Relationship Between Conformation and Antiviral Activity-III. 3′-Azidothymidine (AZT) and 3′-Azido-2′, 3′-dideoxy-5-hydroxymethyluridine
3′-Azido-2′,3′-dideoxy-5-hydroxymethyluridine (AZHMddUrd) was synthesized to improve the potency of 5-hydroxymethyl-2′-deoxyuridine (HMdUrd) against human immunodeficiency virus (HIV). AZHMddUrd was a very poor inhibitor of HIV replication (ED 50 >200 μM) and was also nontoxic up to 400 μM (highe...
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| Veröffentlicht in: | Nucleosides & nucleotides 1995-10, Vol.14 (8), p.1675-1691 |
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| container_title | Nucleosides & nucleotides |
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| creator | Gupta, Sagar V. Kumar, Sashi V.P. Stuart, Allan L. Shi, Ruili Brown, Keith C. Zoghaib, Wajdi M. Li, Jung Delbaere, Louis T.J. |
| description | 3′-Azido-2′,3′-dideoxy-5-hydroxymethyluridine (AZHMddUrd) was synthesized to improve the potency of 5-hydroxymethyl-2′-deoxyuridine (HMdUrd) against human immunodeficiency virus (HIV). AZHMddUrd was a very poor inhibitor of HIV replication (ED
50
>200 μM) and was also nontoxic up to 400 μM (highest concentration tested) to HT4-6C (HeLa CD
4
) cells. AZT was phosphorylated by human cellular thymidine kinase. In contrast, AZHMddUrd and HMdUrd were poor substrates for the kinase. The relationship between molecular conformation and antiretroviral activity for 3′-azidothymidine (AZT), HMdUrd and AZHMddUrd is discussed. |
| doi_str_mv | 10.1080/15257779508009749 |
| format | Article |
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50
>200 μM) and was also nontoxic up to 400 μM (highest concentration tested) to HT4-6C (HeLa CD
4
) cells. AZT was phosphorylated by human cellular thymidine kinase. In contrast, AZHMddUrd and HMdUrd were poor substrates for the kinase. The relationship between molecular conformation and antiretroviral activity for 3′-azidothymidine (AZT), HMdUrd and AZHMddUrd is discussed.</description><identifier>ISSN: 0732-8311</identifier><identifier>DOI: 10.1080/15257779508009749</identifier><language>eng</language><publisher>Taylor & Francis Group</publisher><ispartof>Nucleosides & nucleotides, 1995-10, Vol.14 (8), p.1675-1691</ispartof><rights>Copyright Taylor & Francis Group, LLC 1995</rights><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c211t-d828b9fbb83910f031513a5efcad8ac0c797a8b541e97c90cf6e70d874231d263</citedby><cites>FETCH-LOGICAL-c211t-d828b9fbb83910f031513a5efcad8ac0c797a8b541e97c90cf6e70d874231d263</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/15257779508009749$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/15257779508009749$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,59620,60409</link.rule.ids></links><search><creatorcontrib>Gupta, Sagar V.</creatorcontrib><creatorcontrib>Kumar, Sashi V.P.</creatorcontrib><creatorcontrib>Stuart, Allan L.</creatorcontrib><creatorcontrib>Shi, Ruili</creatorcontrib><creatorcontrib>Brown, Keith C.</creatorcontrib><creatorcontrib>Zoghaib, Wajdi M.</creatorcontrib><creatorcontrib>Li, Jung</creatorcontrib><creatorcontrib>Delbaere, Louis T.J.</creatorcontrib><title>Relationship Between Conformation and Antiviral Activity-III. 3′-Azidothymidine (AZT) and 3′-Azido-2′, 3′-dideoxy-5-hydroxymethyluridine</title><title>Nucleosides & nucleotides</title><description>3′-Azido-2′,3′-dideoxy-5-hydroxymethyluridine (AZHMddUrd) was synthesized to improve the potency of 5-hydroxymethyl-2′-deoxyuridine (HMdUrd) against human immunodeficiency virus (HIV). AZHMddUrd was a very poor inhibitor of HIV replication (ED
50
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4
