Alkyne-linked reduction-activated protecting groups for diverse functionalization on the backbone of oligonucleotides
[Display omitted] A versatile conjugatable/bioreduction-responsive protecting group for phosphodiester moieties was designed, synthesized and incorporated into oligonucleotide strands. Subsequently, controlled pore glass-supported oligonucleotides were conjugated to a variety of functional molecules...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2017-07, Vol.25 (13), p.3350-3356 |
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| container_end_page | 3356 |
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| container_issue | 13 |
| container_start_page | 3350 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 25 |
| creator | Saneyoshi, Hisao Kondo, Kazuhiko Iketani, Koichi Ono, Akira |
| description | [Display omitted]
A versatile conjugatable/bioreduction-responsive protecting group for phosphodiester moieties was designed, synthesized and incorporated into oligonucleotide strands. Subsequently, controlled pore glass-supported oligonucleotides were conjugated to a variety of functional molecules using a copper-catalyzed azide-alkyne cycloaddition reaction. The functionalized protecting groups were deprotected by a nitroreductase/NADH reduction system to give “naked” oligonucleotides. This method allowed the synthesis of oligonucleotide prodrugs bearing the functionalized protecting group at the desired sites and desired residues on oligodeoxyribonucleotide (ODN) backbones. |
| doi_str_mv | 10.1016/j.bmc.2017.04.020 |
| format | Article |
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A versatile conjugatable/bioreduction-responsive protecting group for phosphodiester moieties was designed, synthesized and incorporated into oligonucleotide strands. Subsequently, controlled pore glass-supported oligonucleotides were conjugated to a variety of functional molecules using a copper-catalyzed azide-alkyne cycloaddition reaction. The functionalized protecting groups were deprotected by a nitroreductase/NADH reduction system to give “naked” oligonucleotides. This method allowed the synthesis of oligonucleotide prodrugs bearing the functionalized protecting group at the desired sites and desired residues on oligodeoxyribonucleotide (ODN) backbones.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2017.04.020</identifier><identifier>PMID: 28460887</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Alkynes - chemistry ; Alkynes - metabolism ; Conjugation ; Drug delivery ; Molecular Structure ; NAD - chemistry ; NAD - metabolism ; Nitroreductases - chemistry ; Nitroreductases - metabolism ; Oligonucleotide therapeutics ; Oligonucleotides - chemical synthesis ; Oligonucleotides - chemistry ; Oligonucleotides - metabolism ; Oxidation-Reduction ; Prodrugs - chemical synthesis ; Prodrugs - chemistry ; Prodrugs - metabolism ; Protecting group</subject><ispartof>Bioorganic & medicinal chemistry, 2017-07, Vol.25 (13), p.3350-3356</ispartof><rights>2017 Elsevier Ltd</rights><rights>Copyright © 2017 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c419t-3527f36574ea2fc44e9511820c88b6807c39edd40dc504d55ae4a7f78d8835cb3</citedby><cites>FETCH-LOGICAL-c419t-3527f36574ea2fc44e9511820c88b6807c39edd40dc504d55ae4a7f78d8835cb3</cites><orcidid>0000-0003-4061-101X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2017.04.020$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28460887$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Saneyoshi, Hisao</creatorcontrib><creatorcontrib>Kondo, Kazuhiko</creatorcontrib><creatorcontrib>Iketani, Koichi</creatorcontrib><creatorcontrib>Ono, Akira</creatorcontrib><title>Alkyne-linked reduction-activated protecting groups for diverse functionalization on the backbone of oligonucleotides</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
A versatile conjugatable/bioreduction-responsive protecting group for phosphodiester moieties was designed, synthesized and incorporated into oligonucleotide strands. Subsequently, controlled pore glass-supported oligonucleotides were conjugated to a variety of functional molecules using a copper-catalyzed azide-alkyne cycloaddition reaction. The functionalized protecting groups were deprotected by a nitroreductase/NADH reduction system to give “naked” oligonucleotides. This method allowed the synthesis of oligonucleotide prodrugs bearing the functionalized protecting group at the desired sites and desired residues on oligodeoxyribonucleotide (ODN) backbones.