Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum.
Identifieur interne : 000229 ( PubMed/Curation ); précédent : 000228; suivant : 000230Synthesis 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
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: Pour aller vers cette notice dans l'étape Curation :000229
Links to Exploration step
pubmed:26473363Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum.</title>
<author><name sortKey="Rajapakse, Chandima S K" sort="Rajapakse, Chandima S K" uniqKey="Rajapakse C" first="Chandima S K" last="Rajapakse">Chandima S K. Rajapakse</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Lisai, Maryna" sort="Lisai, Maryna" uniqKey="Lisai M" first="Maryna" last="Lisai">Maryna Lisai</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Deregnaucourt, Christiane" sort="Deregnaucourt, Christiane" uniqKey="Deregnaucourt C" first="Christiane" last="Deregnaucourt">Christiane Deregnaucourt</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Sinou, Veronique" sort="Sinou, Veronique" uniqKey="Sinou V" first="Véronique" last="Sinou">Véronique Sinou</name>
<affiliation wicri:level="1"><nlm:affiliation>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Latour, Christine" sort="Latour, Christine" uniqKey="Latour C" first="Christine" last="Latour">Christine Latour</name>
<affiliation wicri:level="1"><nlm:affiliation>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Roy, Dipankar" sort="Roy, Dipankar" uniqKey="Roy D" first="Dipankar" last="Roy">Dipankar Roy</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Schrevel, Joseph" sort="Schrevel, Joseph" uniqKey="Schrevel J" first="Joseph" last="Schrével">Joseph Schrével</name>
<affiliation wicri:level="1"><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>
</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="1"><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>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2015">2015</date>
<idno type="RBID">pubmed:26473363</idno>
<idno type="pmid">26473363</idno>
<idno type="doi">10.1371/journal.pone.0140878</idno>
<idno type="wicri:Area/PubMed/Corpus">000229</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000229</idno>
<idno type="wicri:Area/PubMed/Curation">000229</idno>
<idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000229</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum.</title>
<author><name sortKey="Rajapakse, Chandima S K" sort="Rajapakse, Chandima S K" uniqKey="Rajapakse C" first="Chandima S K" last="Rajapakse">Chandima S K. Rajapakse</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Lisai, Maryna" sort="Lisai, Maryna" uniqKey="Lisai M" first="Maryna" last="Lisai">Maryna Lisai</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Deregnaucourt, Christiane" sort="Deregnaucourt, Christiane" uniqKey="Deregnaucourt C" first="Christiane" last="Deregnaucourt">Christiane Deregnaucourt</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Sinou, Veronique" sort="Sinou, Veronique" uniqKey="Sinou V" first="Véronique" last="Sinou">Véronique Sinou</name>
<affiliation wicri:level="1"><nlm:affiliation>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Latour, Christine" sort="Latour, Christine" uniqKey="Latour C" first="Christine" last="Latour">Christine Latour</name>
<affiliation wicri:level="1"><nlm:affiliation>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Laboratory of Parasitology, Faculty of Pharmacy, UMR-MD3, Aix-Marseille University, Marseille</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Roy, Dipankar" sort="Roy, Dipankar" uniqKey="Roy D" first="Dipankar" last="Roy">Dipankar Roy</name>
<affiliation wicri:level="1"><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>
</affiliation>
</author>
<author><name sortKey="Schrevel, Joseph" sort="Schrevel, Joseph" uniqKey="Schrevel J" first="Joseph" last="Schrével">Joseph Schrével</name>
<affiliation wicri:level="1"><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>
</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="1"><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>
</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 America.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<GrantList CompleteYN="Y"><Grant><GrantID>SC1GM089558</GrantID>
<Acronym>GM</Acronym>
<Agency>NIGMS NIH HHS</Agency>
<Country>United States</Country>
</Grant>
</GrantList>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
<PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2015</Year>
<Month>10</Month>
<Day>16</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>United States</Country>
<MedlineTA>PLoS One</MedlineTA>
<NlmUniqueID>101285081</NlmUniqueID>
<ISSNLinking>1932-6203</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000962">Antimalarials</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>886U3H6UFF</RegistryNumber>
<NameOfSubstance UI="D002738">Chloroquine</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000962" MajorTopicYN="N">Antimalarials</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000493" MajorTopicYN="N">pharmacokinetics</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D002460" MajorTopicYN="N">Cell Line</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D002738" MajorTopicYN="Y">Chloroquine</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000493" MajorTopicYN="N">pharmacokinetics</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004351" MajorTopicYN="N">Drug Resistance</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008956" MajorTopicYN="Y">Models, Chemical</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010963" MajorTopicYN="N">Plasmodium falciparum</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D051381" MajorTopicYN="N">Rats</DescriptorName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year>
<Month>06</Month>
<Day>16</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="accepted"><Year>2015</Year>
<Month>10</Month>
<Day>01</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2015</Year>
<Month>10</Month>
<Day>17</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="pubmed"><Year>2015</Year>
<Month>10</Month>
<Day>17</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2016</Year>
<Month>6</Month>
<Day>3</Day>
