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PubMedDate not supplied

Butyltin and phenyltin compounds in some marine fishery products on the Japanese market.

The degree of butyltin and phenyltin contamination was determined in samples of 11 species of fish products that were representative of the Japanese fish market. We observed high contamination levels of these organotin compounds in cultured marine products. Mean butyltin contamination of natural (nonfarmed) marine products, however, were relatively low, compared with the cultured products. Phenyltin concentrations in the described samples were generally much lower than levels of butyltin compounds. Levels of organotin compounds in these marine products have decreased drastically as a result of legal controls instituted by the Japanese government in 1990. On the basis of calculated tolerable daily intake levels of tributyltin and triphenyltin, we concluded that the levels of organotin compounds in the marine products on the Japanese market were not sufficiently high to have any effect on human health. However, we also determined that some of the cultured marine products were contaminated with undesirable levels of tributyltin.

Animals↗

PubMed1986

Effect of organotins on fecal pollution indicator organisms.

Pure cultures of Escherichia coli and Streptococcus faecalis and environmental water samples were examined for the possibility that pollution involving organotin compounds could decrease the values for indicator organisms when standard methods were applied to the analysis of water samples. (CH3)2SnCl2 and (CH3)3SnCl decreased viable counts at about 10 to 100 mg of Sn liter-1 (8.4 X 10(-5) to 8.4 X 10(-4) mol of Sn liter-1), and tributyltin chloride was effective at about 0.1 to 1.0 mg of Sn liter-1 (8.4 X 10(-7) to 8.4 X 10(-6) mol of Sn liter-1. These concentrations, particularly for the methyltin compounds, are greater than the concentrations reported to date for these compounds in aquatic ecosystems. Thus, organotin compounds alone would not be likely to cause reductions in counts of indicator organisms measured by standard methods. However, it is suggested that, when combined with other environmental stressors or upon long exposure, organotins such as butyltins may contribute to the injury of indicator organisms.

Enterococcus faecalis↗

PubMed2006

Effect of triorganotin compounds on membrane permeability.

Organotin compounds are widely distributed toxicants. They are membrane-active molecules with broad biological toxicity. In this contribution, we study the effect of triorganotin compounds on membrane permeability using phospholipid model membranes and human erythrocytes. Tribultyltin and triphenyltin are able to induce the release of entrapped carboxyfluorescein from large unilamellar vesicles. The rate of release is similar for phosphatidylcholine and phosphatidylserine systems and the presence of equimolar cholesterol decreases the rate of the process. Release of carboxyfluorescein is almost abolished when a non-diffusible anion like gluconate is present in the external medium, and it is restored by addition of chloride. Tributyltin is able to cause hemolysis of human erythrocytes in a dose-dependent manner. Relative kinetics determination shows that potassium leakage occurs simultaneously with hemoglobin release. Hemolysis is reduced when erythrocytes are suspended in a gluconate medium. These results indicate that triorganotin compounds are able to transport organic anions like carboxyfluorescein across phospholipids bilayers by exchange diffusion with chloride and suggest that anion exchange through erythrocyte membrane could be related to the process of hemolysis.

Fluoresceins↗

PubMed2006

Relationships between the abnormalities of the male reproductive organs and the accumulation of phenol compounds in the striped field mouse, Apodemus agrarius, inhabiting Korea.

The relationships between the abnormalities of the male reproductive organs in striped field mice and the accumulation of endocrine-disrupting chemicals were assessed. Most mice collected at three areas were contaminated with phenol or organotin compounds. Fourteen to 42% of the mice at each area had abnormally shrunken reproductive organs, and some of them were contaminated with high levels of phenol compounds. Moreover, all the shrunken reproductive organs were damaged in the histological structure. The damage was observed also from several mice accumulating a high level of phenol compounds even though they had normally developed reproductive organs, although no damage was found in the mice accumulating a high level of organotin compounds. Collectively, the abnormalities of the reproductive organs in the mice seemed to be related to the accumulation of phenol compounds rather than of organotin compounds.

