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Optical, Redox, and DNA-Binding Properties of Phenanthridinium Chromophores : Elucidating the Role of the Phenyl Substituent for Fluorescence Enhancement of Ethidium in the Presence of DNA

Optical, Redox, and DNA-Binding Properties of Phenanthridinium Chromophores : Elucidating the Role of the Phenyl Substituent for Fluorescence Enhancement of Ethidium in the Presence of DNA

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PRUNKL, Christa, Markus PICHLMAIER, Rainer F. WINTER, Vladimir KHARLANOV, Wolfgang RETTIG, Hans-Achim WAGENKNECHT, 2010. Optical, Redox, and DNA-Binding Properties of Phenanthridinium Chromophores : Elucidating the Role of the Phenyl Substituent for Fluorescence Enhancement of Ethidium in the Presence of DNA. In: Chemistry: a European Journal. 16(11), pp. 3392-3402. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.200902823

@article{Prunkl2010Optic-9897, title={Optical, Redox, and DNA-Binding Properties of Phenanthridinium Chromophores : Elucidating the Role of the Phenyl Substituent for Fluorescence Enhancement of Ethidium in the Presence of DNA}, year={2010}, doi={10.1002/chem.200902823}, number={11}, volume={16}, issn={0947-6539}, journal={Chemistry: a European Journal}, pages={3392--3402}, author={Prunkl, Christa and Pichlmaier, Markus and Winter, Rainer F. and Kharlanov, Vladimir and Rettig, Wolfgang and Wagenknecht, Hans-Achim} }

<rdf:RDF xmlns:dcterms="http://purl.org/dc/terms/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#" xmlns:foaf="http://xmlns.com/foaf/0.1/" xmlns:void="http://rdfs.org/ns/void#" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/9897"> <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9897/1/3392_ftp.pdf"/> <dc:creator>Rettig, Wolfgang</dc:creator> <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/9897/1/3392_ftp.pdf"/> <dc:creator>Wagenknecht, Hans-Achim</dc:creator> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:10Z</dc:date> <dc:language>eng</dc:language> <dc:rights>deposit-license</dc:rights> <dcterms:bibliographicCitation>First publ. in: Chemistry: a European Journal 16 (2010), 11, pp. 3392-3402</dcterms:bibliographicCitation> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dc:creator>Prunkl, Christa</dc:creator> <dc:contributor>Winter, Rainer F.</dc:contributor> <dc:contributor>Kharlanov, Vladimir</dc:contributor> <dc:creator>Winter, Rainer F.</dc:creator> <dc:contributor>Rettig, Wolfgang</dc:contributor> <dc:contributor>Prunkl, Christa</dc:contributor> <dcterms:abstract xml:lang="eng">The phenanthridinium chromophores 5-ethyl-6-phenylphenanthridinium (1), 5-ethyl-6-methylphenanthridinium (2), 3,8-diamino-5-ethyl-6-methylphenanthridinium (3), and 3,8-diamino-5-ethyl-6-(4-N,N-diethylaminophenyl)phenanthridinium (4) were characterized by their optical and redox properties. All dyes were applied in titration experiments with a random-sequence 17mer DNA duplex and their binding affinities were determined. The results were compared to well-known ethidium bromide (E). In general, this set of data allows the influence of substituents in positions 3, 6, and 8 on the optical properties of E to be elucidated. Especially, compound 4 was used to compare the weak electron-donating character of the phenyl substituent at position 6 of E with the more electron-donating 4-N,N-diethylaminophenyl group. Analysis of all of the measurements revealed two pairs of chromophores. The first pair, consisting of 1 and 2, lacks the amino groups in positions 3 and 8, and, as a result, these dyes exhibit clearly altered optical and electrochemical properties compared with E. In the presence of DNA, a significant fluorescence quenching was observed. Their binding affinity to DNA is reduced by nearly one order of magnitude. The electronic effect of the phenyl group in position 6 on this type of dye is rather small. The properties of the second set, 3 and 4, are similar to E due to the presence of the two strongly electron-donating amino groups in positions 3 and 8. However, in contrast to 1 and 2, the electron-donating character of the substituent in position 6 of 3 and 4 is critical. The binding, as well as the fluorescence enhancement, is clearly related to the electron-donating effect of this substituent. Accordingly, compound 4 shows the strongest binding affinity and the strongest fluorescence enhancement. Quantum chemical calculations reveal a general mechanism related to the twisted intramolecular charge transfer (TICT) model. Accordingly, an increase of the twist angle between the phenyl ring in position 6 and the phenanthridinium core opens a nonradiative channel in the excited state that depends on the electron-donating character of the phenyl group. Access to this channel is hindered upon binding to DNA.</dcterms:abstract> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dc:creator>Kharlanov, Vladimir</dc:creator> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/9897"/> <dc:contributor>Wagenknecht, Hans-Achim</dc:contributor> <dcterms:issued>2010</dcterms:issued> <dc:format>application/pdf</dc:format> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dc:contributor>Pichlmaier, Markus</dc:contributor> <dcterms:rights rdf:resource="http://nbn-resolving.org/urn:nbn:de:bsz:352-20140905103416863-3868037-7"/> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T18:15:10Z</dcterms:available> <dc:creator>Pichlmaier, Markus</dc:creator> <dcterms:title>Optical, Redox, and DNA-Binding Properties of Phenanthridinium Chromophores : Elucidating the Role of the Phenyl Substituent for Fluorescence Enhancement of Ethidium in the Presence of DNA</dcterms:title> </rdf:Description> </rdf:RDF>

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