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Bifunctional ferrocene derivatives for molecular recognition of DNA duplexes

Lookup NU author(s): Dr Ben Horrocks, Professor Andrew Houlton

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Abstract

Using l, l '-bis(chlorocarbonyl)ferrocene as the starting material the novel amide derivative 1, 1 '-bis(carbamoylmethylcarbamoyl)ferrocene has been isolated. Furthermore, the in situ reaction of l, l'-di(bromomethyl)ferrocene with several amines led to the formation of salt-like and tertiary amine ferrocene compounds. These compounds are all very stable in air and exhibit interesting hydrogen bonding patterns that can complement those of the DNA nucleobases. Differential pulse voltammetry was used to monitor the interactions of the water soluble ferrocene derivatives with DNA oligomers. The three compounds tested bind strongly to the DNA oligomers and the binding constants calculated are similar to those obtained for the [Fe(phen)3]3H2t ions. The interaction results from a combination of hydrogen bonding, electrostatic, hydrophobic and rc-stacking interactions. © The Royal Society of Chemistry 2000.


Publication metadata

Author(s): Georgopoulou AS, Michael D, Mingos P, White AJP, Williams DJ, Horrocks BR, Houlton A

Publication type: Article

Publication status: Published

Journal: Journal of the Chemical Society, Dalton Transactions

Year: 2000

Issue: 17

Pages: 2969-2974

Print publication date: 01/01/2000

ISSN (print): 1472-7773

ISSN (electronic): 1364-5447

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/b004295l

DOI: 10.1039/b004295l


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