Evaluation of Iron(iii)-N(amine)2N(py)2 complexes as potential bioreductively activated carriers for naphthoquinone-based drugs
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Universidade Federal de Minas Gerais
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Artigo de periódico
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Two new iron(III) complexes, [Fe(bhnq)(L1)]NO3·CH3OH·2H2O (1) and [Fe(bhnq)(L2)]ClO4·CH3OH (2) (L1 = N,N′-bis(pyridin-2-ylmethyl)ethylenediamine and L2 = N,N′-dimethyl-N,N′-bis(pyridin-2-ylmethyl)ethylenediamine), were investigated as potential candidates for bioreductively activated prodrugs. These complexes present a distorted octahedral structure with 2,2′-bis(3-hydroxy-1,4-naphthoquinone), (bhnq)2−, coordinated in a bidentate fashion to the iron(III) ion. A reversible wave associated with the Fe3+/Fe2+couple was observed in MeCN for 1 and 2 respectively at −0.05 V and 0.01 V versus SHE. Unlike previously studied cobalt(III)-based analogs and one iron(III) platform that showed efficient bioreductive activation, complexes 1 and 2 undergo fast dissociation in aqueous buffered solutions with immediate release of the bhnq2− ligand. Therefore, we conclude that the labile 3d5 iron(III) ion is a limited bioreducible carrier for naphthoquinone-based prodrugs when coordinated to this [N2NPy2] platform. Considerable modification of the current ligands or the meticulous selection of other alternative ligand platforms may be necessary to attain this goal.
Abstract
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Ferro, Anoxemia
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Bioreductively activated prodrugs, Prodrugs activated by hypoxia, Bioreducible carrier, Iron
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https://www.sciencedirect.com/science/article/pii/S0277538716305393