Antimalarial and Antitumor Evaluation of Novel C-10 Non-Acetal Dimers of 10β-(2-Hydroxyethyl)deoxoartemisinin
Identifieur interne : 001F29 ( Main/Exploration ); précédent : 001F28; suivant : 001F30Antimalarial and Antitumor Evaluation of Novel C-10 Non-Acetal Dimers of 10β-(2-Hydroxyethyl)deoxoartemisinin
Auteurs : J. Prince Jeyadevan [États-Unis] ; Patrick G. Bray [États-Unis] ; James Chadwick [États-Unis] ; Amy E. Mercer [États-Unis] ; Aoife Byrne [États-Unis] ; Stephen A. Ward [États-Unis] ; B. Kevin Park [États-Unis] ; Dominic P. Williams [États-Unis] ; Rick Cosstick [États-Unis] ; Jill Davies [États-Unis] ; Adrian P. Higson [États-Unis] ; Ed Irving [États-Unis] ; Gary H. Posner [États-Unis] ; Paul M. O'Neill [États-Unis, Royaume-Uni]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 2004.
Abstract
Four series of C-10 non-acetal dimers were prepared from key trioxane alcohol 10β-(2-hydroxyethyl)deoxoartemisinin (9b). All of the dimers prepared displayed potent low nanomolar antimalarial activity versus the K1 and HB3 strains of Plasmodium falciparum. The most potent compound assayed was phosphate dimer 14a, which was greater than 50 times more potent than the parent drug artemisinin and about 15 times more potent than the clinically used acetal artemether. In contrast to their potent activity versus malaria parasites, virtually all of the dimers expressed poor anticancer activity apart from the trioxane phosphate ester dimers 14a and 14b, which expressed nanomolar growth inhibitory (GI50) values versus a range of cancer cell lines in the NCI 60 human cell line screen. Further detailed studies on these dimers in vitro in HL60 cells demonstrate that both phosphate ester dimers (14a and 14b) are more potent than the anticancer agent doxorubicin. Interestingly, phosphate ester monomers 9c and 9d, antimalarially active in the low nanomolar region versus P. falciparum, are inactive as anticancer agents even at concentrations in the millimolar region. This observation emphasizes the importance of two trioxane units for high antiproliferative activity, and we propose that the nature of the linker in dimers of this type plays a crucial role in imparting potent anticancer activity.
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DOI: 10.1021/jm030974c
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10β-(2-Hydroxyethyl)deoxoartemisinin</title><author><name sortKey="Jeyadevan, J Prince" sort="Jeyadevan, J Prince" uniqKey="Jeyadevan J" first="J. Prince" last="Jeyadevan">J. Prince Jeyadevan</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Bray, Patrick G" sort="Bray, Patrick G" uniqKey="Bray P" first="Patrick G." last="Bray">Patrick G. Bray</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Chadwick, James" sort="Chadwick, James" uniqKey="Chadwick J" first="James" last="Chadwick">James Chadwick</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Mercer, Amy E" sort="Mercer, Amy E" uniqKey="Mercer A" first="Amy E." last="Mercer">Amy E. Mercer</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Byrne, Aoife" sort="Byrne, Aoife" uniqKey="Byrne A" first="Aoife" last="Byrne">Aoife Byrne</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Ward, Stephen A" sort="Ward, Stephen A" uniqKey="Ward S" first="Stephen A." last="Ward">Stephen A. Ward</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Park, B Kevin" sort="Park, B Kevin" uniqKey="Park B" first="B. Kevin" last="Park">B. Kevin Park</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Williams, Dominic P" sort="Williams, Dominic P" uniqKey="Williams D" first="Dominic P." last="Williams">Dominic P. Williams</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Cosstick, Rick" sort="Cosstick, Rick" uniqKey="Cosstick R" first="Rick" last="Cosstick">Rick Cosstick</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Davies, Jill" sort="Davies, Jill" uniqKey="Davies J" first="Jill" last="Davies">Jill Davies</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Higson, Adrian P" sort="Higson, Adrian P" uniqKey="Higson A" first="Adrian P." last="Higson">Adrian P. Higson</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Irving, Ed" sort="Irving, Ed" uniqKey="Irving E" first="Ed" last="Irving">Ed Irving</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="Posner, Gary H" sort="Posner, Gary H" uniqKey="Posner G" first="Gary H." last="Posner">Gary H. Posner</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation></author><author><name sortKey="O Neill, Paul M" sort="O Neill, Paul M" uniqKey="O Neill P" first="Paul M." last="O'Neill">Paul M. O'Neill</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Maryland</region></placeName><wicri:cityArea>Department of Chemistry, The Robert Robinson