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PubMed2003

Green rust and iron oxide formation influences metolachlor dechlorination during zerovalent iron treatment.

Electron transfer from zerovalent iron (Fe0) to targeted contaminants is affected by initial Fe0 composition, the oxides formed during corrosion, and surrounding electrolytes. We previously observed enhanced metolachlor destruction by Fe0 when iron or aluminum salts were present in the aqueous matrix and Eh/pH conditions favored formation of green rusts. To understand these enhanced destruction rates, we characterized changes in Fe0 composition during treatment of metolachlor with and without iron and aluminum salts. Raman microspectroscopy and X-ray diffraction (XRD) indicated that the iron source was initially coated with a thin layer of magnetite (Fe3O4), maghemite (gamma-Fe2O3), and wüstite (FeO). Time-resolved analysis indicated that akaganeite (beta-FeOOH) was the dominant oxide formed during Fe0 treatment of metolachlor. Goethite (alpha-FeOOH) and some lepidocrocite (gamma-FeOOH) formed when Al2(SO4)3 was present, while goethite and magnetite (Fe3O4) were identified in Fe0 treatments containing FeSO4. Although conditions favoring formation of sulfate green rust (GR(II); Fe6(OH)12SO4) facilitated Fe0-mediated dechlorination of metolachlor, only adsorption was observed when GR(II) was synthesized (without Fe0) in the presence of metolachlor and Eh/pH changed to favor Fe(III)oxyhydroxide or magnetite formation. In contrast, dechlorination occurred when magnetite or natural goethite was amended with Fe(II) (as FeSO4) at pH 8 and continued as long as additional Fe(II) was provided. While metolachlor was not dechlorinated by GR(II) itself during a 48-h incubation, the GR(II) provided a source of Fe(II) and produced magnetite (and other oxide surfaces) that coordinated Fe(II), which then facilitated dechlorination.

Acetamides↗
PubMed2005

Breakage, regrowth, and fractal nature of natural organic matter flocs.

The growth, breakage, regrowth, and fractal nature of flocs was investigated by use of a laser diffraction particle sizing device. A range of coagulants were investigated for the coagulation of natural organic matter (NOM) and compared to other coagulated systems. The results showed NOM floc structural characteristics varied in steady-state size depending upon which coagulant was used. When compared to other systems, the order of floc size was Fe precipitate > Fe-NOM > latex (in NaCl solution). Floc regrowth after exposure to high shear was limited for all of the flocs under investigation other than for latex in an inert electrolyte. This highlighted differences in the internal bonding structure of flocs, with the results suggesting that physical bonds have a capacity to re-form after breakage. Fractal dimension analysis by small-angle laser light scattering (SALLS) had limited applicability to large flocs that dominated all of the systems under investigation, but the degree of compaction increased as flocs were broken in high shear. This provided a possible mechanistic reason for the irreversible breakage seen.

Alum Compounds↗
PubMed2002

Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts: two faces of an Fe(III)-OOH coin.

The oxygenation of carbon-carbon double bonds by iron enzymes generally results in the formation of epoxides, except in the case of the Rieske dioxygenases, where cis-diols are produced. Herein we report a systematic study of olefin oxidations with H(2)O(2) catalyzed by a group of non-heme iron complexes, i.e., [Fe(II)(BPMEN)(CH(3)CN)(2)](2+) (1, BPMEN = N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-diaminoethane) and [Fe(II)(TPA)(CH(3)CN)(2)](2+) (4, TPA = tris(2-pyridylmethyl)amine) and their 6- and 5-methyl-substituted derivatives. We demonstrate that olefin epoxidation and cis-dihydroxylation are different facets of the reactivity of a common Fe(III)-OOH intermediate, whose spin state can be modulated by the electronic and steric properties of the ligand environment. Highly stereoselective epoxidation is favored by catalysts with no more than one 6-methyl substituent, which give rise to low-spin Fe(III)-OOH species (category A). On the other hand, cis-dihydroxylation is favored by catalysts with more than one 6-methyl substituent, which afford high-spin Fe(III)-OOH species (category B). For catalysts in category A, both the epoxide and the cis-diol product incorporate (18)O from H(2)(18)O, results that implicate a cis-H(18)O-Fe(V)=O species derived from O-O bond heterolysis of a cis-H(2)(18)O-Fe(III)-OOH intermediate. In contrast, catalysts in category B incorporate both oxygen atoms from H(2)(18)O(2) into the dominant cis-diol product, via a putative Fe(III)-eta(2)-OOH species. Thus, a key feature of the catalysts in this family is the availability of two cis labile sites, required for peroxide activation. The olefin epoxidation and cis-dihydroxylation studies described here not only corroborate the mechanistic scheme derived from our earlier studies on alkane hydroxylation by this same family of catalysts (Chen, K.; Que, L, Jr. J. Am. Chem. Soc. 2001, 123, 6327) but also further enhance its credibility. Taken together, these reactions demonstrate the catalytic versatility of these complexes and provide a rationale for Nature's choice of ligand environments in biocatalysts that carry out olefin oxidations.

