The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides
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2013Access:
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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, 5642-5655Download Item:
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.
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Science Foundation Ireland (SFI)
RFP 2009
Science Foundation Ireland (SFI)
RFP 2007
Science Foundation Ireland (SFI)
RFP 2006
Science Foundation Ireland (SFI)
PI 2010
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http://people.tcd.ie/jmkellyhttp://people.tcd.ie/gunnlaut
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Author: GUNNLAUGSSON, THORFINNUR; KELLY, JOHN
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Organic and Biomolecular Chemistry11
34
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http://dx.doi.org/10.1039/c3ob40370jMetadata
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