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PubMedDate not supplied

Iron oxide-enhanced MR lymphography: the evaluation of cervical lymph node metastases in head and neck cancer.

Accurate diagnosis of cervical lymph node metastasis is challenging, even with the latest computed tomography or MR equipment and technique. The lack of definitive criteria for distinguishing metastatic from benign nodes is a serious shortcoming of current imaging options. Dextran-coated, ultrasmall superparamagnetic iron oxide is a new MR contrast agent, which accumulates in the reticuloendothelial system of lymph nodes. Small iron oxide particles are taken up by macrophages within normal functioning nodes, reducing their signal on postcontrast MR because of the magnetic susceptibility effects of iron oxide. Metastatic nodes, on the other hand, remain high in signal on postcontrast T2*-weighted gradient echo images. Early clinical experience in cancer patients suggests that iron oxide-enhanced MR lymphography is a valuable imaging technique that may improve diagnostic accuracy for nodal metastases. This article reviews development of superparamagnetic iron oxide compounds, their imaging characteristics, and clinical experience for evaluating head and neck cancer metastases.

Carcinoma, Squamous Cell↗
PubMed2006

The Poulos-Kraut mechanism of Compound I formation in horseradish peroxidase: a QM/MM study.

QM/MM calculations are used to elucidate the Poulos-Kraut (Poulos, T. L.; Kraut, J. J. Biol. Chem. 1980, 255, 8199-8205) mechanism of O-O bond activation and Compound I (Cpd I) formation in HRP, in conditions corresponding to neutral to basic pH. Attempts to generate Compound I directly from the Fe(H2O2) complex by migrating the proton from the proximal oxygen to the distal one (1,2- proton shift) result in high barriers. The lowest energy mechanism was found to involve initial deprotonation of ferric hydrogen peroxide complex (involving spin crossover from the quartet to the doublet state) by His42 to form ferric-hydroperoxide (Cpd 0). Subsequently, the distal OH group of Cpd 0 is pulled by Arg38 and reprotonated by His42(H+) to form Cpd I and a water molecule that bridges the two residues. The structures of the intermediate and the transition state reveal the manner by which the Arg-His residues promote cooperatively the electronic reorganization that is required to attend the heterolytic O-O cleavage.

Ferric Compounds↗
PubMed2000

Assessment of iron absorption from ferric trimaltol.

Therapeutic iron compounds have limited absorption and often have side-effects, which limits patient compliance. Iron trimaltol is a novel, stable complex, formed between ferric iron (Fe3+) and maltol (3-hydroxy-2-methyl-4-pyrone), and is effective in the treatment of iron deficiency anaemia with few side-effects. However, the kinetics of iron absorption from ferric trimaltol and the reliability of normal colorimetric analysis in detecting iron absorbed from this complex have not been established. We measured increases in serum iron levels in 12 volunteers following oral challenge with four different pharmaceutical formulations of ferric trimaltol in a double-blind, cross-over, randomized study. The conventional colorimetric method for detecting serum iron was compared with thermal analyses after trichloroacetic acid (TCA) treatment of serum. Measurements of serum iron levels by TCA treatment and thermal analysis closely agreed with measurements by colorimetry. For all formulations, serum iron levels peaked at 90 min with a plateau of at least 5 h [mean (standard deviation) peak absorption 8.3% (6.3%) of ingested dose, n=48]. Absorption of iron, based on peak serum values or area under the serum curve, was not different for the four formulations (n=12 each) and correlated with the individual's iron status, as assessed by serum ferritin values (r = -0.6; P < 0.001). Normal colorimetry is suitable for analysis of serum iron levels following ingestion of ferric trimaltol. There is rapid and sustained absorption of iron from ferric trimaltol and, as with ferrous iron, uptake appears to be controlled through normal mechanisms of iron acquisition that depend upon body iron stores.

Adult↗
PubMed2004

Amelioration by active hexose correlated compound of endocrine disturbances induced by oxidative stress in the rat.

