Issue 21, 2007
From the journal:

Dalton Transactions

Synthesis and preliminary DNA-binding studies of diimineplatinum(ii) complexes containing 3- or 4-pyridineboronic acid†

H. Y. Vincent Ching,a   Jack K. Cleggb  and  Louis M. Rendina*a  

* Corresponding authors

a School of Chemistry, The University of Sydney, Sydney, NSW, Australia
E-mail: rendina@chem.usyd.edu.au
Fax: +61 2 9351 3329
Tel: +61 2 9351 4781

b Crystal Structure Analysis Facility, School of Chemistry, The University of Sydney, Sydney, NSW, Australia

Abstract

A series of platinum(II) complexes of the type [Pt(NN)(pyB)2](NO3)2 (NN = bipy, phen; pyB = 3- or 4-pyridineboronic acid) were successfully prepared and fully characterised by 1D- and 2D-multinuclear NMR spectroscopy and ESI-MS. Using VT 1H NMR spectroscopy, rotational isomers for [Pt(NN)(3-pyB)2](NO3)2 were identified and the free energies of activation for rotation of 3-pyB about the Pt–N bond were determined to be ΔG‡310 = 69.2 ± 0.1 kJ mol–1 and ΔG‡305 = 66.0 ± 0.1 kJ mol–1 for [Pt(bipy)(3-pyB)2](NO3)2 and [Pt(phen)(3-pyB)2](NO3)2, respectively. The 3- and 4-pyB ligands readily deboronate in boiling H2O to afford [Pt(NN)(py)2](NO3)2; the structure of [Pt(phen)(py)2]2+ (as its PF6– salt) was confirmed by X-ray crystallography. Preliminary thermal denaturation studies revealed only minimal interactions between [Pt(NN)(pyB)2](NO3)2 and calf-thymus DNA and is attributed to hydroxylation of the boronic acid groups at pH 7.4 to afford the corresponding zwitterionic boronate species. This was confirmed by means of variable pH 1H and 11B{1H} NMR spectroscopy.

Graphical abstract: Synthesis and preliminary DNA-binding studies of diimineplatinum(ii) complexes containing 3- or 4-pyridineboronic acid

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Article information

DOI
https://doi.org/10.1039/B618668H
Article type
Paper
Submitted
21 Dec 2006
Accepted
13 Mar 2007
First published
30 Mar 2007

Dalton Trans., 2007, 2121-2126

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Synthesis and preliminary DNA-binding studies of diimineplatinum(II) complexes containing 3- or 4-pyridineboronic acid

H. Y. V. Ching, J. K. Clegg and L. M. Rendina, Dalton Trans., 2007, 2121 DOI: 10.1039/B618668H

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