Expanding the SAR of Nontoxic Antiplasmodial Indolyl-3-ethanone Ethers and Thioethers.
Identifieur interne : 000C36 ( Main/Exploration ); précédent : 000C35; suivant : 000C37Expanding the SAR of Nontoxic Antiplasmodial Indolyl-3-ethanone Ethers and Thioethers.
Auteurs : Mayibongwe J. Lunga [Afrique du Sud] ; Ruramai L. Chisango [Afrique du Sud] ; Carli Weyers [Afrique du Sud] ; Michelle Isaacs [Afrique du Sud] ; Dale Taylor [Afrique du Sud] ; Adrienne L. Edkins [Afrique du Sud] ; Setshaba D. Khanye [Afrique du Sud] ; Heinrich C. Hoppe [Afrique du Sud] ; Clinton G L. Veale [Afrique du Sud]Source :
- ChemMedChem [ 1860-7187 ] ; 2018.
Descripteurs français
- KwdFr :
- Antipaludiques (), Antipaludiques (pharmacologie), Antipaludiques (synthèse chimique), Antipaludiques (toxicité), Cellules HeLa, Humains, Hémolyse (), Indoles (), Indoles (pharmacologie), Indoles (synthèse chimique), Indoles (toxicité), Plasmodium falciparum (), Relation structure-activité, Structure moléculaire, Sulfures (), Sulfures (pharmacologie), Sulfures (synthèse chimique), Sulfures (toxicité), Tests de sensibilité parasitaire, Érythrocytes (), Éthers (), Éthers (pharmacologie), Éthers (synthèse chimique), Éthers (toxicité).
- MESH :
- pharmacologie : Antipaludiques, Indoles, Sulfures, Éthers.
- synthèse chimique : Antipaludiques, Indoles, Sulfures, Éthers.
- toxicité : Antipaludiques, Indoles, Sulfures, Éthers.
- Antipaludiques, Cellules HeLa, Humains, Hémolyse, Indoles, Plasmodium falciparum, Relation structure-activité, Structure moléculaire, Sulfures, Tests de sensibilité parasitaire, Érythrocytes, Éthers.
English descriptors
- KwdEn :
- Antimalarials (chemical synthesis), Antimalarials (chemistry), Antimalarials (pharmacology), Antimalarials (toxicity), Erythrocytes (drug effects), Ethers (chemical synthesis), Ethers (chemistry), Ethers (pharmacology), Ethers (toxicity), HeLa Cells, Hemolysis (drug effects), Humans, Indoles (chemical synthesis), Indoles (chemistry), Indoles (pharmacology), Indoles (toxicity), Molecular Structure, Parasitic Sensitivity Tests, Plasmodium falciparum (drug effects), Structure-Activity Relationship, Sulfides (chemical synthesis), Sulfides (chemistry), Sulfides (pharmacology), Sulfides (toxicity).
- MESH :
- chemical , chemical synthesis : Antimalarials, Ethers, Indoles, Sulfides.
- chemical , chemistry : Antimalarials, Ethers, Indoles, Sulfides.
- chemical , pharmacology : Antimalarials, Ethers, Indoles, Sulfides.
- chemical , toxicity : Antimalarials, Ethers, Indoles, Sulfides.
- drug effects : Erythrocytes, Hemolysis, Plasmodium falciparum.
- HeLa Cells, Humans, Molecular Structure, Parasitic Sensitivity Tests, Structure-Activity Relationship.
Abstract
Despite major strides in reducing Plasmodium falciparum infections, this parasite still accounts for roughly half a million annual deaths. This problem is compounded by the decreased efficacy of artemisinin combination therapies. Therefore, the development and optimisation of novel antimalarial chemotypes is critical. In this study, we describe our strategic approach to optimise a class of previously reported antimalarials, resulting in the discovery of 1-(5-chloro-1H-indol-3-yl)-2-[(4-cyanophenyl)thio]ethanone (13) and 1-(5-chloro-1H-indol-3-yl)-2-[(4-nitrophenyl)thio]ethanone (14), whose activity was equipotent to that of chloroquine against the P. falciparum 3D7 strain. Furthermore, these compounds were found to be nontoxic to HeLa cells as well as being non-haemolytic to uninfected red blood cells. Intriguingly, several of our most promising compounds were found to be less active against the isogenic NF54 strain, highlighting possible issues with long-term dependability of malarial strains. Finally compound 14 displayed similar activity against both the NF54 and K1 strains, suggesting that it inhibits a pathway that is uncompromised by K1 resistance.
