Tetraoxane Antimalarials and Their Reaction with Fe(II)
Identifieur interne : 001C16 ( Main/Exploration ); précédent : 001C15; suivant : 001C17Tetraoxane Antimalarials and Their Reaction with Fe(II)
Auteurs : Igor Opsenica [Monténégro] ; Nataša Terzi [Monténégro] ; Dejan Opsenica [Monténégro] ; Goran Angelovski [Monténégro, Allemagne] ; Manfred Lehnig [Monténégro] ; Peter Eilbracht [Monténégro] ; Bernard Tinant [Monténégro] ; Zorica Jurani [Monténégro] ; Kirsten S. Smith [Monténégro] ; Young S. Yang [Monténégro] ; Damaris S. Diaz [Monténégro] ; Philip L. Smith [Monténégro] ; Wilbur K. Milhous [Monténégro] ; Dejan Dokovi [Monténégro] ; Bogdan A. Šolaja [Monténégro]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 2006.
Abstract
Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4‘ ‘) methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg·kg-1·day-1, and 2/5 mice at 50 mg·kg-1·day-1, showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO• radicals were detected by EPR experiments. This finding and the indication of Fe(IV)O species led us to propose that RO• radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.
Url:
DOI: 10.1021/jm050966r
Affiliations:
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xml:lang="en">Tetraoxane Antimalarials and Their Reaction with Fe(II)</title><author><name sortKey="Opsenica, Igor" sort="Opsenica, Igor" uniqKey="Opsenica I" first="Igor" last="Opsenica">Igor Opsenica</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Terzi, Natasa" sort="Terzi, Natasa" uniqKey="Terzi N" first="Nataša" last="Terzi">Nataša Terzi</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Opsenica, Dejan" sort="Opsenica, Dejan" uniqKey="Opsenica D" first="Dejan" last="Opsenica">Dejan Opsenica</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Angelovski, Goran" sort="Angelovski, Goran" uniqKey="Angelovski G" first="Goran" last="Angelovski">Goran Angelovski</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation><affiliation wicri:level="3"><country xml:lang="fr">Allemagne</country><wicri:regionArea> Current address: Max-Planck Institute for Biological Cybernetics,Tübingen</wicri:regionArea><placeName><region type="land" nuts="1">Bade-Wurtemberg</region><region type="district" nuts="2">District de Tübingen</region><settlement type="city">Tübingen</settlement></placeName></affiliation></author><author><name sortKey="Lehnig, Manfred" sort="Lehnig, Manfred" uniqKey="Lehnig M" first="Manfred" last="Lehnig">Manfred Lehnig</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Eilbracht, Peter" sort="Eilbracht, Peter" uniqKey="Eilbracht P" first="Peter" last="Eilbracht">Peter Eilbracht</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Tinant, Bernard" sort="Tinant, Bernard" uniqKey="Tinant B" first="Bernard" last="Tinant">Bernard Tinant</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Jurani, Zorica" sort="Jurani, Zorica" uniqKey="Jurani Z" first="Zorica" last="Jurani">Zorica Jurani</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Smith, Kirsten S" sort="Smith, Kirsten S" uniqKey="Smith K" first="Kirsten S." last="Smith">Kirsten S. Smith</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Yang, Young S" sort="Yang, Young S" uniqKey="Yang Y" first="Young S." last="Yang">Young S. Yang</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Diaz, Damaris S" sort="Diaz, Damaris S" uniqKey="Diaz D" first="Damaris S." last="Diaz">Damaris S. Diaz</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Smith, Philip L" sort="Smith, Philip L" uniqKey="Smith P" first="Philip L." last="Smith">Philip L. Smith</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Milhous, Wilbur K" sort="Milhous, Wilbur K" uniqKey="Milhous W" first="Wilbur K." last="Milhous">Wilbur K. Milhous</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Dokovi, Dejan" sort="Dokovi, Dejan" uniqKey="Dokovi D" first="Dejan" last="Dokovi">Dejan Dokovi</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Solaja, Bogdan A" sort="Solaja, Bogdan A" uniqKey="Solaja B" first="Bogdan A." last="Šolaja">Bogdan A. Šolaja</name><affiliation