Scaffold hybridization strategy towards potent hydroxamate-based inhibitors of Flaviviridae viruses and Trypanosoma species.
Identifieur interne : 000864 ( PubMed/Checkpoint ); précédent : 000863; suivant : 000865Scaffold hybridization strategy towards potent hydroxamate-based inhibitors of Flaviviridae viruses and Trypanosoma species.
Auteurs : Erofili Giannakopoulou [Grèce] ; Vasiliki Pardali [Grèce] ; Efseveia Frakolaki [Grèce] ; Vasileios Siozos [Grèce] ; Vassilios Myrianthopoulos [Grèce] ; Emmanuel Mikros [Grèce] ; Martin C. Taylor [Royaume-Uni] ; John M. Kelly [Royaume-Uni] ; Niki Vassilaki [Grèce] ; Grigoris Zoidis [Grèce]Source :
- MedChemComm [ 2040-2511 ] ; 2019.
Abstract
Infections with Flaviviridae viruses, such as hepatitis C virus (HCV) and dengue virus (DENV) pose global health threats. Infected individuals are at risk of developing chronic liver failure or haemorrhagic fever respectively, often with a fatal outcome if left untreated. Diseases caused by tropical parasites of the Trypanosoma species, T. brucei and T. cruzi, constitute significant socioeconomic burden in sub-Saharan Africa and continental Latin America, yet drug development is under-funded. Anti-HCV chemotherapy is associated with severe side effects and high cost, while dengue has no clinically approved therapy and antiparasitic drugs are outdated and difficult to administer. Moreover, drug resistance is an emerging concern. Consequently, the need for new revolutionary chemotherapies is urgent. By utilizing a molecular framework combination approach, we combined two distinct chemical entities with proven antiviral and trypanocidal activity into a novel hybrid scaffold attached by an acetohydroxamic acid group (CH2CONHOH), aiming at derivatives with dual activity. The novel spiro-carbocyclic substituted hydantoin analogues were rationally designed, synthesized and evaluated for their potency against three HCV genotypes (1b, 3a, 4a), DENV and two Trypanosoma species (T. brucei, T. cruzi). They exhibited significant EC50 values and remarkable selectivity indices. Several modifications were undertaken to further explore the structure activity relationships (SARs) and confirm the pivotal role of the acetohydroxamic acid metal binding group.
DOI: 10.1039/c9md00200f
PubMed: 31303998
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Scaffold hybridization strategy towards potent hydroxamate-based inhibitors of <i>Flaviviridae</i> viruses and <i>Trypanosoma</i> species.</title><author><name sortKey="Giannakopoulou, Erofili" sort="Giannakopoulou, Erofili" uniqKey="Giannakopoulou E" first="Erofili" last="Giannakopoulou">Erofili Giannakopoulou</name><affiliation wicri:level="1"><nlm:affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . 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Email: zoidis@pharm.uoa.gr.</nlm:affiliation><country wicri:rule="url">Grèce</country></affiliation></author><author><name sortKey="Pardali, Vasiliki" sort="Pardali, Vasiliki" uniqKey="Pardali V" first="Vasiliki" last="Pardali">Vasiliki Pardali</name><affiliation wicri:level="1"><nlm:affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</nlm:affiliation><country wicri:rule="url">Grèce</country></affiliation></author><author><name sortKey="Frakolaki, Efseveia" sort="Frakolaki, Efseveia" uniqKey="Frakolaki E" first="Efseveia" last="Frakolaki">Efseveia Frakolaki</name><affiliation wicri:level="1"><nlm:affiliation>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens , Greece.</nlm:affiliation><country xml:lang="fr">Grèce</country><wicri:regionArea>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens </wicri:regionArea><wicri:noRegion>Athens </wicri:noRegion></affiliation></author><author><name sortKey="Siozos, Vasileios" sort="Siozos, Vasileios" uniqKey="Siozos V" first="Vasileios" last="Siozos">Vasileios Siozos</name><affiliation wicri:level="1"><nlm:affiliation>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens , Greece.