Incorporation of arginine mimetic residue into peptides for recognition of double stranded nucleic acid structure: Binding and aggregation studies
[Display omitted] An arginine mimetic, featuring a guanidiniocarbonypyrrol as artificial anion binding site (GCP), was introduced into short peptides to study their binding and aggregation with double stranded DNA and RNA. While the incorporation of this GCP modification did not significantly change...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2017-03, Vol.25 (6), p.1875-1880 |
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| container_issue | 6 |
| container_start_page | 1875 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 25 |
| creator | Li, Mao Matković, Marija Piantanida, Ivo Schmuck, Carsten |
| description | [Display omitted]
An arginine mimetic, featuring a guanidiniocarbonypyrrol as artificial anion binding site (GCP), was introduced into short peptides to study their binding and aggregation with double stranded DNA and RNA. While the incorporation of this GCP modification did not significantly change the overall binding affinity for DNA/RNA, their interactions were more sensitive with respect to the type of polynucleotides. Peptide 4, with four GCP modifications, exhibited amazing fluorescent selectivity for AU- and (to a lesser extent) AT- sequences. GC-containing DNA showed much lower response. Additionally, exclusively tri-GCP modified peptide 3 showed intriguing exciton-coupled bisignate ICD bands for all studied DNA/RNA which suggested that a well-defined GCP-dimer bound into DNA/RNA groove.. |
| doi_str_mv | 10.1016/j.bmc.2017.02.006 |
| format | Article |
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An arginine mimetic, featuring a guanidiniocarbonypyrrol as artificial anion binding site (GCP), was introduced into short peptides to study their binding and aggregation with double stranded DNA and RNA. While the incorporation of this GCP modification did not significantly change the overall binding affinity for DNA/RNA, their interactions were more sensitive with respect to the type of polynucleotides. Peptide 4, with four GCP modifications, exhibited amazing fluorescent selectivity for AU- and (to a lesser extent) AT- sequences. GC-containing DNA showed much lower response. Additionally, exclusively tri-GCP modified peptide 3 showed intriguing exciton-coupled bisignate ICD bands for all studied DNA/RNA which suggested that a well-defined GCP-dimer bound into DNA/RNA groove..</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2017.02.006</identifier><identifier>PMID: 28214233</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Arginine - chemistry ; Arginine mimic ; Chromatography, High Pressure Liquid ; DNA - chemistry ; DNA/RNA recognition ; Hydrogen bonds ; Ion pair ; Molecular Mimicry ; Nucleic Acid Denaturation ; Peptides - chemistry ; Polynucleotide binding ; RNA, Double-Stranded - chemistry ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization ; Spectrum Analysis - methods</subject><ispartof>Bioorganic & medicinal chemistry, 2017-03, Vol.25 (6), p.1875-1880</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-c353t-4ec0947f193ff4564fe9970aea0105ba04d9646d63acd528c8890fdedc44deed3</citedby><cites>FETCH-LOGICAL-c353t-4ec0947f193ff4564fe9970aea0105ba04d9646d63acd528c8890fdedc44deed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2017.02.006$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28214233$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Mao</creatorcontrib><creatorcontrib>Matković, Marija</creatorcontrib><creatorcontrib>Piantanida, Ivo</creatorcontrib><creatorcontrib>Schmuck, Carsten</creatorcontrib><title>Incorporation of arginine mimetic residue into peptides for recognition of double stranded nucleic acid structure: Binding and aggregation studies</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>[Display omitted]
An arginine mimetic, featuring a guanidiniocarbonypyrrol as artificial anion binding site (GCP), was introduced into short peptides to study their binding and aggregation with double stranded DNA and RNA. While the incorporation of this GCP modification did not significantly change the overall binding affinity for DNA/RNA, their interactions were more sensitive with respect to the type of polynucleotides. Peptide 4, with four GCP modifications, exhibited amazing fluorescent selectivity for AU- and (to a lesser extent) AT- sequences. GC-containing DNA showed much lower response. Additionally, exclusively tri-GCP modified peptide 3 showed intriguing exciton-coupled bisignate ICD bands for all studied DNA/RNA which suggested that a well-defined GCP-dimer bound into DNA/RNA groove..