) cells. AZT was phosphorylated by human cellular thymidine kinase. In contrast, AZHMddUrd and HMdUrd were poor substrates for the kinase. The relationship between molecular conformation and antiretroviral activity for 3′-azidothymidine (AZT), HMdUrd and AZHMddUrd is discussed.</description><issn>0732-8311</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><recordid>eNp1kLtOwzAUhj2ARCk8AFtGkHDxJa5tiSVUXCJVQkJlYYkcX1SjNK6ccAkTj8Cz8Eg8CWmDxICYznfOr-8MPwBHGE0wEugMM8I455L1C5I8lTtghDglUFCM98B-0zwixIiU6Qh83NlKtT7UzdKvkwvbvlhbJ7NQuxBX2yBRtUmyuvXPPqoqyfSG2g7meT5J6Nf7J8zevAntslt542ubHGcPi5Ot9ZtC0uPpcDDe2PDaQQaXnYk9rWwvV09xqx-AXaeqxh7-zDG4v7pczG7g_PY6n2VzqAnGLTSCiFK6shRUYuQQxQxTxazTygilkeaSK1GyFFvJtUTaTS1HRvCUUGzIlI4BHv7qGJomWleso1-p2BUYFZsaiz819s754PihnpcQK1O0qqtCdFHV2jcF_V__BqhEf0E</recordid><startdate>19951001</startdate><enddate>19951001</enddate><creator>Gupta, Sagar V.</creator><creator>Kumar, Sashi V.P.</creator><creator>Stuart, Allan L.</creator><creator>Shi, Ruili</creator><creator>Brown, Keith C.</creator><creator>Zoghaib, Wajdi M.</creator><creator>Li, Jung</creator><creator>Delbaere, Louis T.J.</creator><general>Taylor & Francis Group</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19951001</creationdate><title>Relationship Between Conformation and Antiviral Activity-III. 3′-Azidothymidine (AZT) and 3′-Azido-2′, 3′-dideoxy-5-hydroxymethyluridine</title><author>Gupta, Sagar V. ; Kumar, Sashi V.P. ; Stuart, Allan L. ; Shi, Ruili ; Brown, Keith C. ; Zoghaib, Wajdi M. ; Li, Jung ; Delbaere, Louis T.J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c211t-d828b9fbb83910f031513a5efcad8ac0c797a8b541e97c90cf6e70d874231d263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Gupta, Sagar V.</creatorcontrib><creatorcontrib>Kumar, Sashi V.P.</creatorcontrib><creatorcontrib>Stuart, Allan L.</creatorcontrib><creatorcontrib>Shi, Ruili</creatorcontrib><creatorcontrib>Brown, Keith C.</creatorcontrib><creatorcontrib>Zoghaib, Wajdi M.</creatorcontrib><creatorcontrib>Li, Jung</creatorcontrib><creatorcontrib>Delbaere, Louis T.J.</creatorcontrib><collection>CrossRef</collection><jtitle>Nucleosides & nucleotides</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gupta, Sagar V.</au><au>Kumar, Sashi V.P.</au><au>Stuart, Allan L.</au><au>Shi, Ruili</au><au>Brown, Keith C.</au><au>Zoghaib, Wajdi M.</au><au>Li, Jung</au><au>Delbaere, Louis T.J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Relationship Between Conformation and Antiviral Activity-III. 3′-Azidothymidine (AZT) and 3′-Azido-2′, 3′-dideoxy-5-hydroxymethyluridine</atitle><jtitle>Nucleosides & nucleotides</jtitle><date>1995-10-01</date><risdate>1995</risdate><volume>14</volume><issue>8</issue><spage>1675</spage><epage>1691</epage><pages>1675-1691</pages><issn>0732-8311</issn><abstract>3′-Azido-2′,3′-dideoxy-5-hydroxymethyluridine (AZHMddUrd) was synthesized to improve the potency of 5-hydroxymethyl-2′-deoxyuridine (HMdUrd) against human immunodeficiency virus (HIV). AZHMddUrd was a very poor inhibitor of HIV replication (ED
50
>200 μM) and was also nontoxic up to 400 μM (highest concentration tested) to HT4-6C (HeLa CD
4
) cells. AZT was phosphorylated by human cellular thymidine kinase. In contrast, AZHMddUrd and HMdUrd were poor substrates for the kinase. The relationship between molecular conformation and antiretroviral activity for 3′-azidothymidine (AZT), HMdUrd and AZHMddUrd is discussed.</abstract><pub>Taylor & Francis Group</pub><doi>10.1080/15257779508009749</doi><tpages>17</tpages></addata></record> |
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| title | Relationship Between Conformation and Antiviral Activity-III. 3′-Azidothymidine (AZT) and 3′-Azido-2′, 3′-dideoxy-5-hydroxymethyluridine |
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