Effect of Various Pyrimidines Possessing the 1-[(2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl] Moiety, Able To Mimic Natural 2‘-Deoxyribose, on Wild-type and Mutant Hepatitis B Virus Replication
Identifieur interne : 004080 ( Main/Exploration ); précédent : 004079; suivant : 004081Effect of Various Pyrimidines Possessing the 1-[(2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl] Moiety, Able To Mimic Natural 2‘-Deoxyribose, on Wild-type and Mutant Hepatitis B Virus Replication
Auteurs : Rakesh Kumar [Canada] ; Wassila Semaine [Canada] ; Monika Johar [Canada] ; D. Lorne J. Tyrrell [Canada] ; Babita Agrawal [Canada]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 2006.
Descripteurs français
- KwdFr :
- Animaux, Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Canards (virologie), Désoxyribose (), Humains, Lamivudine (pharmacologie), Lignée cellulaire, Lignée cellulaire tumorale, Mimétisme moléculaire, Mutation, Nucléosides pyrimidiques (), Nucléosides pyrimidiques (pharmacologie), Nucléosides pyrimidiques (synthèse chimique), Relation structure-activité, Réplication virale (), Résistance virale aux médicaments, Virus de l'hépatite B (), Virus de l'hépatite B (génétique), Virus de l'hépatite B (isolement et purification).
- MESH :
- génétique : Virus de l'hépatite B.
- isolement et purification : Virus de l'hépatite B.
- pharmacologie : Antiviraux, Lamivudine, Nucléosides pyrimidiques.
- synthèse chimique : Antiviraux, Nucléosides pyrimidiques.
- virologie : Canards.
- Animaux, Antiviraux, Désoxyribose, Humains, Lignée cellulaire, Lignée cellulaire tumorale, Mimétisme moléculaire, Mutation, Nucléosides pyrimidiques, Relation structure-activité, Réplication virale, Résistance virale aux médicaments, Virus de l'hépatite B.
- Pascal (Inist)
- Antiviral, Brome composé organique, Chlore composé organique, In vitro, Lignée cellulaire, Mutation, Nucléoside acyclique, Pyrimidine nucléoside, Relation structure activité, Réplication, Synthèse chimique, Uracile(5-bromo-1-[(2-hydroxy-1-hydroxyméthyléthoxy)méthyl]-6-méthyl), Uracile(5-chloro-1-[(2-hydroxy-1-hydroxyméthyléthoxy)méthyl]), Virus hépatite B, Virus hépatite B canard.
English descriptors
- KwdEn :
- Acyclic nucleoside, Animals, Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Line, Cell Line, Tumor, Cell line, Chemical synthesis, Chlorocebus aethiops, Deoxyribose (chemistry), Drug Resistance, Viral, Duck hepatitis B virus, Ducks (virology), Hepatitis B virus, Hepatitis B virus (drug effects), Hepatitis B virus (genetics), Hepatitis B virus (isolation & purification), Humans, In vitro, Lamivudine (pharmacology), Molecular Mimicry, Mutation, Organic bromine compounds, Organic chlorine compounds, Pyrimidine Nucleosides (chemical synthesis), Pyrimidine Nucleosides (chemistry), Pyrimidine Nucleosides (pharmacology), Pyrimidine nucleoside, Replication, Structure activity relation, Structure-Activity Relationship, Virus Replication (drug effects).
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Pyrimidine Nucleosides.
- chemical , chemistry : Antiviral Agents, Deoxyribose, Pyrimidine Nucleosides.
- chemical , pharmacology : Antiviral Agents, Lamivudine, Pyrimidine Nucleosides.
- drug effects : Hepatitis B virus, Virus Replication.
- genetics : Hepatitis B virus.
- isolation & purification : Hepatitis B virus.
- virology : Ducks.
- Animals, Cell Line, Cell Line, Tumor, Chlorocebus aethiops, Drug Resistance, Viral, Humans, Molecular Mimicry, Mutation, Structure-Activity Relationship.
