Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum.
Identifieur interne : 000316 ( Ncbi/Merge ); précédent : 000315; suivant : 000317Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum.
Auteurs : Chandima S K. Rajapakse [États-Unis] ; Maryna Lisai [États-Unis] ; Christiane Deregnaucourt [France] ; Véronique Sinou [France] ; Christine Latour [France] ; Dipankar Roy [États-Unis] ; Joseph Schrével [France] ; Roberto A. Sánchez-Delgado [États-Unis]Source :
- PloS one [ 1932-6203 ] ; 2015.
Descripteurs français
- KwdFr :
- Animaux, Antipaludiques (), Antipaludiques (pharmacocinétique), Antipaludiques (pharmacologie), Antipaludiques (synthèse chimique), Chloroquine (), Chloroquine (pharmacocinétique), Chloroquine (pharmacologie), Humains, Lignée cellulaire, Modèles chimiques, Plasmodium falciparum (métabolisme), Rats, Résistance aux substances ().
- MESH :
- métabolisme : Plasmodium falciparum.
- pharmacocinétique : Antipaludiques, Chloroquine.
- pharmacologie : Antipaludiques, Chloroquine.
- synthèse chimique : Antipaludiques.
- Animaux, Antipaludiques, Chloroquine, Humains, Lignée cellulaire, Modèles chimiques, Rats, Résistance aux substances.
English descriptors
- KwdEn :
- Animals, Antimalarials (chemical synthesis), Antimalarials (chemistry), Antimalarials (pharmacokinetics), Antimalarials (pharmacology), Cell Line, Chloroquine (chemistry), Chloroquine (pharmacokinetics), Chloroquine (pharmacology), Drug Resistance (drug effects), Humans, Models, Chemical, Plasmodium falciparum (metabolism), Rats.
- MESH :
- chemical , chemical synthesis : Antimalarials.
- chemical , chemistry : Antimalarials, Chloroquine.
- chemical , pharmacokinetics : Antimalarials, Chloroquine.
- chemical , pharmacology : Antimalarials, Chloroquine.
- drug effects : Drug Resistance.
- metabolism : Plasmodium falciparum.
- Animals, Cell Line, Humans, Models, Chemical, Rats.
Abstract
The efficacy of chloroquine, once the drug of choice in the fight against Plasmodium falciparum, is now severely limited due to widespread resistance. Amodiaquine is one of the most potent antimalarial 4-aminoquinolines known and remains effective against chloroquine-resistant parasites, but toxicity issues linked to a quinone-imine metabolite limit its clinical use. In search of new compounds able to retain the antimalarial activity of amodiaquine while circumventing quinone-imine metabolite toxicity, we have synthesized five 4-aminoquinolines that feature rings lacking hydroxyl groups in the side chain of the molecules and are thus incapable of generating toxic quinone-imines. The new compounds displayed high in vitro potency (low nanomolar IC50), markedly superior to chloroquine and comparable to amodiaquine, against chloroquine-sensitive and chloroquine-resistant strains of P. falciparum, accompanied by low toxicity to L6 rat fibroblasts and MRC5 human lung cells, and metabolic stability comparable or higher than that of amodiaquine. Computational studies indicate a unique mode of binding of compound 4 to heme through the HOMO located on a biphenyl moeity, which may partly explain the high antiplasmodial activity observed for this compound.
DOI: 10.1371/journal.pone.0140878
PubMed: 26473363
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pubmed:26473363Le document en format XML
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Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York</wicri:regionArea><placeName><region type="state">État de New York</region></placeName></affiliation></author><author><name sortKey="Schrevel, Joseph" sort="Schrevel, Joseph" uniqKey="Schrevel J" first="Joseph" last="Schrével">Joseph Schrével</name><affiliation wicri:level="3"><nlm:affiliation>Unité Molécules de Communication et Adaptation des Microorganismes, (MCAM, UMR 7245), Sorbonne Universités, Muséum National d'Histoire Naturelle CNRS, Paris, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Unité Molécules de Communication et Adaptation des Microorganismes, (MCAM, UMR 7245), Sorbonne Universités, Muséum National d'Histoire Naturelle CNRS, Paris</wicri:regionArea><placeName><region type="region">Île-de-France</region><region type="old region">Île-de-France</region><settlement type="city">Paris</settlement></placeName></affiliation></author><author><name sortKey="Sanchez Delgado, Roberto A" sort="Sanchez Delgado, Roberto A" uniqKey="Sanchez Delgado R" first="Roberto A" last="Sánchez-Delgado">Roberto A. Sánchez-Delgado</name><affiliation wicri:level="2"><nlm:affiliation>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York, United States of America.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York</wicri:regionArea><placeName><region type="state">État de New York</region></placeName></affiliation></author></analytic><series><title level="j">PloS one</title><idno type="eISSN">1932-6203</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Antimalarials (chemical synthesis)</term><term>Antimalarials (chemistry)</term><term>Antimalarials (pharmacokinetics)</term><term>Antimalarials (pharmacology)</term><term>Cell Line</term><term>Chloroquine (chemistry)</term><term>Chloroquine (pharmacokinetics)</term><term>Chloroquine (pharmacology)</term><term>Drug Resistance (drug effects)</term><term>Humans</term><term>Models, Chemical</term><term>Plasmodium falciparum (metabolism)</term><term>Rats</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antipaludiques ()</term><term>Antipaludiques (pharmacocinétique)</term><term>Antipaludiques (pharmacologie)</term><term>Antipaludiques (synthèse chimique)</term><term>Chloroquine ()</term><term>Chloroquine (pharmacocinétique)</term><term>Chloroquine (pharmacologie)</term><term>Humains</term><term>Lignée cellulaire</term><term>Modèles chimiques</term><term>Plasmodium falciparum (métabolisme)</term><term>Rats</term><term>Résistance aux substances ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antimalarials</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antimalarials</term><term>Chloroquine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacokinetics" xml:lang="en"><term>Antimalarials</term><term>Chloroquine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antimalarials</term><term>Chloroquine</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Drug