Alkenes↗
PubMed2002

Searching for the second oxidant in the catalytic cycle of cytochrome P450: a theoretical investigation of the iron(III)-hydroperoxo species and its epoxidation pathways.

Iron(III)-hydroperoxo, [Por(CysS)Fe(III)-OOH](-), a key species in the catalytic cycle of cytochrome P450, was recently identified by EPR/ENDOR spectroscopies (Davydov, R.; Makris, T. M.; Kofman, V.; Werst, D. E.; Sligar, S. G.; Hoffman, B. M. J. Am. Chem. Soc. 2001, 123, 1403-1415). It constitutes the last station of the preparative steps of the enzyme before oxidation of an organic compound and is implicated as the second oxidant capable of olefin epoxidation (Vaz, A. D. N.; McGinnity, D. F.; Coon, M. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3555-3560), in addition to the penultimate active species, Compound I (Groves, J. T.; Han, Y.-Z. In Cytochrome P450: Structure, Mechanism and Biochemistry, 2nd ed.; Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1995; pp 3-48). In response, we present a density functional study of a model species and its ethylene epoxidation pathways. The study characterizes a variety of properties of iron(III)-hydroperoxo, such as the O-O bonding, the Fe-S bonding, Fe-O and Fe-S stretching frequencies, its electron attachment, and ionization energies. Wherever possible these properties are compared with those of Compound I. The proton affinities for protonation on the proximal and distal oxygen atoms of iron(III)-hydroperoxo, and the effect of the thiolate ligand thereof, are determined. In accordance with previous results (Harris, D. L.; Loew, G. H. J. Am. Chem. Soc. 1998, 120, 8941-8948), iron(III)-hydroperoxo is a strong base (as compared with water), and its distal protonation leads to a barrier-free formation of Compound I. The origins of this barrier-free process are discussed using a valence bond approach. It is shown that the presence of the thiolate is essential for this process, in line with the "push effect" deduced by experimentalists (Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887). Finally, four epoxidation pathways of iron(III)-hydroxperoxo are located, in which the species transfers oxygen to ethylene either from the proximal or from the distal sites, in both concerted and stepwise manners. The barriers for the four mechanisms are 37-53 kcal/mol, in comparison with 14 kcal/mol for epoxidation by Compound I. It is therefore concluded that iron(III)-hydroperoxo, as such, cannot be a second oxidant, in line with its significant basicity and poor electron-accepting capability. Possible versions of a second oxidant are discussed.

Catalysis↗
PubMed2005

Metal-peroxo versus metal-oxo oxidants in non-heme iron-catalyzed olefin oxidations: computational and experimental studies on the effect of water.

Computational and experimental studies show that Fe(BPMEN)-catalyzed olefin oxidation has two (FeIII-OOH and FeV=O) oxidant species, which act with comparable activation barriers. The presence of water favors formation of an HO-FeV=O oxidant via water-assisted O-OH bond cleavage and leads to both epoxide and cis-diol products. In the absence of water, the oxidant is the FeIII-OOH [or (MeCN)FeIII-OOH], and oxidation mainly leads to epoxide. This conclusion differs from that derived from DFT investigations of iron-porphyrin-catalyzed olefin epoxidation, where the FeIII-OOH pathway is deemed too high in energy to be plausible. The difference between these two systems may lie in the more flexible coordination environment of the non-heme iron complex, which has an available adjacent coordination site that contributes to the activation of the peroxide in both wa and nwa pathways.

