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PubMed1989

Contraluminal organic anion and cation transport in the proximal renal tubule: V. Interaction with sulfamoyl- and phenoxy diuretics, and with beta-lactam antibiotics.

In order to study the interaction of sulfamoyl- and phenoxy diuretics as well as of beta-lactam antibiotics with the contraluminal anion and cation transport systems the inhibitory potency of these substances against the influx of 3H-para-aminohippurate, 14C-succinate, 35S-sulfate and 3H-N1-methylnicotinamide into cortical tubular cells have been determined. 1.) 2-, 3- and 4-sulfamoylbenzoate inhibit contraluminal PAH influx. N-dipropyl substitution to yield probenecid or ring-substitution to yield furosemide and piretanide augment the inhibitory potency. However, hydrochlorothiazide and acetazolamide exert only a moderate inhibitory potency. Succinate transport was inhibited by furosemide only. Sulfate transport was inhibited by furosemide and 3-sulfamoyl-4-phenoxybenzoate as well as by probenecid, piretanide, hydrochlorothiazide and acetazolamide. 2.) Phenoxyacetate, -propionate, and -butyrate exert increasing inhibition against PAH transport. The weed-killers 2,4-dichloro-, and 2,4,5-trichlorophenoxyacetate (2,4 D and 2,4,5 T) had a similar inhibitory potency, while ethacrynic acid showed a lower and the uricosuric tienilic acid a higher inhibitory potency. None of the compounds of this group interact with contraluminal succinate transport, and only the multiring-substituted compounds 2,4 D, 2,4,5 T, ethacrynic and tienilic acid interact slightly with the sulfate transporter. 3.) The monocarboxylic penicillins benzylpenicillin and phenoxymethylpenicillin as well as the dicarboxylic ticarcillin interact with the contraluminal PAH transport. The aminopenicillin ampicillin had a lower, and apalcillin a higher inhibitory potency than monocarboxylic penicillin. Benzylpenicillin showed small inhibition against succinate transport and ticarcillin against sulfate transport. 4.) The monocarboxylic cephalosporine, 6315 S Shionogi, and the aminocephalosporines, cephalexin and cefadroxil, showed an app. Ki.PAH as the comparable penicillins. The zwitterions cephaloridine and cefpirome did not interact with the PAH transporter, but with the organic cation (NMN) transporter. Amongst the amino-thiazol-containing compounds cefotaxime, ceftriaxone, and cefodizime, increasing interaction with the PAH transporter was seen dependent of a second ionizable anionic group. Compounds with two ionizable anionic groups (cefsulodin, ceftriaxone, cefodizime) exert also a small inhibitory potency against sulfate transport. None of the cephalosporins interacted with the dicarboxylate transporter. The interaction pattern of the tested compounds is in accordance with the specificity requirements for the contraluminal transporters depending on electrical charge and hydrophobicity.

Animals↗
PubMed2006

catena-Poly[[tetraaquamanganese(II)]-mu-4-(carboxylatomethylsulfanyl)phenoxyacetato].

The title compound, [Mn(C10H8O5S)(H2O)4]n, a one-dimensional manganese(II) complex comprising helical chains bridged by 4-(carboxylatomethylsulfanyl)phenoxyacetate ligands has been characterized by single-crystal X-ray diffraction analysis. Hydrogen-bonding interactions between adjacent chains extend the complex into a three-dimensional supramolecular architecture.

Crystallography, X-Ray↗
PubMed2005

The measurement of urinary hydroxyurea in sickle cell anaemia.

Hydroxyurea is increasingly used in the treatment of sickle cell disease (SCD) although there is little evidence on how best to monitor treatment and compliance. It is also not known why 10-50% patients do not benefit from the drug and whether some of this resistance is because of pharmacokinetic factors. We have developed an assay using mass spectrometry (MS) to measure urinary concentrations of hydroxyurea. We have used this assay to study 12 children and six adults with SCD taking hydroxyurea and found that urinary hydroxyurea was present for at least 12 h following tablet ingestion. Thirty-five urine samples were analysed that were expected to contain hydroxyurea, based on the reported timing of the last dose and hydroxyurea was detected in 29 (83%) of these. There were also marked differences in urinary hydroxyurea concentrations, suggesting pharmacokinetic variability may explain some of the differences in response to hydroxyurea. Urine samples were also analysed by MS for penicillin metabolites and 43 of the 57 (75%) contained phenoxyacetate, suggesting the ingestion of penicillin within the last 12 h. These assays are potentially useful to study hydroxyurea metabolism further, develop optimal dosing regimes and monitor compliance with treatment.

