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| - Design, Synthesis, Physicochemical Properties, and Evaluation of Novel IronChelators with Fluorescent Sensors
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| - The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linkedwith different coumarin substituents is described. These compounds have been developed inorder to provide a series of molecular probes for the quantification of intracellular labile ironpools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelationof iron(III) causes quenching of fluorescence. The relationship between iron(III) concentrationand the extent of fluorescence quenching indicates that the metal is chelated in a complexwith a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compoundswas found to be more efficiently quenched by iron(III) than were the hydroxypyranones. Themetal-to-ligand stoichiometry at which maximum quenching is observed was found to dependon the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III)is markedly influenced by solvent polarity and pH. The permeability of two representativefluorescent chelators across human erythrocyte ghost membranes was investigated. The rateof permeability for a series of probes was found to be related to the corresponding ClogP values.
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