Alkenes↗
PubMed2005

Phenolic antioxidants (hydrolyzable tannins, flavonols, and anthocyanins) identified by LC-ESI-MS and MALDI-QIT-TOF MS from Rosa chinensis flowers.

Rosa chinensis (Yuejihua) is a well-known ornamental plant, and its flowers are commonly used in traditional Chinese medicine. Methanolic crude extracts of dried R. chinensis flowers were used for simultaneous determination of phenolic constituents by liquid chromatography-mass spectrometry (LC-MS) and matrix-assisted laser desorption/ionization quadrupole ion trap time-of-flight mass spectrometry (MALDI-QIT-TOF MS). A total of 36 known and unknown phenolics were identified as hydrolyzable tannins, flavonols, and anthocyanins, mainly including gallotannins (mono-, di-, or trigalloylglucopyranosides), ellagitannins, quercetin, quercetin/kaempferol mono- and diglycosides, and cyanidin/pelargonidin diglycosides. MALDI-QIT-TOF MS was applied not only to verify most phenolics isolated and identified by LC-MS but also to tentatively identify two ellagitannins (rugosins B and C) not isolated and unidentified by LC-MS. This study is the first to demonstrate the rapid and successful use of MALDI-QIT-TOF MS and LC-MS to directly and simultaneously identify phenolics in the crude extracts of R. chinensis flowers without any purification. The antioxidant activity of the crude extracts from R. chinensis flowers was also measured with three assay methods. The results showed that the phenolic antioxidants from R. chinensis flowers exhibited very strong radical scavenging effect and antioxidant power. High levels of flavonols and hydrolyzable tannins might be important bioactive principles in the dried R. chinensis flowers.

Anthocyanins↗
PubMed2003

Factors affecting the catalytic epoxidation of olefins by iron porphyrin complexes and H2O2 in protic solvents.

The catalytic epoxidation of cyclohexene by iron(III) porphyrin complexes and H2O2 has been investigated in alcohol solvents to understand factors affecting the catalyst activity in protic solvents. The yields of cyclohexene oxide and the Fe(III/II) reduction potentials of iron porphyrin complexes were significantly affected by the protic solvents, and there was a close correlation between the product yields and the reduction potentials of the iron porphyrin catalysts. The role of alcohol solvents was proposed to control the electronic nature of iron porphyrin complexes that determines the catalyst activity in the epoxidation of olefins by H2O2. We have also demonstrated that an electron-deficient iron porphyrin complex can catalyze the epoxidation of olefins by H2O2 under conditions of limiting substrate with high conversion efficiency in a solvent mixture of CH3OH and CH2Cl2.

Catalysis↗
PubMed2006

Iron sucrose augments homocysteine-induced endothelial dysfunction in normal subjects.

Intravenous iron is commonly used in conjunction with erythropoietic agents to treat anemia in patients with chronic kidney disease. Iron has been proposed to promote oxidative stress and endothelial dysfunction in vascular tissues. We studied the acute effects of intravenous iron sucrose on homocysteine-induced endothelial dysfunction in the brachial artery of normal human subjects. In all, 40 healthy subjects received intravenous iron sucrose 100 mg or placebo over 30 min immediately before ingestion of 100 mg/kg of oral methionine in a double-blind, randomized study. Flow- and nitroglycerin-mediated dilation in the brachial artery, serum markers of iron stores, and homocysteine and nitrotyrosine levels were measured before and after study drug administration. Intravenous iron significantly increased transferrin saturation and non-transferrin-bound iron (NTBI) when compared with placebo. Flow-mediated dilation significantly decreased from baseline 1 h after administration of iron sucrose when compared with placebo (from 6.66+/-0.47 to 1.93+/-0.35% after iron sucrose vs from 6.00+/-0.40 to 5.61+/-0.46% after placebo, P<0.001), but did not differ between groups at 4 h (1.10+/-0.39 vs 1.33+/-0.51%). Nitroglycerin-mediated vasodilation, and homocysteine and 3-nitrotyrosine levels did not differ after administration of iron sucrose and placebo. Intravenous administration of iron sucrose in the setting of transient hyperhomocysteinemia induced by methionine ingestion significantly increased transferrin saturation and plasma levels of NTBI and significantly attenuated flow-mediated dilation in the brachial artery when compared with placebo. This potential mechanistic link between intravenous iron and endothelial dysfunction warrants further study of cardiovascular effects of intravenous iron in anemic chronic kidney disease populations.

