Xanthine-based acyclic nucleoside phosphonates with potent antiviral activity against varicella-zoster virus and human cytomegalovirus
Identifieur interne : 000D75 ( Main/Exploration ); précédent : 000D74; suivant : 000D76Xanthine-based acyclic nucleoside phosphonates with potent antiviral activity against varicella-zoster virus and human cytomegalovirus
Auteurs : Ond Ej Baszczy Ski [République tchèque] ; Martin Maxmilian Kaiser [République tchèque] ; Michal Esnek [République tchèque] ; Petra B Ehová [République tchèque] ; Petr Jansa [République tchèque] ; Eliška Procházková [République tchèque] ; Martin Dra Nsk [République tchèque] ; Robert Snoeck [Belgique] ; Graciela Andrei [Belgique] ; Zlatko Janeba [République tchèque]Source :
- Antiviral Chemistry & Chemotherapy [ 0956-3202 ] ; 2018.
Abstract
While noncanonic xanthine nucleotides XMP/dXMP play an important role in balancing and maintaining intracellular purine nucleotide pool as well as in potential mutagenesis, surprisingly, acyclic nucleoside phosphonates bearing a xanthine nucleobase have not been studied so far for their antiviral properties. Herein, we report the synthesis of a series of xanthine-based acyclic nucleoside phosphonates and evaluation of their activity against a wide range of DNA and RNA viruses. Two acyclic nucleoside phosphonates within the series, namely 9-[2-(phosphonomethoxy)ethyl]xanthine (PMEX) and 9-[3-hydroxy-2-(phosphonomethoxy)propyl]xanthine (HPMPX), were shown to possess activity against several human herpesviruses. The most potent compound was PMEX, a xanthine analogue of adefovir (PMEA). PMEX exhibited a single digit µM activity against VZV (EC50 = 2.6 µM, TK+ Oka strain) and HCMV (EC50 = 8.5 µM, Davis strain), while its hexadecyloxypropyl monoester derivative was active against HSV-1 and HSV-2 (EC50 values between 1.8 and 4.0 µM). In contrast to acyclovir, PMEX remained active against the TK– VZV 07–1 strain with EC50 = 4.58 µM. PMEX was suggested to act as an inhibitor of viral DNA polymerase and represents the first reported xanthine-based acyclic nucleoside phosphonate with potent antiviral properties.
Url:
DOI: 10.1177/2040206618813050
PubMed: 30497281
PubMed Central: 6287304
Affiliations:
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Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey="Kaiser, Martin Maxmilian" sort="Kaiser, Martin Maxmilian" uniqKey="Kaiser M" first="Martin Maxmilian" last="Kaiser">Martin Maxmilian Kaiser</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey=" Esnek, Michal" sort=" Esnek, Michal" uniqKey=" Esnek M" first="Michal" last=" Esnek">Michal Esnek</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey="B Ehova, Petra" sort="B Ehova, Petra" uniqKey="B Ehova P" first="Petra" last="B Ehová">Petra B Ehová</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey="Jansa, Petr" sort="Jansa, Petr" uniqKey="Jansa P" first="Petr" last="Jansa">Petr Jansa</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey="Prochazkova, Eliska" sort="Prochazkova, Eliska" uniqKey="Prochazkova E" first="Eliška" last="Procházková">Eliška Procházková</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey="Dra Nsk, Martin" sort="Dra Nsk, Martin" uniqKey="Dra Nsk M" first="Martin" last="Dra Nsk">Martin Dra Nsk</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author><author><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><affiliation wicri:level="1"><nlm:aff id="aff2-2040206618813050">Laboratory of Virology and Chemotheraphy, Rega Institute, Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratory of Virology and Chemotheraphy, Rega Institute, Leuven</wicri:regionArea><wicri:noRegion>Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><affiliation wicri:level="1"><nlm:aff id="aff2-2040206618813050">Laboratory of Virology and Chemotheraphy, Rega Institute, Leuven, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Laboratory of Virology and Chemotheraphy, Rega Institute, Leuven</wicri:regionArea><wicri:noRegion>Leuven</wicri:noRegion></affiliation></author><author><name sortKey="Janeba, Zlatko" sort="Janeba, Zlatko" uniqKey="Janeba Z" first="Zlatko" last="Janeba">Zlatko Janeba</name><affiliation wicri:level="3"><nlm:aff id="aff1-2040206618813050">Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague, Czech Republic</nlm:aff><country xml:lang="fr">République tchèque</country><wicri:regionArea>Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Prague</wicri:regionArea><placeName><settlement type="city">Prague</settlement><region type="région" nuts="2">Bohême centrale</region></placeName></affiliation></author></analytic><series><title level="j">Antiviral Chemistry & Chemotherapy</title><idno type="ISSN">0956-3202</idno><idno type="eISSN">2040-2066</idno><imprint><date when="2018">2018</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>While noncanonic xanthine nucleotides XMP/dXMP play an important role in balancing and maintaining intracellular purine nucleotide pool as well as in potential mutagenesis, surprisingly, acyclic nucleoside phosphonates bearing a xanthine nucleobase have not been studied so far for their antiviral properties. Herein, we report the synthesis of a series of xanthine-based acyclic nucleoside phosphonates and evaluation of their activity against a wide range of DNA and RNA viruses. Two acyclic nucleoside phosphonates within the series, namely 9-[2-(phosphonomethoxy)ethyl]xanthine (PMEX) and 9-[3-hydroxy-2-(phosphonomethoxy)propyl]xanthine (HPMPX), were shown to possess activity against several human herpesviruses. The most potent compound was PMEX, a xanthine analogue of adefovir (PMEA). PMEX exhibited a single digit µM activity against VZV (EC<sub>50</sub> = 2.6 µM, TK<sup>+</sup> Oka strain) and HCMV (EC<sub>50</sub> = 8.5 µM, Davis strain), while its hexadecyloxypropyl monoester derivative was active against HSV-1 and HSV-2 (EC<sub>50</sub> values between 1.8 and 4.0 µM). In contrast to acyclovir, PMEX remained active against the TK<sup>–</sup> VZV 07–1 strain with EC<sub>50</sub> = 4.58 µM. PMEX was suggested to act as an inhibitor of viral DNA polymerase and represents the first reported xanthine-based acyclic nucleoside phosphonate with potent antiviral properties.