OBJECTIVE: Active hexose correlated compound (AHCC), an extract derived from fungi of Basidiomycetes family, has been found to be a potent antioxidant. Since the secretion of some hormones can be affected by reactive oxygen species, the objective of this study was to examine how ferric nitrilotriacetate (FeNTA), which generates hydroxyl radicals in vivo, modulates the hormone secretion and the effects of AHCC. METHODS: AHCC at 3 % in drinking water was given to male rats for one week, and the animals were decapitated at different time intervals after the treatment with FeNTA intraperitoneally. Serum levels of hormones (corticosterone, testosterone, thyroxine and triiodothyronine), adrenal ascorbic acid as well as changes in hepatic oxidative status were evaluated by immunoassay and spectrometry. RESULTS: Serum corticosterone levels increased significantly following FeNTA treatment, while AHCC reduced the increased levels to normal. Adrenal ascorbic acid levels that reflect ACTH secretion, were decreased by FeNTA and restored to normal by AHCC. Serum levels of testosterone and thyroxine (T4) decreased rapidly after FeNTA treatment, while AHCC pretreatment prevented this fall. Serum triiodothyroxine (T3) levels remained unchanged either by FeNTA or AHCC treatment. The hepatic oxidized glutathione, glutathione-related enzymes and also serum lipid peroxide were greatly enhanced after FeNTA treatment. All of these changes were restored to normal by AHCC pretreatment. CONCLUSION: FeNTA induces various endocrine disorders and AHCC ameliorates these effects by acting as an antioxidant.

Animals↗
PubMed2001

Alternatives to the oxoferryl porphyrin cation radical as the proposed reactive intermediate of cytochrome P450: two-electron oxidized Fe(III) porphyrin derivatives.

The active intermediates in most heme enzyme-catalyzed oxidations such as epoxidation and hydroxylation have been attributed to the O=Fe(IV) porphyrin pi-cation radical, so-called compound I. This could be correct for many cases, however, alternatives to compound I have been proposed for several oxidations including aliphatic hydroxylation catalyzed by P450. Therefore, two-electron oxidized iron porphyrin complexes other than compound I have been reviewed as candidates for the active species responsible for oxidations catalyzed by heme enzymes.

Alkenes↗
PubMed2006

Quantitative analysis of free fatty acids in rat plasma using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry with meso-tetrakis porphyrin as matrix.

Quantitative analysis of free fatty acids was achieved using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) with a meso-tetrakis porphyrin matrix. Cesium acetate was employed as a cationizing agent. The MALDI signal was reproducible and dominated by cesiated cesium carboxylates [RCOOCs + Cs]+. The addition of two Cs ions resulted in a mass shift of 264.8 Da for each fatty acid and greatly reduced background peaks. A linear relationship between fatty acid concentration and corresponding fatty acid to internal standard peak intensity ratio was observed for three representative fatty acids analyzed across a concentration range from 4.40 to 150 microM, with correlation coefficients between 0.986 and 0.987. The application of this method was demonstrated with the analysis of free fatty acids in nonfasted and fasted rat plasmas. A total of eight free fatty acids (14:0, 16:0, 16:1, 17:0, 18:0, 18:1, 18:2, and 20:4) were detected. The relative peak height ratios of the fatty acids to the internal standard allow quantitative measurements of the free fatty acids. It was shown that the levels of free fatty acids were higher in fasted rats than in rats in a nonfasted state. This method is simple, sensitive, and fast. Thus, it provides an appealing tool for the analysis of free fatty acids or other low-molecular weight compounds during drug discovery and/or development.

Acetates↗
PubMed2003

Tissue-specific MR contrast agents.

The purpose of this review is to outline recent trends in contrast agent development for magnetic resonance imaging. Up to now, small molecular weight gadolinium chelates are the workhorse in contrast enhanced MRI. These first generation MR contrast agents distribute into the intravascular and interstitial space, thus allowing the evaluation of physiological parameters, such as the status or existence of the blood-brain-barrier or the renal function. Shortly after the first clinical use of paramagnetic metallochelates in 1983, compounds were suggested for liver imaging and enhancing a cardiac infarct. Meanwhile, liver specific contrast agents based on gadolinium, manganese or iron become reality. Dedicated blood pool agents will be available within the next years. These gadolinium or iron agents will be beneficial for longer lasting MRA procedures, such as cardiac imaging. Contrast enhanced lymphography after interstitial or intravenous injection will be another major step forward in diagnostic imaging. Metastatic involvement will be seen either after the injection of ultrasmall superparamagnetic iron oxides or dedicated gadolinium chelates. The accumulation of both compound classes is triggered by an uptake into macrophages. It is likely that similar agents will augment MRI of atheriosclerotic plaques, a systemic inflammatory disease of the arterial wall. Thrombus-specific agents based on small gadolinium labeled peptides are on the horizon. It is very obvious that the future of cardiovascular MRI will benefit from the development of new paramagnetic and superparamagnetic substances. The expectations for new tumor-, pathology- or receptor-specific agents are high. However, is not likely that such a compound will be available for daily routine MRI within the next decade.

Animals↗
PubMed1995

Resonance Raman studies of catecholate and phenolate complexes of recombinant human tyrosine hydroxylase.

Human tyrosine hydroxylase isoform 1 (hTH1) was expressed in Escherichia coli, purified as the apoenzyme, and reconstituted with iron. The resonance Raman spectra of hTH1 complexed with dopamine, noradrenaline, tyramine, and catechol have been studied and compared to those obtained for TH isolated from bovine adrenal glands or rat phaeochromocytoma tissue. A TH-phenolate complex is reported for the first time. Using dopamine selectively 18O-labeled in the 3-position or both 3- and 4-hydroxy positions, we have been able to assign unambiguously the origin of the low-frequency vibration bands: the band at 631 cm-1 involves the oxygen in the 4-position; the band at 592 cm-1 involves the oxygen in the 3-position, and the band around 528 cm-1 is shifted by both, suggesting a chelated mode vibration. A small shift of the 1275 cm-1 band and no shift of the 1320 cm-1 band were observed, showing that those two bands involve essentially ring vibrations of the catecholate moiety, rather than the C--O stretching vibration as previously suggested. The spectrum of the catechol-d6-hTH1 complex confirms this assignment. The resonance Raman spectra of the 54Fe, 56Fe, or 57Fe isotope-containing enzymes complexed with dopamine are virtually identical, showing that the component of the iron in the approximately 600 cm-1 vibrations is too small to be observed. These results provide a better understanding of the Raman properties of iron-catecholate complexes in this enzyme, as well as in other metalloproteins and model compounds.

Adrenal Gland Neoplasms↗
PubMed1978

Iron sources used in food fortification and their changes due to food processing.

The effect of food processing on the biological availability of iron in iron-fortified foods is critically reviewed. Studies on changes in the chemistry of the iron in processed foods are examined. Various iron sources currently used in food fortification in the U.S. are defined with emphasis on their biological availabilities under various conditions. The availability of iron in foods depends upon numerous factors, most of which are not fully understood. A factor which is often overlooked is the interaction of the iron with the food during events such as cooking or processing. Chemical changes in the iron compounds occur which may correlate with changes in the biological availability.

Adult↗
PubMed1994

Enhancement of MR angiography with iron oxide: preliminary studies in whole-blood phantom and in animals.

OBJECTIVE: We hypothesized that the previously observed T1 effect of a small monocrystalline iron oxide preparation can be exploited to decrease T1 relaxation time of blood. Such a decrease, particularly if present for a long time, could be used to improve the quality of MR angiograms. To test the hypothesis, we performed phantom studies and in vivo animal experiments. MATERIALS AND METHODS: The effect of the monocrystalline iron oxide preparation on the MR signal intensity (spoiled gradient-recalled acquisition in the steady state pulse sequences, various timing parameters) of human whole blood was first tested in a phantom (dose range of monocrystalline iron oxide preparation, 0-3 mumol Fe/ml). Subsequent experiments were performed in rats (n = 7) and in rabbits (n = 6) to determine whether predicted changes in signal intensity could be observed in vivo. RESULTS: Dose optimization studies in rats indicate that injected doses of 15-50 mumol Fe/kg (0.8-2.8 mg Fe/kg) of monocrystalline iron oxide preparation resulted in threefold to fourfold increases of aortic signal-to-noise ratio. Because of its long plasma half-life (180 min in rats), the iron oxide preparation markedly improved the quality of images of the vasculature of the lungs, abdomen, and extremities. CONCLUSION: Our experimental results suggest that this and possibly other iron oxide preparations are alternatives to compounds containing macromolecular gadolinium and could be useful for clinical MR angiography.

Animals↗
PubMed2005

A phenolate-induced trans influence: crystallographic evidence for unusual asymmetric coordination of an alpha-diimine in ternary complexes of iron(III) possessing biologically relevant hetero-donor N-centered tripodal ligands.

Three mononuclear ternary complexes of iron(III) with an alpha-diimine (bipy or phen) and a derivative of N,N-bis(2-hydroxybenzyl)glycinate (L3-) have been synthesized and characterized by magnetic susceptibility measurements, electron paramagnetic resonance (EPR) spectroscopy, vibrational spectroscopy, and electronic absorption spectroscopy. Single-crystal X-ray structure determinations of the pseudo-octahedral complexes [Fe(bipy)L] x MeCN [L = (3,5-Br2)-L3- or (5,3-Cl,Me)-L3-] revealed a considerable and consistent distortion in the coordination of bipy to iron(III) attributable largely to electronic effects. In both crystal structures, the Fe-N(pyridyl) bond trans to the phenolate oxygen is 0.133 A longer than the other one positioned trans to the tertiary amine nitrogen, a relatively weaker donor. This coordination behavior of bipy is of structural interest and has not been observed previously for iron(III). The electronic and EPR spectra of the compounds [Fe(L'-L')L] x MeCN (L'-L' = bipy or phen) are consistent with the spin state of the central metal atom (S = 5/2). The charge-transfer transitions arising from the strong interactions of the phenolate moieties with the ferric ion have been identified as phenolate (p(pi)) --> iron(III) (d(pi*)) (lambda(max) approximately 500 nm, epsilon approximately 3000 M(-1) cm(-1)) and phenolate (p(pi)) --> iron(III) (d(sigma*) (lambda(max) approximately 320 nm, epsilon approximately 5200 M(-1) cm(-1)). The presence of the phenolate moieties in the quadridentate hetero-donor tripodal ligands, H3L, lends these iron(III) ternary complexes the potential to model the specific metal-coordination, metal-substrate interactions, and physicochemical behaviors of several iron-tyrosinate proteins.

Catalysis↗
PubMed2002

Synthesis of ferroquine enantiomers: first investigation of effects of metallocenic chirality upon antimalarial activity and cytotoxicity.

Ferroquine (FQ) is a new antimalarial agent with a high blood schizotoncidal activity. Previous studies on this compound were done with racemate mixtures. As FQ possesses planar chirality, pure enantiomers were obtained by enzymatic resolution in order to compare their antimalarial activities and cytotoxicities. (+)-FQ and (-)-FQ were equally active in vitro, at nanomolar concentrations. Both enantiomers were slightly less active than the racemate in vivo; cytotoxicities were similar. Actually, the racemate represents the optimal formulation. To the best of our knowledge, this is the first investigation of biological activities of compounds with metallocenic chirality.

Animals↗
PubMed1997

Novel estrogens and their radical scavenging effects, iron-chelating, and total antioxidative activities: 17 alpha-substituted analogs of delta 9(11)-dehydro-17 beta-estradiol.

Antioxidant effects of N,N-dimethyl-p-toluidine, p-cresol, and p-(hydroxy)thioanisol 17 alpha-substituted analogs of 17 beta-estradiol and their delta 9(11)-dehydro homologs were investigated using four different in vitro models: rat synaptosomal lipid peroxidation induced by Fenton's reagent, Fe(II)-chelating activities, the formation of superoxide anion radicals, and total antioxidative activity. Whereas the classical estrogen 17 beta-estradiol as well as selected phenolic compounds was only moderately inhibiting iron-dependent lipid peroxidation and stimulating total antioxidative activity, besides delta 9(11)-dehydro-17 beta-estradiol (J 1213), novel estrogens such as C-17-oriented side chain analogs of 17 beta-estradiol (J 843, J 872, and J 897) and delta 9(11)-dehydro homologs (J 844, J 864, and J 898) directly altered the iron redox chemistry and diminished the formation of superoxide anion radicals generated by a xanthine/xanthine oxidase-dependent luminescence reaction to a great extent. These results suggest that definite modifications in the chemical structure of 17 beta-estradiol, e.g., the introduction of a delta 9(11)-double bond and/or p-cresol as well as p-(hydroxy)thioanisol C-17 substitution, may result in substantial changes in their antioxidant behavior. These compounds may be drug candidates for treating pathologies related to free radical formation.

Animals↗
PubMed2005

Sorption of oxytetracycline to iron oxides and iron oxide-rich soils.

The sorption interactions of oxytetracycline with goethite, hematite, and two iron oxide-rich soils were investigated using batch sorption experiments. Oxytetracycline sorption coefficients for goethite and hematite increased with pH to maximum values at pH approximately 8. The sorption edge shape and desorption treatments were consistent with a surface complexation mechanism and could be described by the interaction of divalent anion species with the oxide surface. Oxytetracycline sorption to Georgeville and Orangeburg Ultisol soils decreased with pH. Chemical digestion treatments were used to deduce that soil sorption occurred by complexation to oxide coatings on clay and quartz grains. These results indicate that sorption models must consider the interaction of oxytetracycline, and other similar ionogenic compounds, with soil oxide components in addition to clays and organic matter when predicting sorption in whole soils.