Animals↗

PubMedDate not supplied

Role of hydrophobic and hydrophilic interactions of organotin and organolead compounds with model lipid membranes.

The present study was conducted to clarify the mechanism of toxicity of organic compounds using lipid model membranes (liposomes and planar lipid membranes). The compounds studied were trialkyltin and trialkyllead chlorides, dialkyltin dichlorides and some inorganic forms of those metals. Two different (anionic and cationic) detergents were also used in the experiments to change the surface properties of liposomes. As a measure of interaction between the compounds studied and model membranes were the release of liposome bound praseodymium and the change in stability of planar membranes under the influence of those compounds. On the basis of the results obtained it was postulated that the mechanism of interaction between tin- and leadorganics and model lipid membranes is a combination of different factors featuring interacting sides. The most important properties determining the behaviour of organic compounds in the interaction were lipophilicity and polarity of different parts of the organics and the steric arrangement they can take in the medium. On the other hand, the surface potential of the lipid bilayer and the environment of the lipid molecules, that play a significant role in the availability of the lipid bilayer to the organics, were important factors in the interaction.

Lead↗

PubMed1999

A study on organotin levels in Canadian drinking water distributed through PVC pipes.

A study on organotin compounds in Canadian drinking water was carried out in winter-spring 1996 (28 sites) and autumn 1996 (21 sites). Approximately 29% and 40% of distribution waters supplied through PVC pipes installed recently (typically less than 6 months) contained organotin compounds in the winter-spring and autumn surveys respectively. Monomethyl-, dimethyl-, monobutyl- and dibutyltin levels ranged up to 291 ng Sn/L, 49.1 ng Sn/L, 28.5 ng Sn/L and 52.3 ng Sn/L, respectively. An additional study in summer 1996, of locations where the highest organotin levels were detected in the winter-spring survey, indicated that organotin levels had decreased in most distribution water samples. Samples of PVC pipe/tubing contained organotin compounds consistent with the organotin patterns found in the distribution water samples.

Canada↗

PubMed1995

Determination of tributyltin and triphenyltin compounds in hair and fish using a hydrolysis technique and gas chromatography with flame photometric detection.

A hydrolysis technique and a GC method are described for the determination of tributyltin and triphenyltin compounds in human hair and fish tissue. A sample was hydrolysed with a potassium hydroxide-ethanol-water solution. Tributyltin and triphenyltin compounds in the hydrolysate were extracted with toluene, and then impurities in the extract were eliminated with anion- and cation-exchange resins. After propylation of the organotin compounds, a yellow impurity was removed with a Sep-Pak florisil cartridge, and the two propylated organotin compounds were separated using a silicone OV-1 GC column and determined by flame photometric detection. The limits of determination of tributyltin and triphenyltin compounds in the sample were 5 and 10 ng g-1, respectively, in their chloride forms. The recoveries of tributyltin chloride from hair samples were 78.8 and 90.8%, respectively, when the spiked amounts were 20 and 200 ng. The recoveries of triphenyltin chloride from hair samples were 71.7 and 72.7%, respectively, when the spiked amounts were 40 and 400 ng. The recoveries of the organotin compounds from fish were similar to the recoveries from hair.

Animals↗

PubMed1987

Organotin-induced hemolysis, shape transformation and intramembranous aggregates in human erythrocytes.

Organotin compounds examined in this study exhibited a relative order of potency for induction of in vitro hemolysis in human erythrocytes as follows: tri-n-butyltin greater than tri-n-propyltin greater than tetra-n-butyltin greater than triphenyltin chloride greater than tri-n-ethyltin bromide greater than dibutyltin dichloride greater than stannous chloride greater than tri-n-methyltin chloride = butyltin chloride dihydroxide. All of the organotin compounds induced erythrocyte shape transformation from the normal discocyte to an echinocyte and, in addition, triphenyltin chloride, tetra-n-butyltin and tri-n-ethyltin bromide also elicited stomatocyte formation at higher concentrations. Select organotin compounds also formed tin-containing aggregates within the plasma membrane. The relative order of effectiveness for organotin induction of intramembranous aggregates was tri-n-butyltin greater than tri-n-propyltin greater than tetra-n-butyltin greater than tri-n-ethyltin bromide, which was based upon the lowest concentration at which they were observed. These results support the previously suggested theory that organotins are membrane effectors because of their comparatively high hydrophobic, lipid partitioning properties. The relatively lipophilic compound, triphenyltin chloride, appeared to be anomalous because it did not readily promote hemolysis or induce the formation of intramembranous aggregates in human erythrocytes. A log-linear statistical model demonstrated an association of hemolysis with both tri-n-butyltin aggregate formation and shape transformation. Select organotin compounds should be useful probes in membrane studies because of their numerous effects.

