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PubMed1999

Quantification of organotin compounds and determination of imposex in populations of dogwhelks (Nucella lapillus) from Norway.

Unintentional effects of the antifouling agent tributyltin (TBT) have been discovered in marine gastropods as the induction of male sex characters in females, known as imposex. The occurrence of imposex in dogwhelks (Nucella lapillus) was investigated in 41 populations sampled in 1993-1995 along the Norwegian coast. A method for quantification of organotin species using gas chromatography and atomic emission detection (GC-AED) was developed. Some degree of imposex occurred in almost all populations of dogwhelks studied, except in four from Northern Norway. The concentration of organotin compounds in the gastropods from the unaffected populations was below the detection limit (7 ng Sn/g d.w.). The concentration of TBT in dogwhelks from affected populations was in the range 48-1096 ng Sn/g d.w. A positive relation between the concentration of TBT in dogwhelks and the degree of imposex was found.

Animals↗
PubMedDate not supplied

Synthesis and evaluation of the in vivo trypanocidal activity of water soluble organotin compounds.

A series of (3-(2-methoxy)ethoxypropyl)tin derivatives were synthesized as potential trypanocidal drugs. The series included an alkyltin trichloride, a dialkyltin dichloride and the corresponding dialkyltin oxide, and six dialkyltin dithio derivatives. Compounds were evaluated for trypanocidal activity using in vitro cultures of Trypanosoma equiperdum and mice infected with the same strain of parasite for in vivo tests. Two of the title derivatives, the bis (3-(2-methoxy)ethoxypropyl)tin dichloride 2 and the corresponding bis (3-(2-methoxy)ethoxypropyl)tin oxide 3, appeared to be water soluble reagents. Furthermore, they are the first examples of organotin compounds presenting interesting in vivo trypanocidal activity.

Animals↗
PubMed1976

Toxicity and health effects of selected organotin compounds: a review.

The toxicity of selected tin compounds is reviewed. Over the years, a variety of uses has been found for organic and inorganic tin compounds, as fungicides, as stablizers in plastics, moluscicides, and miticides; they have also been suggested as insect chemosterilants and for other industrial uses. Many of these products are unpalatable when mixed into diets and have been suggested as rodent repellents. Inhaling tin as dust or fumes may cause a benign pneumoconiosis in exposed workers. The organotin compounds can be divided into alkyltin and aryltin compounds. The trimethyl and triethyltin compounds are well absorbed from the gastrointestinal tract and are the most toxic in this group. Triethyltin particularly produces status spongiosus of the white matter of the central nervous system. Most of the other alkyl and aryl tin compounds are poorly absorbed from the gastrointestinal tract, and are less toxic when given orally than when given parentally. Only one compound, tricyclohexyltin hydroxide, is now registered by the Environmental Protection Agency as a miticide. This product produces skin irritation in rabbits. Studies should be conducted to determine whether it causes contact dermatitis in humans.

Animals↗
PubMed1982

Effects of organotin compounds on maximal electroshock seizure (MES) responsiveness in mice. II. Tricyclohexyltin and triphenyltin.

Male mice (25-30 g) were injected (ip) with either 0, 3.5 X 10(-6), 17.5 X 10(-6), or 26.25 X 10(-6) mol/kg of either tricyclohexyltin bromide (TCT) or triphenyltin acetate (TPhT) in a corn-oil vehicle. The mice were tested for maximal electroshock seizure (MES) at 0.5, 4, 24, and 96 h following exposure to the organotin compounds, and the durations of seizure phases were measured and used to assess seizure severity. No significant changes in seizure-grade distribution, as compared to controls, were observed in any of the TCT- or TPhT-treated groups at any of the time points examined. No significant changes in the duration of seizure phases, as compared to controls, were observed in animals dose with 3.5 X 10(-6) mol/kg of TCT or TPhT at any of the time points evaluated. At 0.5 h following exposure, the mice dosed with the two higher levels of TCT or TPhT exhibited increases in MES severity. At 4 and 24 h following exposures, the mice exposed to the two higher dose levels of TPhT exhibited decreases in MES severity, followed by a recovery of normal seizure severity at 96 h. Conversely, the animals dosed with the higher dose levels of TCT exhibited at increased MES severity at 4, 24, and 96 h following exposure. These results, in combination with those in the preceeding paper (Doctor and Fox, 1982), reveal that at equimolar doses TCT And TPhT possess a different spectrum of action than the tri-n-alkyltins.

Animals↗
PubMedDate not supplied

Survey of organotin compounds in blended wines.

