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PubMed2006

Effects of monomethyltin and dimethyltin compounds on heterologously expressed neuronal ion channels (Xenopus oocytes) and synaptic transmission (hippocampal slices).

The aim of this study was to investigate the effects of monomethyltin trichloride (MMT) and dimethyltin dichloride (DMT) on various neuronal ion channels heterologously expressed in Xenopus oocytes and on synaptic transmission in hippocampal slices of young (14-21 days old) and adult (2-4 months old) rats. The Xenopus oocyte expression system was chosen to allow direct assessment of the effects of MMT and DMT both on glutamate receptors sensitive to AMPA and NMDA and on various voltage-operated potassium and sodium channels. Hippocampal slices were used to analyze the effects of MMT and DMT on synaptic potentials generated by the important excitatory Schaffer collateral-CA1 synapse. In general, MMT and DMT were found to have no effect either on voltage-operated sodium and potassium channels or on the metabotropic glutamate receptor but they did differentially affect the functions of ionotropic glutamate receptors and glutamatergic synaptic transmission. MMT (100 microM) significantly reduced NMDA-mediated ion currents by up to 32%, but had no effect on ion currents through AMPA receptors. In slices of adult rats, MMT had no effect on the amplitudes of evoked fEPSPs and brought about a 35% reduction in the LTP amplitudes. In contrast, in slices of young rats MMT evoked a reversible 30% increase in the amplitudes of fEPSPs but had no effect on LTP induction. DMT (100 microM) reduced ion currents through NMDA-receptor ion channels by up to 29% and those through AMPA-receptor ion channels by up to 7%. In hippocampal slices 100 microM DMT reduced the amplitudes of fEPSPs (adults: 50%; young rats: 70%) and LTP (adults: 40%; young rats: 55%). Neither of the organotins affected the paired-pulse facilitation at this synapse, indicating that the organotins exert their effects at the postsynaptic site. The action of MMT and DMT may contribute to the organotin-induced impairment of behavior patterns in connection with learning and memory.

Animals↗

PubMedDate not supplied

Quantitative analysis of ethyltin compounds in mammalian tissue using HPLC/FAAS.

Measurement of total tin and ethyln tin forms in mammalian tissue is described, using ion-exchange high performance liquid chromatography (HPLC) in tandem with flameless atomic absorption spectrometry (FAAS) for tin-specific detection. All tin forms in whole blood and tissue homogenates were liberated from biological (in vivo) binding by treatment with 6M hydrochloric acid for a period of 4 hr. Ethyln tin species, as the chlorides, were partitioned into chloroform:ethyl acetate (1:1) and analyzed via HPLC using a strong cation exchange column, with fraction collection by a programmable collector and fraction tin measurement by FAAS. Triethyl- and diethyltin were separated and quantitated using 0.167M ammonium citrate in 70:30 methanol:water, while monoethyltin required the use of 0.50M citrate salt in 70:30 water:methanol as mobile phase to effect elution. The difference between total and speciated tin content provides an estimate of remaining tin species, including the inorganic element.

Animals↗

PubMed1998

Accumulation of tributyl- and triphenyltin compounds in Pacific oyster, Crassostrea gigas, from the Chinhae Bay System, Korea.

Butyl- and phenyltin residues were quantified in seawater and Pacific oyster (Crassostrea gigas) from the Chinhae Bay System, Korea. Butyltin compounds were detected in all the seawater and C. gigas samples, whereas phenyltin compounds were not detected in any seawater samples. Tributyltin (TBT) concentrations in seawater ranged <8-35 ng Sn L-1. TBT and triphenyltin (TPhT) concentrations in oysters ranged 95-885 and 155-678 ng Sn g-1, respectively. Spatial distribution of TBT was closely related to boating and dry-docking activities. However, spatial distribution of TPhT was not consistent with that of TBT. The estimated biological concentration factor (BCF) for TBT in C. gigas was about 25,000. Furthermore, 19 and 28% of total body burdens of TBT and TPhT were found in gonadal mass of C. gigas just prior to the spawning period, indicating that a proportional amount of TBT and TPhT would be released with a following reproductive process.

