N7-Guanine as a C+ Mimic in Hairpin aeg/aepPNA-DNA Triplex: Probing Binding Selectivity by UV-Tm and Kinetics by Fluorescence-Based Strand-Invasion Assay
N7-substituted guanine (N7G) has been introduced into aminoethylglycyl bisPNA (7) as a C(+) mimic to achieve pH-independent triplex formation with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl units with C(+) and C(+) mimic N7G in the backbone of bisPNAs (8, 9) i...
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| Veröffentlicht in: | Journal of organic chemistry 2003-05, Vol.68 (11), p.4439-4445 |
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| container_issue | 11 |
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| container_title | Journal of organic chemistry |
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| creator | D'COSTA, Moneesha KUMAR, Vaijayanti A. GANESH, Krishna N. |
| description | N7-substituted guanine (N7G) has been introduced into aminoethylglycyl bisPNA (7) as a C(+) mimic to achieve pH-independent triplex formation with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl units with C(+) and C(+) mimic N7G in the backbone of bisPNAs (8, 9) influenced the recognition of complementary DNA in an orientation-selective manner. A simple fluorescence assay is developed to examine the process of strand invasion of target DNA duplex by these modified bisPNAs and comparative results of the study employing triplex forming polypyrimidine (C/T) (6, 8) and purine-pyrimidine (N7G/T) mixmer-bisPNAs (7, 9) are presented. |
| doi_str_mv | 10.1021/jo034048h |
| format | Article |
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The introduction of chiral, cationic aminoethylprolyl units with C(+) and C(+) mimic N7G in the backbone of bisPNAs (8, 9) influenced the recognition of complementary DNA in an orientation-selective manner. A simple fluorescence assay is developed to examine the process of strand invasion of target DNA duplex by these modified bisPNAs and comparative results of the study employing triplex forming polypyrimidine (C/T) (6, 8) and purine-pyrimidine (N7G/T) mixmer-bisPNAs (7, 9) are presented.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034048h</identifier><identifier>PMID: 12762749</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Base Sequence ; Biological and medical sciences ; DNA, Complementary - chemical synthesis ; DNA, Complementary - chemistry ; DNA, Complementary - metabolism ; Fundamental and applied biological sciences. Psychology ; Guanine - analogs & derivatives ; Hydrogen Bonding ; Interactions. Associations ; Intermolecular phenomena ; Kinetics ; Molecular biophysics ; Molecular Mimicry ; Nucleic Acid Conformation ; Peptide Nucleic Acids - chemical synthesis ; Peptide Nucleic Acids - chemistry ; Peptide Nucleic Acids - metabolism ; Pyrimidines - chemistry ; Pyrimidines - metabolism ; Spectrometry, Fluorescence</subject><ispartof>Journal of organic chemistry, 2003-05, Vol.68 (11), p.4439-4445</ispartof><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14843574$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12762749$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>D'COSTA, Moneesha</creatorcontrib><creatorcontrib>KUMAR, Vaijayanti A.</creatorcontrib><creatorcontrib>GANESH, Krishna N.</creatorcontrib><title>N7-Guanine as a C+ Mimic in Hairpin aeg/aepPNA-DNA Triplex: Probing Binding Selectivity by UV-Tm and Kinetics by Fluorescence-Based Strand-Invasion Assay</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>N7-substituted guanine (N7G) has been introduced into aminoethylglycyl bisPNA (7) as a C(+) mimic to achieve pH-independent triplex formation with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl units with C(+) and C(+) mimic N7G in the backbone of bisPNAs (8, 9) influenced the recognition of complementary DNA in an orientation-selective manner. A simple fluorescence assay is developed to examine the process of strand invasion of target DNA duplex by these modified bisPNAs and comparative results of the study employing triplex forming polypyrimidine (C/T) (6, 8) and purine-pyrimidine (N7G/T) mixmer-bisPNAs (7, 9) are presented.