Synthesis and antimalarial activity of prodigiosenes

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 nitro...

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Bibliographic Details
Published in:	Organic & biomolecular chemistry Vol. 12; no. 24; p. 4132
Main Authors:	Marchal, Estelle, Smithen, Deborah A, Uddin, Md Imam, Robertson, Andrew W, Jakeman, David L, Mollard, Vanessa, Goodman, Christopher D, MacDougall, Kristopher S, McFarland, Sherri A, McFadden, Geoffrey I, Thompson, Alison
Format:	Journal Article
Language:	English
Published:	England 28-06-2014
Subjects:	Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Coordination Complexes - chemical synthesis Coordination Complexes - chemistry Parasitic Sensitivity Tests Plasmodium falciparum - drug effects Prodigiosin - analogs & derivatives Prodigiosin - chemical synthesis Prodigiosin - chemistry Prodigiosin - pharmacology Tin - chemistry Zinc - chemistry
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Summary:	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 free-bases.
ISSN:	1477-0539
DOI:	10.1039/c3ob42548g