Issue 24, 2010
From the journal:

Organic & Biomolecular Chemistry

Understanding the DNA binding of novel non-symmetrical guanidinium/2-aminoimidazolinium derivatives†‡

Padraic S. Nagle,a   Susan J. Quinn,§a   John M. Kelly,a   Daniel H. O'Donovan,a   Amir R. Khan,b   Fernando Rodriguez,a   Binh Nguyen,c   W. David Wilsonc  and  Isabel Rozas*a  

* Corresponding authors

a School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland
E-mail: rozasi@tcd.ie
Fax: +353 1 671 2826
Tel: +353 1 896 3731

b School of Biochemistry and Immunology, University of Dublin, Trinity College, Dublin 2, Ireland

c Department of Chemistry, Georgia State University, USA

Abstract

Biophysical studies have been carried out on a family of asymmetric guanidinium-based diaromatic derivatives to assess their potential as DNA minor groove binding agents. To experimentally assess the binding of these compounds to DNA, solution phase biophysical studies have been performed. Thus, surface plasmon resonance, UV-visible spectroscopy and circular and linear dichroism have been utilized to evaluate binding constants, stoichiometry and mode of binding. In addition, the thermodynamics of the binding process have been determined by using isothermal titration calorimetry. These results show significant DNA binding affinity that correlates with the expected 1 : 1 binding ratio usually observed for minor groove binders. Moreover, a simple computational approach has been devised to assess the potential as DNA binders of this family of compounds.

Graphical abstract: Understanding the DNA binding of novel non-symmetrical guanidinium/2-aminoimidazolinium derivatives

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Article information

DOI
https://doi.org/10.1039/C0OB00428F
Article type
Paper
Submitted
15 Jul 2010
Accepted
03 Sep 2010
First published
15 Oct 2010

Org. Biomol. Chem., 2010,8, 5558-5567

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Understanding the DNA binding of novel non-symmetrical guanidinium/2-aminoimidazolinium derivatives

P. S. Nagle, S. J. Quinn, J. M. Kelly, D. H. O'Donovan, A. R. Khan, F. Rodriguez, B. Nguyen, W. D. Wilson and I. Rozas, Org. Biomol. Chem., 2010, 8, 5558 DOI: 10.1039/C0OB00428F

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