Total Synthesis and Biological Investigation of (-)-Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific

Publication type:
Journal article
Metadata:
Autoren
  • Johannes Krieger
  • Toni Smeilus
  • Marcel Kaiser
  • Ean-Jeong Seo
  • Thomas Efferth
  • Athanassios Giannis
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000436402100067&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/anie.201802015
eISSN
1521-3773
Externe Identifier
  • Clarivate Analytics Document Solution ID: GK7QD
  • PubMed Identifier: 29723442
ISSN
1433-7851
Ausgabe der Veröffentlichung
27
Zeitschrift
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Schlüsselwörter
  • chirality
  • enantiomeric drugs
  • ene reactions
  • malaria
  • trioxanes
Paginierung
8293 - 8296
Datum der Veröffentlichung
2018
Status
Published
Titel
Total Synthesis and Biological Investigation of (-)-Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific
Sub types
  • Article
Ausgabe der Zeitschrift
57

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<jats:title>Abstract</jats:title><jats:p>Here, we describe an efficient and diversity‐oriented entry to both (−)‐artemisinin (<jats:bold>1</jats:bold>) and its natural antipode (+)‐artemisinin, starting from commercially and readily available <jats:italic>S</jats:italic>‐(+)‐ and <jats:italic>R</jats:italic>‐(−)‐citronellene, respectively. Subsequently, we answered the still open question regarding the specificity of artemisinins action. By using a drug‐sensitive <jats:italic>Plasmodium falciparum</jats:italic> NF54 strain, we showed that the antimalarial activity of artemisinin is not stereospecific. Our straightforward and biomimetic approach to this natural endoperoxide enables the synthesis of artemisinin derivatives that are not accessible through applying current methods and may help to address the problem of emerging resistance of <jats:italic>Plasmodium falciparum</jats:italic> towards artemisinin.</jats:p>
Autoren
  • Johannes Krieger
  • Toni Smeilus
  • Marcel Kaiser
  • Ean‐Jeong Seo
  • Thomas Efferth
  • Athanassios Giannis
DOI
10.1002/anie.201802015
eISSN
1521-3773
ISSN
1433-7851
Ausgabe der Veröffentlichung
27
Zeitschrift
Angewandte Chemie International Edition
Sprache
en
Online publication date
2018
Paginierung
8293 - 8296
Datum der Veröffentlichung
2018
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/anie.201802015
Datum der Datenerfassung
2023
Titel
Total Synthesis and Biological Investigation of (−)‐Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific
Ausgabe der Zeitschrift
57

Data source: Crossref

Abstract
Here, we describe an efficient and diversity-oriented entry to both (-)-artemisinin (1) and its natural antipode (+)-artemisinin, starting from commercially and readily available S-(+)- and R-(-)-citronellene, respectively. Subsequently, we answered the still open question regarding the specificity of artemisinins action. By using a drug-sensitive Plasmodium falciparum NF54 strain, we showed that the antimalarial activity of artemisinin is not stereospecific. Our straightforward and biomimetic approach to this natural endoperoxide enables the synthesis of artemisinin derivatives that are not accessible through applying current methods and may help to address the problem of emerging resistance of Plasmodium falciparum towards artemisinin.
Addresses
  • Faculty of Chemistry and Mineralogy, Institute of Organic Chemistry, University of Leipzig, Johannisallee 29, 04301, Leipzig, Germany.
Autoren
  • Johannes Krieger
  • Toni Smeilus
  • Marcel Kaiser
  • Ean-Jeong Seo
  • Thomas Efferth
  • Athanassios Giannis
DOI
10.1002/anie.201802015
eISSN
1521-3773
Externe Identifier
  • PubMed Identifier: 29723442
Open access
false
ISSN
1433-7851
Ausgabe der Veröffentlichung
27
Zeitschrift
Angewandte Chemie (International ed. in English)
Schlüsselwörter
  • Cell Line, Tumor
  • Humans
  • Plasmodium falciparum
  • Monoterpenes
  • Artemisinins
  • Antimalarials
  • Cell Survival
  • Cyclization
  • Drug Resistance, Neoplasm
  • Stereoisomerism
Sprache
eng
Medium
Print-Electronic
Online publication date
2018
Paginierung
8293 - 8296
Datum der Veröffentlichung
2018
Status
Published
Datum der Datenerfassung
2018
Titel
Total Synthesis and Biological Investigation of (-)-Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
57

Data source: Europe PubMed Central

Abstract
Here, we describe an efficient and diversity-oriented entry to both (-)-artemisinin (1) and its natural antipode (+)-artemisinin, starting from commercially and readily available S-(+)- and R-(-)-citronellene, respectively. Subsequently, we answered the still open question regarding the specificity of artemisinins action. By using a drug-sensitive Plasmodium falciparum NF54 strain, we showed that the antimalarial activity of artemisinin is not stereospecific. Our straightforward and biomimetic approach to this natural endoperoxide enables the synthesis of artemisinin derivatives that are not accessible through applying current methods and may help to address the problem of emerging resistance of Plasmodium falciparum towards artemisinin.
Autoren
  • Johannes Krieger
  • Toni Smeilus
  • Marcel Kaiser
  • Ean-Jeong Seo
  • Thomas Efferth
  • Athanassios Giannis
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/29723442
DOI
10.1002/anie.201802015
eISSN
1521-3773
Ausgabe der Veröffentlichung
27
Zeitschrift
Angew Chem Int Ed Engl
Schlüsselwörter
  • chirality
  • enantiomeric drugs
  • ene reactions
  • malaria
  • trioxanes
  • Antimalarials
  • Artemisinins
  • Cell Line, Tumor
  • Cell Survival
  • Cyclization
  • Drug Resistance, Neoplasm
  • Humans
  • Monoterpenes
  • Plasmodium falciparum
  • Stereoisomerism
Sprache
eng
Country
Germany
Paginierung
8293 - 8296
Datum der Veröffentlichung
2018
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2019
Titel
Total Synthesis and Biological Investigation of (-)-Artemisinin: The Antimalarial Activity of Artemisinin Is not Stereospecific.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
57

Data source: PubMed

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