</description><subject>Base Sequence</subject><subject>Biological and medical sciences</subject><subject>DNA, Complementary - chemical synthesis</subject><subject>DNA, Complementary - chemistry</subject><subject>DNA, Complementary - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Guanine - analogs & derivatives</subject><subject>Hydrogen Bonding</subject><subject>Interactions. Associations</subject><subject>Intermolecular phenomena</subject><subject>Kinetics</subject><subject>Molecular biophysics</subject><subject>Molecular Mimicry</subject><subject>Nucleic Acid Conformation</subject><subject>Peptide Nucleic Acids - chemical synthesis</subject><subject>Peptide Nucleic Acids - chemistry</subject><subject>Peptide Nucleic Acids - metabolism</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - metabolism</subject><subject>Spectrometry, Fluorescence</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0Mtu1DAUBmALgehQWPACyBu6QaaOL3HCbjqlF00ZRpop2-jEOSkuiRPipOrs2PIOPB1PgqsO4M0v2Z_OxYS8Tvj7hIvk-LbjUnGVfX1CZokWnKU5V0_JjHMhmBSpPCAvQrjl8Witn5ODRJhUGJXPyK-VYecTeOeRQqBAF-_oJ9c6S52nF-CGPibgzTFgv17N2elqTreD6xu8__D7x0-6HrrS-Rt64nz1kBts0I7uzo07Wu7o9Re2bSn4ii5jh9HZ8HB71kzdgMGit8hOIGBFN-MQFbv0dxBc5-k8BNi9JM9qaAK-2uchuT77uF1csKvP55eL-RVzSc5HBplWPMlEnSYgKkCZCc7zMuFW5AgYd5bcoilrIbTUmte1kACVkLXNUpWW8pAcPdbth-77hGEsWhenaxrw2E2hMFLkihsZ4Zs9nMoWq6IfXAvDrvj7nxG83QMIFpo6LmVd-O9UpqQ2Kjr26FwY8f7fOwzfitRIo4vtelMss1yZzemy4PIPsu-SIg</recordid><startdate>20030530</startdate><enddate>20030530</enddate><creator>D'COSTA, Moneesha</creator><creator>KUMAR, Vaijayanti A.</creator><creator>GANESH, Krishna N.</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20030530</creationdate><title>N7-Guanine as a C+ Mimic in Hairpin aeg/aepPNA-DNA Triplex: Probing Binding Selectivity by UV-Tm and Kinetics by Fluorescence-Based Strand-Invasion Assay</title><author>D'COSTA, Moneesha ; KUMAR, Vaijayanti A. ; GANESH, Krishna N.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i190t-a8540182f61a2dae382009b10c29eae05530ce7bf2253550ff23aad23fc8646b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Base Sequence</topic><topic>Biological and medical sciences</topic><topic>DNA, Complementary - chemical synthesis</topic><topic>DNA, Complementary - chemistry</topic><topic>DNA, Complementary - metabolism</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Guanine - analogs & derivatives</topic><topic>Hydrogen Bonding</topic><topic>Interactions. Associations</topic><topic>Intermolecular phenomena</topic><topic>Kinetics</topic><topic>Molecular biophysics</topic><topic>Molecular Mimicry</topic><topic>Nucleic Acid Conformation</topic><topic>Peptide Nucleic Acids - chemical synthesis</topic><topic>Peptide Nucleic Acids - chemistry</topic><topic>Peptide Nucleic Acids - metabolism</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - metabolism</topic><topic>Spectrometry, Fluorescence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>D'COSTA, Moneesha</creatorcontrib><creatorcontrib>KUMAR, Vaijayanti A.</creatorcontrib><creatorcontrib>GANESH, Krishna N.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>D'COSTA, Moneesha</au><au>KUMAR, Vaijayanti A.</au><au>GANESH, Krishna N.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N7-Guanine as a C+ Mimic in Hairpin aeg/aepPNA-DNA Triplex: Probing Binding Selectivity by UV-Tm and Kinetics by Fluorescence-Based Strand-Invasion Assay</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-05-30</date><risdate>2003</risdate><volume>68</volume><issue>11</issue><spage>4439</spage><epage>4445</epage><pages>4439-4445</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>N7-substituted guanine (N7G) has been introduced into aminoethylglycyl bisPNA (7) as a C(+) mimic to achieve pH-independent triplex formation with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl units with C(+) and C(+) mimic N7G in the backbone of bisPNAs (8, 9) influenced the recognition of complementary DNA in an orientation-selective manner. A simple fluorescence assay is developed to examine the process of strand invasion of target DNA duplex by these modified bisPNAs and comparative results of the study employing triplex forming polypyrimidine (C/T) (6, 8) and purine-pyrimidine (N7G/T) mixmer-bisPNAs (7, 9) are presented.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12762749</pmid><doi>10.1021/jo034048h</doi><tpages>7</tpages></addata></record> |
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| subjects | Base Sequence Biological and medical sciences DNA, Complementary - chemical synthesis DNA, Complementary - chemistry DNA, Complementary - metabolism Fundamental and applied biological sciences. Psychology Guanine - analogs & derivatives Hydrogen Bonding Interactions. Associations Intermolecular phenomena Kinetics Molecular biophysics Molecular Mimicry Nucleic Acid Conformation Peptide Nucleic Acids - chemical synthesis Peptide Nucleic Acids - chemistry Peptide Nucleic Acids - metabolism Pyrimidines - chemistry Pyrimidines - metabolism Spectrometry, Fluorescence |
| title | N7-Guanine as a C+ Mimic in Hairpin aeg/aepPNA-DNA Triplex: Probing Binding Selectivity by UV-Tm and Kinetics by Fluorescence-Based Strand-Invasion Assay |
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