Adolescent↗
PubMed2007

Effect of alpha-asarone and a derivative on lipids, bile flow and Na+/K+-ATPase in ethinyl estradiol-induced cholestasis in the rat.

Administration of ethinyl estradiol (EE), a widely used component of oral contraceptives, has been associated with impairment of bile flow and the capacity to excrete organic anions in man and experimental animals. alpha-Asarone (2,4,5-trimethoxypropenylbenzene) and 2-methoxy-4-(2-propenyl) phenoxyacetic acid (MPPA) have shown hypolipidemic effects. In addition to these effects, we decided to evaluate the properties of these compounds on EE-induced cholestasis. Wistar male rats were injected subcutaneously with 10 mg/kg of EE for 5 days; simultaneously, alpha-asarone or MPPA were also administered and appropriate controls were performed. alpha-asarone and MPPA decreased plasma and bile cholesterol. EE diminished triglycerides total, low-density lipoprotein, high-density lipoprotein and bile cholesterol. MPPA further decreased these lipid parameters. Alkaline phosphatase (an enzyme marker of cholestasis) was increased after administration of EE, but this effect was prevented significantly by alpha-asarone or MPPA administration. Bile flow was importantly decreased by EE and increased by alpha-asarone alone. Furthermore, alpha-asarone or MPPA preserved the normal bile flow in EE-treated rats. EE inhibited the activity of the Na(+)/K(+)-ATPase, while both alpha-asarone and MPPA preserved this enzyme activity. Na(+)/K(+)-ATPase is involved in Na(+)-coupled uptake of bile acids into hepatocytes and, therefore, ultimately is the driving force for the generation of bile flow. Therefore, the anticholestatic effects of alpha-asarone and MPPA, described herein by the first time, may be due to its ability to preserve ATPase activity. This enzyme is negatively regulated by membrane cholesterol, thus the hypolipidemic effects of the compounds tested may be responsible for Na(+)/K(+)-ATPase activity and bile flow maintenance.

Alkaline Phosphatase↗
PubMed1985

Anaerobic degradation of veratrylglycerol-beta-guaiacyl ether and guaiacoxyacetic acid by mixed rumen bacteria.

Veratrylglycerol-beta-guaiacyl ether (0.2 g/liter), a lignin model compound, was found to be degraded by mixed rumen bacteria in a yeast extract medium under strictly anaerobic conditions to the extent of 19% within 24 h. Guaiacoxyacetic acid, 2-(o-methoxyphenoxy)ethanol, vanillic acid, and vanillin were detected as degradation products of veratrylglycerol-beta-guaiacyl ether by thin-layer chromatography, gas chromatography, and gas chromatography-mass spectrometry. Guaiacoxyacetic acid (0.25 g/liter), when added into the medium as a substrate, was entirely degraded within 36 h, resulting in the formation of phenoxyacetic acid, guaiacol, and phenol. These results suggest that the beta-arylether bond, an important intermonomer linkage in lignin, can be cleaved completely by these rumen anaerobes.

Anaerobiosis↗
PubMed1986

Extrapolation of biodegradation results to groundwater aquifers: reductive dehalogenation of aromatic compounds.

The reductive biodegradation of a variety of haloaromatic substrates was monitored in samples from two sites within a shallow anoxic aquifer and was compared with freshwater sediment and sewage sludge. The metabolic capacity existing in methane-producing aquifer material was very similar to that in sediment in that three of four chlorobenzoates, five of seven chlorophenols, and one of two chlorophenoxyacetate herbicides were reductively dehalogenated in both types of incubations. The 2,4-dichlorophenoxyacetate was first converted to a dichlorophenol before dehalogenation occurred. Sewage sludge microorganisms dehalogenated four of seven chlorophenols tested and degraded both phenoxyacetate herbicides by first converting them to the corresponding chlorophenols, but the microorganisms did not transform the chlorobenzoates. In general, the same suite of initial metabolites were produced from a test substrate in all types of samples, as confirmed by cochromatography of the intermediates with authentic material. Aquifer microbiota from a sulfate-reducing site was unable to significantly degrade any of the haloaromatic substrates tested. Biological removal of the sulfate in samples from this site permitted dehalogenation of a model substrate, while stimulation of methanogenesis without removal of sulfate did not. These results demonstrate that dehalogenating microorganisms were present at this site but that their activity was at least partially inhibited by the high sulfate levels.