Animals↗

PubMedDate not supplied

Monomethyl-and trimethyltin compounds induce learning deficiencies in young rats.

Male rat pups were exposed to monomethyltin trichloride (MMTC) and trimethyltin chloride (TMTC) via their dams' drinking water throughout gestation and post partum until 21 days of age. At 11 days of age, the pups were tested for acquisition and extinction learning ability in an appetitive learning paradigm, and at 21 days for learning ability in a one trial swim escape learning test. At 11 days, pups from dams exposed to 120 mg/l Sn as MMTC and to 1.0 mg/l Sn as TMTC displayed statistically significant increases in acquisition time, while all dose groups (12, 40, 120 mg/l MMTC and 0.15, 0.5, 1.0 mg/l TMTC) displayed significant decreases in extinction learning ability as compared to controls. At 21 days of age, animals exposed to 12 mg/l and 120 mg/l MMTC displayed higher escape times than controls, as did animals exposed to 0.5 mg/l TMTC.

Animals↗

PubMed2006

Transplacental transfer of phenyltins from a pregnant Dall's porpoise (Phocoenoides dalli) to her fetus.

The maternal to fetal transfer of monophenyltin (MPT), diphenyltin (DPT), and triphenyltin (TPT) was investigated for the first time in a cetacean species, a mother-fetus pair of Dall's porpoises (Phocoenoides dalli) collected off the Sanriku coast, Japan. The mother individual was contaminated by phenyltin compounds, and the muscle, blubber, and liver accounted for 90% of the total phenyltin burden. A two-generation phenyltin contamination via transplacental transfer was demonstrated. This study revealed that the transfer rate was 0.29% for total phenyltins to a fetus of about 6-month-old. Unlike in the mother, the fetal liver could not be considered the target organ for all the phenyltins studied. In a ca. 100kg-weight mother Dall's porpoise and its fetus of 2.21kg-weight, approximately 153microg (TPT, 139microg; DPT, 9.4microg; MPT, 4.2microg) and 0.44microg of total phenyltins (TPT, 0.38microg; DPT, 0.03microg; MPT, 0.03microg) were found, respectively. The body burden of TPT consisted of 91% and 86% of the total phenyltin burdens in the maternal and fetal bodies, respectively.

Animals↗

PubMedDate not supplied

Daily intakes of tributyltin and triphenyltin compounds from meals.

Daily intakes of tributyltin (TBT) and triphenyltin (TPT) compounds from meals in Shiga Prefecture, Japan, were investigated by 2 methods. Daily intakes of TBT and TPT by the duplicate portion method were, respectively, 4.7 and 0.7 microgram in 1991 and 2.2 and 0.7 microgram in 1992. Those by the market basket method were, respectively, 6.9 and 5.4 micrograms in 1991 and 6.7 and 1.3 micrograms in 1992. Daily intakes of TBT and TPT by the market basket method were higher than those by the duplicate portion method. These values were considerably lower than acceptable daily intakes of 80 micrograms/50 kg body weight specified by the Welfare Ministry of Japan for bis(tri-n-butyltin)oxide and of 25 micrograms/50 kg body weight specified by the Food and Agriculture Organization/World Health Organization for TPT.

Adult↗

PubMed2006

Insertion reaction of carbon dioxide into Sn-OR bond. Synthesis, structure and DFT calculations of di- and tetranuclear isopropylcarbonato tin(IV) complexes.

