A fluorescent peptoid pH-sensor
ABSTRACT Peptoids, N‐substituted glycine oligomers, can adopt stable three‐dimensional structures and have found diverse application as peptide surrogates and as nanomaterials. In this report, we have expanded peptoid function to include pH sensing by coupling pH‐induced peptoid conformational chang...
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| Veröffentlicht in: | Biopolymers 2013-07, Vol.100 (4), p.380-386 |
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| creator | Fuller, Amelia A. Holmes, Courtney A. Seidl, Frederick J. |
| description | ABSTRACT
Peptoids, N‐substituted glycine oligomers, can adopt stable three‐dimensional structures and have found diverse application as peptide surrogates and as nanomaterials. In this report, we have expanded peptoid function to include pH sensing by coupling pH‐induced peptoid conformational changes with fluorescence intensity changes. We report two new peptoids (2 and 3) that comprise carboxylic‐acid functionalized side chains and undergo conformational rearrangement in response to pH. Peptoids 2 and 3 are also labeled at one side‐chain with an environmentally sensitive fluorophore, 4‐N,N‐dimethylamino‐1,8‐naphthalimide (4DMN). The fluorescence intensity of 2 varies 24‐fold over the pH range studied. These spectroscopic properties make 2 a sensitive, biocompatible pH sensor. © 2013 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 100: 380–386, 2013. |
| doi_str_mv | 10.1002/bip.22242 |
| format | Article |
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Peptoids, N‐substituted glycine oligomers, can adopt stable three‐dimensional structures and have found diverse application as peptide surrogates and as nanomaterials. In this report, we have expanded peptoid function to include pH sensing by coupling pH‐induced peptoid conformational changes with fluorescence intensity changes. We report two new peptoids (2 and 3) that comprise carboxylic‐acid functionalized side chains and undergo conformational rearrangement in response to pH. Peptoids 2 and 3 are also labeled at one side‐chain with an environmentally sensitive fluorophore, 4‐N,N‐dimethylamino‐1,8‐naphthalimide (4DMN). The fluorescence intensity of 2 varies 24‐fold over the pH range studied. These spectroscopic properties make 2 a sensitive, biocompatible pH sensor. © 2013 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 100: 380–386, 2013.</description><identifier>ISSN: 0006-3525</identifier><identifier>EISSN: 1097-0282</identifier><identifier>DOI: 10.1002/bip.22242</identifier><identifier>PMID: 23526424</identifier><language>eng</language><publisher>United States: Blackwell Publishing Ltd</publisher><subject>conformational rearrangement ; environmentally sensitive fluorophore ; Glycine - chemistry ; Peptides - chemistry ; peptidomimetic ; peptoid oligomer ; Peptoids - chemistry ; Protein Structure, Secondary</subject><ispartof>Biopolymers, 2013-07, Vol.100 (4), p.380-386</ispartof><rights>Copyright © 2013 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3962-870608612c552e66a8a55d56a16702a31a0e90b2f189243a510527044195e9d83</citedby><cites>FETCH-LOGICAL-c3962-870608612c552e66a8a55d56a16702a31a0e90b2f189243a510527044195e9d83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fbip.22242$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fbip.22242$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23526424$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fuller, Amelia A.</creatorcontrib><creatorcontrib>Holmes, Courtney A.</creatorcontrib><creatorcontrib>Seidl, Frederick J.</creatorcontrib><title>A fluorescent peptoid pH-sensor</title><title>Biopolymers</title><addtitle>Biopolymers</addtitle><description>ABSTRACT