Adult↗
PubMed2006

Proinflammatory effects of iron sucrose in chronic kidney disease.

Inflammation is a central component of progressive chronic kidney disease (CKD). Iron promotes oxidative stress and inflammatory response in animals and promotes progressive CKD. Parenteral iron provokes oxidative stress in patients with CKD; however, its potential to provoke an inflammatory response is unknown. In 20 veterans with CKD, 100 mg iron sucrose was administered intravenously over 5 min and urinary excretion rate and plasma concentration of monocyte chemoattractant protein-1 (MCP-1) were measured at timed intervals over 24 h. Patients were then randomized to placebo or N-acetyl cysteine (NAC) 600 mg b.i.d. and the experiment was repeated at 1 week. Iron sucrose markedly increased plasma concentration and urinary excretion rate of MCP-1 at baseline and at 1 week visits (P < 0.0001 for time effect). Urinary excretion peaked at 30 min and plasma concentration at 15 min. Plasma MCP-1 concentration fell from 164 +/- 17.7 to 135 +/- 17.7 pg/ml with NAC, whereas it remained unchanged from 133 +/- 12.5 to 132 +/- 17.7 pg/ml with placebo (P=0.001 for visit x antioxidant drug interaction). There was a reduction in MCP-1 urinary excretion rate from visit 1 to 2. At the baseline visit, the urinary excretion rate averaged 305 +/- 66 pg/min and at the second visit 245 +/- 67 pg/min (mean difference 60 +/- 28 pg/min, P = 0.030). There was no improvement in urinary MCP-1 excretion with NAC. In conclusion, iron sucrose causes rapid and transient generation and/or release of MCP-1 plasma concentration and increases urinary excretion rate, and systemic MCP-1 level but the urinary excretion rate is not abrogated with the antioxidant NAC. These results may have implications for the progression of CKD with parenteral iron.

Aged↗
PubMed2003

Degradation of supramolecular complexes photoinduced by iron(III): the influence of the host on the reactivity of the guest.

Fe(III)-photoinduced degradation of two different supramolecular host-guest complexes, naphthalene with alpha-cyclodextrin and 4-chloroaniline with p-sulfonic-calix[4]arene; was studied in aqueous solution. The stoichiometries, equilibrium constants and conformations of these complexes were characterized. In both cases, the degradation of the guest could not be accounted for by simple competition kinetics of OH radical attack on the guest and host molecules, respectively. This observation was explained by the occurrence of subsequent radical reactions of transients resulting from an OH attack onto the host molecule, which are assumed to be able to induce additional degradation reactions of the guest. An inhibiting influence of the calix[4]arene host on the abundance of oligomeric degradation intermediates of 4-chloroaniline was observed.

Aniline Compounds↗
PubMed1999

Kinetic analysis of 52Fe-labelled iron(III) hydroxide-sucrose complex following bolus administration using positron emission tomography.

Kinetic analysis of a single intravenous injection of 100 mg iron(III) hydroxide-sucrose complex (Venofer) mixed with 52Fe(III) hydroxide-sucrose as a tracer was followed for 3-6 h in four generally anaesthetized, artificially ventilated minipigs using positron emission tomography (PET). The amount of injected radioactivity ranged from 30 to 200 MBq. Blood radioactivity, measured by PET in the left ventricle of the heart, displayed a fast clearance phase followed by a slow one. In the liver and bone marrow a fast radioactivity uptake occurred during the first 30 min, followed by a slower steady increase. In the liver a slight decrease in radioactivity uptake was noted by the end of the study. A kinetic analysis using a three-compartment (namely blood pool, reversible and irreversible tissue pools) model showed a fairly high distribution volume in the liver as compared with the bone marrow. In conclusion, the pharmacokinetics of the injected complex was clearly visualized with the PET technique. The organs of particular interest, namely the heart (for blood kinetics), liver and bone marrow could all be viewed by a single setting of a PET tomograph with an axial field of view of 10 cm. The half-life (T1/2) of 52Fe (8.3 h) enables a detailed kinetic study up to 24 h. A novel method was introduced to verify the actual 52Fe contribution to the PET images by removing the interfering radioactive daughter 52mMn positron emissions. The kinetic data fitted the three-compartment model, from which rate constants could be obtained for iron transfer from the blood to a pool of iron in bone marrow or liver to which it was bound during the study period. In addition, there was a reversible tissue pool of iron, which in the liver slowly equilibrated with the blood, to give a net efflux from the liver some hours after i.v. administration. The liver uptake showed a relatively long distribution phase, whereas the injected iron was immediately incorporated into the bone marrow. Various transport mechanisms seem to be involved in the handling of the injected iron complex.

