Design and Synthesis of Paromomycin-Related Heterocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay
A good starting point for the design of potent bactericidal compounds is the aminoglycoside paromomycin (1). The A‐ring (shown in red) was replaced with a range of heterocycles. An ESIMS‐based RNA‐binding assay was used to screen the binding affinities of the products.
Gespeichert in:
Veröffentlicht in: | Angewandte Chemie International Edition 2003-07, Vol.42 (29), p.3409-3412 |
---|---|
Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 3412 |
---|---|
container_issue | 29 |
container_start_page | 3409 |
container_title | Angewandte Chemie International Edition |
container_volume | 42 |
creator | Ding, Yili Hofstadler, Steven A. Swayze, Eric E. Risen, Lisa Griffey, Richard H. |
description | A good starting point for the design of potent bactericidal compounds is the aminoglycoside paromomycin (1). The A‐ring (shown in red) was replaced with a range of heterocycles. An ESIMS‐based RNA‐binding assay was used to screen the binding affinities of the products. |
doi_str_mv | 10.1002/anie.200351354 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_73519916</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>73519916</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3794-7e26cea84108ce22430bf438b551e9f9f85f7ca74250c9daf4da07bb7010cbee3</originalsourceid><addsrcrecordid>eNqFkMFu1DAQhi0EoqVw5Yh84pbFjuN1ckxLaSttF-gW9Wg5zmQxJPaScQR5BZ4ar3ZVuHGaGfv7v8NPyGvOFpyx_J3xDhY5Y0JyIYsn5JTLnGdCKfE07YUQmSolPyEvEL8lvizZ8jk54WkpK5Wfkt_vAd3WU-Nbupl9_JpOpKGjn8wYhjDM1vnsDnoToaXXEGEMdrY9ZJupwejitH-vB-fDtp9tQNcCvXUDRGeRnhtMvyHZ6a1BpJsd2Ji0EMeZ3q3r7Nz51vktrRHN_JI860yP8Oo4z8iXD5f3F9fZ6uPVzUW9yqxQVZEpyJcWTFlwVlrI80KwpitE2UjJoeqqrpSdskYVuWS2ak1XtIapplGMM9sAiDPy9uDdjeHHBBj14NBC3xsPYUKtUpdVxZcJXBxAOwbEETq9G91gxllzpvft6337-rH9FHhzNE_NAO1f_Fh3AqoD8NP1MP9Hp-v1zeW_8uyQdRjh12PWjN_1Ugkl9cP6Slcr-fl-xR80E38A3sqjDQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>73519916</pqid></control><display><type>article</type><title>Design and Synthesis of Paromomycin-Related Heterocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay</title><source>Wiley-Blackwell Journals</source><source>MEDLINE</source><creator>Ding, Yili ; Hofstadler, Steven A. ; Swayze, Eric E. ; Risen, Lisa ; Griffey, Richard H.</creator><creatorcontrib>Ding, Yili ; Hofstadler, Steven A. ; Swayze, Eric E. ; Risen, Lisa ; Griffey, Richard H.</creatorcontrib><description>A good starting point for the design of potent bactericidal compounds is the aminoglycoside paromomycin (1). The A‐ring (shown in red) was replaced with a range of heterocycles. An ESIMS‐based RNA‐binding assay was used to screen the binding affinities of the products.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200351354</identifier><identifier>PMID: 12888972</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>aminoglycosides ; Aminoglycosides - chemical synthesis ; Aminoglycosides - chemistry ; Aminoglycosides - metabolism ; antibiotics ; Binding, Competitive ; Carbohydrate Sequence ; Drug Design ; heterocycles ; Ligands ; mass spectrometry ; Models, Chemical ; Molecular Sequence Data ; Molecular Structure ; Paromomycin - chemistry ; RNA, Ribosomal, 16S - chemistry ; RNA, Ribosomal, 16S - metabolism ; RNA, Ribosomal, 18S - chemistry ; RNA, Ribosomal, 18S - metabolism ; Spectrometry, Mass, Electrospray Ionization - methods ; Structure-Activity Relationship ; Substrate Specificity ; synthesis design</subject><ispartof>Angewandte Chemie International Edition, 2003-07, Vol.42 (29), p.3409-3412</ispartof><rights>Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3794-7e26cea84108ce22430bf438b551e9f9f85f7ca74250c9daf4da07bb7010cbee3</citedby><cites>FETCH-LOGICAL-c3794-7e26cea84108ce22430bf438b551e9f9f85f7ca74250c9daf4da07bb7010cbee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.200351354$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12888972$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ding, Yili</creatorcontrib><creatorcontrib>Hofstadler, Steven A.