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PubMed2001

Antioxidant activity of 5-alkoxymethyl-6-chromanols.

The 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols (II) are excellent antioxidants against autoxidising safflower oil (ASO), although not as good as 2,2,5,7,8-pentamethyl-6-chromanol (I), the model compound of alpha-tocopherol. The aim of this work was to determine whether the rate of reaction of (II) with the radicals diphenylpicrylhydrazyl (DPP*) and galvinoxyl (ArO*) was directly proportional to their antioxidant activity against ASO. Compounds (II) reacted faster with DPP* than with ArO* but, in each case, slower than compound (I). The rates of reaction of I and II with both radicals followed the order I > II (R = H) > II (R = CH3) > II (R = other alkyls) and were directly proportional to their antioxidant activity against ASO.

Alkylation↗
PubMed2004

Simultaneous determination of isoflavones and bisphenol A in rat serum by high-performance liquid chromatography coupled with coulometric array detection.

A method for simultaneous detection and quantification is presented to determine the presence of isoflavones and bisphenol A in a biological sample. A coulometric array detector was used with reversed-phase high-performance liquid chromatography (HPLC). Daidzein (1), glycitein (2), genistein (3) and their glucoside conjugates, daidzin (4), glycitin (5) and genistin (6), were measured as phytochemicals. Also assayed here was equol (7), a metabolite from compound 1, and bisphenol A (8), an industrial chemical that acts as an endocrine disrupter. All chemicals were simultaneously detected by using a 600-mV single detection voltage with high efficacy. A mixture of 1, 3 and 8 was orally administered to rats, and the levels of these three chemicals in the serum were clearly increased after a 4 kU beta-glucuronidase treatment. The levels of compounds 1 and 3 in the serum were detected at 1665 and 2040 ng/ml, while 8 was at a low level of 417 ng/ml. Compound 7 in the serum was not detected until after enzymatic hydrolysis (72 ng/ml). These results suggest that this analytical method would be useful for metabolic and pharmacokinetic studies on isoflavones and bisphenol A.

Administration, Oral↗
PubMed2002

Electrochemical DNA biosensor for analysis of wastewater samples.

The application of a disposable electrochemical DNA biosensor to wastewater samples is reported. The DNA biosensor is assembled by immobilising double-stranded calf thymus DNA on the surface of a disposable, carbon screen-printed electrode (SPE). The oxidation signal of the guanine base, obtained by a square wave voltammetric scan, is used as analytical signal. The presence of compounds with affinity for DNA is measured by their effect on the guanine oxidation. The comparison of the results with a toxicity test based on bioluminescent bacteria has confirmed the applicability of the method to real samples.

Animals↗
PubMed2002

Effects of 17beta-estradiol and xenoestrogens on the neuronal survival in an organotypic hippocampal culture.

Xenoestrogens are man-made compounds that mimic the actions of estrogens through interactions with estrogen receptors (ERs). Although xenoestrogens have received a great deal of attention as possible causes of brain disfunctions, little information concerning the effects of xenoestrogens on the central nervous system is available. In this study, we investigated the effects of 17beta-estradiol (E(2)) and four xenoestrogens (17alpha-ethynylestradiol, diethylstilbestrol, p-nonylphenol and bisphenol A (BPA)) on the neuronal survival using organotypic hippocampal slice cultures. When the cultured hippocampal slices were exposed to glutamate (1 mM, 15 min), the CA1-selective neuronal damage was induced. Pretreatment with E(2) and the xenoestrogens (24 h) selectively exacerbated the CA3 neuronal damage caused by glutamate. In spite of the marked difference of binding affinities to ERs, all compounds revealed maximal effects at 1 nM. ER antagonists, tamoxifen and ICI 182,780, did not affect responses to E(2) and the xenoestrogens, indicating that these effects are mediated through mechanisms other than ERs. In spite of the fact that BPA has little interaction with ERs at 1 nM, E(2) and BPA equally increased the expression of N-methyl-D-aspartate receptor in CA3 and upregulated the spine density of the apical portion of CA3 dendrites at 1 nM. These compounds also enhanced the sprouting of mossy fibers to CA3 neurons. These results suggest that exposure to E(2) and xenoestrogens during the developmental stage results in a marked influence on synaptogenesis and neuronal vulnerability through mechanisms other than ERs.

