ChloroquineV1, France, Analysis, bibRecord, 000133

Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum

Identifieur interne : 000133 ( France/Analysis ); précédent : 000132; suivant : 000134

Synthesis 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 ] ; 2015-10-16.

RBID : Hal:hal-01235998

English descriptors

mix :
- AGENTS, AMODIAQUINE, ANALOGS, ANTIMALARIAL ACTIVITY, BETA-HEMATIN, COMPLEXES, DENSITY, ISOQUINE, MALARIA, METABOLISM.

Abstract

The efficacy of chloroquine, once the drug of choice in the fight against Plasmodium falcipa-rum, 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-amino-quinolines 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 IC 50), markedly superior to chloroquine and comparable to amodiaquine, against chloroquine-sensitive and chloroquine-resistant strains of P. falcipa-rum, 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.

Url:

https://hal-amu.archives-ouvertes.fr/hal-01235998

DOI: 10.1371/journal.pone.0140878.s004

Affiliations:

Links toward previous steps (curation, corpus...)

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to stream France, to step Extraction: 000133

Links to Exploration step

Hal:hal-01235998

Le document en format XML

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<author><name sortKey="Roy, Dipankar" sort="Roy, Dipankar" uniqKey="Roy D" first="Dipankar" last="Roy">Dipankar Roy</name>
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<author><name sortKey="Schrevel, Joseph" sort="Schrevel, Joseph" uniqKey="Schrevel J" first="Joseph" last="Schrével">Joseph Schrével</name>
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<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"><hal:affiliation type="laboratory" xml:id="struct-442948" status="INCOMING">          <orgName>Chemistry Department of Brooklyn College and Ph.D. Program in Chemistry</orgName>
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          <orgName type="acronym">The Graduate Center</orgName>
          <desc>            <address>              <addrLine>New York, NY 10016</addrLine>
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          <orgName>City University of New York [New York]</orgName>
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          <desc>            <address>              <addrLine>217 East 42 St, New York, NY 10017</addrLine>
              <country key="US"></country>
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<country>États-Unis</country>
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<idno type="DOI">10.1371/journal.pone.0140878.s004</idno>
<series><title level="j">PLoS ONE</title>
<idno type="ISSN">1932-6203</idno>
<imprint><date type="datePub">2015-10-16</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="mix" xml:lang="en"><term>AGENTS</term>
<term>AMODIAQUINE</term>
<term>ANALOGS</term>
<term>ANTIMALARIAL ACTIVITY</term>
<term>BETA-HEMATIN</term>
<term>COMPLEXES</term>
<term>DENSITY</term>
<term>ISOQUINE</term>
<term>MALARIA</term>
<term>METABOLISM</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">              <p>The efficacy of chloroquine, once the drug of choice in the fight against Plasmodium falcipa-rum, 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-amino-quinolines 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 IC 50), markedly superior to chloroquine and comparable to amodiaquine, against chloroquine-sensitive and chloroquine-resistant strains of P. falcipa-rum, 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.</p>
            </div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
<li>États-Unis</li>
</country>
<region><li>Provence-Alpes-Côte d'Azur</li>
</region>
<settlement><li>Marseille</li>
</settlement>
<orgName><li>Université d'Aix-Marseille</li>
</orgName>
</list>
<tree><country name="États-Unis"><noRegion><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>
</noRegion>
<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. Sánchez-Delgado</name>
</country>
<country name="France"><noRegion><name sortKey="Deregnaucourt, Christiane" sort="Deregnaucourt, Christiane" uniqKey="Deregnaucourt C" first="Christiane" last="Deregnaucourt">Christiane Deregnaucourt</name>
</noRegion>
<name sortKey="Latour, Christine" sort="Latour, Christine" uniqKey="Latour C" first="Christine" last="Latour">Christine Latour</name>
<name sortKey="Schrevel, Joseph" sort="Schrevel, Joseph" uniqKey="Schrevel J" first="Joseph" last="Schrével">Joseph Schrével</name>
<name sortKey="Sinou, Veronique" sort="Sinou, Veronique" uniqKey="Sinou V" first="Véronique" last="Sinou">Véronique Sinou</name>
</country>
</tree>
</affiliations>
</record>

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   |wiki=    Sante
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   |texte=   Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum
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Serveur d'exploration Chloroquine

Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum

Synthesis of New 4-Aminoquinolines and Evaluation of Their In Vitro Activity against Chloroquine-Sensitive and Chloroquine-Resistant Plasmodium falciparum

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