Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange
A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerabili...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-04, Vol.58 (15), p.4891-4895 |
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| creator | Palazzolo, Alberto Feuillastre, Sophie Pfeifer, Viktor Garcia‐Argote, Sébastien Bouzouita, Donia Tricard, Simon Chollet, Céline Marcon, Elodie Buisson, David‐Alexandre Cholet, Sophie Fenaille, François Lippens, Guy Chaudret, Bruno Pieters, Grégory |
| description | A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.
Making the swap: A general approach for the late‐stage hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles using mild reaction conditions and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development. |
| doi_str_mv | 10.1002/anie.201813946 |
| format | Article |
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Making the swap: A general approach for the late‐stage hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles using mild reaction conditions and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>ISSN: 1521-3773</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201813946</identifier><identifier>PMID: 30768844</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Chemical Sciences ; Chromatography, Liquid ; Communication ; Communications ; C−H activation ; Deuteration ; Deuterium - chemistry ; Deuterium Exchange Measurement ; Diagnostic software ; Diagnostic systems ; Drug discovery ; Drugs ; Exchanging ; Hydrogen - chemistry ; isotopes ; isotopic labelling ; Mass Spectrometry ; Nanoparticles ; nucleotides ; Oligonucleotides ; Oligonucleotides - chemistry ; Pharmaceutical Preparations - chemistry ; Pharmaceuticals ; Ruthenium ; Substrates</subject><ispartof>Angewandte Chemie International Edition, 2019-04, Vol.58 (15), p.4891-4895</ispartof><rights>2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Attribution - NonCommercial - NoDerivatives</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6056-40cc4a29ec08ade8dc07128834be61585dcc8c8df47c4d2a7851969536842bf23</citedby><cites>FETCH-LOGICAL-c6056-40cc4a29ec08ade8dc07128834be61585dcc8c8df47c4d2a7851969536842bf23</cites><orcidid>0000-0002-3924-8287 ; 0000-0001-6787-4149 ; 0000-0001-9290-6421 ; 0000-0002-5018-6312 ; 0000-0002-0061-8578 ; 0000-0002-9327-2050 ; 0000-0002-8236-0901</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201813946$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201813946$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30768844$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://cea.hal.science/cea-02075752$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Palazzolo, Alberto</creatorcontrib><creatorcontrib>Feuillastre, Sophie</creatorcontrib><creatorcontrib>Pfeifer, Viktor</creatorcontrib><creatorcontrib>Garcia‐Argote, Sébastien</creatorcontrib><creatorcontrib>Bouzouita, Donia</creatorcontrib><creatorcontrib>Tricard, Simon</creatorcontrib><creatorcontrib>Chollet, Céline</creatorcontrib><creatorcontrib>Marcon, Elodie</creatorcontrib><creatorcontrib>Buisson, David‐Alexandre</creatorcontrib><creatorcontrib>Cholet, Sophie</creatorcontrib><creatorcontrib>Fenaille, François</creatorcontrib><creatorcontrib>Lippens, Guy</creatorcontrib><creatorcontrib>Chaudret, Bruno</creatorcontrib><creatorcontrib>Pieters, Grégory</creatorcontrib><title>Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A general approach for the efficient hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.