</creatorcontrib><creatorcontrib>Swayze, Eric E.</creatorcontrib><creatorcontrib>Risen, Lisa</creatorcontrib><creatorcontrib>Griffey, Richard H.</creatorcontrib><title>Design and Synthesis of Paromomycin-Related Heterocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay</title><title>Angewandte Chemie International Edition</title><addtitle>Angewandte Chemie International Edition</addtitle><description>A good starting point for the design of potent bactericidal compounds is the aminoglycoside paromomycin (1). The A‐ring (shown in red) was replaced with a range of heterocycles. An ESIMS‐based RNA‐binding assay was used to screen the binding affinities of the products.</description><subject>aminoglycosides</subject><subject>Aminoglycosides - chemical synthesis</subject><subject>Aminoglycosides - chemistry</subject><subject>Aminoglycosides - metabolism</subject><subject>antibiotics</subject><subject>Binding, Competitive</subject><subject>Carbohydrate Sequence</subject><subject>Drug Design</subject><subject>heterocycles</subject><subject>Ligands</subject><subject>mass spectrometry</subject><subject>Models, Chemical</subject><subject>Molecular Sequence Data</subject><subject>Molecular Structure</subject><subject>Paromomycin - chemistry</subject><subject>RNA, Ribosomal, 16S - chemistry</subject><subject>RNA, Ribosomal, 16S - metabolism</subject><subject>RNA, Ribosomal, 18S - chemistry</subject><subject>RNA, Ribosomal, 18S - metabolism</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><subject>synthesis design</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFu1DAQhi0EoqVw5Yh84pbFjuN1ckxLaSttF-gW9Wg5zmQxJPaScQR5BZ4ar3ZVuHGaGfv7v8NPyGvOFpyx_J3xDhY5Y0JyIYsn5JTLnGdCKfE07YUQmSolPyEvEL8lvizZ8jk54WkpK5Wfkt_vAd3WU-Nbupl9_JpOpKGjn8wYhjDM1vnsDnoToaXXEGEMdrY9ZJupwejitH-vB-fDtp9tQNcCvXUDRGeRnhtMvyHZ6a1BpJsd2Ji0EMeZ3q3r7Nz51vktrRHN_JI860yP8Oo4z8iXD5f3F9fZ6uPVzUW9yqxQVZEpyJcWTFlwVlrI80KwpitE2UjJoeqqrpSdskYVuWS2ak1XtIapplGMM9sAiDPy9uDdjeHHBBj14NBC3xsPYUKtUpdVxZcJXBxAOwbEETq9G91gxllzpvft6337-rH9FHhzNE_NAO1f_Fh3AqoD8NP1MP9Hp-v1zeW_8uyQdRjh12PWjN_1Ugkl9cP6Slcr-fl-xR80E38A3sqjDQ</recordid><startdate>20030728</startdate><enddate>20030728</enddate><creator>Ding, Yili</creator><creator>Hofstadler, Steven A.</creator><creator>Swayze, Eric E.</creator><creator>Risen, Lisa</creator><creator>Griffey, Richard H.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>7X8</scope></search><sort><creationdate>20030728</creationdate><title>Design and Synthesis of Paromomycin-Related Heterocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay</title><author>Ding, Yili ; Hofstadler, Steven A. ; Swayze, Eric E. ; Risen, Lisa ; Griffey, Richard H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3794-7e26cea84108ce22430bf438b551e9f9f85f7ca74250c9daf4da07bb7010cbee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>aminoglycosides</topic><topic>Aminoglycosides - chemical synthesis</topic><topic>Aminoglycosides - chemistry</topic><topic>Aminoglycosides - metabolism</topic><topic>antibiotics</topic><topic>Binding, Competitive</topic><topic>Carbohydrate