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

Shahrbanou MoradpourHafshejani; Joseph H. Hedley; Alexandra O. Haigh; Andrew R. Pike; Eimer M. Tuite

doi:10.1039/C3RA43090A

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

Shahrbanou MoradpourHafshejani,^a Joseph H. Hedley,^ab Alexandra O. Haigh,^ac Andrew R. Pike*^a and Eimer M. Tuite*^a

* Corresponding authors

^a Chemical Nanoscience Laboratory, School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, UK
E-mail: andrew.pike@ncl.ac.uk, eimer.tuite@ncl.ac.uk

^b QuantuMDx, International Centre for Life, Times Square, Newcastle upon Tyne, UK

^c Churchill Community College, Sixth Form, Churchill Street, Wallsend, UK

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.

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DOI: https://doi.org/10.1039/C3RA43090A
Article type: Paper
Submitted: 09 Apr 2013
Accepted: 09 Jul 2013
First published: 12 Jul 2013
This article is Open Access

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RSC Adv., 2013,3, 18164-18172

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

S. MoradpourHafshejani, J. H. Hedley, A. O. Haigh, A. R. Pike and E. M. Tuite, RSC Adv., 2013, 3, 18164 DOI: 10.1039/C3RA43090A

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

Abstract

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

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