wicri:level="1"><country xml:lang="fr">Monténégro</country><wicri:regionArea>Institute of Chemistry, Technology and Metallurgy, Belgrade, Serbia and Montenegro, Fachbereich Chemie, Organische Chemie I, UniversitätDortmund, D-44221 Dortmund, Germany, Laboratoire de Chimie Physique et de Cristallographie, Université Catholique de Louvain,Louvain-la-Neuve, Belgium, National Cancer Research Institute, Belgrade, Serbia and Montenegro, Division of Experimental Therapeutics,Walter Reed Army Institute of Research, Washington, D.C. 20307-5100, and Faculty of Chemistry, University of Belgrade, Belgrade</wicri:regionArea><wicri:noRegion>Belgrade</wicri:noRegion></affiliation><affiliation></affiliation><affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Medicinal Chemistry</title><title level="j" type="abbrev">J. Med. Chem.</title><idno type="ISSN">0022-2623</idno><idno type="eISSN">1520-4804</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published" when="2006-06-08">2006</date><date when="2006-06-29">2006</date><biblScope unit="vol">49</biblScope><biblScope unit="issue">13</biblScope><biblScope unit="page" from="3790">3790</biblScope><biblScope unit="page" to="3799">3799</biblScope></imprint><idno type="ISSN">0022-2623</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4‘ ‘) methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg·kg-1·day-1, and 2/5 mice at 50 mg·kg-1·day-1, showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO• radicals were detected by EPR experiments. This finding and the indication of Fe(IV)O species led us to propose that RO• radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.</div></front></TEI><affiliations><list><country><li>Allemagne</li><li>Monténégro</li></country><region><li>Bade-Wurtemberg</li><li>District de Tübingen</li></region><settlement><li>Tübingen</li></settlement></list><tree><country name="Monténégro"><noRegion><name sortKey="Opsenica, Igor" sort="Opsenica, Igor" uniqKey="Opsenica I" first="Igor" last="Opsenica">Igor Opsenica</name></noRegion><name sortKey="Angelovski, Goran" sort="Angelovski, Goran" uniqKey="Angelovski G" first="Goran" last="Angelovski">Goran Angelovski</name><name sortKey="Diaz, Damaris S" sort="Diaz, Damaris S" uniqKey="Diaz D" first="Damaris S." last="Diaz">Damaris S. Diaz</name><name sortKey="Dokovi, Dejan" sort="Dokovi, Dejan" uniqKey="Dokovi D" first="Dejan" last="Dokovi">Dejan Dokovi</name><name sortKey="Eilbracht, Peter" sort="Eilbracht, Peter" uniqKey="Eilbracht P" first="Peter" last="Eilbracht">Peter Eilbracht</name><name sortKey="Jurani, Zorica" sort="Jurani, Zorica" uniqKey="Jurani Z" first="Zorica" last="Jurani">Zorica Jurani</name><name sortKey="Lehnig, Manfred" sort="Lehnig, Manfred" uniqKey="Lehnig M" first="Manfred" last="Lehnig">Manfred Lehnig</name><name sortKey="Milhous, Wilbur K" sort="Milhous, Wilbur K" uniqKey="Milhous W" first="Wilbur K." last="Milhous">Wilbur K. Milhous</name><name sortKey="Opsenica, Dejan" sort="Opsenica, Dejan" uniqKey="Opsenica D" first="Dejan" last="Opsenica">Dejan Opsenica</name><name sortKey="Smith, Kirsten S" sort="Smith, Kirsten S" uniqKey="Smith K" first="Kirsten S." last="Smith">Kirsten S. Smith</name><name sortKey="Smith, Philip L" sort="Smith, Philip L" uniqKey="Smith P" first="Philip L." last="Smith">Philip L. Smith</name><name sortKey="Solaja, Bogdan A" sort="Solaja, Bogdan A" uniqKey="Solaja B" first="Bogdan A." last="Šolaja">Bogdan A. Šolaja</name><name sortKey="Terzi, Natasa" sort="Terzi, Natasa" uniqKey="Terzi N" first="Nataša" last="Terzi">Nataša Terzi</name><name sortKey="Tinant, Bernard" sort="Tinant, Bernard" uniqKey="Tinant B" first="Bernard" last="Tinant">Bernard Tinant</name><name sortKey="Yang, Young S" sort="Yang, Young S" uniqKey="Yang Y" first="Young S." last="Yang">Young S. Yang</name></country><country name="Allemagne"><region name="Bade-Wurtemberg"><name sortKey="Angelovski, Goran" sort="Angelovski, Goran" uniqKey="Angelovski G" first="Goran" last="Angelovski">Goran Angelovski</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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