Abstract
Hepatitis B virus (HBV) is the most common cause of chronic liver disease worldwide. Development of drug resistance against clinical anti-HBV drug lamivudine due to long-term use and rebound of viral DNA after cessation of treatment has been a major setback of the current therapy. We have synthesized a series of pyrimidine nucleosides possessing a variety of substituents at the C-5 position, and a 1-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl] flexible acyclic glycosyl moiety at the N-1 position, that have the ability to mimic the natural 2‘-deoxyribosyl moiety. Some of these potential antiviral compounds included variations at both C-5 and C-6 positions of the uracil base. Other variations of the uracil derivatives were the 6-aza congeners. 4-Amino and 4-methoxy pyrimidine derivatives were also made. Compounds in which the base moiety was substituted by 5-chloro- (25), 5-(2-bromovinyl)- (32), or 5-bromo-6-methyl- (37) groups possess significant activity against duck-HBV, wild-type human HBV (2.2.15 cells), and lamivudine-resistant HBV containing single and double mutations. No cytotoxicity was seen in host HepG2 and Vero cells, up to the highest concentration tested. The anti-HBV activity exhibited by compounds 25, 32, and 37 was superior for human HBV and comparable for DHBV to that of the corresponding purine nucleoside, ganciclovir. Further, they were only 10−15-fold less inhibitory against human HBV in 2.2.15 cells than the reference drug, lamivudine. Other compounds in the series were moderately inhibitory against DHBV and wild-type human HBV. The size of the halogen and the electronegativity of the substituents at the 5- and 6-positions are important for antiviral activity toward HBV. These compounds were also evaluated for their antiviral activity for West Nile virus, respiratory syncytial virus, SARS-coronavirus, and hepatitis C virus. They were generally inactive in these antiviral assay systems (at concentrations up to 100 μg/mL). 1-[(2-Hydroxy-1-(hydroxymethyl) ethoxy)methyl]-5-fluorocytosine (34) showed some inhibitory activity against hepatitis C virus. Taken together, these data support our previous observations that the 5-substituted pyrimidine nucleosides containing acyclic glycosyl moieties have potential to serve as a new generation of potent, selective, and nontoxic anti-HBV agents for wild-type and lamivudine-resistant mutant HBV.
Url:
DOI: 10.1021/jm060102l
Affiliations:
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Moiety, Able To Mimic Natural 2‘-Deoxyribose, on Wild-type and Mutant Hepatitis B Virus
Replication</title><author><name sortKey="Kumar, Rakesh" sort="Kumar, Rakesh" uniqKey="Kumar R" first="Rakesh" last="Kumar">Rakesh Kumar</name><affiliation wicri:level="1"><country>Canada</country><wicri:regionArea>Department of Laboratory Medicine and Pathology, 1-41 Medical Sciences Building, Department of Surgery, and Department of MedicalMicrobiology and Immunology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB</wicri:regionArea><wicri:noRegion>AB</wicri:noRegion></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Canada</country></affiliation></author><author><name sortKey="Semaine, Wassila" sort="Semaine, Wassila" uniqKey="Semaine W" first="Wassila" last="Semaine">Wassila Semaine</name><affiliation wicri:level="1"><country>Canada</country><wicri:regionArea>Department of Laboratory Medicine and Pathology, 1-41 Medical Sciences Building, Department of Surgery, and Department of MedicalMicrobiology and Immunology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB</wicri:regionArea><wicri:noRegion>AB</wicri:noRegion></affiliation><affiliation></affiliation><affiliation></affiliation></author><author><name sortKey="Johar, Monika" sort="Johar, Monika" uniqKey="Johar M" first="Monika" last="Johar">Monika Johar</name><affiliation wicri:level="1"><country>Canada</country><wicri:regionArea>Department of Laboratory Medicine and Pathology, 1-41 Medical Sciences Building, Department of Surgery, and Department of MedicalMicrobiology and Immunology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB</wicri:regionArea><wicri:noRegion>AB</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Tyrrell, D Lorne J" sort="Tyrrell, D Lorne J" uniqKey="Tyrrell D" first="D. Lorne J." last="Tyrrell">D. Lorne J. Tyrrell</name><affiliation wicri:level="1"><country>Canada</country><wicri:regionArea>Department of Laboratory Medicine and Pathology, 1-41 Medical Sciences