Antiplasmodial Activity and In Vivo Bio-Distribution of Chloroquine Molecules Released with a 4-(4-Ethynylphenyl)-Triazole Moiety from Organometallo-Cobalamins
Identifieur interne : 000A74 ( Main/Exploration ); précédent : 000A73; suivant : 000A75Antiplasmodial Activity and In Vivo Bio-Distribution of Chloroquine Molecules Released with a 4-(4-Ethynylphenyl)-Triazole Moiety from Organometallo-Cobalamins
Auteurs : Jeremie Rossier ; Sara Nasiri Sovari ; Aleksandar Pavic ; Sandra Vojnovic ; Tameryn Stringer ; Sarah B Ttig ; Gregory S. Smith ; Jasmina Nikodinovic-Runic ; Fabio ZobiSource :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
We have explored the possibility of using organometallic derivatives of cobalamin as a scaffold for the delivery of the same antimalarial drug to both erythro- and hepatocytes. This hybrid molecule approach, intended as a possible tool for the development of multi-stage antimalarial agents, pivots on the preparation of azide-functionalized drugs which, after coupling to the vitamin, are released with a 4-(4-ethynylphenyl)-triazole functionality. Three chloroquine and one imidazolopiperazine derivative (based on the KAF156 structure) were selected as model drugs. One hybrid chloroquine conjugate was extensively studied via fluorescent labelling for in vitro and in vivo bio-distribution studies and gave proof-of-concept for the design. It showed no toxicity in vivo (zebrafish model) as well as no hepatotoxicity, no cardiotoxicity or developmental toxicity of the embryos. All 4-(4-ethynylphenyl)-triazole derivatives of chloroquine were equally active against chloroquine-resistant (CQR) and chloroquine-sensitive (CQS)
Url:
DOI: 10.3390/molecules24122310
PubMed: 31234469
PubMed Central: 6630517
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Antiplasmodial Activity and In Vivo Bio-Distribution of Chloroquine Molecules Released with a 4-(4-Ethynylphenyl)-Triazole Moiety from Organometallo-Cobalamins</title><author><name sortKey="Rossier, Jeremie" sort="Rossier, Jeremie" uniqKey="Rossier J" first="Jeremie" last="Rossier">Jeremie Rossier</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author><author><name sortKey="Nasiri Sovari, Sara" sort="Nasiri Sovari, Sara" uniqKey="Nasiri Sovari S" first="Sara" last="Nasiri Sovari">Sara Nasiri Sovari</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author><author><name sortKey="Pavic, Aleksandar" sort="Pavic, Aleksandar" uniqKey="Pavic A" first="Aleksandar" last="Pavic">Aleksandar Pavic</name><affiliation><nlm:aff id="af2-molecules-24-02310">Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Republic of Serbia;<email>pavicaleksandarr@gmail.com</email> (A.P.);<email>sanvojnov@gmail.com</email> (S.V.)</nlm:aff></affiliation></author><author><name sortKey="Vojnovic, Sandra" sort="Vojnovic, Sandra" uniqKey="Vojnovic S" first="Sandra" last="Vojnovic">Sandra Vojnovic</name><affiliation><nlm:aff id="af2-molecules-24-02310">Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Republic of Serbia;<email>pavicaleksandarr@gmail.com</email> (A.P.);<email>sanvojnov@gmail.com</email> (S.V.)</nlm:aff></affiliation></author><author><name sortKey="Stringer, Tameryn" sort="Stringer, Tameryn" uniqKey="Stringer T" first="Tameryn" last="Stringer">Tameryn Stringer</name><affiliation><nlm:aff id="af3-molecules-24-02310">Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa;<email>STRTAM001@myuct.ac.za</email> (T.S.);<email>gregory.smith@uct.ac.za</email> (G.S.S.)</nlm:aff></affiliation></author><author><name sortKey="B Ttig, Sarah" sort="B Ttig, Sarah" uniqKey="B Ttig S" first="Sarah" last="B Ttig">Sarah B Ttig</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author><author><name sortKey="Smith, Gregory S" sort="Smith, Gregory S" uniqKey="Smith G" first="Gregory S." last="Smith">Gregory S. Smith</name><affiliation><nlm:aff id="af3-molecules-24-02310">Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa;<email>STRTAM001@myuct.ac.za</email> (T.S.);<email>gregory.smith@uct.ac.za</email> (G.S.S.)