Anaerobiosis↗
PubMed1997

Introduction of anaerobic dechlorinating bacteria into soil slurry microcosms and nested-PCR monitoring.

Desulfomonile tiedjei and Desulfitobacterium dehalogenans were chosen as model bacteria to demonstrate the introduction of an anaerobic microbia reductive dechlorination activity into nonsterile soil slurry microcosms by inoculation. De novo 3-chlorobenzoate dechlorination activity was established with the bacterium D. tiedjei in microcosms normally devoid of this dechlorination capacity. The addition of D. tiedjei to microcosms supplemented with 20 mM pyruvate as the cosubstrate resulted in total biotransformation of 1.5 mM 3-chlorobenzoate within 7 days. The introduction of the bacterium Desulfitobacterium dehalogenans into nonsterile microcosms resulted in a shortening of the period required for dechlorination activity to be established. In microcosms inoculated with Desulfitobacterium dehalogenans, total degradation of 6 mM 3-chloro-4-hydroxy phenoxyacetic acid (3-Cl-4-OHPA) was observed after 4 days in contrast to the result in noninoculated microcosms, where the total degradation of 3-Cl-4-OHPA by indigenous microorganisms was observed after 11 days. Both externally introduced bacterial strains were detected in soil slurry microcosms by a nested-PCR methodology.

Acetates↗
PubMed1984

Sensitivity of cAMP-stimulated salt secretion in shark rectal gland to "loop" diuretics.

The secretory response of isolated perfused shark rectal gland was characterized with respect to its inhibition by a chemically related series of 5-sulfamoylbenzoic acid derivatives and certain phenoxyacetic acid derivatives. Maximal fluid and salt secretion was elicited with dibutyryl adenosine 3',5'-cyclic monophosphate and theophylline. The potency series established for the 5-sulfamoylbenzoic acid compounds agreed well with the relative potencies previously established for these agents as inhibitors of Na+-K+-Cl- cotransport in the avian erythrocyte. The most potent compound tested (3-benzylamino-4-phenyl-5-sulfamoylbenzoic acid) had a 50% inhibitory concentration value of approximately 5 X 10(-7) M. This compound was approximately 10-fold more effective than bumetanide and 400-fold as inhibitory as furosemide in this system. Ethacrynic acid (EA; 10(-3) M) was a poor inhibitor of rectal gland secretion and was approximately equipotent with its saturated derivative, dihydro EA. In contrast, EA-L-cysteine was fully effective at 10(-4) M, although the EA-D-cysteine adduct was ineffective. These data also qualitatively agree with results obtained in the inhibition of avian erythrocyte Na+-K+-Cl- cotransport and suggest that the rectal gland possesses a serosally oriented "NaCl cotransport" system with pharmacological and perhaps physiological similarities to the Na+-K+-Cl-cotransporter found in erythrocyte and other cell membranes.

Animals↗
PubMed1976

Inhibitory effect of ethacrynic acid on chloride permeability.

Ethacrynic acid inhibits anion movements in ox red blood cells. The I50 for chloride is 7 X 10(-6) M. The inhibitory effect is instantaneous and completely reversed by washing the cells with a Ringer solution, suggesting that reaction with a membrane SH group is not involved in this process. Direct proof that ethacrynic acid does not act by its reactivity with thiol groups is given by experiments with dihydroethacrynic acid, a derivative that lacks the ability to combine with SH groups: the characteristics of inhibition are strictly identical (instantaneous and reversible; I50 equals 9 X 10(-6) M). All the phenoxyacetic derivatives tested were also more or less inhibitory. The relative activity of all the derivatives was highly correlated with their liposolubility, indicating that hydrophobic interaction is important in determining drug effect and influence of steric factors is minimal. The data suggest that inhibition essentially results from a hydrophobic interaction between ethacrynic acid and apolar regions of the membrane protein allowing chloride transport.

