Natural and Biomimetic Hydroxamic Acid Based Siderophores

Abstract

Introduction Physical and Chemical Properties of Hydroxamate‐Based Siderophores Iron Metabolism Biomimetic Chemistry Natural and Biomimetic Hydroxamic Acid Based Siderophores Siderophore Conjugates Biomimetic Siderophores in Health and Disease Acknowledgments

Enforcement of a high-spin ground state for the first 3d heterometallic 12-metallacrown-4 complex

“…For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4dt02275k high affinity of the hydroxamic acid moiety towards this species. [16][17][18] By contrast, the encapsulation of the Cu(II) ion at the core was fostered by avoiding common bridging anions like carboxylate ligands. Cu(II)(DMF) 2 Cl 2 [12-MC Fe(III)N(Shi) -4]-(DMF) 4 •2DMF (1) ‡ and the homometallic metallacrown (HNEt 3 ) 2 Cu(II)[12-MC Cu(II)N(Shi) -4] (2), as supplementary counterexample for the magnetic properties, were fully characterized by X-ray crystallography, elemental analysis, infrared spectroscopy, UV-Vis spectroscopy, atomic absorption spectroscopy (1), Mößbauer spectroscopy (1), ESI mass spectrometry and SQUID-magnetometry.…”

Biomimetic Analogues of the Desferrioxamine E Siderophore for PET Imaging of Invasive Aspergillosis: Targeting Properties and Species Specificity

“…The retro-positioning of the hydroxamate groups was well tolerated by A. fumigatus Sit1, a behavior observed previously for retro-ferrioxamines 47 and -ferrichromes 38−40 and other retro-analogues of hydroxamate siderophores. 41 Hampering of the biological activity of the analogues might be caused by different constraints, such as less effective iron chelation caused by either increased steric hindrance (in the case of smaller FOX analogues) or greater distance from the donor atoms (larger FOX analogues), suboptimal geometry and conformational freedom of the complex, or inappropriate position of amide groups for noncovalent interactions with the transporter. As demon- Nevertheless, the thermodynamic stability of complexes is exceptional and sufficient to prevent cross-chelation in the presence of other strong ligands, such as transferrin, present under biological conditions.…”

Signal Antagonists SuppressPseudomonas syringaePathogenicity

“…To date, only few natural products containing this motif have been isolated, [46][47][48][49][50][51][52] and their biological activity is commonly attributed to the strong metal-binding ability conferred by the diazeniumdiolate group. 19,49,53,56 Compounds 9 and 10, containing a hydroxamate group also known to have metallophore ability, 70,71 instead of the diazeniumdiolate, showed little to no inhibitory activity. Compound 11, a version of the antagonist 7j with a masked diazeniumdiolate group methylated at the diazeniumdiolate O 2position, 43 exhibited no inhibitory activity and even had a slightly promoting effect, demonstrating the importance of the diazeniumdiolate group for antagonistic activity.…”