An extraction method for butyltin, cyclohexyltin, octyltin and phenyltin compounds in wines was developed using 0.05% tropolone in 75% diethyl ether/pentane. Recoveries averaged 96.8% (range 78-121%). Methyl derivatives made by Grignard reaction were quantitated by gas chromatography (GC)-atomic absorption spectrometry (AAS). Twenty-nine of the 90 samples (32.2%) tested contained at least one of the analytes. Mono- and diocyltin were found in one sample only, at levels of 2.41 and 0.12 ng/ml respectively. Dibutyltin levels ranged from < 0.08 to 1.44 ng/ml. Monobutyl and tributyltin were found less frequently and at lower levels than dibutyltin. GC/mass spectrometric analysis confirmed the presence of butyl- and octyltins. No other organotin compounds were detected by either GC-AAS or GC-MS.

Gas Chromatography-Mass Spectrometry↗
PubMed2003

Tin-carbon cleavage of organotin compounds by pyoverdine from Pseudomonas chlororaphis.

The triphenyltin (TPT)-degrading bacterium Pseudomonas chlororaphis CNR15 produces extracellular yellow substances to degrade TPT. Three substances (F-I, F-IIa, and F-IIb) were purified, and their structural and catalytic properties were characterized. The primary structure of F-I was established using two-dimensional nuclear magnetic resonance techniques; the structure was identical to that of suc-pyoverdine from P. chlororaphis ATCC 9446, which is a peptide siderophore produced by fluorescent pseudomonads. Spectral and isoelectric-focusing analyses revealed that F-IIa and F-IIb were also pyoverdines, differing only in the acyl substituent attached to the chromophore part of F-I. Furthermore, we found that the fluorescent pseudomonads producing pyoverdines structurally different from F-I showed TPT degradation activity in the solid extracts of their culture supernatants. F-I and F-IIa degraded TPT to monophenyltin via diphenyltin (DPT) and degraded DPT and dibutyltin to monophenyltin and monobutyltin, respectively. The total amount of organotin metabolites produced by TPT degradation was nearly equivalent to that of the F-I added to the reaction mixture, whereas DPT degradation was not influenced by monophenyltin production. The TPT degradation activity of F-I was remarkably inhibited by the addition of metal ions chelated with pyoverdine. On the other hand, the activity of DPT was increased 13- and 8-fold by the addition of Cu(2+) and Sn(4+), respectively. These results suggest that metal-chelating ligands common to pyoverdines may play important roles in the Sn-C cleavage of organotin compounds in both the metal-free and metal-complexed states.

Bacterial Proteins↗
PubMed2005

Accumulation of organotin compounds and mercury in harbour porpoises (Phocoena phocoena) from the Danish waters and West Greenland.

The concentrations of butyltin (summation operatorBT=TBT+DBT+MBT) and mercury (Hg) were determined in the liver of 35 harbour porpoises (Phocoena phocoena), which were found dead along the coastlines or caught as by-catch in the Danish North Sea and the Inner Danish waters. In addition, three harbour porpoises hunted in West Greenland were analysed. High levels of butyltin and mercury, within the range of 68-4605 mg BT/kg ww and 0.22-92 mg Hg/kg ww, were found in the liver of the Danish harbour porpoises and both substances tend to accumulate with age. The levels in the harbour porpoise from West Greenland were 2.0-18 mg BT/kg ww and 6.3-6.9 mg Hg/kg ww, respectively. The concentrations of butyltin and mercury were both found to be higher in stranded than in by-caught harbour porpoises but only the butyltin concentration was significantly higher in stranded porpoises in the age group 1-5 years. These substances are suspected of inducing adverse effects on immune and endocrine systems in mammals and they may thereby pose a threat to the animals. This study suggests that organotin compounds are also important, when assessing the risks of contaminants on the health and viability of harbour porpoises in Danish waters.

Animals↗
PubMed2004

The ion channel of F-ATP synthase is the target of toxic organotin compounds.

ATP is the universal energy currency of living cells, and the majority of it is synthesized by the F1F0 ATP synthase. Inhibitors of this enzyme are therefore potentially detrimental for all life forms. Tributyltin chloride (TBT-Cl) inhibits ATP hydrolysis by the Na(+)-translocating ATP synthase of Ilyobacter tartaricus or the H(+)-translocating counterpart of Escherichia coli with apparent Ki of 200 nM. To target the site of this inhibition, we synthesized a tritium-labeled derivative of TBT-Cl in which one of the butyl groups was replaced by a photoactivatable aryldiazirine residue. Upon illumination, subunit a of the ATP synthase becomes specifically modified, and this labeling is suppressed in the presence of the original inhibitor. In case of the Na+ ATP synthase, labeling is also suppressed in the presence of Na+ ions, suggesting an interference in Na+ or TBT-Cl binding to subunit a. This interference is corroborated by the protection of ATP hydrolysis from TBT-Cl inhibition by 105 mM Na+. TBT-Cl strongly inhibits Na+ exchange by the reconstituted I. tartaricus ATP synthase. Taken together these results indicate that the subunit a ion channel is the target site for ATPase inhibition by toxic organotin compounds. An inhibitor interacting specifically with this site has not been reported previously.

Adenosine Triphosphatases↗
PubMed2006

Vertical profile of PCDD/Fs, dioxin-like PCBs, other PCBs, PAHs, chlorobenzenes, DDX, HCHs, organotin compounds and chlorinated ethers in dated sediment/soil cores from flood-plains of the river Elbe, Germany.

Concentrations of polychlorinated dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) and other organic micropollutants were determined in dated sediment/soil cores collected from the flood-plain of the river Elbe near Pevestorf (PT), approximately 125 km upstream of Hamburg, and Heuckenlock (HL) in southeast of Hamburg. Concentrations of PCDD/Fs peaked sharply at PT in the 1950s and at HL at the end of the 1940s. Cluster analyses provide evidence that the region of Bitterfeld-Wolfen (about 350-400 km upstream of Hamburg) could be the source of the PCDD/F contamination existing in the cores PT and HL since the 1940s. Obviously it is caused by sediments of the river Elbe of a similar composition. Whereas the PCDD/Fs, HCHs (hexacyclohexane isomers), DDX (DDT, DDD, DDE), and tetrachlorinated ethers in PT and HL presumably originated predominantly from the Bitterfeld-Wolfen region, organotin compounds in HL and dichlorinated haloethers in HL during the 1940s and 1950s can probably largely be attributed to emissions from the Hamburg region. Although they are separated by a large distance, in both sediment cores PT and HL concentrations and composition patterns of most organic micropollutants analyzed widely match. Inductively it can be concluded that similar contaminations will be found in many of the river bank soils between the Bitterfeld-Wolfen region and Hamburg. Excavation of top soils may uncover highly contaminated materials. Since the dated sediment cores show the variation in contaminants in the Elbe sediments over a defined time period, it is possible to make an approximate assessment of the actual degree of contamination to be expected in areas where in previous decades contaminated dredged sediments from the Elbe and from the Port of Hamburg have been deposited on land and used for building plots or for agricultural purposes.

Benzofurans↗
PubMed2005

Aerobic biodegradation of organotin compounds in activated sludge batch reactors.

The biodegradation behavior of four organotin (OT) compounds, namely tributyltin (TBT), dibutyltin (DBT), monobutyltin (MBT) and triphenyltin (TPhT), was studied in lab-scale activated sludge batch reactors. The activated sludge was spiked with the OT compounds at a level of 100 microg l(-1) as Sn. Determination of the OT compounds by GC-FPD after ethylation in the dissolved and particulate phase revealed that 24 h after the start of the experiments, almost the total of OT compounds has been removed from the dissolved phase and is associated with the suspended solids. Calculation of mass balance in batch reactors showed that OT compounds biodegradation was performed via a sequential dealkylation process. Removals due to biodegradation were differentiated according to the parent compound. In experiments with non-acclimatized biomass, a percentage of 27.1, 8.3, 73.8 and 51.3 was still present as TBT, DBT, MBT and TPhT, respectively, at the end of the experiment (18th day). Half-lives (t1/2) of 10.2 and 5.1 days were calculated for TBT and DBT, respectively, whereas apparent t1/2 values could not be determined for MBT and TPhT (t1/2>18 days). The capacity of activated sludge to biodegrade OT compounds in the absence of supplemental substrate indicated that these compounds can be metabolized as single sources of carbon and energy in activated sludge systems. Excluding TBT, the presence of low concentrations of supplemental substrate did not affect the biodegradation potential of activated sludge. The acclimatization of biomass on OT compounds enhanced significantly biodegradation, resulting in significant decreases of half-lives of OT compounds. As a result in the presence of acclimatized biomass, half-lives of 1.4, 3.6, 9.8 and 5.0 days were calculated for TBT, DBT, MBT and TPhT, respectively.

Biodegradation, Environmental↗
PubMed2003

Trace determination of organotin compounds in water, sediment and mussel samples by low-pressure gas chromatography coupled to tandem mass spectrometry.