Making the swap: A general approach for the late‐stage hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles using mild reaction conditions and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development.</description><subject>Chemical Sciences</subject><subject>Chromatography, Liquid</subject><subject>Communication</subject><subject>Communications</subject><subject>C−H activation</subject><subject>Deuteration</subject><subject>Deuterium - chemistry</subject><subject>Deuterium Exchange Measurement</subject><subject>Diagnostic software</subject><subject>Diagnostic systems</subject><subject>Drug discovery</subject><subject>Drugs</subject><subject>Exchanging</subject><subject>Hydrogen - chemistry</subject><subject>isotopes</subject><subject>isotopic labelling</subject><subject>Mass Spectrometry</subject><subject>Nanoparticles</subject><subject>nucleotides</subject><subject>Oligonucleotides</subject><subject>Oligonucleotides - chemistry</subject><subject>Pharmaceutical Preparations - chemistry</subject><subject>Pharmaceuticals</subject><subject>Ruthenium</subject><subject>Substrates</subject><issn>1433-7851</issn><issn>1521-3773</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>EIF</sourceid><recordid>eNqFks1uEzEURkcIREthyxKNxIYuJvh_PBukqAQSKWpZlLXl2HcSVxM72DOFbCoegWfkSXCSEqAbVrblc4_92bcoXmI0wgiRt9o7GBGEJaYNE4-KU8wJrmhd08d5ziitasnxSfEspZvMS4nE0-KEolpIydhpcTdpW2cc-L4cGwMplX0o38PQQ9Q92FJ7W15H17v96nIwHYSFTlB-Wum41iaTzugu7cGrzi2D3zO9s5DKITm_LKdbG8MS_M_vP2Yp9GED5eSbWWm_hOfFkzZXw4v78az4_GFyfTGt5lcfZxfjeWUE4qJiyBimSQMGSW1BWoNqnMNQtgCBueTWGGmkbVltmCV6l7kRDadCMrJoCT0r3h28m2GxBmty3qg7tYlureNWBe3UvzverdQy3CrBm_yYMgvOD4LVg7LpeK4MaIUIqnnNyS3O7Jv7w2L4MkDq1dolA12nPYQhKYKlzFqKm4y-foDehCH6_BSZagQXWPCdcHSgTAwpRWiPN8BI7dpA7dpAHdsgF7z6O-4R__3vGWgOwFfXwfY_OjW-nE3-yH8Bdq3Bsg</recordid><startdate>20190401</startdate><enddate>20190401</enddate><creator>Palazzolo, Alberto</creator><creator>Feuillastre, Sophie</creator><creator>Pfeifer, Viktor</creator><creator>Garcia‐Argote, Sébastien</creator><creator>Bouzouita, Donia</creator><creator>Tricard, Simon</creator><creator>Chollet, Céline</creator><creator>Marcon, Elodie</creator><creator>Buisson, David‐Alexandre</creator><creator>Cholet, Sophie</creator><creator>Fenaille, François</creator><creator>Lippens, Guy</creator><creator>Chaudret, Bruno</creator><creator>Pieters, Grégory</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><general>John Wiley and Sons Inc</general><scope>24P</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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-3924-8287</orcidid><orcidid>https://orcid.org/0000-0001-6787-4149</orcidid><orcidid>https://orcid.org/0000-0001-9290-6421</orcidid><orcidid>https://orcid.org/0000-0002-5018-6312</orcidid><orcidid>https://orcid.org/0000-0002-0061-8578</orcidid><orcidid>https://orcid.org/0000-0002-9327-2050</orcidid><orcidid>https://orcid.org/0000-0002-8236-0901</orcidid></search><sort><creationdate>20190401</creationdate><title>Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange</title><author>Palazzolo, Alberto ; 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Catalyzed by ruthenium nanoparticles, using mild reaction conditions, and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development: tritiated pharmaceuticals with high specific activities and deuterated oligonucleotides suitable for use as internal standards during LC‐MS quantification.
Making the swap: A general approach for the late‐stage hydrogen‐isotope exchange of nucleobase derivatives is described. Catalyzed by ruthenium nanoparticles using mild reaction conditions and involving either D2 or T2 as isotopic sources, this reaction possesses a wide substrate scope and a high solvent tolerability. This novel method facilitates the access to essential diagnostic tools in drug discovery and development.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>30768844</pmid><doi>10.1002/anie.201813946</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3924-8287</orcidid><orcidid>https://orcid.org/0000-0001-6787-4149</orcidid><orcidid>https://orcid.org/0000-0001-9290-6421</orcidid><orcidid>https://orcid.org/0000-0002-5018-6312</orcidid><orcidid>https://orcid.org/0000-0002-0061-8578</orcidid><orcidid>https://orcid.org/0000-0002-9327-2050</orcidid><orcidid>https://orcid.org/0000-0002-8236-0901</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Chemical Sciences Chromatography, Liquid Communication Communications C−H activation Deuteration Deuterium - chemistry Deuterium Exchange Measurement Diagnostic software Diagnostic systems Drug discovery Drugs Exchanging Hydrogen - chemistry isotopes isotopic labelling Mass Spectrometry Nanoparticles nucleotides Oligonucleotides Oligonucleotides - chemistry Pharmaceutical Preparations - chemistry Pharmaceuticals Ruthenium Substrates |
| title | Efficient Access to Deuterated and Tritiated Nucleobase Pharmaceuticals and Oligonucleotides using Hydrogen‐Isotope Exchange |
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