Animals↗
PubMed2006

Non-Hodgkin lymphoma and pesticide exposure: 25 years of research.

Over the past 40 years, a substantial rise in the incidence of non-Hodgkin lymphoma (NHL) has been observed. Epidemiologic studies aimed at understanding this rise have revealed some association with occupational exposure. NHL is common among farmers, where pesticides have been described as the culprit. The association between pesticides and NHL has been demonstrated mainly in case-control studies, while retrospective cohorts have been less convincing. Pesticides including chlorphenol and phenoxyacetic acid herbicides, organochlorines, and organophosphate insecticides, carbamates, and fungicides have been associated with NHL. Although the causality has not been clearly proven, both genotoxic and nongenotoxic mechanisms for lymphomagenesis have been proposed. The leveling-off of NHL incidence in certain countries may be the result of a favorable change in pesticide usage patterns. Future studies, such as the Agricultural Health Study, may clarify the uncertainties regarding this issue.

Agricultural Workers' Diseases↗
PubMed1983

The metabolism of the anti-inflammatory drug eterylate in rat, dog and man.

Oral doses of 14C-eterylate were well absorbed by rat and man and excreted mainly in the urine (94% dose by rat in three days and 91% by man in five days). Oral doses to dogs were excreted in similar proportions in both the urine and faeces, although faecal 14C was probably derived in part, from biliary-excreted material. Peak plasma 14C and drug concn. were generally reached between one and three hours after oral doses. In humans, only two metabolites, salicylic acid and 4-acetamido-phenoxyacetic acid, were detected in plasma. The latter was cleared more rapidly than the former and hence plasma salicyclate concn. reached a peak (10.9 and 19.8 micrograms/ml in Subjects 1 and 2, respectively) and initially declined with a half-life of about two-three hours. Plasma 4-acetamidophenoxyacetic acid concn. reached a peak (4.3, 10.0 micrograms/ml, respectively) and declined with a half-life of about one hour. Tissue concn. of 14C were generally greater in dogs than in rats. Highest conc. occurred at three hours in dogs and at one hour in rats. Apart from those in the liver and kidneys, tissue concn. were lower than those in the corresponding plasma. Unchanged drug was not detected in urine or plasma of any species and was rapidly metabolized in human plasma. The major 14C components in human urine were identified as salicyluric acid and 4-acetamidophenoxyacetic acid; minor metabolites were salicylic acid, gentisic acid and paracetamol. These metabolites were also detected in rat urine albeit in different proportions to those in human urine. Dog urine contained less of these metabolites and a major proportion of the 14C was associated with relatively non-polar components. Although salicylic acid and 4-acetamidophenoxyacetic acid were the only major circulating metabolites in man and rat, dog plasma also contained the non-polar urine metabolites.

Acetanilides↗
PubMedDate not supplied

Quantitative structure-activity relationship of phenoxy and benzyloxy acid derivatives as antisickling agents.

Quantitative structure activity relationship of Hansch-type has been applied to develop correlation between the calculated physicochemical properties and the in vitro activities of phenoxy and benzyloxyacetic acid derivatives as antisickling agents. The antisickling effect of these compounds was first reported by Abraham et al., and is used as a database of this study. QSAR for these compounds was generated in order to provide more information about the structure requirements for the design of more active antisickling analogs. The solubility ratio A/Ao for 22 phenoxyacetic acids and 15 benzyloxyacetic acids were used to develop equations using hydrophobic (pi), electronic (sigma) and molar refraction (MR) parameters. Equations 1 and 2 with correlation coefficients of 0.872 and 0.894 respectively, were obtained for phenoxy and benzyloxy acetic. Potencies were correlated positively with pi values of ortho, meta and/or para substituents. Positive correlations were also obtained for sigma constants of para and/or meta substituents. Negative correlations, on the other hand, were obtained with the MR values of para substituents in the benzenic ring of the benzyloxy acid series. Using the generated correlation equation 2, three potent antigelling benzyloxyacetic acid derivatives were proposed and reported. These compounds are expected to be very promising antisickling agents having A/A. values of 1.016, 1.124 and 1.138.

