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Issue 34, 2013
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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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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.

Graphical abstract: 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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Publication details

The article was received on 20 Feb 2013, accepted on 26 Jun 2013 and first published on 27 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40370J
Citation: Org. Biomol. Chem., 2013,11, 5642-5655
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    The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides

    S. Banerjee, J. A. Kitchen, T. Gunnlaugsson and J. M. Kelly, Org. Biomol. Chem., 2013, 11, 5642
    DOI: 10.1039/C3OB40370J

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