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Synthesis and binding of proflavine diazides as functional intercalators for directed assembly on DNA

Lookup NU author(s): Shahrbanou Moradpour Hafshejani, Dr Joseph Hedley, Dr Andrew Pike, Dr Eimer TuiteORCiD

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Abstract

Proflavine diazide (PD) with amido-azide substituents on the amine groups and its N-methylated analogue (MePD) bind strongly to DNA by nearest-neighbour intercalation with little sequence selectivity, presenting reactive azide groups in the major groove. PD is neutral in aqueous solution but experiences binding-coupled protonation on interaction with DNA with an apparent pK_a shift of 2.5 units. MePD can be click modified in situ on DNA with alkyne-functionalised thienyl-pyrrole as a precursor for conducting polymer synthesis, and remains intercalated after reaction with the substituents aligned in the groove.

Publication metadata

Author(s): Moradpour Hafshejani S, Hedley JH, Haigh AO, Pike AR, Tuite EM

Publication type: Article

Publication status: Published

Journal: RSC Advances

Year: 2013

Volume: 3

Issue: 39

Pages: 18164-18172

Print publication date: 12/07/2013

Date deposited: 07/08/2014

ISSN (electronic): 2046-2069

Publisher: RSC Publications

URL: http://dx.doi.org/10.1039/C3RA43090A

DOI: 10.1039/C3RA43090A

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