Erythrocyte Aggregation↗

PubMed2004

Biotransformation of tributyltin to tin in freshwater river-bed sediments contaminated by an organotin release.

The largest documented release of organotin compounds to a freshwater river system in the United States occurred in early 2000 in central South Carolina. The release consisted of an unknown volume of various organotin compounds such tetrabutyltin (TTBT), tributyltin (TBT), tetraoctyltin (TTOT), and trioctyl tin (TOT) and resulted in a massive fish kill and the permanent closures of a municipal wastewater treatment plant and a local city's only drinking-water intake. Initial sampling events in 2000 and 2001 indicated that concentrations of the ecologically toxic TTBT and TBT were each greater than 10 000 microg/kg in surface-water bed sediments in depositional areas, such as lakes and beaver ponds downstream of the release. Bed-sediment samples collected between 2001 and 2003, however, revealed a substantial decrease in bed-sediment organotin concentrations and an increase in concentrations of degradation intermediate compounds. For example, in bed sediments of a representative beaver pond located about 1.6 km downstream of the release, total organotin concentrations [the sum of TTBT, TBT, and the TBT degradation intermediates dibutyltin (DBT) and monobutyltin (MBT)] decreased from 38 670 to 298 microg/kg. In Crystal Lake, a large lake about 0.4 km downstream from the beaver pond, total organotin concentrations decreased from 28 300 to less than 5 microg/kg during the same time period. Moreover, bed-sediment inorganic tin concentrations increased from pre-release levels of less than 800 to 32 700 microg/kg during this time. These field data suggest that the released organotin compounds, such as TBT, are being transformed into inorganic tin by bed-sediment microbial processes. Microcosms were created in the laboratory that contained bed sediment from the two sites and were amended with tributyltin (as tributyltin chloride) under an ambient air headspace and sacrificially analyzed periodically for TBT, the biodegradation intermediates DBT and MBT, and tin. TBT concentrations decreased faster [half-life (t1/2) = 28 d] in the organic-rich sediments (21.5%) that characterized the beaver pond as compared to the slower (t1/2 = 78 d) degradation rate in the sandy, organic-poor, sediments (0.43%) of Crystal Lake. Moreover, the concentration of inorganic tin increased in microcosms containing bed sediments from both locations. These field and laboratory results suggest that biotransformation of the released organotins, in particular the ecologically detrimental TBT, does occur in this fresh surface-water system impacted with high concentrations of neat organotin compounds.

Biodegradation, Environmental↗

PubMed2005

Accumulation and trophic transfer of organotins in a marine food web from the Danish coastal waters.

The presence of organotin compounds, e.g., tributyltin (TBT) and triphenyltin (TPhT) including the di- and monosubstituted breakdown products, was studied in a representative marine food web in order to assess the accumulation potential at different trophic levels in Danish coastal waters. This included samples of two species of seaweed, four species of invertebrates, four species of fish, five species of birds and two species of mammals. All organisms were sampled away from harbour areas and the organotin concentrations found in this study can therefore be considered to reflect a general level in organisms living in Danish coastal waters. All the samples analysed contained organotin compounds. The highest hepatic concentrations of butyltins were found in flounder (60-259 ng g-1 wet weight [ww], as Sn), eider duck (12-202 ng g-1 ww) and harbour porpoise (134-2283 ng g-1 ww). The lowest concentrations were found in seaweed and a plant-feeding bird. TPhT or its degradation products were also found in most of the samples with the highest concentrations in flounder (9.8-74 ng g-1 ww), cod (23-28 ng g-1 ww) and great black-backed gull (19-24 ng g-1 ww). This indicates an input of TPhT in the region, probably from the use as antifouling agent. A high variance in accumulation potential was found between the species, even between species at the same trophic level, which probably reflects the species-specific differences in exposure routes and the capabilities to metabolise and eliminate the organotin compounds. This study gives evidence of the importance of biomagnification of butyltin in harbour porpoises and, to a lesser extent, in fish and birds.