DOI: 10.1002/cmdc.201800235
PubMed: 29756273
Affiliations:
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Lunga</name><affiliation wicri:level="1"><nlm:affiliation>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Chisango, Ruramai L" sort="Chisango, Ruramai L" uniqKey="Chisango R" first="Ruramai L" last="Chisango">Ruramai L. Chisango</name><affiliation wicri:level="1"><nlm:affiliation>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Weyers, Carli" sort="Weyers, Carli" uniqKey="Weyers C" first="Carli" last="Weyers">Carli Weyers</name><affiliation wicri:level="1"><nlm:affiliation>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Isaacs, Michelle" sort="Isaacs, Michelle" uniqKey="Isaacs M" first="Michelle" last="Isaacs">Michelle Isaacs</name><affiliation wicri:level="1"><nlm:affiliation>Department of Biochemistry and Microbiology, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Department of Biochemistry and Microbiology, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Taylor, Dale" sort="Taylor, Dale" uniqKey="Taylor D" first="Dale" last="Taylor">Dale Taylor</name><affiliation wicri:level="1"><nlm:affiliation>Division of Clinical Pharmacology, Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory, 7925, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Division of Clinical Pharmacology, Department of Medicine, University of Cape Town, Groote Schuur Hospital, Observatory, 7925</wicri:regionArea><wicri:noRegion>7925</wicri:noRegion></affiliation></author><author><name sortKey="Edkins, Adrienne L" sort="Edkins, Adrienne L" uniqKey="Edkins A" first="Adrienne L" last="Edkins">Adrienne L. Edkins</name><affiliation wicri:level="1"><nlm:affiliation>Department of Biochemistry and Microbiology, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Department of Biochemistry and Microbiology, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Khanye, Setshaba D" sort="Khanye, Setshaba D" uniqKey="Khanye S" first="Setshaba D" last="Khanye">Setshaba D. Khanye</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Department of Chemistry, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Hoppe, Heinrich C" sort="Hoppe, Heinrich C" uniqKey="Hoppe H" first="Heinrich C" last="Hoppe">Heinrich C. Hoppe</name><affiliation wicri:level="1"><nlm:affiliation>Department of Biochemistry and Microbiology, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Department of Biochemistry and Microbiology, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author><author><name sortKey="Veale, Clinton G L" sort="Veale, Clinton G L" uniqKey="Veale C" first="Clinton G L" last="Veale">Clinton G L. Veale</name><affiliation wicri:level="1"><nlm:affiliation>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140, South Africa.</nlm:affiliation><country xml:lang="fr">Afrique du Sud</country><wicri:regionArea>Faculty of Pharmacy, Rhodes University, Grahamstown, 6140</wicri:regionArea><wicri:noRegion>6140</wicri:noRegion></affiliation></author></analytic><series><title level="j">ChemMedChem</title><idno type="eISSN">1860-7187</idno><imprint><date when="2018" type="published">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antimalarials (chemical synthesis)</term><term>Antimalarials (chemistry)</term><term>Antimalarials (pharmacology)</term><term>Antimalarials (toxicity)</term><term>Erythrocytes (drug effects)</term><term>Ethers (chemical synthesis)</term><term>Ethers (chemistry)</term><term>Ethers (pharmacology)</term><term>Ethers (toxicity)</term><term>HeLa Cells</term><term>Hemolysis (drug effects)</term><term>Humans</term><term>Indoles (chemical synthesis)</term><term>Indoles (chemistry)</term><term>Indoles (pharmacology)</term><term>Indoles (toxicity)</term><term>Molecular Structure</term><term>Parasitic Sensitivity Tests</term><term>Plasmodium falciparum (drug effects)</term><term>Structure-Activity Relationship</term><term>Sulfides (chemical synthesis)</term><term>Sulfides (chemistry)</term><term>Sulfides (pharmacology)</term><term>Sulfides (toxicity)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antipaludiques ()</term><term>Antipaludiques (pharmacologie)</term><term>Antipaludiques (synthèse chimique)</term><term>Antipaludiques (toxicité)</term><term>Cellules HeLa</term><term>Humains</term><term>Hémolyse ()</term><term>Indoles ()</term><term>Indoles (pharmacologie)</term><term>Indoles (synthèse chimique)</term><term>Indoles (toxicité)</term><term>Plasmodium falciparum ()</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Sulfures ()</term><term>Sulfures (pharmacologie)</term><term>Sulfures (synthèse chimique)</term><term>Sulfures (toxicité)</term><term>Tests de sensibilité parasitaire</term><term>Érythrocytes ()</term><term>Éthers ()</term><term>Éthers (pharmacologie)</term><term>Éthers (synthèse chimique)</term><term>Éthers (toxicité)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antimalarials</term><term>Ethers</term><term>Indoles</term><term>Sulfides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimalarials</term><term>Ethers</term><term>Indoles</term><term>Sulfides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antimalarials</term><term>Ethers</term><term>Indoles</term><term>Sulfides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Antimalarials</term><term>Ethers</term><term>Indoles</term><term>Sulfides</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Erythrocytes</term><term>Hemolysis</term><term>Plasmodium falciparum</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antipaludiques</term><term>Indoles</term><term>Sulfures</term><term>Éthers</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antipaludiques</term><term>Indoles</term><term>Sulfures</term><term>Éthers</term></keywords><keywords scheme="MESH" qualifier="toxicité" xml:lang="fr"><term>Antipaludiques</term><term>Indoles</term><term>Sulfures</term><term>Éthers</term></keywords><keywords scheme="MESH" xml:lang="en"><term>HeLa Cells</term><term>Humans</term><term>Molecular Structure</term><term>Parasitic Sensitivity Tests</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antipaludiques</term><term>Cellules HeLa</term><term>Humains</term><term>Hémolyse</term><term>Indoles</term><term>Plasmodium falciparum</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Sulfures</term><term>Tests de sensibilité parasitaire</term><term>Érythrocytes</term><term>Éthers</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Despite major strides in reducing Plasmodium falciparum infections, this parasite still accounts for roughly half a million annual deaths. This problem is compounded by the decreased efficacy of artemisinin combination therapies. Therefore, the development and optimisation of novel antimalarial chemotypes is critical. In this study, we describe our strategic approach to optimise a class of previously reported antimalarials, resulting in the discovery of 1-(5-chloro-1H-indol-3-yl)-2-[(4-cyanophenyl)thio]ethanone (13) and 1-(5-chloro-1H-indol-3-yl)-2-[(4-nitrophenyl)thio]ethanone (14), whose activity was equipotent to that of chloroquine against the P. falciparum 3D7 strain. Furthermore, these compounds were found to be nontoxic to HeLa cells as well as being non-haemolytic to uninfected red blood cells. Intriguingly, several of our most promising compounds were found to be less active against the isogenic NF54 strain, highlighting possible issues with long-term dependability of malarial strains. Finally compound 14 displayed similar activity against both the NF54 and K1 strains, suggesting that it inhibits a pathway that is uncompromised by K1 resistance.</div></front></TEI><affiliations><list><country><li>Afrique du Sud</li></country></list><tree><country name="Afrique du Sud"><noRegion><name sortKey="Lunga, Mayibongwe J" sort="Lunga, Mayibongwe J" uniqKey="Lunga M" first="Mayibongwe J" last="Lunga">Mayibongwe J. Lunga</name></noRegion><name sortKey="Chisango, Ruramai L" sort="Chisango, Ruramai L" uniqKey="Chisango R" first="Ruramai L" last="Chisango">Ruramai L. Chisango</name><name sortKey="Edkins, Adrienne L" sort="Edkins, Adrienne L" uniqKey="Edkins A" first="Adrienne L" last="Edkins">Adrienne L. Edkins</name><name sortKey="Hoppe, Heinrich C" sort="Hoppe, Heinrich C" uniqKey="Hoppe H" first="Heinrich C" last="Hoppe">Heinrich C. Hoppe</name><name sortKey="Isaacs, Michelle" sort="Isaacs, Michelle" uniqKey="Isaacs M" first="Michelle" last="Isaacs">Michelle Isaacs</name><name sortKey="Khanye, Setshaba D" sort="Khanye, Setshaba D" uniqKey="Khanye S" first="Setshaba D" last="Khanye">Setshaba D. Khanye</name><name sortKey="Taylor, Dale" sort="Taylor, Dale" uniqKey="Taylor D" first="Dale" last="Taylor">Dale Taylor</name><name sortKey="Veale, Clinton G L" sort="Veale, Clinton G L" uniqKey="Veale C" first="Clinton G L" last="Veale">Clinton G L. Veale</name><name sortKey="Weyers, Carli" sort="Weyers, Carli" uniqKey="Weyers C" first="Carli" last="Weyers">Carli Weyers</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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