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At least 739 records · Page 41Linked to original sources
PubMed2001

Partial oxidation by ozone to remove recalcitrance from wastewaters--a review.

Xenobiotic organics produced by modern industrial processes resist conventional biological wastewater treatment. Ozone pretreatment to improve biodegradation via partial oxidation is a potential solution for this recalcitrance. Ozone forms no additional sludge, removes colour and has two modes of action that can be utilised according to the wastewater constituents. The preozonation of a variety of wastewaters and model compounds is reviewed here. Of the industrial processes examined, the associated recalcitrant organic compounds were generally halogenated heterocyclic or nitrogenous aromatics, aliphatic polymers or polyaromatics. Initial optimisation of ozone dose ensured the occurrence of partial oxidation, where over 90% parent compound transformation was required to give best results in the subsequent biological process. Ozonation intermediate and end-products included ketones, aldehydes and organic acids that were more biodegradable than the parent compounds. Biodegradability improvement was assessed using TOC, COD, BOD, BOD/COD ratio and OUR. Actual process feasibility and performance was evaluated using various combined ozonation-biodegradation trials; textile dying and finishing effluent being one area of application. Kinetic studies of chemical and biological stages facilitated process optimisation and can assist scale-up. The main factors affecting ozonation performance were pH, the nature and concentration of oxidisable organics, ozone dose, competition between the target compound and biodegradable by-products, the presence of oxidant scavengers, and the efficiency of ozone mass transfer. The formation of toxic or recalcitrant by-products has been found to occur in some cases, necessitating knowledge of wastewater constituents and trials on a site-by-site basis.

Biodegradation, Environmental↗
PubMed2003

Effect of halogenated substituents on the metabolism and estrogenic effects of the equine estrogen, equilenin.

Estrogen replacement therapy has been correlated with an increased risk for developing breast and endometrial cancers. One potential mechanism of estrogen carcinogenesis involves metabolism of estrogens to 2- and 4-hydroxylated catechols, which are further oxidized to electrophilic/redox active o-quinones that have the potential to both initiate and promote the carcinogenic process. Previously, we showed that the equine estrogens, equilin and equilenin, which are major components of the estrogen replacement formulation Premarin (Wyeth-Ayerst), are primarily metabolized to the catechol, 4-hydroxyequilenin. This catechol was found to autoxidize to an o-quinone causing oxidation and alkylation of DNA in vitro and in vivo. To block catechol formation from equilenin, 4-halogenated equilenin derivatives were synthesized. These derivatives were tested for their ability to bind to the estrogen receptor, induce estrogen sensitive genes, and their potential to form catechol metabolites. We found that the 4-fluoro derivatives were more estrogenic than the 4-chloro and 4-bromo derivatives as demonstrated by a higher binding affinity for estrogen receptors alpha and beta, an enhanced induction of alkaline phosphatase activity in Ishikawa cells, pS2 expression in S30 cells, and PR expression in Ishikawa cells. Incubation of these compounds with tyrosinase in the presence of GSH showed that the halogenated equilenin compounds formed less catechol GSH conjugates than the parent compounds, equilenin and 17beta-hydroxyequilenin. In addition, these halogenated compounds showed less cytotoxicity in the presence of tyrosinase than the parent compounds in S30 cells. Also, as stated above, the 4-fluoro derivatives showed similar estrogenic effects as compared with parent compounds; however, they were less toxic in S30 cells as compared to equilenin and 17beta-equilenin. Because 17beta-hydroxy-4-halogenated equilenin derivatives showed higher estrogenic effects than the halogenated equilenin derivatives in vitro, we studied the relative ability of the 17beta-hydroxy-4-halogenated equilenin derivatives to induce estrogenic effects in the ovariectomized rat model. The 4-fluoro derivative showed higher activity than 4-chloro and 4-bromo derivatives as demonstrated by inducing higher vaginal cellular differentiation, uterine growth, and mammary gland branching. However, 17beta-hydroxy-4-fluoroequilenin showed a lower estrogenic activity than 17beta-hydroxyequilenin and estradiol, which could be due to alternative pharmacokinetic properties for these compounds. These data suggest that the 4-fluoroequilenin derivatives have promise as alternatives to traditional estrogen replacement therapy due to their similar estrogenic properties with less overall toxicity.

