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

Banerjee, Swagata, Kitchen, Jonathan, Gunnlaugsson, Thorfinnur and Kelly, John M. (2012) Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA. Organic & Biomolecular Chemistry, 10 (15), 3033-3043. (doi:10.1039/c2ob06898b).

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.

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Contributors

Author: Jonathan Kitchen

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