Bone Marrow↗
PubMed1999

Pharmacokinetics and red cell utilization of iron(III) hydroxide-sucrose complex in anaemic patients: a study using positron emission tomography.

The pharmacokinetics of a single intravenous injection of 100 mg iron hydroxide-sucrose complex labelled with a tracer in the form of 52Fe/59Fe was followed in six anaemic patients for a period ranging from 6 to 8 3 h using positron emission tomography (PET). Red cell utilization of the labelled iron was followed for 4 weeks. PET data showed radioactive uptake by the liver, spleen and bone marrow. The uptake by the macrophage-rich spleen demonstrated the reticuloendothelial uptake of this iron preparation, with subsequent effective release of that iron for marrow utilization. Red cell utilization, followed for 4 weeks, ranged from 59% to 97%. The bone marrow influx rate constant was independent of blood iron concentration, indicating non-saturation of the transport system in bone marrow. This implied that higher doses of the iron complex can probably be used in the same setting. A higher influx rate into the marrow compared with the liver seemed to be consistent with higher red cell utilization. This would indicate that early distribution of the injected iron complex may predict the long-term utilization.

Adult↗
PubMed2003

Pharmacokinetics and red cell utilization of 52Fe/59Fe-labelled iron polymaltose in anaemic patients using positron emission tomography.

Parenteral iron-polysaccharide complexes are increasingly applied. The pharmacokinetics of iron sucrose have been assessed by our group using positron emission tomography (PET). A single intravenous injection of 100 mg iron as iron (III) hydroxide-polymaltose complex, labelled with a tracer in the form of 52Fe/59Fe, was similarly assessed in six patients using PET for about 8 h. Red cell utilization was followed for 4 weeks. Iron polymaltose was similarly distributed to the liver, spleen and bone marrow. However, a larger proportion of this complex was rapidly distributed to the bone marrow. The shorter equilibration phase for the liver, about 25 min, indicates the minimal role of the liver for direct distribution. Splenic uptake also reflected the reticuloendothelial handling of this complex. Red cell utilization ranged from 61% to 99%. Despite the relatively higher uptake by the bone marrow, there was no saturation of marrow transport systems at this dose level. In conclusion, high red cell utilization of iron polymaltose occurred in anaemic patients. The major portion of the injected dose was rapidly distributed to the bone marrow. In addition, the reticuloendothelial uptake of this complex may reflect the safety of polysaccharide complexes. Non-saturation of transport systems to the bone marrow indicated the presence of a large interstitial transport pool, which might possibly be transferrin.

Adult↗
PubMed2002

Ferric saccharate induces oxygen radical stress and endothelial dysfunction in vivo.

BACKGROUND: Intravenous iron supplementation is used widely in haemodialysis patients. However, nontransferrin-bound iron (NTBI), which increases after intravenous supplementation of ferric saccharate, has been suggested to act as a catalytic agent in oxygen radical formation in vitro and may thus contribute to endothelial impairment in vivo. MATERIALS AND METHODS: In 20 healthy volunteers the effect of 100 mg ferric saccharate infusion was investigated. Vascular ultrasound was used to assess endothelium-dependent vasodilatation at baseline, and 10 and 240 min after ferric saccharate infusion. Whole blood was collected to measure NTBI and in vivo radical formation was assessed by electron spin resonance. A time-control study was performed using saline infusion. RESULTS: Infusion of ferric saccharate induces a greater than fourfold increase in NTBI, as well as a transient, significant (P < 0.01) reduction of flow-mediated dilatation 10 min after infusion of ferric saccharate, when compared with saline. The generation of superoxide in whole blood increased significantly 10 and 240 min after infusion of ferric saccharate by, respectively, 70 and 53%. CONCLUSIONS: Iron infusion at a currently used therapeutic dose for intravenous iron supplementation leads to increased oxygen radical stress and acute endothelial dysfunction.