Adenocarcinoma↗
PubMed1990

Reactivity of ebselen and related selenoorganic compounds with 1,2-dichloroethane radical cations and halogenated peroxyl radicals.

The reactivity of ebselen, 2-phenyl-1,2-benzisoselenazol-3(2H)one, and structurally related analogues was studied by pulse radiolysis. The rate constant for the reaction of ebselen with trichloromethylperoxyl radicals was determined to be 2.9 X 10(8) M-1 s-1, while its sulfur analogue, 2-phenyl-1,2-benzisothiazol-3(2H)one, was oxidized at much lower rates, k less than or equal to 10(7) M-1 s-1. Among several derivatives studied, the only other compound that exhibited a high rate constant was 2-(methylseleno)-benzoic acid-N-phenylamide. Oxidation of ebselen by other halogenated peroxyl radicals was also carried out and revealed a direct relationship between rate constant and the degree of halogenation of the oxidant. The transient radicals generated during oxidation of ebselen and the analogues were characterized by optical absorption and conductivity measurements and were attributed to one-electron-oxidized radical cations. The oxidation potentials were determined by cyclic voltammetry. Comparative evaluation of the in vitro behavior during microsomal lipid peroxidation revealed ebselen to be the most potent antioxidant of the compounds investigated, 2-(Methylseleno)-benzoic acid-N-phenylamide, despite its high rate constant for oxidation by halogenated peroxyl radicals, was found to be a poor antioxidant. The rate constant of oxidation of ebselen by trichloromethylperoxyl radicals is comparable to that of alpha-tocopherol under similar conditions, underscoring the potential pharmacological interest of ebselen as an antioxidant.

Antioxidants↗
PubMed1996

Synthesis and muscarinic activities of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives.

A series of 3-(pyrazolyl)-1,2,5,6-tetrahydropyridine derivatives (B) was synthesized and tested for muscarinic activity in receptor binding assays using [3H]-oxotremorine-M (3H-OXO-M) and [3H]-pirenzepine (3H-PZ) as ligands. Potential muscarinic agonistic or antagonistic properties of the compounds were determined using binding studies measuring their potencies to inhibit the binding of 3H-OXO-M and 3H-PZ. Preferential inhibition of 3H-OXO-M binding was used as an indicator for potential muscarinic agonistic properties; this potential was confirmed in functional studies on isolated organs. All compounds with agonistic properties showed 3H-PZ/3H-OXO-M potency ratios in excess of 20. In contrast, for antagonists this ratio was found to be close to unity. Mono-halogenation resulted in compounds (4b and 4d) with M3 agonistic properties as shown by their atropine sensitive stimulant properties in the guinea pig ileum, but with very little or no M1 activity. Some minor in vivo effects were observed for both these compounds, with the iodinated compound 4d inducing salivation. Compound 4d also showed some positive mnemonic properties in rats where spatial short-term memory had been compromised by temporary cholinergic depletion. These data indicate that some M3 agonism may be desired in therapeutic agents aimed at the treatment of the cognitive deficits of Alzheimer's disease patients.

1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine↗
PubMed1984

Determination of phenylurea pesticides by high-performance liquid chromatography with UV and photoconductivity detectors in series.

High-performance liquid chromatographic (HPLC) separations of eighteen phenylurea pesticides were investigated using both reversed-phase and normal-phase systems. A photoconductivity detector, which responds selectively to ionic products formed via postcolumn UV irradiation of photolabile analytes, was connected in tandem with a UV detector permitting serial dual detection of these compounds. The photoconductivity detector responded selectively to the thirteen halogen and sulfur containing compounds whereas the UV detector responses were of the same order of magnitude for all eighteen compounds at 250 nm. The HPLC-UV-photoconductivity detection system was successfully applied to the determination of chloroxuron in strawberries at the official tolerance level of 0.5 ppm. The tandem detectors combined with a choice of columns and chromatographic modes offers enhanced selectivity for the HPLC analysis of these pesticides as trace contaminants in complex samples.

Chromatography, High Pressure Liquid↗
PubMed2001

Structural requirements for voltage-dependent block of muscle sodium channels by phenol derivatives.