Laboratories, University of Liverpool, Liverpool L69 7ZD, U.K.,Department of Pharmacology and Therapeutics, University of Liverpool, Liverpool L69 3GE, U.K.,Liverpool School of Tropical Medicine, University of Liverpool, Liverpool L69 3GE, U.K., UFC Ltd., Synergy House,Guildhall Close, Manchester Science Park, Manchester M15 6SY, U.K., and Department of Chemistry,School of Arts and Sciences, The Johns Hopkins University, Baltimore</wicri:cityArea></affiliation><affiliation></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Royaume-Uni</country><wicri:regionArea> To whom correspondence should be addressed. Address: Department of Chemistry, Robert Robinson Laboratories, University ofLiverpool, Liverpool L69 7ZD</wicri:regionArea><wicri:noRegion>Liverpool L69 7ZD</wicri:noRegion></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="2004-01-31">2004</date><date when="2004-02-26">2004</date><biblScope unit="vol">47</biblScope><biblScope unit="issue">5</biblScope><biblScope unit="page" from="1290">1290</biblScope><biblScope unit="page" to="1298">1298</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">Four series of C-10 non-acetal dimers were prepared from key trioxane alcohol 10β-(2-hydroxyethyl)deoxoartemisinin (9b). All of the dimers prepared displayed potent low nanomolar antimalarial activity versus the K1 and HB3 strains of Plasmodium falciparum. The most potent compound assayed was phosphate dimer 14a, which was greater than 50 times more potent than the parent drug artemisinin and about 15 times more potent than the clinically used acetal artemether. In contrast to their potent activity versus malaria parasites, virtually all of the dimers expressed poor anticancer activity apart from the trioxane phosphate ester dimers 14a and 14b, which expressed nanomolar growth inhibitory (GI50) values versus a range of cancer cell lines in the NCI 60 human cell line screen. Further detailed studies on these dimers in vitro in HL60 cells demonstrate that both phosphate ester dimers (14a and 14b) are more potent than the anticancer agent doxorubicin. Interestingly, phosphate ester monomers 9c and 9d, antimalarially active in the low nanomolar region versus P. falciparum, are inactive as anticancer agents even at concentrations in the millimolar region. This observation emphasizes the importance of two trioxane units for high antiproliferative activity, and we propose that the nature of the linker in dimers of this type plays a crucial role in imparting potent anticancer activity.</div></front></TEI><affiliations><list><country><li>Royaume-Uni</li><li>États-Unis</li></country><region><li>Maryland</li></region></list><tree><country name="États-Unis"><region name="Maryland"><name sortKey="Jeyadevan, J Prince" sort="Jeyadevan, J Prince" uniqKey="Jeyadevan J" first="J. Prince" last="Jeyadevan">J. Prince Jeyadevan</name></region><name sortKey="Bray, Patrick G" sort="Bray, Patrick G" uniqKey="Bray P" first="Patrick G." last="Bray">Patrick G. Bray</name><name sortKey="Byrne, Aoife" sort="Byrne, Aoife" uniqKey="Byrne A" first="Aoife" last="Byrne">Aoife Byrne</name><name sortKey="Chadwick, James" sort="Chadwick, James" uniqKey="Chadwick J" first="James" last="Chadwick">James Chadwick</name><name sortKey="Cosstick, Rick" sort="Cosstick, Rick" uniqKey="Cosstick R" first="Rick" last="Cosstick">Rick Cosstick</name><name sortKey="Davies, Jill" sort="Davies, Jill" uniqKey="Davies J" first="Jill" last="Davies">Jill Davies</name><name sortKey="Higson, Adrian P" sort="Higson, Adrian P" uniqKey="Higson A" first="Adrian P." last="Higson">Adrian P. Higson</name><name sortKey="Irving, Ed" sort="Irving, Ed" uniqKey="Irving E" first="Ed" last="Irving">Ed Irving</name><name sortKey="Mercer, Amy E" sort="Mercer, Amy E" uniqKey="Mercer A" first="Amy E." last="Mercer">Amy E. Mercer</name><name sortKey="O Neill, Paul M" sort="O Neill, Paul M" uniqKey="O Neill P" first="Paul M." last="O'Neill">Paul M. O'Neill</name><name sortKey="Park, B Kevin" sort="Park, B Kevin" uniqKey="Park B" first="B. Kevin" last="Park">B. Kevin Park</name><name sortKey="Posner, Gary H" sort="Posner, Gary H" uniqKey="Posner G" first="Gary H." last="Posner">Gary H. Posner</name><name sortKey="Ward, Stephen A" sort="Ward, Stephen A" uniqKey="Ward S" first="Stephen A." last="Ward">Stephen A. Ward</name><name sortKey="Williams, Dominic P" sort="Williams, Dominic P" uniqKey="Williams D" first="Dominic P." last="Williams">Dominic P. Williams</name></country><country name="Royaume-Uni"><noRegion><name sortKey="O Neill, Paul M" sort="O Neill, Paul M" uniqKey="O Neill P" first="Paul M." last="O'Neill">Paul M. O'Neill</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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