<Hour>6</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>epublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">26473363</ArticleId>
<ArticleId IdType="doi">10.1371/journal.pone.0140878</ArticleId>
<ArticleId IdType="pii">PONE-D-15-26404</ArticleId>
<ArticleId IdType="pmc">PMC4608832</ArticleId>
</ArticleIdList>
<ReferenceList><Reference><Citation>J Pharmacol Exp Ther. 2002 Feb;300(2):399-407</Citation>
<ArticleIdList><ArticleId IdType="pubmed">11805197</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Bioorg Med Chem Lett. 2010 Feb 1;20(3):1078-80</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20034790</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2011 Jan 13;54(1):131-42</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21141892</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Parasitol Res. 2009 Sep;105(3):609-27</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19593586</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Am J Trop Med Hyg. 2004 May;70(5):474-80</Citation>
<ArticleIdList><ArticleId IdType="pubmed">15155978</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Comput Chem. 2009 Dec;30(16):2785-91</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19399780</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Clin Pharmacokinet. 1996 Oct;31(4):257-74</Citation>
<ArticleIdList><ArticleId IdType="pubmed">8896943</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Bioorg Med Chem. 2008 Jul 15;16(14):6813-23</Citation>
<ArticleIdList><ArticleId IdType="pubmed">18562202</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Eur J Med Chem. 2013 Nov;69:338-47</Citation>
<ArticleIdList><ArticleId IdType="pubmed">24077524</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Science. 1976 Aug 20;193(4254):673-5</Citation>
<ArticleIdList><ArticleId IdType="pubmed">781840</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>ACS Med Chem Lett. 2013 Oct 01;4(12):1198-202</Citation>
<ArticleIdList><ArticleId IdType="pubmed">24900630</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Malar J. 2007;6:44</Citation>
<ArticleIdList><ArticleId IdType="pubmed">17437625</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Bioorg Med Chem. 2012 Oct 1;20(19):5965-79</Citation>
<ArticleIdList><ArticleId IdType="pubmed">22917857</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Antimicrob Chemother. 2013 Apr;68(4):786-8</Citation>
<ArticleIdList><ArticleId IdType="pubmed">23169890</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2009 Apr 9;52(7):1828-44</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19284751</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 1994 Apr 29;37(9):1362-70</Citation>
<ArticleIdList><ArticleId IdType="pubmed">8176713</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Bioorg Med Chem. 2010 Sep 15;18(18):6625-33</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20797868</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 1997 Feb 14;40(4):437-48</Citation>
<ArticleIdList><ArticleId IdType="pubmed">9046333</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2013 Jun 13;56(11):4811-5</Citation>
<ArticleIdList><ArticleId IdType="pubmed">23701465</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789</Citation>
<ArticleIdList><ArticleId IdType="pubmed">9944570</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 1999 Jul 29;42(15):2747-51</Citation>
<ArticleIdList><ArticleId IdType="pubmed">10425085</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Nature. 2000 Mar 16;404(6775):307-10</Citation>
<ArticleIdList><ArticleId IdType="pubmed">10749217</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2010 Apr 22;53(8):3214-26</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20329733</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Dalton Trans. 2012 Mar 7;41(9):2764-73</Citation>
<ArticleIdList><ArticleId IdType="pubmed">22249579</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Parasitol. 1979 Jun;65(3):418-20</Citation>
<ArticleIdList><ArticleId IdType="pubmed">383936</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2011 Oct 13;54(19):6956-68</Citation>
<ArticleIdList><ArticleId IdType="pubmed">21875063</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Bioorg Med Chem Lett. 2010 Dec 1;20(23):7059-63</Citation>
<ArticleIdList><ArticleId IdType="pubmed">20951034</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Phys Chem B. 2009 May 7;113(18):6378-96</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19366259</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2003 Nov 6;46(23):4933-45</Citation>
<ArticleIdList><ArticleId IdType="pubmed">14584944</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Inorg Chem. 2009 Feb 2;48(3):1122-31</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19119867</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>Antimicrob Agents Chemother. 1979 Dec;16(6):710-8</Citation>
<ArticleIdList><ArticleId IdType="pubmed">394674</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>PLoS One. 2012;7(5):e37259</Citation>
<ArticleIdList><ArticleId IdType="pubmed">22649514</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2012 Dec 13;55(23):10387-404</Citation>
<ArticleIdList><ArticleId IdType="pubmed">23145816</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2009 Mar 12;52(5):1408-15</Citation>
<ArticleIdList><ArticleId IdType="pubmed">19222165</ArticleId>
</ArticleIdList>
</Reference>
<Reference><Citation>J Med Chem. 2004 Oct 7;47(21):5204-9</Citation>
<ArticleIdList><ArticleId IdType="pubmed">15456263</ArticleId>
</ArticleIdList>
</Reference>
</ReferenceList>
</PubmedData>
</pubmed>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/ChloroquineV1/Data/PubMed/Curation
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000229 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Curation/biblio.hfd -nk 000229 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Sante |area= ChloroquineV1 |flux= PubMed |étape= Curation |type= RBID |clé= pubmed:26473363 |texte= Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Curation/RBID.i -Sk "pubmed:26473363" \ | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Curation/biblio.hfd \ | NlmPubMed2Wicri -a ChloroquineV1
![]() | This area was generated with Dilib version V0.6.33. | ![]() |