Animals↗
PubMed2002

Antioxidant ortho-benzoyloxyphenyl acetic acid ester, vaccihein A, from the fruit of rabbiteye blueberry (Vaccinium ashei).

A new ortho-benzoyloxyphenyl acetic acid ester, called vaccihein A (1), was isolated from the fruit of rabbiteye blueberry (Vaccinium ashei). The chemical structure was determined on the basis of spectroscopic data. Compound 1 had antioxidative activity using the ferric thiocyanate method. In addition, 1 showed a scavenging effect on the stable free radical 1,1-diphenyl-2-picrylhydrazyl.

Acetates↗
PubMed1983

[Asthma induced by diphenylmethane diisocyanate].

Isocyanates have been widely used in the plastic industry as a curing agent. Tolylene diisocyanate (TDI) is the representative compound popularly used. It may induce respiratory symptoms in some factory workers. Diphenylmethane diisocyanate (MDI) is relatively safer than TDI, and rarely causes symptoms. Here we report four workers frequently exposed to MDI during work. Three of them became asthmatics. Among the asthmatics, two were proven by bronchoprovocation tests to be sensitive to MDI or its compound, and the third one was not sensitive to them. The fourth had no respiratory symptoms, and was not sensitive to isocyanate compound by provocation test. The results indicate a wide range of individual variation in isocyanate sensitivity. The mechanism of this sensitivity is discussed in detail.

Adult↗
PubMed2006

Structure-activity relationships of substituted N-benzyl piperidines in the GBR series: Synthesis of 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-1-(2-trifluoromethylbenzyl)piperidine, an allosteric modulator of the serotonin transporter.

A series of 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-(substituted benzyl) piperidines with substituents at the ortho and meta positions in the aromatic ring of the N-benzyl side chain were synthesized and their affinities and selectivities for the dopamine transporter (DAT), serotonin transporter (SERT), and norepinephrine transporter (NET) were determined. One analogue, 4-(2-(bis(4-fluorophenyl)methoxy)ethyl)-1-(2-trifluoromethylbenzyl)piperidine (the C(2)-trifluoromethyl substituted compound), has been found to act as an allosteric modulator of hSERT binding and function. It had little affinity for any of the transporters. Several compounds showed affinity for the DAT in the low nanomolar range and displayed a broad range of SERT/DAT selectivity ratios and very little affinity for the NET. The pharmacological tools provided by the availability of compounds with varying transporter affinity and selectivity could be used to obtain additional information about the properties a compound should have to act as a useful pharmacotherapeutic agent for cocaine addiction and help unravel the pharmacological mechanisms relevant to stimulant abuse.

Allosteric Regulation↗
PubMed2002

Drugs under investigation for attention-deficit hyperactivity disorder.

There has been substantial development of pharmacological treatments for attention-deficit hyperactivity disorder (ADHD) recently. The greatest change is the approval of new delivery systems for methylphenidate (MPH) and amphetamine (AMP) that permit once a day dosing. There are also a number of new compounds under development for the disorder, including several non-stimulant agents. These compounds target the noradrenergic, histaminergic and dopaminergic systems. The recent developments in the pharmacological treatment of ADHD should increase therapeutic options and the percentage of individuals with the disorder who can be effectively treated.

Animals↗
PubMed2006

Effects of bisphenol A and ethynyl estradiol exposure on enzyme activities, growth and development in the fourth instar larvae of Chironomus riparius (Diptera, Chironomidae).

This study was conducted to determine the toxic effects of bisphenol A (BPA) and ethynyl estradiol (EE), well-known endocrine disruptors, on Chironomus riparius under controlled laboratory conditions. Mortality, enzyme activities, and growth/development parameters were studied as acute, biochemical, and physiological toxicities, respectively. The results of the present study showed activation of catalase and glutathione-S-transferase after BPA and EE exposure, as well as increased emergence failure after EE exposure. This study on the effects of BPA and EE on C. riparius can be an important addition to the knowledge that has been obtained regarding the toxicology of BPA and EE in aquatic organism, on which limited data are available. The data obtained from this study, however, are not sufficient to establish any correlation or casual relationship between these two compounds and the response of C. riparius. Thus, further research is required to come up with direct experimental demonstrations of the wider relationship between the biochemical effects of BPA and EE on C. riparius and their consequences at higher levels of biological organization.