We have studied the effects of four different phenol derivatives, with methyl and halogen substituents, on heterologously expressed human skeletal muscle sodium channels, in order to find structural determinants of blocking potency. All compounds blocked skeletal muscle sodium channels in a concentration-dependent manner. The methylated phenol 3-methylphenol and the halogenated phenol 4-chlorophenol blocked sodium currents on depolarization from -100 mV to 0 mV with IC(50) values of 2161 and 666 microM respectively. Methylation of the halogenated compound further increased potency, reducing the IC(50) to 268 microM in 2-methyl-4-chlorophenol and to 150 microM in 3,5-dimethyl-4-chlorophenol. Membrane depolarization before the test depolarization increased sodium channel blockade. When depolarizations were started from -70 mV or when a 2.5 s prepulse was introduced before the test pulse inducing slow inactivation, the IC(50) was reduced more than 3 fold in all compounds. The values of K(D) for the fast-inactivated state derived from drug-induced shifts in steady-state availability curves were 14 microM for 3,5-dimethyl-4-chlorophenol, 19 microM for 2-methyl-4-chlorophenol, 26 microM for 4-chlorophenol and 115 microM for 3-methylphenol. All compounds accelerated the current decay during depolarization and slowed recovery from fast inactivation. No relevant frequency-dependent block after depolarizing pulses applied at 10, 50 and 100 Hz was detected for any of the compounds. All the phenol derivatives that we examined are effective blockers of skeletal muscle sodium channels, especially in conditions that are associated with membrane depolarization. Blocking potency is increased by halogenation and by methylation with increasing numbers of methyl groups.

Cell Line↗
PubMed1975

Mechanism of induction of RNA tumor viruses by halogenated pyrimidines.

Frome these studies on JLS V-9 cells, a number of conclusions can be drawn about the mechanism of MuLV induction by halogenated pyrimidines. The compounds can induce virus from otherwise healthy cells as long as deoxycytidine is present along with the inducing agent. The compounds must be present during the S phase of the cell cycle and must be incorporated into DNA in order to induce virus (Teich et al. 1973). Only one strand of DNA need be substituted by BrdU or IdU in order to induce virus, because a one-hour period of incorporation leads to induction. From these results it is possible to construct a model for how halogenated pyrimidines are able to induce viruses from otherwise uninfected cells. Because the critical period for the incorporation of the compound is a restricted segment of the S phase of the cell, there would appear to be a critical segment of the genetic information of the cell which, when substituted with BrdU or IdU, leads to a transcriptional derepression. Presumably the critical segment of DNA is either a controlling element of the integrated provirus or it is a separate gene which controls the expression of the integrated provirus. Whichever is true, these results strongly imply that the search for specific repressors of the segments of mammalian DNA is likely to be successful and that RNA tumor viruses may offer a system in which such repression systems can be identified and investigated.

Bromodeoxyuridine↗
PubMed1991

Use of artificial intelligence in structure-affinity correlations of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) receptor ligands.

The Computer-Automated Structure Evaluation (CASE) Program, an expert system that automatically selects relevant descriptors for structure-activity relationships, has been used to analyze the binding of various ligands to the tetrachloro-dibenzo-p-dioxin (TCDD) receptor or Ah receptor. Two databases were analyzed. One database contained 136 polycyclic aromatic hydrocarbons (PAH), substituted dibenzo-p-dioxins, dibenzofurans and biphenyls whose binding affinities were measured by a sucrose density gradient technique. The other 87 compound database contained PAH, nitro-PAH, halo-PAH and N-heterocycles. Their binding affinities were measured by the electrofocusing assay. Within each training set significant correlations between the affinity for the TCDD receptor and relevant molecular fragments identified by the CASE program were observed. Among the halogenated aromatic hydrocarbons, fragments containing lateral halogens and a longitudinal hydrogen appeared important for TCDD receptor binding. The fragments of PAH and heterocyclic compounds that were most activating with respect to TCDD receptor binding were found to contain the classical 'bay' region and were in fact identical to the fragments found previously to be related to carcinogenicity. It was found that the activating fragments from PAH and heterocyclic compounds were different from those found within the halogenated compounds such as dibenzo-p-dioxins, dibenzofurans and biphenyls. One interpretation of the data is that two different recognition sites may be involved in Ah receptor binding.

Artificial Intelligence↗
PubMed1992

Structure and function of vanadium compounds in living organisms.

Vanadium has been recognized as a metal of biological importance only recently. In this mini-review, its main functions uncovered during the past few years are addressed. These encompass (i) the regulation of phosphate metabolizing enzymes (which is exemplified for the inhibition of ribonucleases by vanadate), (ii) the halogenation of organic compounds by vanadate-dependent non-heme peroxidases from seaweeds, (iii) the reductive protonation of nitrogen (nitrogen fixation) by alternative, i.e. vanadium-containing, nitrogenases from N2-fixing bacteria, (iv) vanadium sequestering by sea squirts (ascidians), and (v) amavadine, a low molecular weight complex of V(IV) accumulated in the fly agaric and related toadstools. The function of vanadium, while still illusive in ascidians and toadstools, begins to be understood in vanadium-enzyme interaction. Investigations into the structure and function of model compounds play an increasingly important role in elucidating the biological significance of vanadium.

Animals↗
PubMed1998

[Effect of halogenated quaternary ammonium on cultured tumor cells].

This work reports the action of one halogenic quaternary ammonium compound on the in-vitro proliferation of different lines of human cancer cells. IC 50 inhibition growth was observed at a concentration of 2.10(-6) mol and T1 growth at 3.10(-6)-5.10(-5) mol. These results seem to indicate that halogenic quaternary ammoniums present a potent growth inhibitory activity on different cancer cells lines. The presence of a quaternary ammonium group, responsible for some alkylating effect, could explain such a result.

Cell Division↗
PubMed1995

Synthesis and anti-HIV-1 activity of 4,5,6,7-tetrahydro-5-methylimidazo-[4,5,1-jk][1,4]benzodiazepin- 2(1H)-one (TlBO) derivatives. 4.

In previous papers, we have described the discovery of a new series of compounds, 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1 H)- ones, TlBO (1 and 1a), with potent anti-HIV-1 activity and the synthesis of analogues to better define the structure-activity relationships (SAR) in terms of changes in substituents at the N-6 position and variations of the five-membered urea ring as well as the seven-membered diazepine ring. This paper describes the synthesis of TlBO analogues with various substitutents on the aromatic ring and their SAR in terms of anti-HIV-1 properties. Substituents on the 8-position furnished the most rewarding results and gave a large improvement in potency versus the parent compound. These included halogen, thiomethyl, and methyl. Analogues like 8-cyano, -methoxy, and -acetylene were equipotent, while 8-amino, -acetylamino, -dimethylamino, and -nitro were inactive (Table 1). Substituents at the 9-position tended to have little effect on activity, and 10-substituents decreased activity. The 8-chloro compound 6a with IC50 = 0.0043 microM is currently under clinical development.

Antiviral Agents↗
PubMed2004

Fate of chlorinated fatty acids in migrating sockeye salmon and their transfer to arctic grayling.

To investigate whether biotransport constitutes an entry route into pristine ecosystems for nonpersistent, nonvolatile xenobiotic compounds, extractable organically bound halogen in sockeye salmon (Oncorhynchus nerka) from Alaska was determined before and after spawning migration. The major organohalogen compounds in the salmon were halogenated fatty acids, predominantly chlorinated species that accounted for up to 35% of the extractable, organically bound chlorine (EOCl) in the fish tissues. The amount of chlorinated fatty acids in the salmon muscle decreased as a result of spawning migration. The decrease was correlated with that of triacylglycerols in the salmon muscle, indicating the chlorinated fatty acids to be mobilized and metabolized to approximately the same extent as the other fatty acids. Chlorinated fatty acids were also transferred to the maturing roe in a manner similar to that of the unchlorinated fatty acids. Lipids of the Arctic grayling (Thymallus arcticus), a fish resident to the spawning lake of the salmon, contained higher concentrations of chlorinated fatty acids than grayling in a lake without migratory salmon. This may reflect a food-chain transfer of the chlorinated fatty acids originating from the salmon, demonstrating a long-range transport route for this type of pollutants to pristine areas.

Animals↗