Building, Department of Surgery, and Department of MedicalMicrobiology and Immunology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB</wicri:regionArea><wicri:noRegion>AB</wicri:noRegion></affiliation><affiliation></affiliation></author><author><name sortKey="Agrawal, Babita" sort="Agrawal, Babita" uniqKey="Agrawal B" first="Babita" last="Agrawal">Babita Agrawal</name><affiliation wicri:level="1"><country>Canada</country><wicri:regionArea>Department of Laboratory Medicine and Pathology, 1-41 Medical Sciences Building, Department of Surgery, and Department of MedicalMicrobiology and Immunology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, AB</wicri:regionArea><wicri:noRegion>AB</wicri:noRegion></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Canada</country></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Medicinal Chemistry</title><title level="j" type="abbrev">J. Med. Chem.</title><idno type="ISSN">0022-2623</idno><idno type="eISSN">1520-4804</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published">2006</date><date type="published">2006</date><biblScope unit="vol">49</biblScope><biblScope unit="issue">12</biblScope><biblScope unit="page" from="3693">3693</biblScope><biblScope unit="page" to="3700">3700</biblScope></imprint><idno type="ISSN">0022-2623</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acyclic nucleoside</term><term>Animals</term><term>Antiviral</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Cell Line</term><term>Cell Line, Tumor</term><term>Cell line</term><term>Chemical synthesis</term><term>Chlorocebus aethiops</term><term>Deoxyribose (chemistry)</term><term>Drug Resistance, Viral</term><term>Duck hepatitis B virus</term><term>Ducks (virology)</term><term>Hepatitis B virus</term><term>Hepatitis B virus (drug effects)</term><term>Hepatitis B virus (genetics)</term><term>Hepatitis B virus (isolation & purification)</term><term>Humans</term><term>In vitro</term><term>Lamivudine (pharmacology)</term><term>Molecular Mimicry</term><term>Mutation</term><term>Organic bromine compounds</term><term>Organic chlorine compounds</term><term>Pyrimidine Nucleosides (chemical synthesis)</term><term>Pyrimidine Nucleosides (chemistry)</term><term>Pyrimidine Nucleosides (pharmacology)</term><term>Pyrimidine nucleoside</term><term>Replication</term><term>Structure activity relation</term><term>Structure-Activity Relationship</term><term>Virus Replication (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Canards (virologie)</term><term>Désoxyribose ()</term><term>Humains</term><term>Lamivudine (pharmacologie)</term><term>Lignée cellulaire</term><term>Lignée cellulaire tumorale</term><term>Mimétisme moléculaire</term><term>Mutation</term><term>Nucléosides pyrimidiques ()</term><term>Nucléosides pyrimidiques (pharmacologie)</term><term>Nucléosides pyrimidiques (synthèse chimique)</term><term>Relation structure-activité</term><term>Réplication virale ()</term><term>Résistance virale aux médicaments</term><term>Virus de l'hépatite B ()</term><term>Virus de l'hépatite B (génétique)</term><term>Virus de l'hépatite B (isolement et purification)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Pyrimidine Nucleosides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Deoxyribose</term><term>Pyrimidine Nucleosides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Lamivudine</term><term>Pyrimidine Nucleosides</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Hepatitis B virus</term><term>Virus Replication</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Hepatitis B virus</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Virus de l'hépatite B</term></keywords><keywords scheme="MESH" qualifier="isolation & purification" xml:lang="en"><term>Hepatitis B virus</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Virus de l'hépatite B</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Lamivudine</term><term>Nucléosides pyrimidiques</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Nucléosides pyrimidiques</term></keywords><keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Canards</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Ducks</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Cell Line</term><term>Cell Line, Tumor</term><term>Chlorocebus aethiops</term><term>Drug Resistance, Viral</term><term>Humans</term><term>Molecular Mimicry</term><term>Mutation</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Antiviraux</term><term>Désoxyribose</term><term>Humains</term><term>Lignée cellulaire</term><term>Lignée cellulaire tumorale</term><term>Mimétisme moléculaire</term><term>Mutation</term><term>Nucléosides pyrimidiques</term><term>Relation structure-activité</term><term>Réplication virale</term><term>Résistance virale aux médicaments</term><term>Virus de l'hépatite B</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Antiviral</term><term>Brome composé organique</term><term>Chlore composé organique</term><term>In vitro</term><term>Lignée cellulaire</term><term>Mutation</term><term>Nucléoside acyclique</term><term>Pyrimidine nucléoside</term><term>Relation structure activité</term><term>Réplication</term><term>Synthèse chimique</term><term>Uracile(5-bromo-1-[(2-hydroxy-1-hydroxyméthyléthoxy)méthyl]-6-méthyl)</term><term>Uracile(5-chloro-1-[(2-hydroxy-1-hydroxyméthyléthoxy)méthyl])</term><term>Virus hépatite B</term><term>Virus hépatite B canard</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract">Hepatitis B virus (HBV) is the most common cause of chronic liver disease worldwide. Development of drug resistance against clinical anti-HBV drug lamivudine due to long-term use and rebound of viral DNA after cessation of treatment has been a major setback of the current therapy. We have synthesized a series of pyrimidine nucleosides possessing a variety of substituents at the C-5 position, and a 1-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl] flexible acyclic glycosyl moiety at the N-1 position, that have the ability to mimic the natural 2‘-deoxyribosyl moiety. Some of these potential antiviral compounds included variations at both C-5 and C-6 positions of the uracil base. Other variations of the uracil derivatives were the 6-aza congeners. 4-Amino and 4-methoxy pyrimidine derivatives were also made. Compounds in which the base moiety was substituted by 5-chloro- (25), 5-(2-bromovinyl)- (32), or 5-bromo-6-methyl- (37) groups possess significant activity against duck-HBV, wild-type human HBV (2.2.15 cells), and lamivudine-resistant HBV containing single and double mutations. No cytotoxicity was seen in host HepG2 and Vero cells, up to the highest concentration tested. The anti-HBV activity exhibited by compounds 25, 32, and 37 was superior for human HBV and comparable for DHBV to that of the corresponding purine nucleoside, ganciclovir. Further, they were only 10−15-fold less inhibitory against human HBV in 2.2.15 cells than the reference drug, lamivudine. Other compounds in the series were moderately inhibitory against DHBV and wild-type human HBV. The size of the halogen and the electronegativity of the substituents at the 5- and 6-positions are important for antiviral activity toward HBV. These compounds were also evaluated for their antiviral activity for West Nile virus, respiratory syncytial virus, SARS-coronavirus, and hepatitis C virus. They were generally inactive in these antiviral assay systems (at concentrations up to 100 μg/mL). 1-[(2-Hydroxy-1-(hydroxymethyl) ethoxy)methyl]-5-fluorocytosine (34) showed some inhibitory activity against hepatitis C virus. Taken together, these data support our previous observations that the 5-substituted pyrimidine nucleosides containing acyclic glycosyl moieties have potential to serve as a new generation of potent, selective, and nontoxic anti-HBV agents for wild-type and lamivudine-resistant mutant HBV.</div></front></TEI><affiliations><list><country><li>Canada</li></country></list><tree><country name="Canada"><noRegion><name sortKey="Kumar, Rakesh" sort="Kumar, Rakesh" uniqKey="Kumar R" first="Rakesh" last="Kumar">Rakesh Kumar</name></noRegion><name sortKey="Agrawal, Babita" sort="Agrawal, Babita" uniqKey="Agrawal B" first="Babita" last="Agrawal">Babita Agrawal</name><name sortKey="Agrawal, Babita" sort="Agrawal, Babita" uniqKey="Agrawal B" first="Babita" last="Agrawal">Babita Agrawal</name><name sortKey="Johar, Monika" sort="Johar, Monika" uniqKey="Johar M" first="Monika" last="Johar">Monika Johar</name><name sortKey="Kumar, Rakesh" sort="Kumar, Rakesh" uniqKey="Kumar R" first="Rakesh" last="Kumar">Rakesh Kumar</name><name sortKey="Semaine, Wassila" sort="Semaine, Wassila" uniqKey="Semaine W" first="Wassila" last="Semaine">Wassila Semaine</name><name sortKey="Tyrrell, D Lorne J" sort="Tyrrell, D Lorne J" uniqKey="Tyrrell D" first="D. Lorne J." last="Tyrrell">D. Lorne J. Tyrrell</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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