dc.contributor.author | GUNNLAUGSSON, THORFINNUR | en |
dc.contributor.author | KELLY, JOHN | en |
dc.date.accessioned | 2013-12-11T10:01:48Z | |
dc.date.available | 2013-12-11T10:01:48Z | |
dc.date.issued | 2013 | en |
dc.date.submitted | 2013 | en |
dc.identifier.citation | Banerjee, S., Kitchen, J.A., Gunnlaugsson, T., Kelly, J.M., The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides, Organic and Biomolecular Chemistry, 11, 34, 2013, 5642-5655 | en |
dc.identifier.other | Y | en |
dc.identifier.uri | http://hdl.handle.net/2262/67731 | |
dc.description | PUBLISHED | en |
dc.description.abstract | The synthesis and characterisation of two cationic pyridinium based 4-amino-1,8-naphthalimide derivatives (2 and 3) are described and compared to those of compound 1. The photophysical properties of 2 and 3 are shown to vary greatly with the solvent polarity and H-bonding ability. The dimethylamino substitution in 3 results in a weak quantum yield of fluorescence emission due to faster non-radiative deactivation of the excited singlet state than that seen for 2. As with 1, the fluorescence of 2 was found to be enhanced in its 1:1 complex with 5?-adenosine-monophosphate (5?-AMP) while it was partially quenched in its complex with 5?-guanosine-monophosphate (5?-GMP). In contrast, the fluorescence of 3 was enhanced ('switched on') in the presence of both adenine and guanine rich sequences. Linear and circular dichroism studies showed that each of 1, 2 and 3 binds to double-stranded DNA by intercalation. However, 2 and 3 do not show the preference for AT-rich DNA observed for 1. Comparative fluorescence studies with double stranded DNA show that the emission of 3 was 16 times enhanced in its DNA bound form, suggesting potential use of this structure as a spectroscopic probe for studying nucleic acid structure. | en_US |
dc.description.sponsorship | Financial support from Science Foundation Ireland (SFI) for
RFP 2006, RFP 2007, RFP 2009, and PI 2010 grants and PRTLI
for Cycle 4 funding to CSCB is acknowledged. JAK thanks
IRCSET for a postdoctoral fellowship. We would like to thank
particularly Dr John O
?
Brien and Dr Martin Feeney for their
help with NMR and MS, respectively | en_US |
dc.format.extent | 5642-5655 | en |
dc.language.iso | en | en |
dc.relation.ispartofseries | Organic and Biomolecular Chemistry | en |
dc.relation.ispartofseries | 11 | en |
dc.relation.ispartofseries | 34 | en |
dc.rights | Y | en |
dc.subject | DNA | en_US |
dc.title | The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides | en |
dc.type | Journal Article | en |
dc.type.supercollection | scholarly_publications | en |
dc.type.supercollection | refereed_publications | en |
dc.identifier.peoplefinderurl | http://people.tcd.ie/jmkelly | en |
dc.identifier.peoplefinderurl | http://people.tcd.ie/gunnlaut | en |
dc.identifier.rssinternalid | 89989 | en |
dc.identifier.doi | http://dx.doi.org/10.1039/c3ob40370j | en |
dc.rights.ecaccessrights | OpenAccess | |
dc.contributor.sponsor | Science Foundation Ireland (SFI) | en |
dc.contributor.sponsorGrantNumber | RFP 2009 | en |
dc.contributor.sponsor | Science Foundation Ireland (SFI) | en |
dc.contributor.sponsorGrantNumber | RFP 2007 | en |
dc.contributor.sponsor | Science Foundation Ireland (SFI) | en |
dc.contributor.sponsorGrantNumber | RFP 2006 | en |
dc.contributor.sponsor | Science Foundation Ireland (SFI) | en |
dc.contributor.sponsorGrantNumber | PI 2010 | en |