Antisickling Agents↗
PubMed1992

[Physiological characteristics of the strains of Cryptococcus deffluens--producers of penicillin acylase].

A fermentation medium balanced by the main components was developed for Cryptococcus diffluens strains producing penicillin-V-acylases (PA). It was shown that the culture needed for production of the enzyme was inductor, which was phenoxyacetic acid (POAA). Additional introduction of ethanol to the medium provided an increase in production of PA by 36 per cent and the culture growth by 25 per cent. Introduction of one of the following substances to the medium with POAA and ethanol i.e. (CN3COO)2Ca, FeSO4, proline or asparagine provided an additional increase in the production level of PA by 24 to 94 per cent. The use of the medium varieties will permit one to isolate highly productive cells of the culture.

Amino Acids↗
PubMed2006

[Study of a newly synthesized substance with a potential to stimulate beta3-adrenergic receptors].

beta3-Adrenoreceptor agonists can stimulate lipolysis in the white adipose tissue and thermogenesis in the brown adipose tissue. These activities could be useful in the treatment of obesity and the associated metabolic syndrome. The effects of six-week oral administration of the newly synthesized substance B496 (methyl-4-[2-[2-hydroxy-3-(4-ethylcarbamoyl)phenoxyprophyl]amino]etyl)-phenoxyacetate hydrochloride) on serum glucose, triglycerides, total cholesterol, and leptin levels were studied in male Wistar rats fed with a high-fat diet. The animals were divided into a group treated with B496 (5 mg dissolved in 1 litre of water) and a control group. The results indicated a significant reduction in serum glucose levels (-26 %, p<0,01), triacylglyceride levels (-21 %, p<0,05) and leptin levels (-43 %, p<0,01). Further the effect of a single intraperitoneal dose (1 mg/kg) of B496 and BRL-37344 on serum leptin levels in the C57Bl/6J mouse was investigated. Administration of BRL-37344 resulted in a significant decrease in serum leptin levels (-55 %, p<0,001). This reduction was not demonstrated by newly synthesized substance B496.

Adrenergic beta-Agonists↗
PubMed1978

Treatment of arterial hypertension with tienilic acid, a new diuretic with uricosuric properties.

Tienilic acid--2,3-dichloro-4-(2-thienyl-carbonyl)phenoxyacetic acid--is a new diuretic with uricosuric properties. Nineteen patients with moderate arterial hypertension were treated for 5 consecutive weeks in a randomized fashion in a double-blind study with either tienilic acid or hydrochlorothiazide. Blood pressure was significantly reduced and to the same degree with both drugs. In 7 of the 11 patients receiving tienilic acid the daily dose was increased from 250 to 500 mg after 2 weeks, and in 2 of the 8 patients taking hydrochlorothiazide the daily dose was increased from 50 to 100 mg. Because of the potent uricosuric action of tienilic acid the mean serum urate concentration decreased from 6.3 to 3.3 mg/dL in the patients taking the drug. In contrast, the patients receiving hydrochlorothiazide the mean serum urate concentration increased from 6.1 to 7.8 mg/dL. Moderate hypokalemia of almost identical degree (mean serum potassium values 3.6 and 3.5 mmol/L) and mild metabolic alkalosis were observed in both groups. Tienilic acid had a marked hypocalciuric effect, which was of the same magnitude as the observed with hydrochlorothiazide. During the 5 weeks of treatment no significant change in renal or liver function was observed in either group. There were no hematologic complications and the drug was remarkably well tolerated. Tienilic acid, because of its unique character as a diuretic, hypouricemic and antihypertensive agent, should become the preferred drug for the treatment of arterial hypertension.

Adult↗
PubMed1987

Soft tissue sarcoma and non-Hodgkin's lymphoma in relation to phenoxyherbicide and chlorinated phenol exposure in western Washington.