The reaction of carbon dioxide with the stannane nBu2Sn(OiPr)2 and distannoxane [nBu2(iPrO)Sn]2O leads to the selective insertion into one Sn-OiPr bond generating the corresponding nBu2Sn(OiPr)(OCO2(i)Pr) and nBu2(iPrO)SnOSn(OCO2(i)Pr)nBu2 species. Both compounds are characterised by multinuclear NMR, FT-IR and single-crystal X-ray crystallography. In the solid state, they adopt a dimeric arrangement with bridging isopropoxy and terminal isopropylcarbonato ligands. The X-ray crystal structure of the dinuclear stannane shows that the Sn2O2 ring and the two Sn-OCO2C fragments are nearby coplanar. The same holds for the ladder-type tetranuclear distannoxane. The dimeric structures are also evidenced by solution NMR in non-coordinating solvents. Interestingly, the assignment of the exo and endo tin resonances of the dimeric distannoxane is unambiguous using a labeled 13CO2 experiment. The stability of the dimeric association has been probed in the stannane series on the basis of DFT calculations.

Carbon Dioxide↗

PubMed1991

The antitumor activity and the structure of bis(adeninato-N9) diphenyltin(IV).

Bis(adeninato-N9)diphenyltin(IV) has been selected as a tumor panel compound by the U.S. National Cancer Institute and tested against a number of tumors according to standard protocols. The activity criteria were not passed. The solid state structure of the environment of tin in the complex has been definitely established to be of the tetrahedral type by means of 119Sn Mössbauer-Zeeman spectroscopy; this configuration has been assumed to be maintained also in aqueous suspensions of the drug, in conditions corresponding to the administration to mice. The occurrence of strong Sn-N bonds, consistently resistant to hydrolytic processes, has been assumed, and correlated to the observed low toxicity of the drug. The extent of the antitumor action corresponds to the standard response to Ph2SnIV moieties.

Adenine↗

PubMed2004

Monitoring the degradation and solubilisation of butyltin compounds during in vitro gastrointestinal digestion using "triple spike" isotope dilution GC-ICP-MS.

An in vitro gastrointestinal digestion approach in combination with species-specific isotope dilution analysis has been employed for the first time to study the transformation reactions as well as the solubilisation of butyltin species throughout a simulated human digestion. Different sample preparation procedures were assayed in order to avoid problems derived from lack of isotope equilibration between the endogenous and the isotopically-enriched added species. A "triple spike" approach, which can be used to calculate the corrected concentrations of mono-, di-, and tributyltin (MBT, DBT and TBT, respectively), as well as six interconversions, was employed throughout this work. In order to calculate and compare the species degradation factors, a triple spike solution containing each butyltin species enriched in a different isotope was added to the simulated gastric and intestinal fluids before the digestion procedures in the presence and in the absence of a solid biological matrix (commercial mussel tissue). Additionally, by analysing the soluble and insoluble fractions resulting from the simulated digestion of a commercial mussel tissue (gastric and gastric plus intestinal digestion), total mass balances for each butyltin compound could be derived. For this purpose, the isotopically-enriched species were added after the enzymatic digestions in order to avoid problems derived from lack of isotope equilibration. The mass balances provided information not only about the solubilisation but also about the degradation of the butyltin species during the digestion procedures. Good agreement between the degradation factors calculated under all experiments performed in this work and between those reported in previous works were obtained. The most serious degradation observed was that of DBT to produce MBT, whereas slight degradations of TBT and MBT were detected. Moreover, a worrying 61% of the original total butyltin content present in a commercial mussel tissue was found to be solubilised after complete simulated gastrointestinal digestion, with minimal degradation of TBT.

Gas Chromatography-Mass Spectrometry↗

PubMed2005

Characterization of transboundary POP contamination in aquatic ecosystems of Pearl River delta.

During the past two decades, the rapid development of the Pearl River delta leads to substantial accumulation of various toxic organic compounds. This study aims to give a preliminary characterization of the existing state of contamination in this region and to provide insight into the possible fate of persistent organic pollutants (POPs) in this estuary. The available data on POPs in water, river, estuarine sediments, soil, and marine organisms within the Pearl River delta are compiled. It is shown that it may lead to transboundary POP pollution problems at both Hong Kong and Macau Special Administration Regions located at the downstream end of the region. It is noted that the levels of DDTs and HCHs in various environmental media are at alerting levels and that fresh DDT might still be applied illegally within the region. A systematic research is required to determine both the temporal and spatial variations of all POPs in various carrying media of the Pearl River delta as a whole.

China↗

PubMed2005

Bis{mu-2-[(2,3-dichlorophenyl)amino]benzoato-kappaO}di-mu2-ethoxo-octamethyldi-mu3-oxo-tetratin(IV).

The title compound, [Sn4(CH3)8(C13H8Cl2NO2)2(C2H5O)2O2], is a centrosymmetric dimer, with three linearly fused four-membered Sn-O-Sn-O rings. The coordination polyhedron of the Sn atom bonded to the carboxylate can be described as trigonal-bipyramidal distorted toward square-pyramidal. That of the second Sn atom is similar, but the distortion towards square-pyramidal geometry is greater. The Sn-O and Sn-C distances are 2.020 (2)-2.226 (2) and 2.096 (4)-2.114 (4) A, respectively. The benzene rings of the 2-[(2,3-dichlorophenyl)amino]benzoate ligand subtend an angle of 50.49 (17) degrees; the conformation of the ligand is stabilized by intramolecular N-H...Cl and N-H...O hydrogen bonds. The structure is assembled via pi-pi stacking interactions to form chains parallel to [120].

Anti-Inflammatory Agents↗

PubMed1990

Effects of chemically induced maternal toxicity on prenatal development in the rat.

The hypothesis that chemically induced overt maternal toxicity induces a characteristic syndrome of adverse developmental effects in the rat was investigated. Pregnant animals (Sprague-Dawley strain) were dosed by oral gavage with one of a series of compounds on days 6-15 of gestation. These chemicals were diquat (DIQ), ethylene-bis-isothiocyanate (EBIS), toxaphene (TOX), styrene (STY), 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4,5-trichlorophenol (2,4,5-Tr), triphenyl tin hydroxide (TPTH), and cacodylic acid (CAC). The compounds were chosen because they exhibited little or no developmental toxicity in previous studies. Dosage levels producing maternal weight loss and/or lethality were determined from preliminary toxicity studies. Significant maternal weight reductions were noted during the course of treatment with all compounds except CAC and 2,4,5-Tr. Maternal lethality was produced by EBIS, TOX, 2,4,-D, and 2,4,5-Tr. The main treatment-related developmental toxicity noted in litters at term consisted of increased lethality (EBIS, TPTH) and decreased fetal weight (EBIS and CAC). Treatment-related anomalies were seen in litters treated with 2,4-D and TOX (supernumerary ribs) and with EBIS and STY (enlarged renal pelvis). No significant developmental effects were produced with DIQ, or 2,4,5-Tr. This study indicates that overt maternal toxicity as defined by weight loss or mortality is not always associated with the same defined syndrome of adverse developmental effects in the rat.

2,4,5-Trichlorophenoxyacetic Acid↗

PubMed2004

Butyltins in water, biofilm, animals and sediments of the west coast of India.

