalarials
- Antiviral Agents
- Molecular Structure
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2015
- Paginierung
- 5452 - 5458
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Datum der Datenerfassung
- 2015
- Titel
- Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities.
- Sub types
- Research Support, Non-U.S. Gov't
- Journal Article
- Ausgabe der Zeitschrift
- 23
Data source: Europe PubMed Central
- Abstract
- New pharmaceutically active compounds can be obtained by modification of existing drugs to access more effective agents in the wake of drug resistance amongst others. To achieve this goal the concept of hybridization was established during the last decade. We employed this concept by coupling two artemisinin-derived precursors to obtain dimers or trimers with increased in vitro activity against Plasmodiumfalciparum 3D7 strain, leukemia cells (CCRF-CEM and multidrug-resistant subline CEM/ADR5000) and human cytomegalovirus (HCMV). Dimer 4 (IC50 of 2.6 nM) possess superior antimalarial activity compared with its parent compound artesunic acid(3) (IC50 of 9.0 nM). Dimer5 and trimers6 and 7 display superior potency against both leukemia cell lines (IC50 up to 0.002 μM for CCRF-CEM and IC50 up to 0.20 μM for CEM/ADR5000) and are even more active than clinically used doxorubicin (IC50 1.61 μM for CEM/ADR5000). With respect to anti-HCMV activity, trimer6 is the most efficient hybrid (IC50 0.04 μM) outperforming ganciclovir (IC50 2.6 μM), dihydroartemisinin(IC50 >10 μM) and artesunic acid (IC50 3.8 μM).
- Date of acceptance
- 2015
- Autoren
- Christoph Reiter
- Tony Fröhlich
- Lisa Gruber
- Corina Hutterer
- Manfred Marschall
- Cornelia Voigtländer
- Oliver Friedrich
- Barbara Kappes
- Thomas Efferth
- Svetlana B Tsogoeva
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/26260339
- DOI
- 10.1016/j.bmc.2015.07.048
- eISSN
- 1464-3391
- Ausgabe der Veröffentlichung
- 17
- Zeitschrift
- Bioorg Med Chem
- Schlüsselwörter
- Anticancer activity
- Antimalarial activity
- Antiviral activity
- Artemisinin-derived dimers
- Artemisinin-derived hybrids
- Artemisinin-derived trimers
- Antimalarials
- Antineoplastic Agents, Phytogenic
- Antiviral Agents
- Artemisinins
- Humans
- Molecular Structure
- Sprache
- eng
- Country
- England
- Paginierung
- 5452 - 5458
- PII
- S0968-0896(15)00632-X
- Datum der Veröffentlichung
- 2015
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2016
- Titel
- Highly potent artemisinin-derived dimers and trimers: Synthesis and evaluation of their antimalarial, antileukemia and antiviral activities.
- Sub types
- Journal Article
- Research Support, Non-U.S. Gov't
- Ausgabe der Zeitschrift
- 23
Data source: PubMed
- Beziehungen:
- Property of