</description><subject>Alkynes - chemistry</subject><subject>Alkynes - metabolism</subject><subject>Conjugation</subject><subject>Drug delivery</subject><subject>Molecular Structure</subject><subject>NAD - chemistry</subject><subject>NAD - metabolism</subject><subject>Nitroreductases - chemistry</subject><subject>Nitroreductases - metabolism</subject><subject>Oligonucleotide therapeutics</subject><subject>Oligonucleotides - chemical synthesis</subject><subject>Oligonucleotides - chemistry</subject><subject>Oligonucleotides - metabolism</subject><subject>Oxidation-Reduction</subject><subject>Prodrugs - chemical synthesis</subject><subject>Prodrugs - chemistry</subject><subject>Prodrugs - metabolism</subject><subject>Protecting group</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9P4zAQxS3EihZ2PwAX5COXhHHiJI44IcQuSJX2snu2HHtS3KZ2sZNK8OlxaeGINNL80XtPmh8hlwxyBqy-WeXdRucFsCYHnkMBJ2TOeM2zsmzZKZlDW4sMRFvPyHmMKwAoeMvOyKwQvAYhmjmZ7ob1q8NssG6NhgY0kx6td5lKbafGdNsGP2La3JIug5-2kfY-UGN3GCLSfnIfBjXYN7UfaKrxGWmn9LrzDqnvqR_s0rtJD-hHazD-JD96NUT8dewX5P_vh3_3j9ni75-n-7tFpjlrx6ysiqYv66rhqIpec45txZgoQAvR1QIaXbZoDAejK-CmqhRy1fSNMEKUle7KC3J9yE0_vEwYR7mxUeMwKId-ipKJllcFKxuepOwg1cHHGLCX22A3KrxKBnJPW65koi33tCVwmWgnz9Uxfuo2aL4cn3iT4PYgwPTkzmKQUVt0Go0NCak03n4T_w7jVJJ4</recordid><startdate>20170701</startdate><enddate>20170701</enddate><creator>Saneyoshi, Hisao</creator><creator>Kondo, Kazuhiko</creator><creator>Iketani, Koichi</creator><creator>Ono, Akira</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>7X8</scope><orcidid>https://orcid.org/0000-0003-4061-101X</orcidid></search><sort><creationdate>20170701</creationdate><title>Alkyne-linked reduction-activated protecting groups for diverse functionalization on the backbone of oligonucleotides</title><author>Saneyoshi, Hisao ; Kondo, Kazuhiko ; Iketani, Koichi ; Ono, Akira</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c419t-3527f36574ea2fc44e9511820c88b6807c39edd40dc504d55ae4a7f78d8835cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkynes - chemistry</topic><topic>Alkynes - metabolism</topic><topic>Conjugation</topic><topic>Drug delivery</topic><topic>Molecular Structure</topic><topic>NAD - chemistry</topic><topic>NAD - metabolism</topic><topic>Nitroreductases - chemistry</topic><topic>Nitroreductases - metabolism</topic><topic>Oligonucleotide therapeutics</topic><topic>Oligonucleotides - chemical synthesis</topic><topic>Oligonucleotides - chemistry</topic><topic>Oligonucleotides - metabolism</topic><topic>Oxidation-Reduction</topic><topic>Prodrugs - chemical synthesis</topic><topic>Prodrugs - chemistry</topic><topic>Prodrugs - metabolism</topic><topic>Protecting group</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Saneyoshi, Hisao</creatorcontrib><creatorcontrib>Kondo, Kazuhiko</creatorcontrib><creatorcontrib>Iketani, Koichi</creatorcontrib><creatorcontrib>Ono, Akira</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Saneyoshi, Hisao</au><au>Kondo, Kazuhiko</au><au>Iketani, Koichi</au><au>Ono, Akira</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alkyne-linked reduction-activated protecting groups for diverse functionalization on the backbone of oligonucleotides</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2017-07-01</date><risdate>2017</risdate><volume>25</volume><issue>13</issue><spage>3350</spage><epage>3356</epage><pages>3350-3356</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
A versatile conjugatable/bioreduction-responsive protecting group for phosphodiester moieties was designed, synthesized and incorporated into oligonucleotide strands. Subsequently, controlled pore glass-supported oligonucleotides were conjugated to a variety of functional molecules using a copper-catalyzed azide-alkyne cycloaddition reaction. The functionalized protecting groups were deprotected by a nitroreductase/NADH reduction system to give “naked” oligonucleotides. This method allowed the synthesis of oligonucleotide prodrugs bearing the functionalized protecting group at the desired sites and desired residues on oligodeoxyribonucleotide (ODN) backbones.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>28460887</pmid><doi>10.1016/j.bmc.2017.04.020</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-4061-101X</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2017-07, Vol.25 (13), p.3350-3356 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Alkynes - chemistry Alkynes - metabolism Conjugation Drug delivery Molecular Structure NAD - chemistry NAD - metabolism Nitroreductases - chemistry Nitroreductases - metabolism Oligonucleotide therapeutics Oligonucleotides - chemical synthesis Oligonucleotides - chemistry Oligonucleotides - metabolism Oxidation-Reduction Prodrugs - chemical synthesis Prodrugs - chemistry Prodrugs - metabolism Protecting group |
| title | Alkyne-linked reduction-activated protecting groups for diverse functionalization on the backbone of oligonucleotides |
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