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Issue 15, 2012
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Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

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Abstract

The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and H-bonding ability. The fluorescence of 1 is enhanced and blue-shifted in its 1 : 1 complex with 5′-adenosine-monophosphate while it is partially quenched and red-shifted in its complex with 5′-guanosine-monophosphate. Linear and circular dichroism measurements show that 1 binds to double-stranded DNA by intercalation. Comparative UV-visible and fluorescence studies with double stranded synthetic polynucleotides poly(dA–dT)2 and poly(dG–dC)2 show that 1 binds much more strongly to the AT polymer; 1 also has a strong preference for A–T rich sequences in natural DNA. Thermal denaturation measurements also reveal a much greater stabilisation of the double-stranded poly(dA–dT)2 than of natural DNA.

Graphical abstract: Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

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Publication details

The article was received on 10 Nov 2011, accepted on 26 Jan 2012 and first published on 26 Jan 2012


Article type: Paper
DOI: 10.1039/C2OB06898B
Citation: Org. Biomol. Chem., 2012,10, 3033-3043
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    Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

    S. Banerjee, J. A. Kitchen, T. Gunnlaugsson and J. M. Kelly, Org. Biomol. Chem., 2012, 10, 3033
    DOI: 10.1039/C2OB06898B

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