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Thiophene-based DNA binders for sensing, nano-bioelectronics, and therapeutic purposes

Dorin, Irina Mihaela 2010. Thiophene-based DNA binders for sensing, nano-bioelectronics, and therapeutic purposes. PhD Thesis, Cardiff University.

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The development of cationic conjugated oligohetero-aromatics as building blocks for conjugated polymeric DNA binders with exciting spectroscopic and electronic properties is a prerequisite for genosensors and programmable self assembly of nanobioelectronic systems. As an example of such systems, we have synthesised a series of cationic conjugated oligoheteroaromatics using Pd cross-coupling reactions such as the Suzuki-Mirayaura and Stille cross-coupling in combination with microwave-assisted Pd catalysis to synthesise the conjugated oligoheteroaromatic frameworks. The interactions of these oligoheteroaromatics with duplex DNA were studied and all the compounds showed interesting optoelectronic properties which change markedly upon binding to duplex DNA. As a result, these cationic conjugated oligoheteroaromatics are able to detect double-stranded DNA. The affinities of the studied oligoheteroaromatics are typically in the order of 104 M'1 and binding modes vary between groove binding and intercalation. Additionally, we have demonstrated that cationic conjugated oligoheteroaromatics self assemble in aqueous solutions, forming various aggregate structures such as micelles via n-n stacking interactions. Self aggregation of cationic oligoheteroaromatics in aqueous solution needs to be taken in account when quantifying the binding of cationic oligoheteroaromatics with duplex DNA, but the resulting quantitative information on the self assembly of cationic oligoheteroaromatics can also open new interesting prospects for material science.

Item Type: Thesis (PhD)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
ISBN: 9781303222429
Date of First Compliant Deposit: 30 March 2016
Last Modified: 10 Jan 2018 01:00

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