Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity

Basha, Maram T., Chartres, Jy D., Pantarat, Namfon, Ali, Mohammad Akbar, Mirza, Aminul Huq, Kalinowski, Danuta S., Richardson, Des R. and Bernhardt, Paul V. (2012) Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity. Dalton Transactions, 41 21: 6536-6548. doi:10.1039/c2dt12387h

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Author Basha, Maram T.
Chartres, Jy D.
Pantarat, Namfon
Ali, Mohammad Akbar
Mirza, Aminul Huq
Kalinowski, Danuta S.
Richardson, Des R.
Bernhardt, Paul V.
Title Heterocyclic dithiocarbazate iron chelators: Fe coordination chemistry and biological activity
Journal name Dalton Transactions   Check publisher's open access policy
ISSN 1477-9226
Publication date 2012-06-07
Sub-type Article (original research)
DOI 10.1039/c2dt12387h
Open Access Status File (Publisher version)
Volume 41
Issue 21
Start page 6536
End page 6548
Total pages 13
Place of publication Cambridge, U.K.
Publisher Royal Society of Chemistry
Collection year 2013
Language eng
Formatted abstract
The iron coordination and biological chemistry of a series of heterocyclic dithiocarbazate Schiff base ligands is reported with regard to their activity as Fe chelators for the treatment of Fe overload and also cancer. The ligands are analogous to tridentate heterocyclic hydrazone and thiosemicarbazone chelators we have studied previously which bear NNO and NNS donor sets. The dithiocarbazate Schiff base ligands in this work also are NNS chelators and form stable low spin ferric and ferrous complexes and both have been isolated. In addition an unusual hydroxylated ligand derivative has been identified via an Fe-induced oxidation reaction. X-ray crystallographic and spectroscopic characterisation of these complexes has been carried out and also the electrochemical properties have been investigated. All Fe complexes exhibit totally reversible FeIII/II couples in mixed aqueous solvents at potentials higher than found in analogous thiosemicarbazone Fe complexes. The ability of the dithiocarbazate Schiff base ligands to mobilise Fe from cells and also to prevent Fe uptake from transferrin was examined and all ligands were effective in chelating intracellular Fe relative to known controls such as the clinically important Fe chelator desferrioxamine. The Schiff base ligands derived from 2-pyridinecarbaldehyde were non-toxic to SK-N-MC neuroepithelioma (cancer) cells but those derived from the ketones 2-acetylpyridine and di-2-pyridyl ketone exhibited significant antiproliferative activity.
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Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
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Citation counts: TR Web of Science Citation Count  Cited 17 times in Thomson Reuters Web of Science Article | Citations
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Created: Wed, 30 May 2012, 10:21:10 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences