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PubMed2003

Antiplatelet properties of a novel, non-NO-based soluble guanylate cyclase activator, BAY 41-2272.

Nitric oxide (NO) plays an important role in cardiovascular homeostasis, particularly in the regulation of vascular tone and the reactivity of platelets and circulating cells. Soluble guanylate cyclase (sGC) acts as the principal biological target for NO and catalyses the formation of the intracellular second messenger cyclic GMP (cGMP); activation of this enzyme is thought to be responsible for the majority of cardiovascular actions of NO. In the present study, we have evaluated the antiplatelet effects of a novel non-NO-based sGC activator, BAY 41-2272, in vitro and in vivo. BAY 41-2272 produced a marked inhibition of platelet aggregation in washed platelets with a potency (IC(50) approximately 100 nM) some threefold less than the NO donor S-nitrosoglutathione. BAY 41-2272 also prevented aggregation in platelet-rich plasma (PRP), albeit with a much lower potency. Both NO and prostacyclin exhibited synergistic activity with BAY 41-2272 to inhibit platelet aggregation. In vivo, at doses of BAY 41-2272 that significantly reduced blood pressure, the compound had little effect on FeCl(3)-induced thrombosis. These data confirm that intraplatelet sGC activation results in inhibition of aggregation and suggests that novel non-NO-based sGC activators, which possess both hypotensive and antiplatelet activities, may be useful as therapeutic agents.

Adenosine Diphosphate↗
PubMed2006

De novo formation of chloroethyne in soil.

To date, chloroethyne in the environment has been proposed to occur as a reactive intermediate during the reductive dechlorination of tri- and tetrachloroethene with zerovalent metals. Such artificial conditions might possibly be found at organohalide-contaminated sites that are surrounded by remediation barriers made of metallic iron. In this paper, it is shown that the highly reactive chloroethyne is also a product of natural processes in soil. Soil air samples from three differentterrestrial ecosystems of Northern Germany showed significant chloroethyne concentrations, besides other naturally produced monochlorinated compounds, such as chloromethane, chloroethane and chloroethene. Measured amounts range from 5 to 540 pg chloroethyne in air purged from 1 L of soil. A possible route of chloroethyne formation in soil is discussed, where chloroethyne is probably produced as a byproduct of the oxidative halogenation of aromatic compounds in soil. A series of laboratory studies, using the redox-sensitive catechol as a discrete organic model compound, showed the formation of chloroethyne when Fe3+ and hydrogen peroxide were added to the system. We therefore propose that the natural formation of chloroethyne in soil proceeds via oxidative cleavage of a quinonic system in the presence of the ubiquitous soil component chloride.

Alkynes↗
PubMed1989

Lipid peroxidation of human granulocytes (PMN) and monocytes by iron complexes.

Because the phagocytic function of non-stimulated human polymorphonuclear granulocytes (PMN) is impaired after incubation with either polynuclear Fe(III) or Fe(II), we decided to study lipid peroxidation of PMN and monocytes by these iron complexes. Lipid peroxidation was assessed by measuring thiobarbituric acid reactive substances and fluorescent compounds. In this study we report that monocytes, isolated in the standard way (EDTA-mediated detachment), release significantly more thiobarbituric acid reactive substances after incubation with iron than PMN. Monocytes, however, isolated without EDTA release the same amount after incubation with iron as PMN. The iron complexes shown to impair phagocyte function also stimulated the peroxidation of membrane lipids. Ascorbic acid in high concentrations enhanced iron-induced lipid peroxidation. Lipid peroxidation induced by ferrous ascorbate (1:20) could be inhibited by catalase, the iron chelators deferoxamine and transferrin, and the hydroxyl radical scavenger thiourea. Mononuclear complexes (ferric citrate 1:20) did not impair granulocyte function and did not induce lipid peroxidation. Our results suggest that impaired phagocyte function in patients with iron overload may be due to non-transferrin bound iron-mediated peroxidation of membrane lipids. However, the lowest amount of ferrous ascorbate (1:20) capable of inducing lipid peroxidation (50 microM) was significantly higher than that which impaired phagocyte function (10 microM).

Ferric Compounds↗
PubMed2003

Degradation of 2-fluorophenol by the brown-rot fungus Gloeophyllum striatum: evidence for the involvement of extracellular Fenton chemistry.

Iron-containing liquid cultures of the brown-rot basidiomycete Gloeophyllum striatum degraded 2-fluorophenol. Two simultaneously appearing degradation products, 3-fluorocatechol and catechol, were identified by gas chromatography and mass spectrometry (GC-MS). Concomitantly, fluoride was produced at approximately 50% of the amount that theoretically could be achieved upon complete dehalogenation. Defluorination was strongly inhibited in the presence of either the hydroxyl radical scavenger mannitol or superoxide dismutase, as well as in the absence of iron. The addition of the natural iron chelator oxalate caused a clear but less extensive inhibition, whereas supplementation with the artificial iron chelator nitrilotriacetic acid increased fluoride production. Extracellular 2-fluorophenol degradation was evidenced by defluorination, observed upon addition of 2-fluorophenol to cell-free culture supernatants derived from iron-containing fungal cultures. Ultrafiltered culture supernatants oxidized methanol to formaldehyde, known as a product of the reaction of methanol with hydroxyl radical. In addition, G. striatum was found to produce metabolites extractable with ethyl acetate that are capable of reducing Fe3+. GC-MS analysis of such extracts revealed the presence of several compounds. The mass spectrum of a prominent peak matched those previously reported for 2,5-dimethoxyhydroquinone and 4,5-dimethoxycatechol, fungal metabolites implicated to drive hydroxyl radical production in Gloeophyllum. Taken together, these findings further support an extracellular Fenton-type mechanism operative during halophenol degradation by G. striatum.

Biodegradation, Environmental↗
PubMed1983

Iron-binding compounds of Mycobacterium avium, M. intracellulare, M. scrofulaceum, and mycobactin-dependent M. paratuberculosis and M. avium.

Fifty-three strains of M. avium and related species all produced one or more exochelins, the extracellular iron-binding compounds of the mycobacteria, when grown iron deficiently. Only those strains which could grow without the addition of mycobactin (i.e., mycobactin independent) produced mycobactin, the intracellular iron-binding compound of the mycobacteria. Exochelins varied from 20 to 2,000 micrograms per g of cell dry weight; mycobactins were between 1 and 10 mg per g of cell dry weight. M. paratuberculosis (13 strains) and 13 strains of M. avium, both species dependent upon mycobactin for growth, failed to produce spectrophotometrically detectable amounts of mycobactin (less than 0.2 microgram per g of cell dry weight), although mycobactin could be recognized in one strain of M. avium grown with an additional supply of salicylate and examined by a radiolabeling technique. On repeated subculture three of the mycobactin-dependent strains of M. avium, but none of those of M. paratuberculosis, lost their mycobactin dependence and on reexamination were found to produce their own mycobactin at 0.3 mg per g of cell dry weight. It is concluded that mycobactin biosynthesis is probably strongly repressed in the mycobactin-dependent strains rather than being a genetic deletion. The exochelins, when examined by high-pressure thin-layer chromatography were revealed as being multiples of similar compounds, with up to 20 individual iron-binding compounds being recognizable with some strains. It is argued that the exochelins represent the single most important means of iron acquisition in mycobacteria growing in vitro and in vivo, and their elaboration by the fastidious M. paratuberculosis and related species explains how these organisms are able to grow in vivo in the absence of an external supply of mycobactin.

Chromatography, Thin Layer↗
PubMed2006

Removal of pharmaceuticals in drinking water treatment: effect of chemical coagulation.

The removal of selected pharmaceuticals (diclofenac, ibuprofen, bezafibrate, carbamazepine and sulfamethoxazole) by chemical coagulation was studied. Jar test experiments were done in MilliQ water, in lake water and in commercial humic acid solutions using aluminium (pH 6) and ferric sulphate (pH 4.5). The concentrations of the pharmaceuticals in the studied water samples were determined by HPLC analysis and UV detection. In MilliQ water coagulation, the pharmaceuticals were poorly removed (< 10%) with the exception of diclofenac, which was removed up to 66% with ferric sulphate. This compound was also the only pharmaceutical removed (30%) during the lake water coagulation with ferric sulphate. In the presence of dissolved humic matter, diclofenac as well as ibuprofen and bezafibrate could be removed by ferric sulphate coagulation. The removal of diclofenac reached a maximum of 77%, while 50% of ibuprofen and 36% of bezafibrate were removed. Hence, a high amount of high-molecular-weight dissolved organic matter enhanced the removal of ionisable pharmaceuticals. The non-ionisable compounds, carbamazepine and sulfamethoxazole, were not affected by the coagulation processes studied. Although conditions such as high humic material content, low coagulation pH and ferric coagulant increase the removal of certain ionic pharmaceuticals, it can be concluded that by coagulation it is not possible to entirely remove pharmaceuticals from water.

Alum Compounds↗
PubMed1975

Kinetic studies on the specificity of chelate-iron uptake in Aspergillus.

Three strains of the fungus Aspergillus, Aspergillus quadricinctus (E. Yuill), A. fumigatus (Fresenius), and A. melleus (Yukawa), each producing different iron-chelating compounds during iron-deficient cultivation, were used for 55Fe3+ uptake measurements. Iron from chelates of the ferrichrome-type family was taken up by young mycelia of all strains tested, irrespective of the ferrichrome-type compound these strains predominantly produce in low-iron cultures. Ferrichrysin-producing strains, however, seem to favor ferrichrysin iron uptake, whereas ferrichrome, ferricrocin, and even ferrirubin showed similar iron transport properties in all of these strains. Compared to iron uptake from ferrichrome-type compounds (Km approximately 4 uM) iron uptake from fusigen revealed completely different kinetic values (Km approximately 50 to 80 muM). Iron from exogenous chelates, e.g., from coprogen produced by Neurospora crassa for ferrioxamine B produced by Streptomyces pilosus, can obviously not be taken up by Aspergillus, confirming the pronounced specificity of chelate-iron transport in fungi.

Aspergillus↗
PubMed2005

Synthesis and chloroquine-enhancing activity of Na-deacetyl-ferrocenoyl-strychnobrasiline.

Several strychnobrasiline derivatives have been synthesized to overcome the lack of in vivo reversal activity of the parent compound. In the present study, N(a)-deacetyl-ferrocenoyl-strychnobrasiline was synthesized by condensing N(a)-deacetyl-strychnobrasiline with ferrocenic acid previously treated with oxalyl chloride. While the in vitro antiplasmodial activity of the test compound (IC(50)=4.83 microg/mL) was increased 15-fold compared to that of strychnobrasiline, and the in vitro enhancing activity was found to be similar to that of the parent compound, the compound was devoid of any in vivo potentiating effect, and an antagonistic effect was even observed at higher doses. Based on the overall results on the hemisynthesis of strychnobrasiline derivatives for better reversal activity, this strategy has appeared to be of little value for useful drugs.

Alkaloids↗
PubMed1991

High-performance liquid chromatographic separation of racemic and diastereomeric mixtures of 2,4-pentadienoate-iron tricarbonyl derivatives.

beta-Cyclodextrin chiral stationary phase facilitates the chiral separation of the (+/-)-methyl-5-formyl-2,4-pentadienoate-iron tricarbonyl (1) racemic mixture. The separation of oxazolidine derivatives 2 and 3 diastereomers were achieved with a C18 column but the compounds underwent in-column hydrolysis to give (-)- and (+)-1, respectively. This hydrolysis was exploited for the determination of 2 and 3 by the beta-cyclodextrin column, namely 2 and 3 were initially and completely hydrolyzed in the column to give (-)- and (+)-1 and this racemic mixture was then separated by this chiral column.

Chromatography, High Pressure Liquid↗
PubMed1981

Factors affecting the absorption of iron from Fe(III)EDTA.

1. The modification of iron absorption from Fe(III)EDTA by agents known to promote or inhibit absorption was examined in 101 volunteer multiparous Indian women. Fe absorption from Fe(III)EDTA was compared with absorption of intrinsic food Fe in a further twenty-eight subjects. Finally the urinary excretion of radio-Fe after oral administration of 59Fe(III)EDTA was studied in twenty-four subjects and evidence of intraluminal exchange of Fe was examined. 2. Fe absorption from maize porridge fortified with Fe(III)EDTA was more than twice that from porridge fortified with FeSO4 . 7H2O. 3. Although bran decreased Fe absorption from FeSO4 . 7H2O approximately 11-fold, it had no significant effect on Fe absorption from Fe(III)EDTA. Nevertheless tea, which is a more potent inhibitor of Fe absorption, decreased absorption from Fe(III)EDTA 7-fold. 4. Fe absorption from Fe(III)EDTA given in water was only increased 40% by addition of 3 mol ascorbic acid/mol Fe but by 7-fold when the relative proportions were increased to 6:1. This enhancing effect was blunted when the Fe(III)EDTA was given with maize porridge. In these circumstances, an ascorbate:iron value of 3:1 (which doubles absorption from FeSO4 . 7H2O) produced no significant increase in Fe absorption, while a value of 6:1 produced only a 2 . 5-fold increase. 5. Fe absorption from Fe(III)EDTA was not altered by addition of maize porridge unless ascorbic acid was present. 6. Less than 1% of 59Fe administered as 59Fe(III)EDTA was excreted in the urine and there was no inverse relationship between Fe absorption and the amounts excreted (r 0 . 58, P less than 0 . 05). 7. Isotope exchange between 59Fe(III)EDTA and 59FeSO4 . 7H2O was demonstrated by finding a similar relative value for the two isotopes in urine and erythrocytes when the two labelled compounds were given together orally. This finding was confirmed by in vitro studies, which showed enhanced 59Fe solubilization from 59FeSO4 . 7H2O in maize porridge when unlabelled Fe(III)EDTA was added. 8. Although Fe absorption from Fe(III)EDTA was marginally higher it appeared to form a common pool with intrinsic food iron in most studies. It is postulated that the mechanism whereby Fe(III)EDTA forms a common pool with intrinsic food Fe differs from that occurring with simple Fe salts. When Fe is present in the chelated form it remains in solution and is relatively well absorbed because it is protected from inhibitory ligands. Simple Fe salts, however, are not similarly protected and are absorbed as poorly as the intrinsic food Fe. 9. It is concluded that Fe(III)EDTA may be a useful compound for food fortification of cereals because the Fe is well absorbed and utilized for haemoglobin synthesis. The substances in cereals which inhibit absorption of simple Fe salts do not appear to inhibit absorption of Fe from Fe(III)EDTA.

Adult↗
PubMed2004

Synthesis and characterization of carboxylate-rich complexes having the [Fe2(mu-OH)2(mu-O2CR)]3+ and [Fe2(mu-O)(mu-O2CR)]3+ cores of O2-dependent diiron enzymes.

The {Fe2(mu-OH)2(mu-O2CR)}3+ and {Fe2(mu-O)(mu-O2CR)}3+ cores of the carboxylate-bridged diiron(III) centers in the enzyme active sites were reproduced by small molecule model complexes that were prepared through direct oxygenation of the mononuclear iron(II) complexes. Upon oxygenation of [Fe(O2CArTol)2(Hdmpz)2], where -O2CArTol is 2,6-di(p-tolyl)benzoate and Hdmpz is 3,5-dimethylpyrazole, [Fe2(mu-OH)2(mu-O2CArTol)(O2CArTol)3(OH2)(Hdmpz)2] was generated and characterized to share close physical properties with sMMOHox, including delta = 0.45 (2) mm/s, DeltaEQ = 1.21 (2) mm/s, and J = -7.2 (2) cm-1. The compound [Fe2(mu-O)(mu-O2CAr4-FPh)(O2CAr4-FPh)3(Hdmpz)3], where -O2CAr4-FPh is 2,6-di(4-fluorophenyl)benzoate, with delta = 0.51 (2) mm/s, DeltaEQ = 1.26 (2) mm/s, and J = -117.4 (1) cm-1, was isolated as the oxygenation product of [Fe(O2CAr4-FPh)2(Hdmpz)2].

Binding Sites↗
PubMed1990

Isolation of a guanine-malondialdehyde adduct from rat and human urine.

A 1:1 adduct of guanine with malondialdehyde (MDA) was isolated from rat and human urine. This compound was shown to be identical to a synthetic adduct prepared according to the procedure of Seto et al. (Bull. Chem. Soc. Jpn. 58, 3431-3435, 1985). The UV, NMR and other characteristics of the compound were consistent with the tricyclic pyrimidinopurine structure proposed by these investigators. Its endogenous origin is indicated by its presence in the urine of rats fed an MDA-free diet, and by the observation that its excretion increased following iron or carbon tetrachloride administration. It may serve as a marker for nucleic acid modification caused by lipid peroxidation in vivo.

Animals↗
PubMed2004

Chromium removal from aqueous solution by the ferrite process.

This research summarises the results of the study on the removal of chromium by applying the ferrite process to the solutions obtained from two different Cr(VI) reduction processes utilising sodium sulphite and ferrous sulphate as reducing agents. For both solutions containing trivalent chromium ions, the optimum treatment conditions were determined. The generated sludges were characterised by XRD analysis and physical tests. In addition, to explore the dissolution properties of the sludges obtained, they were contacted with the solutions of sulphuric, citric, tartaric, oxalic and ascorbic acids and EDTA. Also, the sludge samples were subjected to standard toxicity characterisation leaching procedure (TCLP) test of USEPA in order to determine the pollution potential. An efficient Cr(III) removal (about 100%) in the solution from the Cr(VI) reduction process utilising sodium sulphite as reducing agent was achieved when the solution was treated at pH 9 and 50 degrees C for 60 min in the presence of Fe2+/Cr3+ weight ratio of 16. For the other Cr(III) solution prepared from Cr(VI) reduction by ferrous sulphate, a Fe2+/Cr3+ weight ratio of 17.9 at the same conditions was found to produce complete removal of Cr(III). It was determined that the spynel chromium-iron compounds obtained in the process were in the form of chromite (Cr2FeO4). Dissolution experiments and TCLP tests show that the concentrations of the chromium dissolved from both sludges were below the limit given as 5 mg l(-1) by USEPA. The results showed that Cr(III) removal through ferrite process provides the advantages that the sludges generated are non-voluminous, easily separable and environmentally stable.

Chromium↗
PubMed2006

Bis[bis(2-pyridylcarbonyl)aminato]iron(III) perchlorate acetonitrile disolvate.

The title compound, [Fe(C12H8N3O2)2]ClO4.2C2H3N, contains Fe(III) in a distorted octahedral coordination environment, with the Fe-N(pyridine) bonds significantly longer than the Fe-N(amine) bonds. The crystal packing involves a bifurcated C-H...(O,O) contact that is also found in all other [M(C12H8N3O2)2] complexes reported previously.

Acetonitriles↗
PubMed1998

Effect of modified hemes on the spectral properties and activity of manganese peroxidase.

Recombinant manganese peroxidase (rMnP), expressed in Escherichia coli as apo-protein, was constituted with Fe(III) protoporphyrin IX, Fe(III) protoporphyrin IX dimethyl ester (DME), Fe(III) deuteroporphyrin (Deut), Fe(III) etioporphyrin III (Etio), and Fe(III) methylpyrrolporphyrin XXI (MPP). The electronic absorption spectra of these hemoproteins were similar to those of native MnP, but absorption maxima were shifted to longer wavelengths in the order of Deut-rMnP, MPP-rMnP, Etio-rMnP, DME-rMnP, and rMnP. All enzymes contained a high-spin, pentacoordinate heme iron as evidenced by the characteristic charge transfer bands in the visible region. The hemoproteins exhibited reduced catalytic activity while maintaining similar substrate Km values compared to native MnP. Compounds I, II, and III were obtained for these hemin-analogue enzymes except for Deut-rMnP. We concluded that the spectral properties of MnP are strongly influenced by porphyrin alpha- and beta-meso edge substituents and manganese oxidation is affected by the gamma-meso edge groups, suggesting a role for the heme propionates in electron transfer during catalysis.

Enzyme Activation↗
PubMed1993

Iron-reducing and free-radical-scavenging properties of apomorphine and some related benzylisoquinolines.

The scavenging and iron-reducing properties of a series of benzylisoquinolines of natural and synthetic origin have been studied. Bulbocapnine, boldine, glaucine, and stepholidine acted as scavengers of hydroxyl radical in the deoxyribose degradation by Fe(3+)-EDTA + H2O2. On the contrary, laudanosoline, apomorphine, protopapaverine, anonaine, and tetrahydroberberine increased deoxyribose degradation by a mechanism related to generation of superoxide anion. Only apomorphine had a stimulating effect in the system using citrate instead of ethylenediaminetetraacetic acid (EDTA) as well as in the absence of chelator. Apomorphine also stimulated DNA damage by Cu2+. The iron-ion reducing ability of apomorphine and laudanosoline was confirmed using cytochrome c. Both compounds scavenged peroxyl radicals in an aqueous medium, while in Fe(3+)-induced microsomal lipid peroxidation apomorphine acted as an inhibitor and laudanosoline stimulated the process. It is suggested that in microsomes the chain-breaking antioxidant properties of apomorphine overcome its possible influence on redox cycling of iron, or prooxidant properties.

Animals↗
PubMed2003

Synthesis, X-ray crystal structure, and redox and electronic properties of iron(III)-polyimidazole complexes relevant to the metal sites of iron proteins.

A new tripod N(3) ligand (L), containing three imidazole rings, was synthesized in good yield. At variance with usual aromatic ligands with N(2) or N(3) donor sets such as pyridine or pyrazole derivatives, L stabilizes the Fe(III) oxidation state. The corresponding iron(III) complexes [Fe(L)Cl(3)] (1) and [Fe(L)(2)](ClO(4))(3) (2) were prepared and characterized by X-ray structural analysis and spectroscopic methods. The coordination environment around all the Fe(III) centers has a distorted octahedral geometry. [Fe(L)Cl(3)] (1) belongs to the monoclinic system, space group P2(1)/n, a = 9.7406(5) A, b = 17.207(2) A, c = 14.615(2) A, beta = 104.448(9)(o) Z = 4, V = 2372.1(4) A(3); R = 0.044, R(w) = 0.055. [Fe(L)(2)](ClO(4))(3) (2) belongs to the monoclinic system, space group P2(1)/c, a = 16.1057(15) A, b = 11.1079(12) A, c = 26.283(2) A, beta = 102.062(10)(o), Z = 4, V = 4598.2(8) A(3); R = 0.0465, R(w) = 0.0902. The Fe-N((i)PrIm) bond lengths are systematically longer than the Fe-N(MeIm) ones. Compound 2 is a highly anisotropic low-spin Fe(III) complex displaying a rather unusual EPR spectrum with a sharp signal at g = 3.5 and a broad one at g approximately 1.6. The fitting of this EPR spectrum is discussed.

Crystallography, X-Ray↗
PubMed2001

Pathways for extracellular Fenton chemistry in the brown rot basidiomycete Gloeophyllum trabeum.

The brown rot fungus Gloeophyllum trabeum uses an extracellular hydroquinone-quinone redox cycle to reduce Fe(3+) and produce H(2)O(2). These reactions generate extracellular Fenton reagent, which enables G. trabeum to degrade a wide variety of organic compounds. We found that G. trabeum secreted two quinones, 2,5-dimethoxy-1,4-benzoquinone (2,5-DMBQ) and 4,5-dimethoxy-1,2-benzoquinone (4,5-DMBQ), that underwent iron-dependent redox cycling. Experiments that monitored the iron- and quinone-dependent cleavage of polyethylene glycol by G. trabeum showed that 2,5-DMBQ was more effective than 4,5-DMBQ in supporting extracellular Fenton chemistry. Two factors contributed to this result. First, G. trabeum reduced 2,5-DMBQ to 2,5-dimethoxyhydroquinone (2,5-DMHQ) much more rapidly than it reduced 4,5-DMBQ to 4,5-dimethoxycatechol (4,5-DMC). Second, although both hydroquinones reduced ferric oxalate complexes, the predominant form of Fe(3+) in G. trabeum cultures, the 2,5-DMHQ-dependent reaction reduced O(2) more rapidly than the 4,5-DMC-dependent reaction. Nevertheless, both hydroquinones probably contribute to the extracellular Fenton chemistry of G. trabeum, because 2,5-DMHQ by itself is an efficient reductant of 4,5-DMBQ.

Benzoquinones↗