An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing

An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing

Pyrrole- and indole-linked C(8)-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ∼ 10-fold brighter and shows prom...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2011-01, Vol.9 (5), p.1565-1571
Hauptverfasser: Schlitt, Katherine M, Millen, Andrea L, Wetmore, Stacey D, Manderville, Richard A
Format: Artikel
Sprache:eng
Schlagworte:
Base Pairing
Deoxyguanosine - chemistry
DNA - chemistry
Fluorescence
Fluorescent Dyes - chemistry
Hydrogen Bonding
Indoles - chemistry
Models, Molecular
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1571
container_issue 5
container_start_page 1565
container_title Organic & biomolecular chemistry
container_volume 9
creator Schlitt, Katherine M
Millen, Andrea L
Wetmore, Stacey D
Manderville, Richard A
description Pyrrole- and indole-linked C(8)-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ∼ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing.
doi_str_mv 10.1039/c0ob00883d
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1468369921</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1468369921</sourcerecordid><originalsourceid>FETCH-LOGICAL-c319t-387046b0243ba83edc16bc2939b168424b3b9b1faefd21a3c55ff3bb82622d263</originalsourceid><addsrcrecordid>eNpFkE1Lw0AQhhdRbK1e_AGyRxGi-9XN5liKWqHgRfEY9mNSYtPduJuI9dcbaa3MwDyHh5fhReiSkltKeHFnSTCEKMXdERpTkecZmfLi-MCMjNBZSu-E0CKX4hSNGGWCDDNG3zOPa-9CA1lT-zU4PFeZg_C1XfXah1R7wL63DQzoAGvbJayHxVXThwjJgu9whDbEDiIOFX7TXQo-m8farvEnxNQnvAhhlToAj41OgFtdx9qvztFJpZsEF_s7Qa8P9y_zRbZ8fnyaz5aZ5bToMq5yIqQhTHCjFQdnqTSWFbwwVCrBhOFmwEpD5RjV3E6nVcWNUUwy5pjkE3S9y21j-OghdeWmHv5uGu0h9KmkQioui4LRQb3ZqTaGlCJUZRvrjY7bkpLyt-vyv-tBvtrn9mYD7qD-lct_ABpve5w</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1468369921</pqid></control><display><type>article</type><title>An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing</title><source>MEDLINE</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Schlitt, Katherine M ; Millen, Andrea L ; Wetmore, Stacey D ; Manderville, Richard A</creator><creatorcontrib>Schlitt, Katherine M ; Millen, Andrea L ; Wetmore, Stacey D ; Manderville, Richard A</creatorcontrib><description>Pyrrole- and indole-linked C(8)-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ∼ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c0ob00883d</identifier><identifier>PMID: 21240404</identifier><language>eng</language><publisher>England</publisher><subject>Base Pairing ; Deoxyguanosine - chemistry ; DNA - chemistry ; Fluorescence ; Fluorescent Dyes - chemistry ; Hydrogen Bonding ; Indoles - chemistry ; Models, Molecular</subject><ispartof>Organic &amp; biomolecular chemistry, 2011-01, Vol.9 (5), p.1565-1571</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-387046b0243ba83edc16bc2939b168424b3b9b1faefd21a3c55ff3bb82622d263</citedby><cites>FETCH-LOGICAL-c319t-387046b0243ba83edc16bc2939b168424b3b9b1faefd21a3c55ff3bb82622d263</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21240404$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schlitt, Katherine M</creatorcontrib><creatorcontrib>Millen, Andrea L</creatorcontrib><creatorcontrib>Wetmore, Stacey D</creatorcontrib><creatorcontrib>Manderville, Richard A</creatorcontrib><title>An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Pyrrole- and indole-linked C(8)-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ∼ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing.</description><subject>Base Pairing</subject><subject>Deoxyguanosine - chemistry</subject><subject>DNA - chemistry</subject><subject>Fluorescence</subject><subject>Fluorescent Dyes - chemistry</subject><subject>Hydrogen Bonding</subject><subject>Indoles - chemistry</subject><subject>Models, Molecular</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1Lw0AQhhdRbK1e_AGyRxGi-9XN5liKWqHgRfEY9mNSYtPduJuI9dcbaa3MwDyHh5fhReiSkltKeHFnSTCEKMXdERpTkecZmfLi-MCMjNBZSu-E0CKX4hSNGGWCDDNG3zOPa-9CA1lT-zU4PFeZg_C1XfXah1R7wL63DQzoAGvbJayHxVXThwjJgu9whDbEDiIOFX7TXQo-m8farvEnxNQnvAhhlToAj41OgFtdx9qvztFJpZsEF_s7Qa8P9y_zRbZ8fnyaz5aZ5bToMq5yIqQhTHCjFQdnqTSWFbwwVCrBhOFmwEpD5RjV3E6nVcWNUUwy5pjkE3S9y21j-OghdeWmHv5uGu0h9KmkQioui4LRQb3ZqTaGlCJUZRvrjY7bkpLyt-vyv-tBvtrn9mYD7qD-lct_ABpve5w</recordid><startdate>20110101</startdate><enddate>20110101</enddate><creator>Schlitt, Katherine M</creator><creator>Millen, Andrea L</creator><creator>Wetmore, Stacey D</creator><creator>Manderville, Richard A</creator><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></search><sort><creationdate>20110101</creationdate><title>An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing</title><author>Schlitt, Katherine M ; Millen, Andrea L ; Wetmore, Stacey D ; Manderville, Richard A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-387046b0243ba83edc16bc2939b168424b3b9b1faefd21a3c55ff3bb82622d263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Base Pairing</topic><topic>Deoxyguanosine - chemistry</topic><topic>DNA - chemistry</topic><topic>Fluorescence</topic><topic>Fluorescent Dyes - chemistry</topic><topic>Hydrogen Bonding</topic><topic>Indoles - chemistry</topic><topic>Models, Molecular</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schlitt, Katherine M</creatorcontrib><creatorcontrib>Millen, Andrea L</creatorcontrib><creatorcontrib>Wetmore, Stacey D</creatorcontrib><creatorcontrib>Manderville, Richard A</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schlitt, Katherine M</au><au>Millen, Andrea L</au><au>Wetmore, Stacey D</au><au>Manderville, Richard A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2011-01-01</date><risdate>2011</risdate><volume>9</volume><issue>5</issue><spage>1565</spage><epage>1571</epage><pages>1565-1571</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Pyrrole- and indole-linked C(8)-deoxyguanosine nucleosides act as fluorescent reporters of H-bonding specificity. Their fluorescence is quenched upon Watson-Crick H-bonding to dC, while Hoogsteen H-bonding to G enhances emission intensity. The indole-linked probe is ∼ 10-fold brighter and shows promise as a fluorescent reporter of Hoogsteen base pairing.</abstract><cop>England</cop><pmid>21240404</pmid><doi>10.1039/c0ob00883d</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2011-01, Vol.9 (5), p.1565-1571
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_1468369921
source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Base Pairing
Deoxyguanosine - chemistry
DNA - chemistry
Fluorescence
Fluorescent Dyes - chemistry
Hydrogen Bonding
Indoles - chemistry
Models, Molecular
title An indole-linked C8-deoxyguanosine nucleoside acts as a fluorescent reporter of Watson-Crick versus Hoogsteen base pairing
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-05T11%3A08%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=An%20indole-linked%20C8-deoxyguanosine%20nucleoside%20acts%20as%20a%20fluorescent%20reporter%20of%20Watson-Crick%20versus%20Hoogsteen%20base%20pairing&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Schlitt,%20Katherine%20M&rft.date=2011-01-01&rft.volume=9&rft.issue=5&rft.spage=1565&rft.epage=1571&rft.pages=1565-1571&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c0ob00883d&rft_dat=%3Cproquest_cross%3E1468369921%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1468369921&rft_id=info:pmid/21240404&rfr_iscdi=true