Peptoids, N‐substituted glycine oligomers, can adopt stable three‐dimensional structures and have found diverse application as peptide surrogates and as nanomaterials. In this report, we have expanded peptoid function to include pH sensing by coupling pH‐induced peptoid conformational changes with fluorescence intensity changes. We report two new peptoids (2 and 3) that comprise carboxylic‐acid functionalized side chains and undergo conformational rearrangement in response to pH. Peptoids 2 and 3 are also labeled at one side‐chain with an environmentally sensitive fluorophore, 4‐N,N‐dimethylamino‐1,8‐naphthalimide (4DMN). The fluorescence intensity of 2 varies 24‐fold over the pH range studied. These spectroscopic properties make 2 a sensitive, biocompatible pH sensor. © 2013 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 100: 380–386, 2013.</description><subject>conformational rearrangement</subject><subject>environmentally sensitive fluorophore</subject><subject>Glycine - chemistry</subject><subject>Peptides - chemistry</subject><subject>peptidomimetic</subject><subject>peptoid oligomer</subject><subject>Peptoids - chemistry</subject><subject>Protein Structure, Secondary</subject><issn>0006-3525</issn><issn>1097-0282</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkE1PwkAURSdGI4gu_APKUheFN28-2i6RKKBEXWBcToZ2mlQLrTNtlH_vaIGdiauXvJx7c3MIOacwoAA4XObVABE5HpAuhTgMACM8JF0AkAETKDrkxLk3AM4ZhWPSQf-UHHmXXI76WdGU1rjErOt-Zaq6zNN-NQ2cWbvSnpKjTBfOnG1vj7zc3S7G02D-NJmNR_MgYbHEIApBQiQpJkKgkVJHWohUSE1lCKgZ1WBiWGJGoxg504KCwNDvobEwcRqxHrlqeytbfjTG1WqV-0lFodembJyinHGg0uf-gVIqUVLBPXrdooktnbMmU5XNV9puFAX1o055depXnWcvtrXNcmXSPblz5YFhC3zmhdn83aRuZs-7yqBN5K42X_uEtu9KhiwU6vVxohb34Zg_yKkC9g0CZoHD</recordid><startdate>201307</startdate><enddate>201307</enddate><creator>Fuller, Amelia A.</creator><creator>Holmes, Courtney A.</creator><creator>Seidl, Frederick J.</creator><general>Blackwell Publishing Ltd</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>201307</creationdate><title>A fluorescent peptoid pH-sensor</title><author>Fuller, Amelia A. ; Holmes, Courtney A. ; Seidl, Frederick J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3962-870608612c552e66a8a55d56a16702a31a0e90b2f189243a510527044195e9d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>conformational rearrangement</topic><topic>environmentally sensitive fluorophore</topic><topic>Glycine - chemistry</topic><topic>Peptides - chemistry</topic><topic>peptidomimetic</topic><topic>peptoid oligomer</topic><topic>Peptoids - chemistry</topic><topic>Protein Structure, Secondary</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fuller, Amelia A.</creatorcontrib><creatorcontrib>Holmes, Courtney A.</creatorcontrib><creatorcontrib>Seidl, Frederick J.</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Biopolymers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fuller, Amelia A.</au><au>Holmes, Courtney A.</au><au>Seidl, Frederick J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A fluorescent peptoid pH-sensor</atitle><jtitle>Biopolymers</jtitle><addtitle>Biopolymers</addtitle><date>2013-07</date><risdate>2013</risdate><volume>100</volume><issue>4</issue><spage>380</spage><epage>386</epage><pages>380-386</pages><issn>0006-3525</issn><eissn>1097-0282</eissn><abstract>ABSTRACT
Peptoids, N‐substituted glycine oligomers, can adopt stable three‐dimensional structures and have found diverse application as peptide surrogates and as nanomaterials. In this report, we have expanded peptoid function to include pH sensing by coupling pH‐induced peptoid conformational changes with fluorescence intensity changes. We report two new peptoids (2 and 3) that comprise carboxylic‐acid functionalized side chains and undergo conformational rearrangement in response to pH. Peptoids 2 and 3 are also labeled at one side‐chain with an environmentally sensitive fluorophore, 4‐N,N‐dimethylamino‐1,8‐naphthalimide (4DMN). The fluorescence intensity of 2 varies 24‐fold over the pH range studied. These spectroscopic properties make 2 a sensitive, biocompatible pH sensor. © 2013 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 100: 380–386, 2013.</abstract><cop>United States</cop><pub>Blackwell Publishing Ltd</pub><pmid>23526424</pmid><doi>10.1002/bip.22242</doi><tpages>7</tpages></addata></record> |
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| ispartof | Biopolymers, 2013-07, Vol.100 (4), p.380-386 |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | conformational rearrangement environmentally sensitive fluorophore Glycine - chemistry Peptides - chemistry peptidomimetic peptoid oligomer Peptoids - chemistry Protein Structure, Secondary |
| title | A fluorescent peptoid pH-sensor |
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