Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA
[Display omitted] A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure–activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding to...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2016-09, Vol.24 (17), p.3947-3952 |
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| container_issue | 17 |
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| container_title | Bioorganic & medicinal chemistry |
| container_volume | 24 |
| creator | Wynn, Jessica E. Zhang, Wenyu Tebit, Denis M. Gray, Laurie R. Hammarskjold, Marie-Louise Rekosh, David Santos, Webster L. |
| description | [Display omitted]
A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure–activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding towards RRE IIB, and the peptide demonstrates selectivity towards RRE IIB in the presence of tRNA. Footprinting studies suggest a binding site on the upper stem and internal loop regions of the RNA, which induces enzymatic cleavage of the internal loops of RRE IIB upon binding. |
| doi_str_mv | 10.1016/j.bmc.2016.04.009 |
| format | Article |
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A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure–activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding towards RRE IIB, and the peptide demonstrates selectivity towards RRE IIB in the presence of tRNA. Footprinting studies suggest a binding site on the upper stem and internal loop regions of the RNA, which induces enzymatic cleavage of the internal loops of RRE IIB upon binding.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2016.04.009</identifier><identifier>PMID: 27091070</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anti-HIV Agents - chemistry ; Anti-HIV Agents - pharmacology ; Boronic acids ; Boronic Acids - chemistry ; Boronic Acids - pharmacology ; Branched peptides ; HeLa Cells ; HIV Core Protein p24 - antagonists & inhibitors ; HIV-1 ; HIV-1 - drug effects ; HIV-1 - genetics ; Humans ; Integrase Inhibitors - pharmacology ; Lamivudine - pharmacology ; Nucleic Acid Conformation ; p24 inhibition ; Peptide Library ; Peptides - chemistry ; Peptides - pharmacology ; Quinolones - pharmacology ; Raltegravir Potassium - pharmacology ; Response Elements ; RNA, Viral - chemistry ; RNA, Viral - genetics ; RNA, Viral - metabolism ; RRE RNA ; Structure-Activity Relationship ; Virus Replication - drug effects ; Zidovudine - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 2016-09, Vol.24 (17), p.3947-3952</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c451t-ab7125c3ee2b945f718071869981634624ca02a43f5743ff7a32711263c7efbb3</citedby><cites>FETCH-LOGICAL-c451t-ab7125c3ee2b945f718071869981634624ca02a43f5743ff7a32711263c7efbb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2016.04.009$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,777,781,882,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27091070$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wynn, Jessica E.</creatorcontrib><creatorcontrib>Zhang, Wenyu</creatorcontrib><creatorcontrib>Tebit, Denis M.</creatorcontrib><creatorcontrib>Gray, Laurie R.</creatorcontrib><creatorcontrib>Hammarskjold, Marie-Louise</creatorcontrib><creatorcontrib>Rekosh, David</creatorcontrib><creatorcontrib>Santos, Webster L.</creatorcontrib><title>Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure–activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding towards RRE IIB, and the peptide demonstrates selectivity towards RRE IIB in the presence of tRNA. Footprinting studies suggest a binding site on the upper stem and internal loop regions of the RNA, which induces enzymatic cleavage of the internal loops of RRE IIB upon binding.</description><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Boronic acids</subject><subject>Boronic Acids - chemistry</subject><subject>Boronic Acids - pharmacology</subject><subject>Branched peptides</subject><subject>HeLa Cells</subject><subject>HIV Core Protein p24 - antagonists & inhibitors</subject><subject>HIV-1</subject><subject>HIV-1 - drug effects</subject><subject>HIV-1 - genetics</subject><subject>Humans</subject><subject>Integrase Inhibitors - pharmacology</subject><subject>Lamivudine - pharmacology</subject><subject>Nucleic Acid Conformation</subject><subject>p24 inhibition</subject><subject>Peptide Library</subject><subject>Peptides - chemistry</subject><subject>Peptides - pharmacology</subject><subject>Quinolones - pharmacology</subject><subject>Raltegravir Potassium - pharmacology</subject><subject>Response Elements</subject><subject>RNA, Viral - chemistry</subject><subject>RNA, Viral - genetics</subject><subject>RNA, Viral - metabolism</subject><subject>RRE RNA</subject><subject>Structure-Activity Relationship</subject><subject>Virus Replication - drug effects</subject><subject>Zidovudine - pharmacology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kNFKAzEQRYMotlY_wBfJD-w6yaabBkEopdpCUSjqa8hms25quynZWKlfb0q16IsPkxmYe8-Qi9AlgZQAya8XabHSKY1jCiwFEEeoS1jOkiwT5Bh1QeSDBAYi76Cztl0AAGWCnKIO5SAIcOiit1GtvNLBePupgnUNVk2JbYM3NniH48bGaYtdhRUuvGp0bUq8NutgS4ML511jdZTZEodaheiMqOhq8YcNNZ5MXxKC5_Mxnj8Mz9FJpZatufjuPfR8N34aTZLZ4_10NJwlmvVJSFTBCe3rzBhaCNavOBlArFyIAckzllOmFVDFsqrP41NxlVFOCM0zzU1VFFkP3e656_diZUptmuDVUq69XSm_lU5Z-XfT2Fq-uo1kgkcSiwCyB2jv2tab6uAlIHfJy4WMyctd8hKYjMlHz9XvowfHT9RRcLMXmPj1jTVettqaRpvSeqODLJ39B_8F1SaUXw</recordid><startdate>20160901</startdate><enddate>20160901</enddate><creator>Wynn, Jessica E.</creator><creator>Zhang, Wenyu</creator><creator>Tebit, Denis M.</creator><creator>Gray, Laurie R.</creator><creator>Hammarskjold, Marie-Louise</creator><creator>Rekosh, David</creator><creator>Santos, Webster L.</creator><general>Elsevier Ltd</general><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>5PM</scope></search><sort><creationdate>20160901</creationdate><title>Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA</title><author>Wynn, Jessica E. ; Zhang, Wenyu ; Tebit, Denis M. ; Gray, Laurie R. ; Hammarskjold, Marie-Louise ; Rekosh, David ; Santos, Webster L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c451t-ab7125c3ee2b945f718071869981634624ca02a43f5743ff7a32711263c7efbb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Boronic acids</topic><topic>Boronic Acids - chemistry</topic><topic>Boronic Acids - pharmacology</topic><topic>Branched peptides</topic><topic>HeLa Cells</topic><topic>HIV Core Protein p24 - antagonists & inhibitors</topic><topic>HIV-1</topic><topic>HIV-1 - drug effects</topic><topic>HIV-1 - genetics</topic><topic>Humans</topic><topic>Integrase Inhibitors - pharmacology</topic><topic>Lamivudine - pharmacology</topic><topic>Nucleic Acid Conformation</topic><topic>p24 inhibition</topic><topic>Peptide Library</topic><topic>Peptides - chemistry</topic><topic>Peptides - pharmacology</topic><topic>Quinolones - pharmacology</topic><topic>Raltegravir Potassium - pharmacology</topic><topic>Response Elements</topic><topic>RNA, Viral - chemistry</topic><topic>RNA, Viral - genetics</topic><topic>RNA, Viral - metabolism</topic><topic>RRE RNA</topic><topic>Structure-Activity Relationship</topic><topic>Virus Replication - drug effects</topic><topic>Zidovudine - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wynn, Jessica E.</creatorcontrib><creatorcontrib>Zhang, Wenyu</creatorcontrib><creatorcontrib>Tebit, Denis M.</creatorcontrib><creatorcontrib>Gray, Laurie R.</creatorcontrib><creatorcontrib>Hammarskjold, Marie-Louise</creatorcontrib><creatorcontrib>Rekosh, David</creatorcontrib><creatorcontrib>Santos, Webster L.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wynn, Jessica E.</au><au>Zhang, Wenyu</au><au>Tebit, Denis M.</au><au>Gray, Laurie R.</au><au>Hammarskjold, Marie-Louise</au><au>Rekosh, David</au><au>Santos, Webster L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2016-09-01</date><risdate>2016</risdate><volume>24</volume><issue>17</issue><spage>3947</spage><epage>3952</epage><pages>3947-3952</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure–activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding towards RRE IIB, and the peptide demonstrates selectivity towards RRE IIB in the presence of tRNA. Footprinting studies suggest a binding site on the upper stem and internal loop regions of the RNA, which induces enzymatic cleavage of the internal loops of RRE IIB upon binding.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>27091070</pmid><doi>10.1016/j.bmc.2016.04.009</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology Boronic acids Boronic Acids - chemistry Boronic Acids - pharmacology Branched peptides HeLa Cells HIV Core Protein p24 - antagonists & inhibitors HIV-1 HIV-1 - drug effects HIV-1 - genetics Humans Integrase Inhibitors - pharmacology Lamivudine - pharmacology Nucleic Acid Conformation p24 inhibition Peptide Library Peptides - chemistry Peptides - pharmacology Quinolones - pharmacology Raltegravir Potassium - pharmacology Response Elements RNA, Viral - chemistry RNA, Viral - genetics RNA, Viral - metabolism RRE RNA Structure-Activity Relationship Virus Replication - drug effects Zidovudine - pharmacology |
| title | Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA |
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