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Bennett, Bd" uniqKey="Bennett B">BD Bennett</name></author><author><name sortKey="Kimball, Eh" uniqKey="Kimball E">EH Kimball</name></author><author><name sortKey="Gao, M" uniqKey="Gao M">M Gao</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wheeler, Lj" uniqKey="Wheeler L">LJ Wheeler</name></author><author><name sortKey="Rajagopal, I" uniqKey="Rajagopal I">I Rajagopal</name></author><author><name sortKey="Mathews, Ck" uniqKey="Mathews C">CK. 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De Clercq</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey=" Esnek, M" uniqKey=" Esnek M">M Česnek</name></author><author><name sortKey="Masojidkova, M" uniqKey="Masojidkova M">M Masojídková</name></author><author><name sortKey="Hol, A" uniqKey="Hol A">A Holý</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Yu, Kl" uniqKey="Yu K">KL Yu</name></author><author><name sortKey="Bronson, Jj" uniqKey="Bronson J">JJ Bronson</name></author><author><name sortKey="Yang, H" uniqKey="Yang H">H Yang</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hol, A" uniqKey="Hol A">A. Holý</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Baszczy Ski, O" uniqKey="Baszczy Ski O">O Baszczyňski</name></author><author><name sortKey="Hockova, D" uniqKey="Hockova D">D Hocková</name></author><author><name sortKey="Janeba, Z" uniqKey="Janeba Z">Z Janeba</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Franchetti, P" uniqKey="Franchetti P">P Franchetti</name></author><author><name sortKey="Sheikha, Ga" uniqKey="Sheikha G">GA Sheikha</name></author><author><name sortKey="Cappellacci, L" uniqKey="Cappellacci L">L Cappellacci</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hol, A" uniqKey="Hol A">A Holý</name></author><author><name sortKey="Masojidkova, M" uniqKey="Masojidkova M">M. Masojídková</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hol, A" uniqKey="Hol A">A Holý</name></author><author><name sortKey="Votruba, I" uniqKey="Votruba I">I Votruba</name></author><author><name sortKey="Tlous Ova, E" uniqKey="Tlous Ova E">E Tloušťová</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Reiser, H" uniqKey="Reiser H">H Reiser</name></author><author><name sortKey="Wang, J" uniqKey="Wang J">J Wang</name></author><author><name sortKey="Chong, L" uniqKey="Chong L">L Chong</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Daluge, Sm" uniqKey="Daluge S">SM Daluge</name></author><author><name sortKey="Good, Ss" uniqKey="Good S">SS Good</name></author><author><name sortKey="Faletto, Mb" uniqKey="Faletto M">MB Faletto</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Painter, Gr" uniqKey="Painter G">GR Painter</name></author><author><name sortKey="Almond, Mr" uniqKey="Almond M">MR Almond</name></author><author><name sortKey="Trost, Lc" uniqKey="Trost L">LC Trost</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Jansa, P" uniqKey="Jansa P">P Jansa</name></author><author><name sortKey="Baszczy Ski, O" uniqKey="Baszczy Ski O">O Baszczyňski</name></author><author><name sortKey="Dra Nsk, M" uniqKey="Dra Nsk M">M Dračínský</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Hol, A" uniqKey="Hol A">A Holý</name></author><author><name sortKey="Rosenberg, I" uniqKey="Rosenberg I">I. Rosenberg</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Belgique</li><li>République tchèque</li></country><region><li>Bohême centrale</li></region><settlement><li>Prague</li></settlement></list><tree><country name="République tchèque"><region name="Bohême centrale"><name sortKey="Baszczy Ski, Ond Ej" sort="Baszczy Ski, Ond Ej" uniqKey="Baszczy Ski O" first="Ond Ej" last="Baszczy Ski">Ond Ej Baszczy Ski</name></region><name sortKey=" Esnek, Michal" sort=" Esnek, Michal" uniqKey=" Esnek M" first="Michal" last=" Esnek">Michal Esnek</name><name sortKey="B Ehova, Petra" sort="B Ehova, Petra" uniqKey="B Ehova P" first="Petra" last="B Ehová">Petra B Ehová</name><name sortKey="Dra Nsk, Martin" sort="Dra Nsk, Martin" uniqKey="Dra Nsk M" first="Martin" last="Dra Nsk">Martin Dra Nsk</name><name sortKey="Janeba, Zlatko" sort="Janeba, Zlatko" uniqKey="Janeba Z" first="Zlatko" last="Janeba">Zlatko Janeba</name><name sortKey="Jansa, Petr" sort="Jansa, Petr" uniqKey="Jansa P" first="Petr" last="Jansa">Petr Jansa</name><name sortKey="Kaiser, Martin Maxmilian" sort="Kaiser, Martin Maxmilian" uniqKey="Kaiser M" first="Martin Maxmilian" last="Kaiser">Martin Maxmilian Kaiser</name><name sortKey="Prochazkova, Eliska" sort="Prochazkova, Eliska" uniqKey="Prochazkova E" first="Eliška" last="Procházková">Eliška Procházková</name></country><country name="Belgique"><noRegion><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name></noRegion><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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