DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides
The binding of four phenanthridine-guanidine peptides to DNA/RNA was evaluated via spectrophotometric/microcalorimetric methods and computations. The minor structural modifications-the type of the guanidine group (pyrrole guanidine (GCP) and arginine) and the linker length (presence or absence of gl...
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| Veröffentlicht in: | International journal of biological macromolecules 2019-08, Vol.134, p.422-434 |
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| creator | Matić, Josipa Šupljika, Filip Tandarić, Tana Dukši, Marko Piotrowski, Patryciusz Vianello, Robert Brozovic, Anamaria Piantanida, Ivo Schmuck, Carsten Stojković, Marijana Radić |
| description | The binding of four phenanthridine-guanidine peptides to DNA/RNA was evaluated via spectrophotometric/microcalorimetric methods and computations. The minor structural modifications-the type of the guanidine group (pyrrole guanidine (GCP) and arginine) and the linker length (presence or absence of glycine)-greatly affected the conformation of compounds and consequently the binding to double- (ds-) and single-stranded (ss-) polynucleotides. GCP peptide with shorter linker was able to distinguish between RNA (A-helix) and DNA (B-helix) by different circular dichroism response at 295 nm and thus can be used as a chiral probe. Opposed to the dominant stretched conformation of GCP peptide with shorter linker, the more flexible and longer linker of its analogue enabled the molecule to adopt the intramolecularly stacked form which resulted in weaker yet selective binding to DNA. Beside efficient organization of ss-polynucleotide structures, GCP peptide with shorter linker bound stronger to ss-DNA/RNA compared to arginine peptides which emphasize the importance of GCP unit.
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| doi_str_mv | 10.1016/j.ijbiomac.2019.05.063 |
| format | Article |
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[Display omitted]</description><identifier>ISSN: 0141-8130</identifier><identifier>EISSN: 1879-0003</identifier><identifier>DOI: 10.1016/j.ijbiomac.2019.05.063</identifier><identifier>PMID: 31082420</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Base Pairing ; Circular Dichroism ; DNA - chemistry ; DNA/RNA chiral probe ; DNA/RNA recognition ; Glycine - chemistry ; Guanidine - chemistry ; Molecular Conformation ; Nucleic Acid Conformation ; Peptides - chemistry ; Phenanthridines - chemistry ; Pyrrole guanidine peptide ; RNA - chemistry ; Spectrum Analysis ; Thermodynamics</subject><ispartof>International journal of biological macromolecules, 2019-08, Vol.134, p.422-434</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright © 2019 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c416t-65b93630aa7542a29d91eabe1f5cb8c02986bd7766f51122e58bd76f136b64143</citedby><cites>FETCH-LOGICAL-c416t-65b93630aa7542a29d91eabe1f5cb8c02986bd7766f51122e58bd76f136b64143</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ijbiomac.2019.05.063$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31082420$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matić, Josipa</creatorcontrib><creatorcontrib>Šupljika, Filip</creatorcontrib><creatorcontrib>Tandarić, Tana</creatorcontrib><creatorcontrib>Dukši, Marko</creatorcontrib><creatorcontrib>Piotrowski, Patryciusz</creatorcontrib><creatorcontrib>Vianello, Robert</creatorcontrib><creatorcontrib>Brozovic, Anamaria</creatorcontrib><creatorcontrib>Piantanida, Ivo</creatorcontrib><creatorcontrib>Schmuck, Carsten</creatorcontrib><creatorcontrib>Stojković, Marijana Radić</creatorcontrib><title>DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides</title><title>International journal of biological macromolecules</title><addtitle>Int J Biol Macromol</addtitle><description>The binding of four phenanthridine-guanidine peptides to DNA/RNA was evaluated via spectrophotometric/microcalorimetric methods and computations. The minor structural modifications-the type of the guanidine group (pyrrole guanidine (GCP) and arginine) and the linker length (presence or absence of glycine)-greatly affected the conformation of compounds and consequently the binding to double- (ds-) and single-stranded (ss-) polynucleotides. GCP peptide with shorter linker was able to distinguish between RNA (A-helix) and DNA (B-helix) by different circular dichroism response at 295 nm and thus can be used as a chiral probe. Opposed to the dominant stretched conformation of GCP peptide with shorter linker, the more flexible and longer linker of its analogue enabled the molecule to adopt the intramolecularly stacked form which resulted in weaker yet selective binding to DNA. Beside efficient organization of ss-polynucleotide structures, GCP peptide with shorter linker bound stronger to ss-DNA/RNA compared to arginine peptides which emphasize the importance of GCP unit.