</nlm:affiliation><country xml:lang="fr">Grèce</country><wicri:regionArea>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens </wicri:regionArea><wicri:noRegion>Athens </wicri:noRegion></affiliation></author><author><name sortKey="Myrianthopoulos, Vassilios" sort="Myrianthopoulos, Vassilios" uniqKey="Myrianthopoulos V" first="Vassilios" last="Myrianthopoulos">Vassilios Myrianthopoulos</name><affiliation wicri:level="1"><nlm:affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</nlm:affiliation><country wicri:rule="url">Grèce</country></affiliation></author><author><name sortKey="Mikros, Emmanuel" sort="Mikros, Emmanuel" uniqKey="Mikros E" first="Emmanuel" last="Mikros">Emmanuel Mikros</name><affiliation wicri:level="1"><nlm:affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</nlm:affiliation><country wicri:rule="url">Grèce</country></affiliation></author><author><name sortKey="Taylor, Martin C" sort="Taylor, Martin C" uniqKey="Taylor M" first="Martin C" last="Taylor">Martin C. Taylor</name><affiliation wicri:level="1"><nlm:affiliation>Department of Pathogen Molecular Biology , London School of Hygiene and Tropical Medicine , Keppel Street , London WC1E 7HT , UK.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Pathogen Molecular Biology , London School of Hygiene and Tropical Medicine , Keppel Street , London WC1E 7HT </wicri:regionArea><wicri:noRegion>London WC1E 7HT </wicri:noRegion></affiliation></author><author><name sortKey="Kelly, John M" sort="Kelly, John M" uniqKey="Kelly J" first="John M" last="Kelly">John M. Kelly</name><affiliation wicri:level="1"><nlm:affiliation>Department of Pathogen Molecular Biology , London School of Hygiene and Tropical Medicine , Keppel Street , London WC1E 7HT , UK.</nlm:affiliation><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Department of Pathogen Molecular Biology , London School of Hygiene and Tropical Medicine , Keppel Street , London WC1E 7HT </wicri:regionArea><wicri:noRegion>London WC1E 7HT </wicri:noRegion></affiliation></author><author><name sortKey="Vassilaki, Niki" sort="Vassilaki, Niki" uniqKey="Vassilaki N" first="Niki" last="Vassilaki">Niki Vassilaki</name><affiliation wicri:level="1"><nlm:affiliation>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens , Greece.</nlm:affiliation><country xml:lang="fr">Grèce</country><wicri:regionArea>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens </wicri:regionArea><wicri:noRegion>Athens </wicri:noRegion></affiliation></author><author><name sortKey="Zoidis, Grigoris" sort="Zoidis, Grigoris" uniqKey="Zoidis G" first="Grigoris" last="Zoidis">Grigoris Zoidis</name><affiliation wicri:level="1"><nlm:affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</nlm:affiliation><country wicri:rule="url">Grèce</country></affiliation></author></analytic><series><title level="j">MedChemComm</title><idno type="eISSN">2040-2511</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Infections with <i>Flaviviridae</i> viruses, such as hepatitis C virus (HCV) and dengue virus (DENV) pose global health threats. Infected individuals are at risk of developing chronic liver failure or haemorrhagic fever respectively, often with a fatal outcome if left untreated. Diseases caused by tropical parasites of the <i>Trypanosoma</i> species, <i>T. brucei</i> and <i>T. cruzi</i>, constitute significant socioeconomic burden in sub-Saharan Africa and continental Latin America, yet drug development is under-funded. Anti-HCV chemotherapy is associated with severe side effects and high cost, while dengue has no clinically approved therapy and antiparasitic drugs are outdated and difficult to administer. Moreover, drug resistance is an emerging concern. Consequently, the need for new revolutionary chemotherapies is urgent. By utilizing a molecular framework combination approach, we combined two distinct chemical entities with proven antiviral and trypanocidal activity into a novel hybrid scaffold attached by an acetohydroxamic acid group (CH<sub>2</sub>CONHOH), aiming at derivatives with dual activity. The novel spiro-carbocyclic substituted hydantoin analogues were rationally designed, synthesized and evaluated for their potency against three HCV genotypes (1b, 3a, 4a), DENV and two <i>Trypanosoma</i> species (<i>T. brucei</i>, <i>T. cruzi</i>). They exhibited significant EC<sub>50</sub> values and remarkable selectivity indices. Several modifications were undertaken to further explore the structure activity relationships (SARs) and confirm the pivotal role of the acetohydroxamic acid metal binding group.