Spectral properties and G-quadruplex DNA binding selectivities of a series of unsymmetrical perylene diimides

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dc.contributor.authorDincalp, Haluk
dc.contributor.authorAvcibasi, Nesibe
dc.contributor.authorIcli, Siddik
dc.date.accessioned2019-10-27T19:38:24Z
dc.date.available2019-10-27T19:38:24Z
dc.date.issued2007
dc.departmentEge Üniversitesien_US
dc.description.abstractA series of new unsymmetrical perylene diimides have been synthesized to investigate their binding selectivities to G-quadruplex DNA structure, a unique four-stranded DNA motif, which is significant to the regulation of telomerase activity. The structures of the perylene diimides have been characterized by IR spectrophotometer, H-1 NMR, C-13 NMR, MS, TGA and time-resolved instruments. Spectrochemical behaviors have been investigated by visible absorption and fluorescence emission spectra. The spectral characterization of the compounds has been investigated in five common organic solvents of different polarity and in water (in 170 mM phosphate buffer at pH 6). Marked red shifts of absorbance and fluorescence emission bands of the compounds in aqueous solution are compared with the other organic solutions. The fluorescence quantum yields are determined low in more polar solvents and also calculated to be about less than about 0.05 in aqueous solution because of the aggregation effects. Photodegradation rate constants (k(p)) of the synthesized compounds have been compared under xenon lamp irradiation in acetonitrile solution. Binding abilities of the synthesized perylene diimides to different form of DNA strands have been investigated by visible absorption and fluorescence spectroscopy in the phosphate buffer solutions. Also, pH-dependent aggregation and G-quadruplex DNA binding selectivity of these ligands have been compared. Among these ligands, N-(2,6-diisopropylphenyl)-N'-(4-pyridyl)-perylene-3,4,9,10-tetracarboxylic diimide (PYPER) has been found to be the most selective interactive ligand for G-quadruplex formed in the G4'-DNA structure. PYPER has shown a significant selectivity to G4'-DNA which is comprised of d(TTAGGG) repeats, known as human telomeres, in the phosphate buffer at pH 6. The absorption maximum of the PYPER/G4'-DNA complex has given bathochromic shift of 7 nm with respect to the absorption maximum of DNA-free solution of PYPER in phosphate buffer at pH 6. Fluorescence quenching experiments between PYPER and G4'-DNA show that PYPER demonstrates about a 9.3-fold selectivity for binding to G4'-DNA versus ds-DNA base pairs with the bimolecular rate constant of 0.95 x 10(12) M-1 s(-1). (c) 2006 Elsevier B.V. All rights reserved.en_US
dc.identifier.doi10.1016/j.jphotochem.2006.04.035
dc.identifier.endpage12en_US
dc.identifier.issn1010-6030
dc.identifier.issn1010-6030en_US
dc.identifier.issue1en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage1en_US
dc.identifier.urihttps://doi.org/10.1016/j.jphotochem.2006.04.035
dc.identifier.urihttps://hdl.handle.net/11454/40080
dc.identifier.volume185en_US
dc.identifier.wosWOS:000242913200001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevier Science Saen_US
dc.relation.ispartofJournal of Photochemistry and Photobiology A-Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectperylene diimideen_US
dc.subjectfluorescence quenchingen_US
dc.subjectG-quadruplex DNAen_US
dc.subjecthuman telomeraseen_US
dc.subjectanti-cancer agenten_US
dc.titleSpectral properties and G-quadruplex DNA binding selectivities of a series of unsymmetrical perylene diimidesen_US
dc.typeArticleen_US

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