Animals↗

PubMed2001

Speciation of butyltin compounds in marine sediments with headspace solid phase microextraction and gas chromatography mass spectrometry.

A method for the determination of organotin compounds (monobutyl = MBT, dibutyl = DBT, and tributyltin = TBT) in marine sediments by headspace Solid Phase Microextraction (SPME) has been developed. The analytical procedure involved 1) extraction of TBT, DBT and MBT from sediments with HCl and methanol mixture, 2) in situ derivatization with sodium tetraethylborate and 3) headspace SPME extraction using a fiber coated with poly(dimethylsiloxane). The derivatized organotin compounds were desorbed into the splitless injector and simultaneously analyzed by gas chromatography - mass spectrometry. The analytical method was optimized with respect to derivatization reaction and extraction conditions. The detection limits obtained for MBT, DBT and TBT ranged from 730 to 969 pg/g as Sn dry weight. Linear calibration curves were obtained for all analytes in the range of 30-1000 ng/L as Sn. Analysis of a standard reference sediment (CRM 462) demonstrates the suitability of this method for the determination of butyltin compounds in marine sediments. The application to the determination of TBT, DBT and MBT in a coastal marine sediment is shown.

Gas Chromatography-Mass Spectrometry↗

PubMed1999

Organotin(IV) compounds as intramolecular transesterification catalysts in thermal depolymerization of poly(L-lactic acid) oligomer to form LL-lactide.

Mono-, di-, and tetraalkyl tin(IV) compounds were evaluated for the intramolecular transesterification reaction of the thermal depolymerization of poly(L-lactic acid) oligomer forming lactide by gas chromatography using a beta-cyclodextrin stationary phase capillary column. The most active catalyst was found to be monobutyltin trichloride (BuSnCl3) (8), which contains tin-halogen bonds, and the least effective was the coordinatively saturated monoorganotin derivative, monobutyltin tris(2-ethylhexanoate) (7). Coordination of the carbonyl group in the oligomer to the tin catalysts is an important factor influencing its activity.

Catalysis↗

PubMed2001

[Current status of organotin studied in China and abroad].

The toxicity of organotin compounds and the current pollution status in China and abroad is discussed. Regulations and limitations on the usage of organotin compounds in western countries are introduced briefly in this paper. The examination results showed that the most Chinese harbors, rivers as well as larger lakes were contaminated by organotin, especially by tribuyltin compounds. Regulations for limiting the use of butyltin compounds as antifouling paints in Chinese marine industries are imperatively needed. Actions toward for the investigation of organotin contamination levels in food chains and in household commodities are also highly desired.

Animals↗

PubMed2001

Electrospray ionization mass spectrometry of tribenzyltin substituted-phenoxyacetate compounds.