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">31303998</PMID><DateRevised><Year>2020</Year><Month>02</Month><Day>25</Day></DateRevised><Article PubModel="Electronic-eCollection"><Journal><ISSN IssnType="Electronic">2040-2511</ISSN><JournalIssue CitedMedium="Internet"><Volume>10</Volume><Issue>6</Issue><PubDate><Year>2019</Year><Month>Jun</Month><Day>01</Day></PubDate></JournalIssue><Title>MedChemComm</Title><ISOAbbreviation>Medchemcomm</ISOAbbreviation></Journal><ArticleTitle>Scaffold hybridization strategy towards potent hydroxamate-based inhibitors of <i>Flaviviridae</i> viruses and <i>Trypanosoma</i> species.</ArticleTitle><Pagination><MedlinePgn>991-1006</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1039/c9md00200f</ELocationID><Abstract><AbstractText>Infections with <i>Flaviviridae</i> viruses, such as hepatitis C virus (HCV) and dengue virus (DENV) pose global health threats. Infected individuals are at risk of developing chronic liver failure or haemorrhagic fever respectively, often with a fatal outcome if left untreated. Diseases caused by tropical parasites of the <i>Trypanosoma</i> species, <i>T. brucei</i> and <i>T. cruzi</i>, constitute significant socioeconomic burden in sub-Saharan Africa and continental Latin America, yet drug development is under-funded. Anti-HCV chemotherapy is associated with severe side effects and high cost, while dengue has no clinically approved therapy and antiparasitic drugs are outdated and difficult to administer. Moreover, drug resistance is an emerging concern. Consequently, the need for new revolutionary chemotherapies is urgent. By utilizing a molecular framework combination approach, we combined two distinct chemical entities with proven antiviral and trypanocidal activity into a novel hybrid scaffold attached by an acetohydroxamic acid group (CH<sub>2</sub>CONHOH), aiming at derivatives with dual activity. The novel spiro-carbocyclic substituted hydantoin analogues were rationally designed, synthesized and evaluated for their potency against three HCV genotypes (1b, 3a, 4a), DENV and two <i>Trypanosoma</i> species (<i>T. brucei</i>, <i>T. cruzi</i>). They exhibited significant EC<sub>50</sub> values and remarkable selectivity indices. Several modifications were undertaken to further explore the structure activity relationships (SARs) and confirm the pivotal role of the acetohydroxamic acid metal binding group.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Giannakopoulou</LastName><ForeName>Erofili</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Pardali</LastName><ForeName>Vasiliki</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Frakolaki</LastName><ForeName>Efseveia</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens , Greece.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Siozos</LastName><ForeName>Vasileios</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens , Greece.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Myrianthopoulos</LastName><ForeName>Vassilios</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Mikros</LastName><ForeName>Emmanuel</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . Email: zoidis@pharm.uoa.gr.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Taylor</LastName><ForeName>Martin C</ForeName><Initials>MC</Initials><AffiliationInfo><Affiliation>Department of Pathogen Molecular Biology , London School of Hygiene and Tropical Medicine , Keppel Street , London WC1E 7HT , UK.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kelly</LastName><ForeName>John M</ForeName><Initials>JM</Initials><AffiliationInfo><Affiliation>Department of Pathogen Molecular Biology , London School of Hygiene and Tropical Medicine , Keppel Street , London WC1E 7HT , UK.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Vassilaki</LastName><ForeName>Niki</ForeName><Initials>N</Initials><AffiliationInfo><Affiliation>Molecular Virology Laboratory , Hellenic Pasteur Institute , Vas. Sofias Avenue , GR-11521 , Athens , Greece.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zoidis</LastName><ForeName>Grigoris</ForeName><Initials>G</Initials><Identifier Source="ORCID">0000-0002-9442-5186</Identifier><AffiliationInfo><Affiliation>School of Health Sciences , Faculty of Pharmacy , Department of Pharmaceutical Chemistry , National and Kapodistrian University of Athens , Panepistimiopolis-Zografou , GR-15771 Athens , Greece . 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