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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

Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA
Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8-naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA
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.
1477-0520
3033-3043
Banerjee, Swagata
54596b4a-a93c-4da5-8f4c-719af50f9c26
Kitchen, Jonathan
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Kelly, John M.
f7c8a7e0-2e28-43e0-b8b1-ae53b2b28a08
Banerjee, Swagata
54596b4a-a93c-4da5-8f4c-719af50f9c26
Kitchen, Jonathan
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Kelly, John M.
f7c8a7e0-2e28-43e0-b8b1-ae53b2b28a08

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).

Record type: Article

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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More information

Published date: 21 April 2012
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 352483
URI: https://eprints.soton.ac.uk/id/eprint/352483
ISSN: 1477-0520
PURE UUID: 6e8c4128-cce7-4d44-aefb-a3e27133cb74
ORCID for Jonathan Kitchen: ORCID iD orcid.org/0000-0002-7139-5666

Catalogue record

Date deposited: 14 May 2013 13:18
Last modified: 18 Jul 2017 04:13

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