Hydrolysis products of organotin compounds RC(6)H(4)OCH(2)COOSn(CH(2)ph)(3) (R = o-NO(2), 1; m-NO(2), 2; p-NO(2), 3; o-CH(3), 4; o-OCH(3), 5; o-Cl, 6; o-Br, 7) and RC(6)H(3)OCH(2)COOSn(CH(2)ph)(3) (R = o,o-2CH(3), 8, o-OCH(3), p-CHO, 9; o,p-2Cl, 10), produced in aqueous acetonitrile solution, have been investigated by electrospray mass spectrometry (MS) and MS(n) techniques. The complexes [Y(2)SnXR'](-), [Y(3)SnXR'](-), [Y(3)SnX(2)R'](-), [Y(2)SnX(3)R'](-), and fragment ions of [Y(3)SnR'](-), plus abundant RC(6)H(4)(or RC(6)H(3))OCH(2)COO(-) and RC(6)H(4)(or RC(6)H(3))O(-) ions are observed in negative mode, whereas the protonated molecular ion [M + H](+), complexes [Y(2)SnXR'](+), [Y(3)SnXR'](+), [Y(2)SnX(2)R'](+), [Y(3)SnX(2)R'](+), [Y(2)SnX(3)R'](+), [Y(3)SnX(3)R'](+), as well as [YSnXR'](+), [M - CH(2)ph](+), XSn(+), (phCH(2))(3)Sn(+), phCH(2)Sn(+) (Y = &bond;CH(2)ph, X = &bond;OOCCH(2)OC(6)H(4)R(or C(6)H(3)R)) are detected in the positive mode. Water adduct ions are seen in both modes. The assignments are facilitated by agreement between observed and calculated isotopic patterns and tandem mass spectrometry studies.

Journal Article↗

PubMedDate not supplied

Comparative organotin toxicity in the developing rat: somatic and morphological changes and relationship to accumulation of total tin.

The effect of the structure of organotin compounds on their toxicity and neurotoxicity to the developing rat has been studied. Oral administration was used after selection of a vehicle that gave uniform organotin solubilization as evidenced by toxicity and chemical solubility data. This vehicle was milk plus Tween-80. Eight different organotin compounds were systematically surveyed for effects in the neonatal rat. Trimethyl- and triethyltin were most toxic, and were somewhat more toxic than tri-n-propyltin. Tri-n-butyltin was somewhat less toxic, while tricyclohexyl-, triphenyl-, diethyl- and dimethyltin were least toxic. Some higher doses of trimethyl- or triethyltin caused neuropathological changes that were characteristic for each compound, these changes being absent for the other agents. Regardless of their toxicity, significant amounts of tin, as the element, were found in brain, kidney, and liver after treatment with all agents. However, detectable blood values were only obtained for trimethyl- and triethyltin.

Administration, Oral↗

PubMed2005

Triphenyltin and Tributyltin inhibit pig testicular 17beta-hydroxysteroid dehydrogenase activity and suppress testicular testosterone biosynthesis.

We previously reported that tributyltin chloride (TBT) and triphenyltin chloride (TPT) powerfully suppressed human chorionic gonadotropin- and 8-bromo-cAMP-stimulated testosterone production in pig Leydig cells at concentrations that were not cytotoxic [Nakajima Y, Sato Q, Ohno S, Nakajin S. Organotin compounds suppress testosterone production in Leydig cells from neonatal pig testes. J Health Sci 2003;49:514-9]. This study investigated the effects of these organotin compounds on the activity of enzymes involved in testosterone biosynthesis in pig testis. At relatively low concentrations of TPT, 17beta-hydroxysteroid dehydrogenase (17beta-HSD; IC(50)=2.6microM) and cytochrome P450 17alpha-hydroxylase/C(17-20) lyase (IC(50)=117microM) activities were inhibited, whereas cholesterol side-chain cleavage cytochrome P450 and 3beta-HSD/Delta(4)-Delta(5) isomerase activities were less sensitive. Overall, TPT was more effective than TBT. TPT also inhibited both ferredoxin reductase and P450 reductase activities at concentrations over 30microM; however, TBT had no effect, even at 100microM. The IC(50) values of TPT were estimated to be 25.7 and 22.8microM for ferredoxin reductase and P450 reductase, respectively. The inhibitory effect of TPT (30microM) on microsomal 17beta-HSD activity from pig testis was eliminated by pretreatment with the reducing agents dithiothreitol (1mM) and dithioerythritol (1mM). On the other hand, TPT (0.03microM) or TBT (0.1microM) exposure suppressed the testosterone production from androstenedione in pig Leydig cells indicating that these organotins inhibit 17beta-HSD activity in vivo as well as in vitro, and the IC(50) values of TPT and TBT for 17beta-HSD activity were estimated to be 48 and 114nM, respectively. Based on these results, it appears possible that the effects of TBT and TPT are largely due to direct inhibition of 17beta-HSD activity in vivo.