</nlm:aff></affiliation></author><author><name sortKey="Nikodinovic Runic, Jasmina" sort="Nikodinovic Runic, Jasmina" uniqKey="Nikodinovic Runic J" first="Jasmina" last="Nikodinovic-Runic">Jasmina Nikodinovic-Runic</name><affiliation><nlm:aff id="af2-molecules-24-02310">Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Republic of Serbia;<email>pavicaleksandarr@gmail.com</email> (A.P.);<email>sanvojnov@gmail.com</email> (S.V.)</nlm:aff></affiliation></author><author><name sortKey="Zobi, Fabio" sort="Zobi, Fabio" uniqKey="Zobi F" first="Fabio" last="Zobi">Fabio Zobi</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31234469</idno><idno type="pmc">6630517</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6630517</idno><idno type="RBID">PMC:6630517</idno><idno type="doi">10.3390/molecules24122310</idno><date when="2019">2019</date><idno type="wicri:Area/Pmc/Corpus">000715</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000715</idno><idno type="wicri:Area/Pmc/Curation">000715</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000715</idno><idno type="wicri:Area/Pmc/Checkpoint">000A03</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000A03</idno><idno type="wicri:Area/Ncbi/Merge">000724</idno><idno 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sortKey="Nasiri Sovari, Sara" sort="Nasiri Sovari, Sara" uniqKey="Nasiri Sovari S" first="Sara" last="Nasiri Sovari">Sara Nasiri Sovari</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author><author><name sortKey="Pavic, Aleksandar" sort="Pavic, Aleksandar" uniqKey="Pavic A" first="Aleksandar" last="Pavic">Aleksandar Pavic</name><affiliation><nlm:aff id="af2-molecules-24-02310">Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Republic of Serbia;<email>pavicaleksandarr@gmail.com</email> (A.P.);<email>sanvojnov@gmail.com</email> (S.V.)</nlm:aff></affiliation></author><author><name sortKey="Vojnovic, Sandra" sort="Vojnovic, Sandra" uniqKey="Vojnovic S" first="Sandra" last="Vojnovic">Sandra Vojnovic</name><affiliation><nlm:aff id="af2-molecules-24-02310">Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Republic of Serbia;<email>pavicaleksandarr@gmail.com</email> (A.P.);<email>sanvojnov@gmail.com</email> (S.V.)</nlm:aff></affiliation></author><author><name sortKey="Stringer, Tameryn" sort="Stringer, Tameryn" uniqKey="Stringer T" first="Tameryn" last="Stringer">Tameryn Stringer</name><affiliation><nlm:aff id="af3-molecules-24-02310">Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa;<email>STRTAM001@myuct.ac.za</email> (T.S.);<email>gregory.smith@uct.ac.za</email> (G.S.S.)</nlm:aff></affiliation></author><author><name sortKey="B Ttig, Sarah" sort="B Ttig, Sarah" uniqKey="B Ttig S" first="Sarah" last="B Ttig">Sarah B Ttig</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author><author><name sortKey="Smith, Gregory S" sort="Smith, Gregory S" uniqKey="Smith G" first="Gregory S." last="Smith">Gregory S. Smith</name><affiliation><nlm:aff id="af3-molecules-24-02310">Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa;<email>STRTAM001@myuct.ac.za</email> (T.S.);<email>gregory.smith@uct.ac.za</email> (G.S.S.)</nlm:aff></affiliation></author><author><name sortKey="Nikodinovic Runic, Jasmina" sort="Nikodinovic Runic, Jasmina" uniqKey="Nikodinovic Runic J" first="Jasmina" last="Nikodinovic-Runic">Jasmina Nikodinovic-Runic</name><affiliation><nlm:aff id="af2-molecules-24-02310">Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, Vojvode Stepe 444a, 11000 Belgrade, Republic of Serbia;<email>pavicaleksandarr@gmail.com</email> (A.P.);<email>sanvojnov@gmail.com</email> (S.V.)