Acetylcholinesterase↗
PubMedDate not supplied

Identification of derivatives of bisphenol A diglycidyl ether and novolac glycidyl ether in can coatings by liquid chromatography/ion trap mass spectrometry.

A reversed-phase liquid chromatographic method combined with fluorescence and multiple mass spectrometric detection in series is presented for the separation and structure elucidation of bisphenol A diglycidyl ether (BADGE) and novolac glycidyl ether (NOGE) derivatives. Atmospheric pressure chemical ionization in the positive ion mode and collision induced fragmentation in the ion trap allowed identification of BADGE- and NOGE-related compounds originating from reactions of the glycidyl ethers with bisphenols, solvents, and chain stoppers. Two extracts from food-can coatings were investigated in detail. It was possible to elucidate the structures of many substances and consequently to draw conclusions about the production of the lacquers.

Acetates↗
PubMed2004

Transfer of maternally injected endocrine disruptors through breast milk during lactation induces neonatal Calbindin-D9k in the rat model.

The uterus is a highly estrogen-responsive tissue, which can be measured through changes in CaBP-9k expression. In this study, we investigated the potential for estrogenic compounds 4-tert-octylphenol (OP), nonylphenol (NP), bisphenol A (BPA), diethylstilbestrol (DES) and 17beta-estradiol (E2) to be transferred through breast milk from dam to neonate during lactation using the induction of CaBP-9k in uterine tissue as a biomarker. Dams were treated with OP, NP and BPA, dissolved in corn oil, at doses of 200, 400 and 600 mg/kg body weight per day l for 5 days after delivery. Dams and neonates were euthanized after 24h. Treatment with these estrogenic compounds increased the expression of CaBP-9k mRNA in the maternal uterus, in a dose-dependent manner. All doses of estrogenic compounds resulted in an increase in CaBP-9k protein levels. These compounds have an estrogenic effect on the maternal uterus during the lactation period as shown by the induction of both CaBP-9k mRNA and protein. In the neonatal uterus, the expression of CaBP-9k mRNA and protein significantly increased with DES exposure. There was a significant increase in CaBP-9k mRNA in neonatal uterus when the dams were treated with high doses of estrogenic compounds, but protein levels of CaBP-9k were undetectable. Taken together, these findings suggest that maternally injected estrogenic compounds may be transferred to neonates through breast milk and thus affecting uterine function, as shown by the induction of CaBP-9k gene expression in the neonatal uterus.

Animals↗
PubMed2002

Toxic effects of endocrine disrupters on freshwater sponges: common developmental abnormalities.

Endocrine disrupters are of substantial concern, in large part because effects of these compounds on the growth and development of many aquatic organisms are unknown. We examined toxic effects of three substances (ethylbenzene, nonylphenol, and bisphenol A), that are known to be hormonally active in many animals, on growth and development of two species of freshwater sponge. A common developmental abnormality was observed when sponges were treated with each of these compounds. The three compounds also caused significant reductions in growth rates. Lower concentrations resulted in malformed water vascular systems in several replicates. The utility of freshwater sponge bioassays is discussed as it relates to understanding possible mechanisms of action of endocrine disrupters on aquatic invertebrates.

Animals↗
PubMed1993

Glycosylated derivatives of benzophenone, benzhydrol, and benzhydril as potential venous antithrombotic agents.

A series of glycosylated derivatives of benzophenone, benzhydrol, and benzhydril has been synthesized and evaluated for potential activity as venous antithrombotic agents. Studies on structure-activity relationships revealed that compounds having an electron-withdrawing group in the benzhydril or benzhydrol moiety, and specifically those having the beta-D-xylopyranosyl structure in the sugar moiety, were good antithrombotic agents in a rat model of venous thrombosis.

Administration, Oral↗
PubMed2004

[Chemiluminescent assay for biological substances--chemiluminescent assay for alkaline phosphatase using lucigenin and its application to enzyme immunoassay].

The chemiluminescent reaction of lucigenin with various biological substances has been studied. Chemiluminescence of lucigenin is produced by the addition of organic reducing compounds to lucigenin in alkaline solution. On the basis of this reaction, we have developed highly sensitive chemiluminescent methods for the detection of enzyme immunoassay, especially using alkaline phosphatase (ALP) as a label enzyme. The detection limits of enzyme was 10(-19)-10(-20) mol per assay.