A fast method for the determination of eight organotin compounds (OTs), monobutyltin (MBT), dibutyltin (DBT), tributyltin (TBT), tetrabutyltin (TeBT), monophenyltin (MPhT), diphenyltin (DPhT), triphenyltin (TPhT) and tetraphenyltin (TePhT), in water, sediments and mussels, was developed using low-pressure gas chromatography/tandem mass spectrometry (LPGC/MS/MS). The method is based on sodium diethyldithiocarbamate (DDTC) complexation of the ionic organotins, followed by extraction of the target matrices and derivatization by a Grignard reagent, as described in a previously published method for water samples. Solid-phase extraction was selected as extraction method from water samples after comparison with liquid-liquid extraction, but extraction of the OTs from sediment and mussel samples was performed using toluene. Matrix-matched calibration standards were used to minimize matrix effects. The analytical process was validated by the analysis of spiked blank samples. Performance characteristics such as linearity, detection limit (LOD), quantitation limit (LOQ), precision, and recovery were determined. Recoveries of OTs in spiked matrices ranged from 86-108% in water and from 78-110% in sediments and mussels, with precision values lower than 18%. Detection limits ranged from 0.1-9.6 ng L(-1) in water, and 0.03-6.10 microg kg(-1) in the other matrices. The present implementation of LPGC rather than conventional capillary GC permitted use of large-volume injection and reduced analysis time by a factor of two. The proposed methodology was applied to the determination of OTs in real samples of water, marine sediments and mussels from the west coast of the Mediterranean Sea (Spain).

Animals↗
PubMed2006

Development of an analytical method for organotin compounds in fortified flour samples using microwave-assisted extraction and normal-phase HPLC with UV detection.

The normal high-performance liquid chromatography with UV detection was applied for the determination of tributyltin chloride (TBT), triphenyltin chloride (TPhT), tetraphenyltin (TrPhT), triethyltin chloride (TET) and tetraethyltin (TrET) from flour samples. The separation was performed in the isocratic mode on cyanopropyl column with a mobile phase of hexane-acetonitrile-THF (97/1/2). Under the experimental conditions used, quantitative limit of TBT, TPhT, TrPhT, TET and TrET are 0.95, 0.46, 0.97, 0.75 and 0.96 microg/ml, respectively. Microwave-assisted extraction of organotin (OT) compounds at 100 degrees C with an extraction time of 3 min was described. The extraction of organotin can be finished in acetic acid-hexane (20/80) medium. The quantitative extraction of five organotin compounds was achieved with recoveries ranging from 88 to 101% R.S.D. 3-8%.

Analytic Sample Preparation Methods↗
PubMed2004

Contamination and biomethylation of organotin compounds in pearl/fish culture areas in Japan.

Uwakai of Japan is famous for pearl and yellowtail fish culture. Recently, pearl culture farming in that region has suffered from a low production of pearls. An illegal use of organotin antifouling paints on fishing nets was reported. In the line of pollution studies, thus, the present investigation was carried out to examine the contamination status and fate of organotin compounds. Totally, 23 water, 10 sediment and 8 pearl oyster tissue samples were analyzed for tributyltin (TBT), triphenyltin (TPT), and their breakdown products (di- and mono compounds) by gas chromatography combined with inductively coupled plasma mass spectrometry (GC/ICP-MS). The results show that the TBT concentrations in water, sediment and biota were in the range from 0.11 to 10.6 ng Sn l(-1), 0.35 to 2500 ng Sn g(-1), and 50.4 to 181 ng Sn g(-1), respectively. The values for sediment and biota are expressed on the dry-weight basis. Triphenyltin in water, sediment and biota were in the range from 0.009 to 0.108 ng l(-1), non-detect to 12.7 ng g(-1), and non-detect to 6.83 ng g(-1), respectively. Although the TBT concentration in seawater is below the tentative assessment level of 10 ng l(-1) set by the Japanese Environment Agency in 1992, it may cause endocrine disruption/other effects in aquatic organisms. Octyltin compounds (mono-, di- and trioctyltin) were also quantified in seawater and sediment. The detection of dibutyldimethyltin (DBDMT) and tributylmonomethyltin (TBMMT) in sediment (methylated butyltins comprised 2.8-31% of total butyltins), and TBMMT in seawater suggested that biomethylation of anthropogenic tributyltins is a significant transformation pathway in the coastal environment.

Animals↗
PubMed1982

Effects of organotin compounds on maximal electroshock seizure (MES) responsiveness in mice. I. TRI(n-alkyl)tin compounds.