17-Hydroxysteroid Dehydrogenases↗

PubMed2003

Ecotoxicological problems associated with contaminated sites.

Contamination sites pose significant environmental hazards for terrestrial and aquatic ecosystems. They are important sources of pollution and may result in ecotoxicological effects. At severely contaminated sites acute effects occur, but the core problem lies in possible long-term chronic effects. Ecotoxicological effects occur at all levels of the biological organization, from the molecular to the ecosystem level. Not only certain organisms may be affected, but the ecosystems as a whole in its function and structure. Contaminants at large contaminated sites often share critical properties such as toxicity, high environmental persistence, often high mobility prone to contamination of groundwater, and high lipophilicity resulting in bioaccumulation in food webs. Contaminants present at polluted sites occur as mixtures; therefore, interactions between individual compounds may be of importance. The bioavailability is a key factor responsible for ecotoxicological effects of contaminants: only the bioavailable fraction induces ecotoxicological effects, as shown for organotin compounds. Organotins belong to the most toxic pollutants known so far for aquatic life. Widespread contamination of harbor sediments occurs globally due to the ongoing use of organotins in antifouling paints on large ships. In lake sediments, tributyl- and triphenyltin are very persistent and bioavailable to biota even after a long time. The bioavailability of organotins is dependent on the pH and the content of organic matter. Organotins accumulate in sediments, but remobilization occurs during disturbance and dredging. A key question in dealing with contaminated sites is whether, and to what extent ecotoxicity occurs. Usually, established OECD tests and whole effluent toxicity tests are performed for an ecotoxicological evaluation and for risk assessment. However, these assays are often expensive, laborious and sometimes not sensitive enough. As a consequence, we have used rapid and inexpensive in vitro systems such as fish cell lines for the evaluation of sediments and landfill leachates, which were contaminated by polycyclic aromatic hydrocarbons (PAHs). The determination of cytotoxicity as a measure for acute toxicity, and the induction of cytochrome P4501A (CYP1A) as a biomarker of exposure and effects were found to be important measures, which can be used for hazard and risk assessment. We have developed a concept for the ecotoxicological evaluation of PAH contamination based on induction equivalents, which can be applied for aquatic and terrestrial ecosystems. One of the key question and present gaps, however, includes the long-term chronic ecotoxicological effects of single compounds and mixtures on soil and aquatic biota at contaminated sites. This should be addressed in the future.

Animals↗

PubMed1999

Caspase involvement in the induction of apoptosis by the environmental toxicants tributyltin and triphenyltin.

Organotin compounds such as tributyltin (TBT) and triphenyltin (TPT) can kill target cells by triggering apoptosis. The mechanism by which these environmental toxicants activate the apoptotic program is currently unclear. We have studied the effect of TBT and TPT in the human Hut-78 and Jurkat T-lymphocyte cell lines. Within 1 h there was a 30-fold increase in caspase activity, as measured by the cleavage of the fluorescent peptide DEVD-AMC. Morphological changes characteristic of apoptosis, such as membrane blebbing and nuclear fragmentation, were readily detectable. Blocking caspase activity with the peptide inhibitor z-VAD-fmk prevented all subsequent apoptotic changes. The optimal concentration range for induction of apoptosis was 0.5 to 5 microM TBT. TPT was also able to trigger caspase activity in the lymphocyte cell lines, but it took over 2 h to detect and occurred at a lower concentration range of 0.01 to 1 microM. Higher concentrations of TBT and TPT caused cell necrosis, and we showed that these concentrations were able to inhibit caspase activity in apoptotic cells. TBT and TPT were able interact with a vicinal thiol compound, similar to the known caspase inhibitor phenylarsine oxide, providing a potential mechanism for caspase inhibition. We propose that vicinal thiol proteins may be a general biological target of these organotin compounds, leading to the induction of caspase activity and apoptosis at low concentrations, and more extensive cell damage and necrotic cell death at higher concentrations.

Apoptosis↗