Ferrichromes analogs

In the following, we describe the various ferrichrome analogs according to their order. 

The EFF calculations yielded a single Cs-symmetric conformation for each type of ferrichrome analog (Figure 4), both with a A-cis configuration of the hydroxamates about the metal when L-amino acids were used. Taken together with the spectroscopic data, pronounced differences were observed for the conformations of these iron complexes. Inspection of the calculated conformations showed that the backbone amide groups may... 

Since the 1,2-HOPO chelators form neutral complexes while the catecholates form charged complexes, it is reasonable to assume that charged species are essential for the enterobactin receptor recognition. The lack of recognition by the ferrichrome analog may well be attributed to the bulky substituents on the hydroxamate moiety in agreement with early observations by Emery and Emery and others ... 

Incubation of Pseudomonas putida with anthracene-labeled carbon-base ferrichrome analog Fe(lll) complex 173 resulted in cellular iron uptake and the appearance of anthracene fluorescence in the culture medium identical to the Fe-ferrichrome uptake. Incubation with the alanyl analog 174 failed to show any significant iron uptake or fiuorescence. This is consistent with the tests described above on the unlabeled analogs. Remarkably, other strains such as Pseudomonas fluorescens S680 or WCS3742 also did not show any iron uptake or culture fluorescence. 

The second group of hydroxamate-based chelators consists of biomimetic ferrichrome analogs modified by introducing hydrophobic amino acids between the template and the hydroxamic acid binding sites 59, 60, 66, 68, 70, 199 and 200. Since they function to withhold iron from cells in contrast to their original function of iron delivery, they were named reversed siderophores (RSF) . ... 

There is a considerable difference in the antimalarial action of desferrioxamine B (DFO) and the hydrophobic chelators based on ferrichrome analogs. While the former is limited to mature forms in the life cycle of P. falciparum (trophozoites and schizonts), the latter effects to a greater extent early developing stages (ring). Therefore, studies explored... 

A new class of lipophilic ferrichrome analogs carrying acetoxymethyl ester moieties 203 has been synthesized and shown to penetrate rapidly through cell membranes. Intracellular esterase mediated hydrolysis transformed the lipophilic termini from hydrophobic to hydrophilic. The intracellular retention was visualized in hepatoma cells by labeling these analogs with a fluorescent naphthy-imide probe . Their fluorescence analogs retained their fluorescent properties for extended periods in comparison to hydrophobic derivatives 204 lacking the cleavable substituents. 

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