Biofilm, fish, oyster, mussel, clam, surface seawater, suspended particulate matter (SPM), and sediment samples were collected from marine and/or estuarine waters of the west coast of India. These samples were analysed for butyltin derivatives such as dibutyltin (DBT) and tributyltin (TBT). The concentrations DBT plus TBT varied between 2.4 and 8.3, 163 and 363 ng/l, 5 and 2853 ng/g dry wt in the SPM, seawater and sediment samples, respectively, of the Marmugao harbour. The values of DBT plus TBT ranged between 0.60 and 29, 123 and 242 ng/l and 1.4 and 65 ng/g dry wt in SPM, water and sediment samples, respectively, collected from the Mandovi estuary. In the Dona Paula Bay the DBT plus TBT varied from 10 to 89 ng/l in surface seawater, and TBT from 10 to 513 ng/g in biofilm samples. For the coastal sediment samples the concentration of DBT plus TBT ranged between 36 and 133 ng/g dry wt of sediment. For the animal samples the DBT plus TBT ranged between 58 and 825 ng/g dry wt of the tissue. Mussel tissues contained the highest amount of DBT plus TBT (825 ng/g dry wt tissue), whereas highest TBT concentration was recorded in the oyster (732 ng/g dry wt). TBT was generally the most abundant butyltin compound in most of the samples suggesting fresh inputs and/or less degradation of TBT. A wide range of the observed butyltin concentrations suggests the presence of localized areas of contamination. Leaching of tributyltin-containing antifouling paints from the ocean going ships, fishing and recreational boats, barges, and the inputs of TBT from the Goa shipyard and dry dock facility situated in the harbour are the probable sources of the DBT and TBT in the samples of the west coast of India. Higher levels of TBT were observed in biofilm relative to that in the surrounding seawater. When fed on TBT contaminated biofilm of the diatom Navicula subinflata, butyltin concentrations in the clam Paphia malabarica increased over the period of feeding suggesting the importance of biofilm in the transfer of butyltins to higher group of organisms.

Animals↗

PubMed2001

Butyltin exposure causes a rapid decrease in cyclic AMP levels in human lymphocytes.

Natural killer (NK) cells are a subset of lymphocytes that are capable of killing tumor cells, virally infected cells, and antibody-coated cells. Butyltins (BTs) are used in a variety of consumer products and industrial applications. Tributyltin (TBT) is found in dairy products, meat, and fish. Dibutyltin (DBT) is found in plastic products, beverages stored in PVC pipes during manufacturing, and poultry products. BTs appear to increase the risk of cancer and viral infections in exposed individuals. This increased risk may be due in part to the inhibitory effect of these compounds on the cytotoxic function of NK cells. A 24-h exposure of NK cells to 200 nM TBT or 1.5 microM DBT decreased the cytotoxic function of NK cells by greater than 90%. Higher concentrations of TBT and DBT decreased the cytotoxic function of NK cells (by greater than 90%) after only a 1-h exposure. A 24-h exposure to either TBT or DBT decreased intracellular ATP levels by about 30%. However, as much as a 1-h exposure to either 300 nM TBT or 10 microM DBT caused no significant decrease in ATP levels. Thus, a decrease in ATP levels is a longer-term consequence of BT exposure. Intracellular levels of cAMP are decreased by as much as 80% within 5 min of exposure to either TBT or DBT. This rapid decline in cAMP levels in NK cells may be a consequence of BT exposure that is related to the rapid decrease in the cytotoxic function of NK cells.

Adenosine Triphosphate↗

PubMed2001

Butyltin compounds in sediments from the commercial harbor of Alexandria City, Egypt.

Tributyltin (TBT), dibutyltin (DBT), and monobutyltin (MBT) compounds were quantitatively determined in surface-sediment samples collected from 23 sites in the commercial harbor of Alexandria City, Egypt. Butyltin concentrations in sediments varied widely depending on the sample location, ranging from less than 0.1 to 186 ng g(-1) of Sn for MBT, less than 0.1 to 379 ng g(-1) of Sn for DBT, and 1 to 2,067 ng g(-1) of Sn for TBT Elevated TBT concentrations, ranging from 727 to 2,067 ng g(-1) of Sn were observed in harbors, marinas, and near ship-repair facilities, indicating that the butyltin-containing, antifouling paints of boats and vessels are the major source of butyltin contamination. The TBT concentration decreased rapidly away from potential source areas of boat docking and repair facilities. The high relative concentrations of TBT in the sediments indicated that degradation processes in the sediments are minor, probably due to the anoxic sedimentary conditions at the sampling sites and/or relatively fresh input of TBT to these sites.

Biodegradation, Environmental↗

PubMed2005

Effects of fentin hydroxide on reproduction of the Japanese quail (Coturnix coturnix japonica).

