Literature DB >> 12120518

Alkylation of heme by the antimalarial drug artemisinin.

Anne Robert1, Yannick Coppel, Bernard Meunier.   

Abstract

The peroxide function of artemisinin has been activated by iron(II)-heme generated in situ from iron(III)-protoporphyrin-IX and glutathione, a biologically relevant reductant. In mild conditions, this reaction produced a high yield (85%) of heme derivatives alkylated at alpha-, beta-, and delta-meso positions by a C4-centered radical derived from artemisinin.

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Year:  2002        PMID： 12120518     DOI： 10.1039/b110817b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  23 in total

1.  Reaction of artemisinin with haemoglobin: implications for antimalarial activity.

Authors:  Rangiah Kannan; Krishan Kumar; Dinkar Sahal; Shrikant Kukreti; Virander S Chauhan
Journal:  Biochem J       Date:  2005-01-15       Impact factor: 3.857

2.  The role of heme and the mitochondrion in the chemical and molecular mechanisms of mammalian cell death induced by the artemisinin antimalarials.

Authors:  Amy E Mercer; Ian M Copple; James L Maggs; Paul M O'Neill; B Kevin Park
Journal:  J Biol Chem       Date:  2010-11-08       Impact factor: 5.157

3.  Synthesis and Study of the Antimalarial Cardamom Peroxide.

Authors:  Xirui Hu; Pharath Lim; Rick M Fairhurst; Thomas J Maimone
Journal:  Tetrahedron       Date:  2018-03-26       Impact factor: 2.457

4.  Probing the antimalarial mechanism of artemisinin and OZ277 (arterolane) with nonperoxidic isosteres and nitroxyl radicals.

Authors:  Matthias A Fügi; Sergio Wittlin; Yuxiang Dong; Jonathan L Vennerstrom
Journal:  Antimicrob Agents Chemother       Date:  2009-12-22       Impact factor: 5.191

5.  Artemisinin-Based Drugs Target the Plasmodium falciparum Heme Detoxification Pathway.

Authors:  Kaleab A Ribbiso; Laura E Heller; Abigail Taye; Erin Julian; Andreas V Willems; Paul D Roepe
Journal:  Antimicrob Agents Chemother       Date:  2021-03-18       Impact factor: 5.191

6.  Characterization of noncovalent complexes of antimalarial agents of the artemisinin-type and FE(III)-heme by electrospray mass spectrometry and collisional activation tandem mass spectrometry.

Authors:  Vlada A Pashynska; Hilde Van den Heuvel; Magda Claeys; Marina V Kosevich
Journal:  J Am Soc Mass Spectrom       Date:  2004-08       Impact factor: 3.109

7.  Artemisinin as a Chinese medicine, selectively induces apoptosis in pancreatic tumor cell line.

Authors:  Shokoofe Noori; Zuhair M Hassan; Vida Farsam
Journal:  Chin J Integr Med       Date:  2013-06-15       Impact factor: 1.978

8.  Peroxide bond-dependent antiplasmodial specificity of artemisinin and OZ277 (RBx11160).

Authors:  Marcel Kaiser; Sergio Wittlin; Angela Nehrbass-Stuedli; Yuxiang Dong; Xiaofang Wang; Andrew Hemphill; Hugues Matile; Reto Brun; Jonathan L Vennerstrom
Journal:  Antimicrob Agents Chemother       Date:  2007-06-11       Impact factor: 5.191

Review 9.  1,4-naphthoquinones and other NADPH-dependent glutathione reductase-catalyzed redox cyclers as antimalarial agents.

Authors:  Didier Belorgey; Don Antoine Lanfranchi; Elisabeth Davioud-Charvet
Journal:  Curr Pharm Des       Date:  2013       Impact factor: 3.116

10.  Correlation between Plasmodium yoelii nigeriensis susceptibility to artemisinin and alkylation of heme by the drug.

Authors:  Anne Robert; Catherine Claparols; Benoit Witkowski; Françoise Benoit-Vical
Journal:  Antimicrob Agents Chemother       Date:  2013-06-10       Impact factor: 5.191
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