</description><subject>Arginine - chemistry</subject><subject>Arginine mimic</subject><subject>Chromatography, High Pressure Liquid</subject><subject>DNA - chemistry</subject><subject>DNA/RNA recognition</subject><subject>Hydrogen bonds</subject><subject>Ion pair</subject><subject>Molecular Mimicry</subject><subject>Nucleic Acid Denaturation</subject><subject>Peptides - chemistry</subject><subject>Polynucleotide binding</subject><subject>RNA, Double-Stranded - chemistry</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><subject>Spectrum Analysis - methods</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>eNp9kc2O1DAQhC0EYoeFB-CCfOSS0E48nhhO7IqflVbiAmfLY3eiHiV2sB0kXoMnxqPZ5cipJfdXZbuKsdcCWgFCvTu1x8W1HYhDC10LoJ6wnZBKNn2vxVO2A62GBgatrtiLnE8A0EktnrOrbuiE7Pp-x_7cBRfTGpMtFAOPI7dpokAB-UILFnI8YSa_IadQIl9xLeQx8zGmunFxCvSo9HE7zshzSTZ49DxsbsZqYB358-nmypbwPb-h4ClMvFLcTlPC6XJ5LpsnzC_Zs9HOGV89zGv24_On77dfm_tvX-5uP943rt_3pZHoQMvDKHQ_jnKv5IhaH8CiBQH7owXptZLKq946v-8GNwwaxvouJ6VH9P01e3vxXVP8uWEuZqHscJ5twLhlIwaltVLDASoqLqhLMeeEo1kTLTb9NgLMuQpzMrUKc67CQGdqFVXz5sF-Oy7o_ykes6_AhwuA9ZO_CJPJjjA49FSDLcZH-o_9X5DGnY8</recordid><startdate>20170315</startdate><enddate>20170315</enddate><creator>Li, Mao</creator><creator>Matković, Marija</creator><creator>Piantanida, Ivo</creator><creator>Schmuck, Carsten</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></search><sort><creationdate>20170315</creationdate><title>Incorporation of arginine mimetic residue into peptides for recognition of double stranded nucleic acid structure: Binding and aggregation studies</title><author>Li, Mao ; Matković, Marija ; Piantanida, Ivo ; Schmuck, Carsten</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c353t-4ec0947f193ff4564fe9970aea0105ba04d9646d63acd528c8890fdedc44deed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Arginine - chemistry</topic><topic>Arginine mimic</topic><topic>Chromatography, High Pressure Liquid</topic><topic>DNA - chemistry</topic><topic>DNA/RNA recognition</topic><topic>Hydrogen bonds</topic><topic>Ion pair</topic><topic>Molecular Mimicry</topic><topic>Nucleic Acid Denaturation</topic><topic>Peptides - chemistry</topic><topic>Polynucleotide binding</topic><topic>RNA, Double-Stranded - chemistry</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><topic>Spectrum Analysis - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Mao</creatorcontrib><creatorcontrib>Matković, Marija</creatorcontrib><creatorcontrib>Piantanida, Ivo</creatorcontrib><creatorcontrib>Schmuck, Carsten</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>Li, Mao</au><au>Matković, Marija</au><au>Piantanida, Ivo</au><au>Schmuck, Carsten</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Incorporation of arginine mimetic residue into peptides for recognition of double stranded nucleic acid structure: Binding and aggregation studies</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2017-03-15</date><risdate>2017</risdate><volume>25</volume><issue>6</issue><spage>1875</spage><epage>1880</epage><pages>1875-1880</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>[Display omitted]
An arginine mimetic, featuring a guanidiniocarbonypyrrol as artificial anion binding site (GCP), was introduced into short peptides to study their binding and aggregation with double stranded DNA and RNA. While the incorporation of this GCP modification did not significantly change the overall binding affinity for DNA/RNA, their interactions were more sensitive with respect to the type of polynucleotides. Peptide 4, with four GCP modifications, exhibited amazing fluorescent selectivity for AU- and (to a lesser extent) AT- sequences. GC-containing DNA showed much lower response. Additionally, exclusively tri-GCP modified peptide 3 showed intriguing exciton-coupled bisignate ICD bands for all studied DNA/RNA which suggested that a well-defined GCP-dimer bound into DNA/RNA groove..</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>28214233</pmid><doi>10.1016/j.bmc.2017.02.006</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2017-03, Vol.25 (6), p.1875-1880 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Arginine - chemistry Arginine mimic Chromatography, High Pressure Liquid DNA - chemistry DNA/RNA recognition Hydrogen bonds Ion pair Molecular Mimicry Nucleic Acid Denaturation Peptides - chemistry Polynucleotide binding RNA, Double-Stranded - chemistry Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Spectrum Analysis - methods |
| title | Incorporation of arginine mimetic residue into peptides for recognition of double stranded nucleic acid structure: Binding and aggregation studies |
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