Male mice (25-30 g) were injected (ip) with 0, 3.5 X 10(-6), or 17.5 X 10(-6) mol trimethyltin bromide (TMT), triethyltin bromide (TET), tri-n-propyltin chloride (TPT), or tri-n-butyltin bromide (TBT) per kg. Additional groups of mice were also injected (ip) with either 0 or 17.5 X 10(-6) mol sodium bromide (NaBr) or 17.5 X 10(-6) mol stannic bromide (SnBr4) per kg. The mice were tested with maximal electroshock seizure (MES) at 0.5, 4, 21-24, and 96 h following exposure to the organotin compounds. Mice exposed to TMT, TET, TPT, or TBT exhibited dose-dependent decreases in MES severity as evaluated by seizure-grade distributions and duration of tonic seizure phases. The tri-n-alkyltin compounds exhibited a structure-activity relationship in their ability to decreased maximal responsiveness to the MES test. In order of decreasing ability they were: TMT greater than TET greater than TPT greater than TBT. Administration of NaBr and SnBr4 did not alter MES responsiveness, indicating the essential role of the alkyl moieties of the tri-n-alkyltin compounds in producing alterations in central nervous system function.

Animals↗
PubMed2003

Isotope dilution analysis as a definitive tool for the speciation of organotin compounds.

Different spike solutions available for the determination of butyltin compounds by isotope dilution analysis are described and applied for the determination of butyltin compounds in PACS-2 certified reference material. Additionally, those spike solutions were evaluated during the course of an interlaboratory exercise organised by the National Research Council of Canada and the Laboratory of the Government Chemist (UK) in order to quantify tributyltin in a pilot sediment. The aim of this project was to evaluate the capabilities of isotope dilution mass spectrometry to reduce the uncertainty in the certification of Reference Materials for the speciation of organotin compounds. All participants were supplied with a 17Sn-enriched TBT solution from the Laboratory of the Government Chemist (UK). In our case, we performed the analysis of the pilot sediment also using a 119Sn enriched spike (mixed mono-, di- and tributyltin) and a 118Sn-119Sn double spike. The use of these additional spike solutions not only allowed the determination of monobutyltin and dibutyltin in the pilot sediment but also the evaluation and correction of possible extraction-derived rearrangement reactions. An excellent agreement amongst our results and between the participants was obtained with a precision of 8.4% RSD at a level of ca. 80 ng TBT g(-1) (as Sn).

Journal Article↗
PubMed1984

Developmental neuropathology of organotin compounds.

The literature concerning the developmental neuropathology of organotins is reviewed. To date, neuropathological effects have been convincingly demonstrated for trimethyltin (TMT) and triethyltin (TET). Both compounds may damage the developing CNS; however they have different cellular targets. TMT is a neuronotoxin which damages areas of the limbic system, cerebral cortex, and brainstem. TET is a myelinotoxin which causes massive myelinic edema by yet undetermined mechanisms. Neuronal death is also seen following TET intoxication during the neonatal period, possibly as a result of elevated intracranial pressure. The neuropathological features of TMT and TET intoxication during early life are presented. Neurochemical and behavioral alterations resulting from congenital and/or neonatal exposure to organotins are also discussed.

Animals↗
PubMed1995

Speciation of organotin compounds by capillary electrophoresis using indirect ultraviolet absorbance detection.

Capillary electrophoresis (CE) with indirect photometric detection was investigated for the separation of organotin species. Compounds such as dimethyltin (DMT), dibutyltin (DBT), and tributyltin (TBT) are important pollutants in the aqueous environment and techniques are needed to analyze directly aqueous environmental samples quickly and economically. By adjusting the mobile phase to pH 2.65 by HCl, tributyltin, dibutyltin and dimethyltin in aqueous solutions were separated by capillary electrophoresis using indirect ultraviolet (UV) absorbance detection. Pyridine was used as the UV absorption additive at 254 nm and separation was achieved in 6 min. Peak tailing obtained at higher pH suggests strong interaction between the dimethyltin cation and the negatively charged capillary wall. Cetyltrimethylammonium bromide (CTAB) was added to the mobile phase to improve the peak shapes when the pH of the mobile phase was greater than 3.5. Separations of organotin species in mobile phases with or without CTAB were compared. The change of electrophoretic mobility in mobile phases with different pH values indicates that DMT and DBT start to undergo hydrolysis at a pH 3.0. It was also found that the choice of the buffer anions is critical in the separation of the tin compounds as complexes appear to form with DMT and DBT in the presence of oxalate and citrate.

Electrophoresis, Capillary↗