</nlm:aff></affiliation></author><author><name sortKey="Zobi, Fabio" sort="Zobi, Fabio" uniqKey="Zobi F" first="Fabio" last="Zobi">Fabio Zobi</name><affiliation><nlm:aff id="af1-molecules-24-02310">Department of Chemistry, University of Fribourg, Chemin du Musée 10, 1700 Fribourg, Switzerland;<email>jeremie.rossier@unifr.ch</email> (J.R.);<email>sara.nasirisovari@unifr.ch</email> (S.N.S.);<email>sarah.baettig@unifr.ch</email> (S.B.)</nlm:aff></affiliation></author></analytic><series><title level="j">Molecules</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>We have explored the possibility of using organometallic derivatives of cobalamin as a scaffold for the delivery of the same antimalarial drug to both erythro- and hepatocytes. This hybrid molecule approach, intended as a possible tool for the development of multi-stage antimalarial agents, pivots on the preparation of azide-functionalized drugs which, after coupling to the vitamin, are released with a 4-(4-ethynylphenyl)-triazole functionality. Three chloroquine and one imidazolopiperazine derivative (based on the KAF156 structure) were selected as model drugs. One hybrid chloroquine conjugate was extensively studied via fluorescent labelling for in vitro and in vivo bio-distribution studies and gave proof-of-concept for the design. It showed no toxicity in vivo (zebrafish model) as well as no hepatotoxicity, no cardiotoxicity or developmental toxicity of the embryos. All 4-(4-ethynylphenyl)-triazole derivatives of chloroquine were equally active against chloroquine-resistant (CQR) and chloroquine-sensitive (CQS) <italic>Plasmodium falciparum</italic> strains.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Alonso, P L" uniqKey="Alonso P">P.L. Alonso</name></author><author><name sortKey="Brown, G" uniqKey="Brown G">G. Brown</name></author><author><name sortKey="Arevalo Herrera, M" uniqKey="Arevalo Herrera M">M. Arevalo-Herrera</name></author><author><name sortKey="Binka, F" uniqKey="Binka F">F. Binka</name></author><author><name sortKey="Chitnis, C" uniqKey="Chitnis C">C. Chitnis</name></author><author><name sortKey="Collins, F" uniqKey="Collins F">F. Collins</name></author><author><name sortKey="Doumbo, O K" uniqKey="Doumbo O">O.K. Doumbo</name></author><author><name sortKey="Greenwood, B" uniqKey="Greenwood B">B. 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Li</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list></list><tree><noCountry><name sortKey="B Ttig, Sarah" sort="B Ttig, Sarah" uniqKey="B Ttig S" first="Sarah" last="B Ttig">Sarah B Ttig</name><name sortKey="Nasiri Sovari, Sara" sort="Nasiri Sovari, Sara" uniqKey="Nasiri Sovari S" first="Sara" last="Nasiri Sovari">Sara Nasiri Sovari</name><name sortKey="Nikodinovic Runic, Jasmina" sort="Nikodinovic Runic, Jasmina" uniqKey="Nikodinovic Runic J" first="Jasmina" last="Nikodinovic-Runic">Jasmina Nikodinovic-Runic</name><name sortKey="Pavic, Aleksandar" sort="Pavic, Aleksandar" uniqKey="Pavic A" first="Aleksandar" last="Pavic">Aleksandar Pavic</name><name sortKey="Rossier, Jeremie" sort="Rossier, Jeremie" uniqKey="Rossier J" first="Jeremie" last="Rossier">Jeremie Rossier</name><name sortKey="Smith, Gregory S" sort="Smith, Gregory S" uniqKey="Smith G" first="Gregory S." last="Smith">Gregory S. Smith</name><name sortKey="Stringer, Tameryn" sort="Stringer, Tameryn" uniqKey="Stringer T" first="Tameryn" last="Stringer">Tameryn Stringer</name><name sortKey="Vojnovic, Sandra" sort="Vojnovic, Sandra" uniqKey="Vojnovic S" first="Sandra" last="Vojnovic">Sandra Vojnovic</name><name sortKey="Zobi, Fabio" sort="Zobi, Fabio" uniqKey="Zobi F" first="Fabio" last="Zobi">Fabio Zobi</name></noCountry></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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