Adult↗
PubMed2002

Nontransferrin-bound iron in the plasma of haemodialysis patients after intravenous iron saccharate infusion.

BACKGROUND: Many haemodialysis patients treated with recombinant human erythropoietin (r-HuEPO) receive intravenous iron supplementation on a regular basis. It has been shown previously that this may result in a transient "oversaturation" of transferrin. METHODS: Ten stable haemodialysis patients on r-HuEPO treatment received 100 mg iron saccharate in 60 min, and 1 week later 100 mg in 6 min. Conventional iron metabolism parameters and nontransferrin-bond iron, detected with HPLC after addition of nitrilotriacetate and pretreatment with cobalt, were measured. Also, iron was measured in dialysate. RESULTS: Serum iron increased from 9.6 +/- 6.2 to 213.7 +/- 49.4 micromol L(-1) (P < 0.001) when iron was given in 60 min, and from 11.1 +/- 4.7 to 219.3 +/- 43.7 micromol L(-1) (P < 0.001) when iron was given in 6 min. Transferrin saturation increased from 0.22 +/- 0.18 to 4.75 +/- 1.35 in protocol 1 and 0.26 +/- 0.16 to 4.91 +/- 1.38 in protocol 2. Nontransferrin-bound iron increased from 0.74 +/- 0.69 to 3.79 +/- 1.41 micromol L(-1) in protocol 1, and from 0.90 +/- 0.92 to 2.90 +/- 0.96 micromol L(-1) in protocol 2. No significant iron concentrations were found in dialysate before or during the iron saccharate infusion. CONCLUSION: Nontransferrin-bound iron exists in plasma of dialysis patients after infusion of iron saccharate. There was no difference when 100 mg iron was given in 60 min or in 6 min. Before iron infusion, appreciable concentrations of nontransferrin-bound iron could already be detected. The clinical significance is not clear, but the findings may be important since nontransferrin-bound iron can act as a catalytic agent in the formation of hydroxyl radicals, thus potentially inducing cell damage and atherosclerosis.

Anemia↗
PubMed2003

High-dose parenteral iron sucrose depresses neutrophil intracellular killing capacity.

BACKGROUND: Iron is essential for the formation of hemoglobin. During long-term treatment with human recombinant erythropoietin (rhEPO), the majority of end-stage renal disease (ESRD) patients will not respond adequately to rhEPO unless substituted with intravenous iron. However, concern exists about possible detrimental effects of parenteral iron on cellular host defense and iron-mediated increments of oxidative stress. METHODS: We analyzed phagocytic functions of polymorphonuclear leukocytes (PMN) isolated from 20 ESRD patients on peritoneal dialysis in response to 300 mg of iron sucrose or placebo administered intravenously over two hours in a randomized, double-blind manner. We evaluated Fc gamma R-dependent phagocytosis and killing (primary outcome variable) of opsonized Escherichia coli, Fc gamma R-dependent oxidative burst capacity, and complement receptor 3 (CR3, Mac1, CD11b/CD18)/tumor necrosis factor alpha (TNFalpha)-mediated release of bactericidal lactoferrin before, during, one hour, and two days after administration. RESULTS: The absolute count and the percentage of E. coli killed by PMN of iron sucrose-treated peritoneal dialysis patients decreased significantly over time in comparison to placebo-treated patients (F = 3.48, df = 4, P = 0.008; F = 3.99, df = 4, P = 0.006, respectively). All secondary outcome variables were not different between both groups over time. CONCLUSIONS: Killing capacity of PMN isolated from ESRD patients decreases in response to high-dose parenteral iron sucrose, possibly in part explaining reported higher hospitalization rates and lower survival rates of dialysis patients receiving frequent and high-dose parenteral iron.

Anemia↗