A population-based case-control study was conducted in western Washington State to evaluate the relationship between occupational exposure of men aged 20-79 to phenoxyacetic acid herbicides and chlorinated phenols and the risks of developing soft tissue sarcoma (STS) and non-Hodgkin's lymphoma (NHL). Occupational histories and other data were obtained by personal interviews for 128 STS cases and 576 NHL cases, diagnosed between 1981 and 1984, and for 694 randomly selected controls without cancer. Among the study subjects with any past occupational exposure to phenoxyherbicides, the estimated relative risk and 95% confidence interval of developing STS was 0.80 (0.5-1.2), and of developing NHL, 1.07 (0.8-1.4). Risk estimates of developing STS and NHL associated with past chlorophenol exposure were 0.99 (0.7-1.5) and 0.99 (0.8-1.2), respectively. No increasing risk of either cancer was associated with overall duration or intensity of chemical exposure or with exposure to any specific phenoxyherbicide per se. However, estimated risks of NHL were elevated among men who had been farmers, 1.33 (1.03-1.7), forestry herbicide applicators, 4.80 (1.2-19.4), and for those potentially exposed to phenoxyherbicides in any occupation for 15 years or more during the period prior to 15 years before cancer diagnosis, 1.71 (1.04-2.8). Increased risks of NHL were also observed among those with occupational exposure to organochlorine insecticides, such as DDT [1.82 (1.04-3.2)] and organic solvents [1.35 (1.06-1.7)], and to other chemicals typically encountered in the agricultural, forestry, or wood products industries. These results demonstrate small but significantly increased risks of developing NHL in association with some occupational activities where phenoxyherbicides have been used in combination with other types of chemicals, particularly for prolonged periods. They do not demonstrate a positive association between increased cancer risks and exposure to any specific phenoxyherbicide product alone. Moreover, these findings provide no evidence of increased risks of developing NHL associated with chlorinated phenol exposure or of developing STS associated with exposure to either class of chemical.

Adult↗
PubMed1976

[Increasing the threshold sensitivity of the spot detection reaction on a chromatogram].

A known analytical procedure was used for increasing the sensitivity threshold of the reaction of the zone opening on chromatogrammes. The procedure was the following: the carboxylic acid admixtures determined chromatographically were previously extracted from dry samples of the test-compounds into an optimal solvent. The expediency of the procedure was shown on examples of phenylacetic, phenoxyacetic and isoxasolcarboxylic acids present as admixtures in semisynthetic penicillins and raw materials used for their preparation. The threshold sensitivity was increased by 6 to 9 times. The chromatographic separation was performed in a fixed layer of Silica Gel KSK treated with a buffer. The mobile phase was used in the form of a solvent system: n-heptan-glacial acetic acid (95:5).

Carboxylic Acids↗
PubMed1996

Differential eudismic ratios in the antagonism of human platelet function by phenoxy- and thiophenoxyacetic acids.

The antilipidemic drug clofibric acid (CPIB) exhibits antiplatelet effects. In order to examine the role of enantioselectivity and hydrophobicity, the mono(desmethyl) enantiomers of 2-(4-chlorophenoxy)propanoic acid (CPPA), related butanoate homologs, 2-(4-chlorophenoxy)butanoic acid (CPBA), thioether relatives, 2-(4-chlorothiophenoxy)propanoic acid (CTPA) and corresponding butanoate homologs, 2-(4-chlorothiophenoxy)butanoic acid (CTBA) were studied. All compounds inhibit prostaglandin-dependent human platelet aggregation and serotonin secretion induced by ADP. For the phenoxy acid series, (+)-(R)-CPPA is 5-fold more potent than either (-)-(S)-CPPA or CPIB giving a rank order potency of (+)-(R)-CPPA > (+)-(R)-CPBA > (-)-(S)-CPPA > (-)-(S)-CPBA. With the exception of (-)-(S)-CTPA, all thiophenoxy acid enantiomers are less potent than their respective phenoxy acid isomers [(+)-(R)-CTPA > (-)-(S)-CTPA > (+)-(R)-CTBA > (-)-(S)-CTBA]. The same rank order of potencies are observed against responses induced by arachidonic acid (AA) with the exception of CPIB which is inactive. However, inhibition of thrombin-induced [3H]-AA release by phenoxyacetic acids is not stereoselective but correlates with hydrophobicity.

Arachidonic Acid↗