Acetone↗
PubMed1992

Structure-activity studies on benzhydrol-containing nipecotic acid and guvacine derivatives as potent, orally-active inhibitors of GABA uptake.

The introduction of lipophilic groups onto the ring nitrogen of nipecotic acid and guvacine, two known GABA uptake inhibitors, afforded potent, orally-active anticonvulsant drugs. A series of compounds is reported which explores the structure-activity relationships (SAR) in this series. Among the areas explored: side-chain SAR (aromatic-, heterocyclic-, and tricyclic-containing side chains) and modifications to the tetrahydropyridine ring. The benzhydrol ether-containing side chains afforded the most potent compounds with several exhibiting in vitro IC50 values for GABA uptake of < 1 microM (including 5, Table I; 37, 43, Table IV; and 44, Table V). Compound 44 was selected for extensive evaluation and subsequently progressed to Phase 1 clinical trials with severe adverse effects seen after single dose administration to humans.

Administration, Oral↗
PubMed1997

Cephalosporin 3'-phloroglucide esters and 7-(phloroglucidamido) cephalosporins as novel antibacterial agents.

Two series of new phloroglucide derivatives were synthesized that possessed antibacterial activities. The first series includes cephalosporin 3'-phloroglucide esters 19 and 20, which were obtained by condensation of cephalosporin 16 with bioactive phloroglucides 14 and 15, respectively. They exhibited a dual mode of antibacterial action. In comparison with cephalosporins 26 and 27, bearing an acetoxy unit at the C-3' position, the bifunctional cephalosporins 19 and 20 showed a broadened spectrum of activity. Results from the consistent valence force field (CVFF) calculations indicate that the most stable conformational isomer of phenolic acid 14, holding a cis-syn-syn geometry, possessed a cavity. It provides an ideal environment to accommodate metal ions of holoenzymes. Phenolic keto acid 15, however, possessed a trans-anti-syn conformation, which allowed chelation between metal ions and the phenolic hydroxyl groups as well as the carbonyl functionalities. Our biological results show that the cavity formed in phloroglucides plays an important role. The second series includes 7-(phloroglucidamido)cephalosporins 24 and 25, which were synthesized by condensation of cephalosporin 21 with 14 and 15, respectively. Results from the CVFF calculations indicate that cephalosporin 24 also possessed a cavity. Unlike cephalosporin 3'-phloroglucide esters 19 and 20, cephalosporins 24 and 25 were found resistant to beta-lactamases from Staphylococcus aureus 95 and Pseudomonas aeruginosa 18S-H. These new compounds, however, showed notable activities against S. aureus FDA 209P, S. aureus 95, Candida albicans, P. aeruginosa 1101-75, and P. aeruginosa 18S-H.

Anti-Bacterial Agents↗
PubMed2004

Adsorption of bisphenol-A, 17 beta-estradiole and 17 alpha-ethinylestradiole to sewage sludge.

Adsorption of bisphenol-A (CAS 85-05-7), 17 beta-estradiole (CAS 50-28-2) and 17 alpha-ethinylestradiole (CAS 57-63-6) to activated and to inactivated sludge from wastewater treatment plants (WWTPs) was investigated, thus allowing to distinguish between pure adsorption and biosorption. For the investigated substances the determination of the adsorption kinetics is based on experiments performed according to the OECD guideline 106 and on free concentration measurements in the liquid phase. The description of the adsorption behaviour occurred via Freundlich Adsorption Isotherms. Additionally specific adsorption coefficients KD, KOM and KOC were calculated. The results of these calculations were compared to KOC values obtained with a HPLC method according to the OECD guideline 121. All substances showed a high adsorption affinity to the adsorbent and in spite of the application of very high initial concentrations no saturation level could be reached. Within a contact time of 24 h, no difference between the adsorption to activated and inactivated sludge could be detected. The calculated KD values were within a range of about KD = 1000 l kg(-1) for the investigated compounds and showed a clear concentration dependency in the case of bisphenol-A. Adsorption was also found to depend on pH. The experimentally determined KOC values of the investigated substances were significantly higher than the results obtained with the HPLC method described in OECD guideline 121.

Adsorption↗