[Display omitted]</description><subject>Base Pairing</subject><subject>Circular Dichroism</subject><subject>DNA - chemistry</subject><subject>DNA/RNA chiral probe</subject><subject>DNA/RNA recognition</subject><subject>Glycine - chemistry</subject><subject>Guanidine - chemistry</subject><subject>Molecular Conformation</subject><subject>Nucleic Acid Conformation</subject><subject>Peptides - chemistry</subject><subject>Phenanthridines - chemistry</subject><subject>Pyrrole guanidine peptide</subject><subject>RNA - chemistry</subject><subject>Spectrum Analysis</subject><subject>Thermodynamics</subject><issn>0141-8130</issn><issn>1879-0003</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE9v1DAQxS0EotvCV6h85JLUY8de58aqlD9SVSQEZ8uxJ10viR3sbKX99mSVliun0bx5b0bzI-QaWA0M1M2hDocupNG6mjNoayZrpsQrsgG9bSvGmHhNNgwaqDQIdkEuSzksqpKg35ILAUzzhrMN2X962N38eNjRjC49xjCHFKlLcc5pGNDT7kTnPdLH4eRCRDqE-BsztdGv8tHG4M-DMQWcTzT1dNpjtHHe53Uw4TQHj-UdedPboeD753pFfn2--3n7tbr__uXb7e6-cg2ouVKya4USzNqtbLjlrW8BbYfQS9dpx3irVee3W6V6CcA5Sr20qgehOtVAI67Ih3XvlNOfI5bZjKE4HAYbMR2L4VyAblqu5WJVq9XlVErG3kw5jDafDDBzpmwO5oWyOVM2TJqF8hK8fr5x7Eb0_2IvWBfDx9WAy6dPAbMpLmB06MPCeTY-hf_d-Askt5GZ</recordid><startdate>20190801</startdate><enddate>20190801</enddate><creator>Matić, Josipa</creator><creator>Šupljika, Filip</creator><creator>Tandarić, Tana</creator><creator>Dukši, Marko</creator><creator>Piotrowski, Patryciusz</creator><creator>Vianello, Robert</creator><creator>Brozovic, Anamaria</creator><creator>Piantanida, Ivo</creator><creator>Schmuck, Carsten</creator><creator>Stojković, Marijana Radić</creator><general>Elsevier B.V</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>20190801</creationdate><title>DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides</title><author>Matić, Josipa ; Šupljika, Filip ; Tandarić, Tana ; Dukši, Marko ; Piotrowski, Patryciusz ; Vianello, Robert ; Brozovic, Anamaria ; Piantanida, Ivo ; Schmuck, Carsten ; Stojković, Marijana Radić</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c416t-65b93630aa7542a29d91eabe1f5cb8c02986bd7766f51122e58bd76f136b64143</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Base Pairing</topic><topic>Circular Dichroism</topic><topic>DNA - chemistry</topic><topic>DNA/RNA chiral probe</topic><topic>DNA/RNA recognition</topic><topic>Glycine - chemistry</topic><topic>Guanidine - chemistry</topic><topic>Molecular Conformation</topic><topic>Nucleic Acid Conformation</topic><topic>Peptides - chemistry</topic><topic>Phenanthridines - chemistry</topic><topic>Pyrrole guanidine peptide</topic><topic>RNA - chemistry</topic><topic>Spectrum Analysis</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matić, Josipa</creatorcontrib><creatorcontrib>Šupljika, Filip</creatorcontrib><creatorcontrib>Tandarić, Tana</creatorcontrib><creatorcontrib>Dukši, Marko</creatorcontrib><creatorcontrib>Piotrowski, Patryciusz</creatorcontrib><creatorcontrib>Vianello, Robert</creatorcontrib><creatorcontrib>Brozovic, Anamaria</creatorcontrib><creatorcontrib>Piantanida, Ivo</creatorcontrib><creatorcontrib>Schmuck, Carsten</creatorcontrib><creatorcontrib>Stojković, Marijana Radić</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>International journal of biological macromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matić, Josipa</au><au>Šupljika, Filip</au><au>Tandarić, Tana</au><au>Dukši, Marko</au><au>Piotrowski, Patryciusz</au><au>Vianello, Robert</au><au>Brozovic, Anamaria</au><au>Piantanida, Ivo</au><au>Schmuck, Carsten</au><au>Stojković, Marijana Radić</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides</atitle><jtitle>International journal of biological macromolecules</jtitle><addtitle>Int J Biol Macromol</addtitle><date>2019-08-01</date><risdate>2019</risdate><volume>134</volume><spage>422</spage><epage>434</epage><pages>422-434</pages><issn>0141-8130</issn><eissn>1879-0003</eissn><abstract>The binding of four phenanthridine-guanidine peptides to DNA/RNA was evaluated via spectrophotometric/microcalorimetric methods and computations. The minor structural modifications-the type of the guanidine group (pyrrole guanidine (GCP) and arginine) and the linker length (presence or absence of glycine)-greatly affected the conformation of compounds and consequently the binding to double- (ds-) and single-stranded (ss-) polynucleotides. GCP peptide with shorter linker was able to distinguish between RNA (A-helix) and DNA (B-helix) by different circular dichroism response at 295 nm and thus can be used as a chiral probe. Opposed to the dominant stretched conformation of GCP peptide with shorter linker, the more flexible and longer linker of its analogue enabled the molecule to adopt the intramolecularly stacked form which resulted in weaker yet selective binding to DNA. Beside efficient organization of ss-polynucleotide structures, GCP peptide with shorter linker bound stronger to ss-DNA/RNA compared to arginine peptides which emphasize the importance of GCP unit.
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| subjects | Base Pairing Circular Dichroism DNA - chemistry DNA/RNA chiral probe DNA/RNA recognition Glycine - chemistry Guanidine - chemistry Molecular Conformation Nucleic Acid Conformation Peptides - chemistry Phenanthridines - chemistry Pyrrole guanidine peptide RNA - chemistry Spectrum Analysis Thermodynamics |
| title | DNA/RNA recognition controlled by the glycine linker and the guanidine moiety of phenanthridine peptides |
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