Resistance</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Plasmodium falciparum</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Plasmodium falciparum</term></keywords><keywords scheme="MESH" qualifier="pharmacocinétique" xml:lang="fr"><term>Antipaludiques</term><term>Chloroquine</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antipaludiques</term><term>Chloroquine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antipaludiques</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Cell Line</term><term>Humans</term><term>Models, Chemical</term><term>Rats</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Antipaludiques</term><term>Chloroquine</term><term>Humains</term><term>Lignée cellulaire</term><term>Modèles chimiques</term><term>Rats</term><term>Résistance aux substances</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The efficacy of chloroquine, once the drug of choice in the fight against Plasmodium falciparum, is now severely limited due to widespread resistance. Amodiaquine is one of the most potent antimalarial 4-aminoquinolines known and remains effective against chloroquine-resistant parasites, but toxicity issues linked to a quinone-imine metabolite limit its clinical use. In search of new compounds able to retain the antimalarial activity of amodiaquine while circumventing quinone-imine metabolite toxicity, we have synthesized five 4-aminoquinolines that feature rings lacking hydroxyl groups in the side chain of the molecules and are thus incapable of generating toxic quinone-imines. The new compounds displayed high in vitro potency (low nanomolar IC50), markedly superior to chloroquine and comparable to amodiaquine, against chloroquine-sensitive and chloroquine-resistant strains of P. falciparum, accompanied by low toxicity to L6 rat fibroblasts and MRC5 human lung cells, and metabolic stability comparable or higher than that of amodiaquine. Computational studies indicate a unique mode of binding of compound 4 to heme through the HOMO located on a biphenyl moeity, which may partly explain the high antiplasmodial activity observed for this compound. </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">26473363</PMID><DateCompleted><Year>2016</Year><Month>06</Month><Day>02</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Electronic-eCollection"><Journal><ISSN IssnType="Electronic">1932-6203</ISSN><JournalIssue CitedMedium="Internet"><Volume>10</Volume><Issue>10</Issue><PubDate><Year>2015</Year></PubDate></JournalIssue><Title>PloS one</Title><ISOAbbreviation>PLoS ONE</ISOAbbreviation></Journal><ArticleTitle>Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum.</ArticleTitle><Pagination><MedlinePgn>e0140878</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1371/journal.pone.0140878</ELocationID><Abstract><AbstractText>The efficacy of chloroquine, once the drug of choice in the fight against Plasmodium falciparum, is now severely limited due to widespread resistance. Amodiaquine is one of the most potent antimalarial 4-aminoquinolines known and remains effective against chloroquine-resistant parasites, but toxicity issues linked to a quinone-imine metabolite limit its clinical use. In search of new compounds able to retain the antimalarial activity of amodiaquine while circumventing quinone-imine metabolite toxicity, we have synthesized five 4-aminoquinolines that feature rings lacking hydroxyl groups in the side chain of the molecules and are thus incapable of generating toxic quinone-imines. The new compounds displayed high in vitro potency (low nanomolar IC50), markedly superior to chloroquine and comparable to amodiaquine, against chloroquine-sensitive and chloroquine-resistant strains of P. falciparum, accompanied by low toxicity to L6 rat fibroblasts and MRC5 human lung cells, and metabolic stability comparable or higher than that of amodiaquine. Computational studies indicate a unique mode of binding of compound 4 to heme through the HOMO located on a biphenyl moeity, which may partly explain the high antiplasmodial activity observed for this compound. </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Rajapakse</LastName><ForeName>Chandima S K</ForeName><Initials>CS</Initials><AffiliationInfo><Affiliation>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York, United States of America.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lisai</LastName><ForeName>Maryna</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York, United States of America.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Deregnaucourt</LastName><ForeName>Christiane</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Unité Molécules de Communication et Adaptation des Microorganismes, (MCAM, UMR 7245), Sorbonne Universités, Muséum National d'Histoire Naturelle CNRS, Paris, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sinou</LastName><ForeName>Véronique</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Latour</LastName><ForeName>Christine</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Roy</LastName><ForeName>Dipankar</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York, United States of America.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Schrével</LastName><ForeName>Joseph</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Unité Molécules de Communication et Adaptation des Microorganismes, (MCAM, UMR 7245), Sorbonne Universités, Muséum National d'Histoire Naturelle CNRS, Paris, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sánchez-Delgado</LastName><ForeName>Roberto A</ForeName><Initials>RA</Initials><AffiliationInfo><Affiliation>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry, The Graduate Center of The City University of New York, New York, New York, United States of 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last="Rajapakse">Chandima S K. Rajapakse</name></region><name sortKey="Lisai, Maryna" sort="Lisai, Maryna" uniqKey="Lisai M" first="Maryna" last="Lisai">Maryna Lisai</name><name sortKey="Roy, Dipankar" sort="Roy, Dipankar" uniqKey="Roy D" first="Dipankar" last="Roy">Dipankar Roy</name><name sortKey="Sanchez Delgado, Roberto A" sort="Sanchez Delgado, Roberto A" uniqKey="Sanchez Delgado R" first="Roberto A" last="Sánchez-Delgado">Roberto A. 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