Adsorption↗
PubMed2005

Potential toxicity.

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Aluminum Compounds↗
PubMedDate not supplied

The microaerophilic nature of Treponema pallidum: enhanced survival and incorporation of tritiated adenine under microaerobic conditions in the presence or absence of reducing compounds.

Treponema pallidum, although sensitive to atmospheric concentrations of O2, requires low levels of O2 for optimal survival and metabolic activity. The addition of 0.0125-0.2 mg/ml of sodium metabisulfite to a basal medium consisting of Eagle's minimal essential medium and 50% fresh, heat-inactivated normal rabbit serum was found to have an effect similar to that of dithiothreitol in extending the survival of T. pallidum (Nichols strain) under 3% O2. Detailed analysis of the effect of O2 tension revealed that 50% motility was retained longest at atmospheric O2 concentrations of 1-5%, whether or not dithiothreitol or sodium metabisulfite were present. Concentrations of O2 of 3-10% were optimal for nucleic acid synthesis, as determined by [3H]adenine incorporation during the first 24 hr of incubation. Sodium metabisulfite was less effective than dithiothreitol in stimulating nucleic acid synthesis. Neither sodium metabisulfite nor dithiothreitol at their effective concentrations had any effect on levels of dissolved O2. During incubation under 3% O2, motility was maintained at > 50% for 15 days and virulence for at least 13 days by dilution of the treponemal suspensions every three days with fresh medium containing sodium metabisulfite. The optimal retention of motility and nucleic acid synthesis under microaerobic conditions in the absence of reducing compounds provides further evidence that T. pallidum is a microaerophilic organism.

Adenine↗
PubMed1991

[Evaluation of the fibrogenic effect of coke dust on the lungs and internal organs of experimental animals].

Based on the data collected by the Provincial Regional Administration Unit for Control of Epidemics and Hygiene in Katowice, dust concentration at the MAKOSZOWY Coking Plant in Zabrze at 18 work-places exceeded the TLV's. The purpose of this study was to determine changes within the respiratory systems of experimental animals exposed to intratracheal administration of MAKOSZOWY Coking Plant dust, sampled at the charging larry 3-4 operating stand and at the battery roof. After pulverization the dusts contained 98.1% and 99.6% respirable particles, and 6.5% and 6.0% of SiO2, respectively, determined with the Polezhajev method. They also contained aluminum and iron compounds. Hydroxyproline content in the lungs of the animals following the intratracheal administration of 50 mg of the dusts investigated 3-6 months after the experiment was determined. Determination of Hypro contend within the animals' lungs was pursued with the Stegemann method as modified by Hurych and Chvapil. The biochemical investigation results obtained were statistically analyzed with the t-Student's Test. Single intratracheal administration of dust from the battery roof work stand of the MAKOSZOWY Coking Plant caused within 6 months a statistically significant increase in the lung Hydroxyproline level in experimental animals (t = 13.10). An almost triole Hypro increase with respect to the control group was observed. No analogy between lung Hypro level increase (12.833 mg) and histological change was noted. Such a significant lung Hydroxyproline level increase could have been due to the SiO2 content of dust (6%), as well as to the presence of iron compounds in it (4.98%).(ABSTRACT TRUNCATED AT 250 WORDS)

Air Pollutants↗
PubMed1982

Properties and proteolysis of ferric enterobactin outer membrane receptor in Escherichia coli K12.

A protein with a relative subunit molecular weight of 81000 (81K) has been isolated in virtually pure form from the outer membrane of low iron grown cells of Escherichia coli K12. The 81K protein, which is part of the receptor complex for translocation of the siderophore ferric enterobactin, displays activity in vitro for binding both ferric enterobactin and colicin B. The dissociation constant for the 81K-ferric enterobactin compound at 4 degrees C in 2% Triton-0.1 M Tris, pH 7, was determined to be 10 nM. The N-terminal amino acid was identified as phenylalanine, and the amino acid composition was shown to be similar to that published for the ferric aerobactin-cloacin receptor of Enterobacter cloacae. A plasmid-bearing strain of E. coli was employed to confirm that degradation of 81K to a slightly smaller, inactive form (81K) is performed by a second outer membrane component, protein a. The endoproteolytic action of protein a was verified by the finding of alanine as the N-terminal residue of 81K. A survey of enteric species suggests that the 81K-protein a interaction is confined to the K12 strain of E. coli.

Amino Acids↗