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Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium

Identifieur interne : 000094 ( Hal/Checkpoint ); précédent : 000093; suivant : 000095

Discovery of new thienopyrimidinone derivatives displaying antimalarial properties toward both erythrocytic and hepatic stages of Plasmodium

Auteurs : Anita Cohen [France] ; Peggy Suzanne [France] ; Jean-Charles Lancelot [France] ; Pierre Verhaeghe [France] ; Aurélien Lesnard [France] ; Louise Basmaciyan [France] ; Sébastien Hutter [France] ; Michèle Laget [France] ; Aurélien Dumètre [France] ; Lucie Paloque [France] ; Eric Deharo [France] ; Maxime D. Crozet [France] ; Pascal Rathelot [France] ; Patrick Dallemagne [France] ; Audrey Lorthiois [France] ; Carol Hopkins Sibley [États-Unis] ; Patrice Vanelle [France] ; Alexis Valentin [France] ; Dominique Mazier [France] ; Sylvain Rault [France] ; Nadine Azas [France]

Source :

RBID : Hal:hal-01460555

Abstract

A preliminary in vitro screening of compounds belonging to various chemical families from our library revealed the thieno[3,2-d]pyrimidin-4(3H)-one scaffold displayed a promising profile against Plasmodium falciparum. Then, 120 new derivatives were synthesized and evaluated in vitro; compared to drug references, 40 showed good activity toward chloroquine sensitive (IC50 35-344 nM) and resistant (IC50 45-800 nM) P. falciparum strains. They were neither cytotoxic (CC50 15-50 mu M) toward HepG2 and CHO cells, nor mutagenic. Structure activity relationships were defined. The lead-compound also appeared active against the Plasmodium liver stages (Plasmodium yoelii IC50 = 35 nM) and a preliminary in vivo evaluation indicated the in vitro activity was preserved (45% reduction in parasitemia compared to untreated infected mice). A mechanistic study demonstrated these molecules do not involve any of the pathways described for commercial drugs and exert a specific activity on the ring and trophozoite stages. 2015 Elsevier Masson SAS. All rights reserved.


Url:
DOI: 10.1016/j.ejmech.2015.03.011

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<p>A preliminary in vitro screening of compounds belonging to various chemical families from our library revealed the thieno[3,2-d]pyrimidin-4(3H)-one scaffold displayed a promising profile against Plasmodium falciparum. Then, 120 new derivatives were synthesized and evaluated in vitro; compared to drug references, 40 showed good activity toward chloroquine sensitive (IC50 35-344 nM) and resistant (IC50 45-800 nM) P. falciparum strains. They were neither cytotoxic (CC50 15-50 mu M) toward HepG2 and CHO cells, nor mutagenic. Structure activity relationships were defined. The lead-compound also appeared active against the Plasmodium liver stages (Plasmodium yoelii IC50 = 35 nM) and a preliminary in vivo evaluation indicated the in vitro activity was preserved (45% reduction in parasitemia compared to untreated infected mice). A mechanistic study demonstrated these molecules do not involve any of the pathways described for commercial drugs and exert a specific activity on the ring and trophozoite stages. 2015 Elsevier Masson SAS. All rights reserved.</p>
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<surname>Crozet</surname>
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<idno type="halauthorid">67145</idno>
<affiliation ref="#struct-258556"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Pascal</forename>
<surname>Rathelot</surname>
</persName>
<idno type="halauthorid">795693</idno>
<affiliation ref="#struct-258556"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Patrick</forename>
<surname>Dallemagne</surname>
</persName>
<email type="md5">e2720beed5ff2d3091ccace6c74ac4f2</email>
<email type="domain">unicaen.fr</email>
<idno type="idhal" notation="string">patrick-dallemagne</idno>
<idno type="idhal" notation="numeric">182895</idno>
<idno type="halauthorid">349358</idno>
<idno type="ORCID">https://orcid.org/0000-0002-4845-615X</idno>
<idno type="ResearcherId">http://www.researcherid.com/rid/D-3237-2013 </idno>
<affiliation ref="#struct-207951"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Audrey</forename>
<surname>Lorthiois</surname>
</persName>
<idno type="halauthorid">1091468</idno>
<affiliation ref="#struct-246601"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Carol Hopkins</forename>
<surname>Sibley</surname>
</persName>
<idno type="halauthorid">241917</idno>
<affiliation ref="#struct-558772"></affiliation>
<affiliation ref="#struct-22573"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Patrice</forename>
<forename type="middle">J</forename>
<surname>Vanelle</surname>
</persName>
<idno type="halauthorid">1441437</idno>
<affiliation ref="#struct-258556"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Alexis</forename>
<surname>Valentin</surname>
</persName>
<idno type="halauthorid">235550</idno>
<affiliation ref="#struct-192672"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Dominique</forename>
<surname>Mazier</surname>
</persName>
<idno type="halauthorid">217412</idno>
<affiliation ref="#struct-246601"></affiliation>
<affiliation ref="#struct-167009"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Sylvain</forename>
<surname>Rault</surname>
</persName>
<idno type="halauthorid">350166</idno>
<affiliation ref="#struct-207951"></affiliation>
<affiliation ref="#struct-455934"></affiliation>
</author>
<author role="aut">
<persName>
<forename type="first">Nadine</forename>
<surname>Azas</surname>
</persName>
<idno type="halauthorid">795694</idno>
<affiliation ref="#struct-220808"></affiliation>
</author>
</analytic>
<monogr>
<idno type="halJournalId" status="VALID">12364</idno>
<idno type="issn">0223-5234</idno>
<idno type="eissn">1768-3254</idno>
<title level="j">European Journal of Medicinal Chemistry</title>
<imprint>
<publisher>Elsevier</publisher>
<biblScope unit="volume">95</biblScope>
<biblScope unit="pp">16-28</biblScope>
<date type="datePub">2015-05</date>
</imprint>
</monogr>
<idno type="doi">10.1016/j.ejmech.2015.03.011</idno>
</biblStruct>
</sourceDesc>
<profileDesc>
<langUsage>
<language ident="en">English</language>
</langUsage>
<textClass>
<classCode scheme="halDomain" n="chim">Chemical Sciences</classCode>
<classCode scheme="halTypology" n="ART">Journal articles</classCode>
</textClass>
<abstract xml:lang="en">
<p>A preliminary in vitro screening of compounds belonging to various chemical families from our library revealed the thieno[3,2-d]pyrimidin-4(3H)-one scaffold displayed a promising profile against Plasmodium falciparum. Then, 120 new derivatives were synthesized and evaluated in vitro; compared to drug references, 40 showed good activity toward chloroquine sensitive (IC50 35-344 nM) and resistant (IC50 45-800 nM) P. falciparum strains. They were neither cytotoxic (CC50 15-50 mu M) toward HepG2 and CHO cells, nor mutagenic. Structure activity relationships were defined. The lead-compound also appeared active against the Plasmodium liver stages (Plasmodium yoelii IC50 = 35 nM) and a preliminary in vivo evaluation indicated the in vitro activity was preserved (45% reduction in parasitemia compared to untreated infected mice). A mechanistic study demonstrated these molecules do not involve any of the pathways described for commercial drugs and exert a specific activity on the ring and trophozoite stages. 2015 Elsevier Masson SAS. All rights reserved.</p>
</abstract>
</profileDesc>
</hal>
</record>

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