Sequence</topic><topic>Drug Design</topic><topic>heterocycles</topic><topic>Ligands</topic><topic>mass spectrometry</topic><topic>Models, Chemical</topic><topic>Molecular Sequence Data</topic><topic>Molecular Structure</topic><topic>Paromomycin - chemistry</topic><topic>RNA, Ribosomal, 16S - chemistry</topic><topic>RNA, Ribosomal, 16S - metabolism</topic><topic>RNA, Ribosomal, 18S - chemistry</topic><topic>RNA, Ribosomal, 18S - metabolism</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><topic>Structure-Activity Relationship</topic><topic>Substrate Specificity</topic><topic>synthesis design</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ding, Yili</creatorcontrib><creatorcontrib>Hofstadler, Steven A.</creatorcontrib><creatorcontrib>Swayze, Eric E.</creatorcontrib><creatorcontrib>Risen, Lisa</creatorcontrib><creatorcontrib>Griffey, Richard H.</creatorcontrib><collection>Istex</collection><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>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ding, Yili</au><au>Hofstadler, Steven A.</au><au>Swayze, Eric E.</au><au>Risen, Lisa</au><au>Griffey, Richard H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and Synthesis of Paromomycin-Related Heterocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angewandte Chemie International Edition</addtitle><date>2003-07-28</date><risdate>2003</risdate><volume>42</volume><issue>29</issue><spage>3409</spage><epage>3412</epage><pages>3409-3412</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A good starting point for the design of potent bactericidal compounds is the aminoglycoside paromomycin (1). The A‐ring (shown in red) was replaced with a range of heterocycles. An ESIMS‐based RNA‐binding assay was used to screen the binding affinities of the products.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>12888972</pmid><doi>10.1002/anie.200351354</doi><tpages>4</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 1433-7851 |
ispartof | Angewandte Chemie International Edition, 2003-07, Vol.42 (29), p.3409-3412 |
issn | 1433-7851 1521-3773 |
language | eng |
recordid | cdi_proquest_miscellaneous_73519916 |
source | Wiley-Blackwell Journals; MEDLINE |
subjects | aminoglycosides Aminoglycosides - chemical synthesis Aminoglycosides - chemistry Aminoglycosides - metabolism antibiotics Binding, Competitive Carbohydrate Sequence Drug Design heterocycles Ligands mass spectrometry Models, Chemical Molecular Sequence Data Molecular Structure Paromomycin - chemistry RNA, Ribosomal, 16S - chemistry RNA, Ribosomal, 16S - metabolism RNA, Ribosomal, 18S - chemistry RNA, Ribosomal, 18S - metabolism Spectrometry, Mass, Electrospray Ionization - methods Structure-Activity Relationship Substrate Specificity synthesis design |
title | Design and Synthesis of Paromomycin-Related Heterocycle-Substituted Aminoglycoside Mimetics Based on a Mass Spectrometry RNA-Binding Assay |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T07%3A36%3A17IST&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=Design%20and%20Synthesis%20of%20Paromomycin-Related%20Heterocycle-Substituted%20Aminoglycoside%20Mimetics%20Based%20on%20a%20Mass%20Spectrometry%20RNA-Binding%20Assay&rft.jtitle=Angewandte%20Chemie%20International%20Edition&rft.au=Ding,%20Yili&rft.date=2003-07-28&rft.volume=42&rft.issue=29&rft.spage=3409&rft.epage=3412&rft.pages=3409-3412&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.200351354&rft_dat=%3Cproquest_cross%3E73519916%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=73519916&rft_id=info:pmid/12888972&rfr_iscdi=true |