Disease relevance of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• The hydroxamic acid siderophore ferrioxamine B [FeIII(HDFB)+] and the iron complex of diethylenetri-aminepentaacetic acid [FeIII(DTPA)2-] protected mice against death by septic shock induced by Corynebacterium parvum + lipopolysaccharide [1].
• Ferrioxamine uptake in Yersinia enterocolitica: characterization of the receptor protein FoxA [2].
• The gene for the high-affinity outer membrane ferrioxamine receptor FoxA of Yersinia enterocolitica was cloned in Escherichia coli K-12 [2].
• Of particular interest is the observation that 1a was utilized by the uptake system of ferrioxamine B in Yersinia enterocolitica (FoxA) but failed to use the ferrioxamine uptake route in Pseudomonas putida [3].
• Our observations indicate that biliary excretion of intravenously administered ferrioxamine and aluminoxamine is negligible even in renal failure [4].

High impact information on N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• This enabled us to identify iron uptake gene clusters that likely serve in transport of ferric citrate and ferrioxamine [5].
• Mean +/- SEM steady state concentrations of desferrioxamine B + ferrioxamine were 6.90 +/- 0.60 mumol/L at 36 hours and 7.72 +/- 0.68 mumol/L at 72 hours; in vitro, the ID50 has been reported to be approximately 4 to 20 mumol/L [6].
• In addition, pretreatment of cells with desferrioxamine, but not ferrioxamine, blocked the FeTF-induced increase in PKC-beta transcripts [7].
• One of these, Arn3p/Sit1p, facilitates the uptake of ferrioxamine B, a siderophore of the hydroxamate class [8].
• Analogues 1a and 1d were utilized by the ferrioxamine B uptake system (FoxA), while 1b and 1c either used different uptake systems or were transported to the microbial cell nonspecifically by diffusion via the cell membrane [3].

Chemical compound and disease context of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• The heterologous siderophores ferrioxamine B and ferrichrome activate signaling pathways in Pseudomonas aeruginosa [9].
• FoxB of Pseudomonas aeruginosa Functions in the Utilization of the Xenosiderophores Ferrichrome, Ferrioxamine B, and Schizokinen: Evidence for Transport Redundancy at the Inner Membrane [10].
• The value of rapid, contrast-enhanced, diuretic magnetic resonance (MR) imaging (using ferrioxamine B and furosemide) in demonstrating partial unilateral ureteral obstruction and the potential of such MR imaging in differentiating obstructive from nonobstructive hydronephrosis was assessed in six micropigs [11].
• We previously reported that the 78-kDa outer membrane receptor for ferrioxamine B is induced in iron-starved Vibrio vulnificus cells when desferrioxamine B was supplied exogenously [12].

Biological context of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• This was due to the iron-binding function of the molecule, as the iron-saturated form, ferrioxamine B mesylate, did not affect virulence [13].
• The addition of desferrioxamine prevented both ferrioxamine- and tert-butyl hydroperoxide-induced lipid peroxidation and cytotoxicity [14].
• Escherichia coli fhuF mutants, a sufS::MudI mutant, and a sufD::MudI mutant were found to have the same phenotype: the inability to use ferrioxamine B as an iron source in a plate assay [15].
• Addition of ferrioxamine (iron saturated DF) instead of DF to PMA-induced cells did not affect gene expression, indicating that diminished expression was due to iron deprivation, not nonspecific toxicity [16].
• The Fct protein has 36% sequence homology with the E. coli ferrichrome receptor FhuA and the Yersinia enterocolitica ferrioxamine receptor FoxA [17].

Anatomical context of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• The distribution volume of aluminoxamine and ferrioxamine appeared to be confined to the extracellular space and their renal excretion correlated with renal function [4].
• The uptake of iron and generation of ferrioxamine were markedly reduced by 5 mM-methylamine, which prevented endosome acidification and uncoupling of iron from endocytosed transferrin [18].
• Chelation of transferrin iron by desferrioxamine in K562 cells. The partition of iron between ferrioxamine and ferritin [18].
• We have shown that rat liver microsomes catalyse NADPH-dependent reduction of Fe3+ without chelator, as well as Fe3+(ADP), Fe3+(ATP), Fe3+(citrate), Fe3+(EDTA), and ferrioxamine in N2 [19].
• Administration of deferoxamine mesylate or ferrioxamine mesylate IV to ewes was not accompanied by measurable deferoxamine or ferrioxamine in fetal blood [20].

Associations of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide with other chemical compounds

• Deletion of ARN3 did not prevent yeast from using ferrioxamine B as an iron source; however, deletion of ARN3 and FET3, a component of the high affinity ferrous iron transport system, did prevent uptake of ferrioxamine-bound iron and growth on ferrioxamine as an iron source [21].
• Ionophore-siderophore host-guest assemblies composed of 18-crown-6 and ferrioxamine B, benzo-18-crown-6 and ferrioxamine B, and cis-syn-cis-dicyclohexano-18-crown-6 and ferrioxamine B were successfully crystallized, and their structures were determined by single-crystal X-ray diffraction [22].
• The siderophores ferrioxamine B, ferrichrome, triacetylfusarinine, coprogen, enterobactin and pyoverdine sustained growth of the cells under iron-limited conditions, and siderophore iron was incorporated into the major iron protein of T. foetus, ferredoxin [23].
• Flow injection analysis of the siderophores with detection by ESI-MS produced detection limits of 1.9 fmol for FO, 31.1 fmol for FC and 524 fmol for FR [24].
• Effects of the magnetic resonance contrast medium ferrioxamine methanesulfonate on systemic and renal hemodynamics in the anesthetized dog [25].

Gene context of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• Sed1p interacts with Arn3p physically and mediates ferrioxamine B uptake in Saccharomyces cerevisiae [26].
• A combination of preenrichment in buffered peptone water supplemented with ferrioxamine E and amplification of iroB by magnetic immuno-PCR allowed detection of S. enterica in albumen within 24 h [27].
• However, only the transport of ferrioxamine G was dependent on the energy-transducing protein TonB, since growth stimulation of a tonB strain by ferrioxamines B and E was observed, albeit at lower efficiencies than in the parental strain [28].
• Expression of the inner membrane protein FoxB (PA2465) of Pseudomonas aeruginosa in mutants of Sinorhizobium meliloti that are defective in the utilization of ferrichrome, ferrioxamine B, and schizokinen resulted in the restoration of siderophore utilization [10].
• The iron- and cAMP-regulated gene SIT1 influences ferrioxamine B utilization, melanization and cell wall structure in Cryptococcus neoformans [29].

Analytical, diagnostic and therapeutic context of N'-[5-(acetyl-oxido-amino)pentyl]-N-[5-[3-(5-aminopentyl-oxido-carbamoyl)propanoylamino]pentyl]-N-oxido-butanediamide

• Analysis of water microcosms with the Bioscreen C apparatus confirmed that these supplements enhanced recovery of cells in stressed populations; enterobacterial autoinducer was the most effective, promoting resuscitation in populations that were so heavily stressed that ferrioxamine E or Oxyrase had no effect [30].
• Determination of desferoxamine and ferrioxamine by high-performance liquid chromatography with direct serum injection and pre-column enrichment [31].
• Ferrioxamine as a magnetic resonance contrast agent. Preclinical studies and phase I and II human clinical trials [32].
• Validated HPLC assay for iron determination in biological matrices based on ferrioxamine formation [33].

References