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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

The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides
The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides
The synthesis and characterisation of two cationic pyridinium based 4-amino-1,8-naphthalimide derivatives ( and ) are described and compared to those of compound . The photophysical properties of and are shown to vary greatly with the solvent polarity and H-bonding ability. The dimethylamino substitution in results in a weak quantum yield of fluorescence emission due to faster non-radiative deactivation of the excited singlet state than that seen for . As with , the fluorescence of 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 was enhanced ('switched on') in the presence of both adenine and guanine rich sequences. Linear and circular dichroism studies showed that each of , and binds to double-stranded DNA by intercalation. However, and do not show the preference for AT-rich DNA observed for . Comparative fluorescence studies with double stranded DNA show that the emission of was 16 times enhanced in its DNA bound form, suggesting potential use of this structure as a spectroscopic probe for studying nucleic acid structure.
1477-0520
5642-5655
Banerjee, Swagata
54596b4a-a93c-4da5-8f4c-719af50f9c26
Kitchen, Jonathan A.
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 A.
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Kelly, John M.
f7c8a7e0-2e28-43e0-b8b1-ae53b2b28a08

Banerjee, Swagata, Kitchen, Jonathan A., Gunnlaugsson, Thorfinnur and Kelly, John M. (2013) The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides. Organic & Biomolecular Chemistry, 11 (34), 5642-5655. (doi:10.1039/C3OB40370J). (PMID:23873271)

Record type: Article

Abstract

The synthesis and characterisation of two cationic pyridinium based 4-amino-1,8-naphthalimide derivatives ( and ) are described and compared to those of compound . The photophysical properties of and are shown to vary greatly with the solvent polarity and H-bonding ability. The dimethylamino substitution in results in a weak quantum yield of fluorescence emission due to faster non-radiative deactivation of the excited singlet state than that seen for . As with , the fluorescence of 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 was enhanced ('switched on') in the presence of both adenine and guanine rich sequences. Linear and circular dichroism studies showed that each of , and binds to double-stranded DNA by intercalation. However, and do not show the preference for AT-rich DNA observed for . Comparative fluorescence studies with double stranded DNA show that the emission of 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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Published date: 7 August 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 356252
URI: https://eprints.soton.ac.uk/id/eprint/356252
ISSN: 1477-0520
PURE UUID: 0942f13e-8b47-4221-9204-924ab140b2ae
ORCID for Jonathan A. Kitchen: ORCID iD orcid.org/0000-0002-7139-5666

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Date deposited: 30 Aug 2013 13:20
Last modified: 18 Jul 2017 03:40

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Contributors

Author: Swagata Banerjee
Author: Jonathan A. Kitchen ORCID iD
Author: Thorfinnur Gunnlaugsson
Author: John M. Kelly

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