Journal article
Synthesis and antimalarial activity of prodigiosenes
Estelle Marchal, Deborah A Smithen, Md Imam Uddin, Andrew W Robertson, David L Jakeman, Vanessa Mollard, Christopher D Goodman, Kristopher S MacDougall, Sherri A McFarland, Geoffrey I McFadden, Alison Thompson
Organic and Biomolecular Chemistry | Royal Society of Chemistry | Published : 2014
DOI: 10.1039/c3ob42548g
Abstract
Several analogues of the natural compound prodigiosin with modified A- and C-rings were synthesised as were some of their tin, cobalt, boron and zinc complexes. The antimalarial activity of these prodigiosenes was evaluated in vitro using the 3D7 Plasmodium falciparum strain. The presence of a nitrogen atom in the A-ring is needed for antimalarial activity but the presence of an alkyl group at the β′-position of the C-ring seems detrimental. Dibutyl tin complexes exhibit IC50 values mostly in the nanomolar range with equal or improved activity compared to the free-base prodigiosene ligand, despite the fact that the general toxicity of such tin complexes is demonstrably lower than that of the..
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Funding Acknowledgements
E. Marchal is supported by a trainee award from The Beatrice Hunter Cancer Research Institute with funds provided by Cancer Care Nova Scotia as part of The Terry Fox Foundation Strategic Health Research Training Program in Cancer Research at CIHR. G. McFadden is supported by a Program Grant from the National Health and Medical Research Council of Australia and a Discovery Project from the Australian Research Council. We thank the Australian Red Cross for supplying human blood.