Are 5′- O-Carbamate-2′,3′-dideoxythiacytidine New Anti-HIV and Anti-HBV nucleoside Drugs or Prodrugs?
In contrast to 5′- O-carbonate 3TC derivatives ( 23, 24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates ( 15– 21 and 25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infecte...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2003-08, Vol.13 (15), p.2459-2463 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Anastasi, Carole Vlieghe, Patrick Hantz, Olivier Schorr, Olivier Pannecouque, Christophe Witvrouw, Myriam De Clercq, Erik Clayette, Pascal Dereuddre-Bosquet, Nathalie Dormont, Dominique Gondois-Rey, Françoise Hirsch, Ivan Kraus, Jean-Louis |
| description | In contrast to 5′-
O-carbonate 3TC derivatives (
23,
24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (
15–
21 and
25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated.
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| doi_str_mv | 10.1016/S0960-894X(03)00496-7 |
| format | Article |
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O-carbonate 3TC derivatives (
23,
24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (
15–
21 and
25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated.
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O-carbonate 3TC derivatives (
23,
24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (
15–
21 and
25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated.
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Drug treatments</subject><subject>Prodrugs - metabolism</subject><subject>Prodrugs - pharmacology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhi0EosvCI4ByoaIShnHsOPGpWrbAVlpRJKDiZnntCTVk42InLXvjmXgknoSkG7VHTuP59f3j0fyEPGXwigGTrz-BkkArJb6-AH4EIJSk5T0yY0IKygUU98nsFjkgj1L6DsAECPGQHLC8KnIl-Iz8WETMir-__9DsjC5N3Jit6ZDmg_KSj7LzDsOvXXfhjd113vkWsw94nS3aztPV6XlmWjc1b86ztrcNhjR4spPYf0tZiNnHGNz4Pn5MHtSmSfhkqnPy5d3bz8sVXZ-9P10u1tSKvOiocmigYg4YiJw7U0oFdQ7VRvJqk1fCYgkKytwa5WppLAdXlkpyJ8Faxy2fk6P93AvT6MvotybudDBerxZrPWoAHATn7IoN7OGevYzhZ4-p01ufLDaNaTH0SZdcSFXwESz2oI0hpYj17WQGekxE3ySix3Nr4PomkcE-J8-mD_rNFt2da4pgAJ5PgEnWNHU0rfXpjhOqZKwcFzjeczic7spj1Ml6bC06H9F22gX_n1X-AYTtqEY</recordid><startdate>20030804</startdate><enddate>20030804</enddate><creator>Anastasi, Carole</creator><creator>Vlieghe, Patrick</creator><creator>Hantz, Olivier</creator><creator>Schorr, Olivier</creator><creator>Pannecouque, Christophe</creator><creator>Witvrouw, Myriam</creator><creator>De Clercq, Erik</creator><creator>Clayette, Pascal</creator><creator>Dereuddre-Bosquet, Nathalie</creator><creator>Dormont, Dominique</creator><creator>Gondois-Rey, Françoise</creator><creator>Hirsch, Ivan</creator><creator>Kraus, Jean-Louis</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-6080-1286</orcidid></search><sort><creationdate>20030804</creationdate><title>Are 5′- O-Carbamate-2′,3′-dideoxythiacytidine New Anti-HIV and Anti-HBV nucleoside Drugs or Prodrugs?</title><author>Anastasi, Carole ; Vlieghe, Patrick ; Hantz, Olivier ; Schorr, Olivier ; Pannecouque, Christophe ; Witvrouw, Myriam ; De Clercq, Erik ; Clayette, Pascal ; Dereuddre-Bosquet, Nathalie ; Dormont, Dominique ; Gondois-Rey, Françoise ; Hirsch, Ivan ; Kraus, Jean-Louis</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c425t-9dea081d010423da7690f208b638b284ce709072ca9df6ac30d77963d60ccd3c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Anti-HIV Agents - metabolism</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - metabolism</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Chemical Sciences</topic><topic>Culture Media</topic><topic>Deoxycytidine - analogs & derivatives</topic><topic>Deoxycytidine - metabolism</topic><topic>Deoxycytidine - pharmacology</topic><topic>Hepatitis B virus - drug effects</topic><topic>HIV-1 - drug effects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Medicinal Chemistry</topic><topic>Pharmacology. 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23,
24), which are clearly 3TC prodrugs, the corresponding 3TC carbamates (
15–
21 and
25), found to be very stable compounds with respect to enzymatic hydrolysis (cellular lysates and culture cell media) and still active on both HIV-1 and HBV infected cells, may not be 3TC prodrugs. The antiviral properties as well as the mechanism of action of 3TC analogues have been studied and evaluated.
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| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2003-08, Vol.13 (15), p.2459-2463 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_00304331v1 |
| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Anti-HIV Agents - metabolism Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - metabolism Antiviral Agents - pharmacology Biological and medical sciences Cell Line Chemical Sciences Culture Media Deoxycytidine - analogs & derivatives Deoxycytidine - metabolism Deoxycytidine - pharmacology Hepatitis B virus - drug effects HIV-1 - drug effects Humans Medical sciences Medicinal Chemistry Pharmacology. Drug treatments Prodrugs - metabolism Prodrugs - pharmacology |
| title | Are 5′- O-Carbamate-2′,3′-dideoxythiacytidine New Anti-HIV and Anti-HBV nucleoside Drugs or Prodrugs? |
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