In a one-generation reproductive study, the fungicidal compound triphenyltin hydroxide (fentin) was administered to adult Japanese quail for 6 weeks at dietary levels of 3 and 30 ppm. Reproduction was significantly impaired in the high-dose group. The principal adverse finding was a marked increase in embryonic mortality, resulting in a lower hatch rate. Furthermore, a reduction in egg production was observed with ongoing duration of treatment. Most of the other reproduction-related parameters were not affected. The in ovo losses are assumed to result from a direct toxic effect of the test substance on chick embryos. At the low dietary level, reproduction was not altered. In contrast to the obvious reproductive toxicity, there was only limited evidence of adverse treatment-related findings in the adult birds. However, because such minor effects as an increase in mean liver weight, which was accompanied by macroscopic liver findings and a decrease in T4 serum concentration, were still seen at 3 ppm, a no-observed-effect level could not be established.

Animals↗

PubMed2001

pH dependence of the partitioning of triphenyltin and tributyltin between phosphatidylcholine liposomes and water.

Triorganotin compounds are very toxic contaminants. The site of their basic mechanism of action of acute toxicity is the biomembrane. Liposome-water distribution ratios of triphenyltin and tributyltin were determined between pH 3 and pH 8 with the equilibrium dialysis method in the micromolar concentration range, which is the concentration range where acute toxicity is observed. In addition, biomembrane-water distribution ratios of tributyltin were determined with chromatophores of Rhodobacter sphaeroides that contain approximately 70% protein intercalated in the lipid bilayer. The liposome-water distribution of both compounds showed only weak pH dependence. For tributyltin, the apparent distribution ratio decreased from 4100 at low pH to 2000 at high pH, while this ratio decreased from 70 000 to 22 000 for TPT. The distribution ratio of the triorganotin cation exceeded that of the neutral hydroxo complex by a factor of 2. The distribution ratio of both the cation and the hydroxo complex of triphenyltin exceeded that of tributyltin by a factor of 10. It is postulated that the sorption of the cation is governed by complex formation with ligands in the phospholipids, presumably the phosphate group. The biomembrane-water distribution ratio of tributyltin was found to be lower than the liposome-water distribution ratio at high pH. The hydroxo complex appears to partition only to the lipid fraction of the biomembrane. Yet, at low pH the biomembrane-water distribution ratio exceeded the liposome-water distribution ratio, which is attributed to complex formation of the cationic species with ligands of the protein fraction.

Anti-Infective Agents↗

PubMed2006

Accumulation of butyltin compounds in cobia Rachycentron canadum raised in offshore aquaculture sites.

Butyltin residues (monobutyltin, MBT; dibutyltin, DBT; tributyltin, TBT; tetrabutyltin, TeBT) in the sea water and in the cobia (Rachycentron canadum) from aquaculture sites located offshore of Penhu island, Taiwan, were collected and quantified. The average concentrations of MBT, DBT, TBT and TeBT in sea water were n.d.-28+/-3, 4.0+/-0.6-88+/-13, n.d.-43+/-4, and n.d.-7+/-1 ng l(-1), respectively. The total butyltin (sum of MBT, DBT, TBT, TeBT) residues in the skin, dorsal muscle, ventral muscle, dark muscle, and liver of the cobia were in the range of 72+/-12-2270+/-85, 79+/-11-688+/-33, 82+/-14-1715+/-104, 93+/-13-803+/-47, and n.d.-52,745+/-252 ng g(-1) (wet weight), respectively. Although in this study in most cases, the highest concentration of total butyltin residues was found in liver or skin, in some cases, the highest concentration was found in muscle tissue. The crude lipid content in the skin, dorsal muscle, ventral muscle, dark muscle, and liver of these cobia was in the range of 7.9+/-0.1-28+/-1%, 11.7+/-0.8-29+/-1%, 11.5+/-0.3-44+/-3%, 24.2+/-0.4-48.4+/-0.4%, and 55.7+/-0.1-87.7+/-0.4% (wet weight), respectively. The concentrations of crude lipid content, and the concentrations of total butyltin residues in these tissues were not correlated.

Animals↗