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PubMed1991

Accumulation of tri-n-butyltin chloride and triphenyltin chloride by oral and via gill intake of goldfish (Carassius auratus).

1. The bioconcentration factors (BCF) of both chemicals via gill intake of goldfish reached plateaux after 21 days of exposure. The average BCF values of Bu3SnCl and Ph3SnCl (N = 2) were 1976 and 1384, respectively, after 21-28 days of exposure. 2. The BCF values by oral intake of goldfish reached plateaux after 28 days for Bu3SnCl but did not for Ph3SnCl. The BCF values of Bu3SnCl and Ph3SnCl were 0.04 and 0.10, respectively, after 35 days. 3. The order of the BCF values via gill intake was reversed compared with that by oral intake. Further, the contamination of freshwater fish by these compounds was discussed using the results of these experiments.

Administration, Oral↗
PubMed2006

Masculinization of female gastropod mollusks induced by organotin compounds, focusing on mechanism of actions of tributyltin and triphenyltin for development of imposex.

Imposex, the superimposition of male-type genital organs (penis and vas deferens) on female gastropods, is cause-specific and induced by low concentrations of certain organotins, such as tributyltin (TBT) and triphenyltin (TPT) from antifouling paints. Reproductive failure may be observed at severely affected stages. The history of imposex study and the legislation of organotins are summarized. The present statuses of gastropod imposex and organotin pollution in Japan, together with endocrine disruption observed in abalones, are also summarized, on the basis of the results of the field studies of the rock shell (Thais clavigera) conducted at 174 locations along the Japan coast between January 1999 and November 2001, the histopathological and analytical chemical studies of the ivory shell (Babylonia japonica), and both field and laboratory studies of the abalone (Haliotis madaka and H. gigantea). The fundamental knowledge of the endocrinology of gastropod mollusks is briefly described. Four hypotheses, such as that of aromatase-inhibition, regarding the induction mechanism of imposex induced by organotins in gastropods are reviewed. Finally, a new hypothesis that states that retinoid X receptor (RXR) plays an important role in inducing the development of imposex, i.e., the differentiation and growth of male-type genital organs in female gastropods, is reviewed and discussed to clarify the entire mode of action of TBT or TPT in the development of imposex in gastropods.

Animals↗
PubMed1989

Effect of tributyltin on Escherichia coli: role of modifying factors.

The effects of inorganic and organic tin compounds and various factors affecting the toxicity of the latter to Escherichia coli were studied. In comparison to stannous chloride, tributyltin chloride (TBTC) was more inhibitory to the growth of the test organism; this may be due to its greater liposolubility and ready absorption through the bacterial membrane. The toxicity of TBTC to E. coli was modulated by various factors, such as pH, sulfate and chloride ions, and the presence of glucose, succinate, and reducing agents like cysteine and dithiothreitol (DTT). TBTC was more toxic to cells in minimal than in complex media. Similarly, this compound was more inhibitory to the growth of E. coli at acid pH than at basic pH. Succinate in contrast to glucose, when used as a carbon source, made the bacterium more sensitive to TBTC. Cysteine and DTT (both at a final concentration of 0.5 mM) partially protected the cells against the inhibitory effect of this agent.

Chlorides↗
PubMedDate not supplied

Collection and analysis of butyltin compounds in air at nanogram-per-cubic-meter levels.

An analytical method for determining butyltin chlorides in air at low nanogram-per-cubic-meter levels was developed. Butyltin chlorides investigated were mono-n-butyltin trichloride (MBTC), di-n-butyltin dichloride (DBTC), and tri-n-butyltin chloride (TBTC). These tin chlorides were trapped on cartridges packed with Porapak-N, eluted with methylene chloride containing 0.3% HCl, hydridized with sodium borohydride, and analyzed by capillary gas chromatography with flame photometric detection. On the basis of a 20 m3 sample, a detection limit of 0.05 ng/m3 can be achieved.

Air Pollutants↗
PubMed1974

Inhibition and uncoupling of photophosphorylation in isolated chloroplasts by organotin, organomercury and diphenyleneiodonium compounds.

1. Trialkyltin, triphenyltin and diphenyleneiodonium compounds inhibited ADP-stimulated O(2) evolution by isolated pea chloroplasts in the presence of phosphate or arsenate. Tributyltin and triphenyltin were the most effective inhibitors, which suggests a highly hydrophobic site of action. Phenylmercuric acetate was a poor inhibitor of photophosphorylation, which suggests that thiol groups are not involved. 2. Triethyltin was a potent uncoupler of photophosphorylation by isolated chloroplasts in media containing Cl(-), but had little uncoupling activity when Cl(-) was replaced by NO(3) (-) or SO(4) (2-), which are inactive in the anion-hydroxide exchange. It is suggested that uncoupling by triethyltin is a result of the Cl(-)-OH(-) exchange together with a natural uniport of Cl(-). Tributyltin, triphenyltin and phenylmercuric acetate had low uncoupling activity, probably because in these compounds the uncoupling activity is partially masked by inhibitory effects. 3. At high concentrations the organotin compounds caused inhibition of electron transport uncoupled by carbonyl cyanide m-chlorophenylhydrazone or NH(4)Cl. At these high concentrations the organotin compounds may be producing a detergent-like disorganization of the membrane structure. In contrast, diphenyleneiodonium sulphate inhibited uncoupled electron transport at low concentrations; however, this inhibition is less than the inhibition of photophosphorylation, which suggests that the compound also inhibits the phosphorylation reactions as well as electron transport. 4. The effects of these compounds on basal electron transport were complex and depended on the pH of the reaction media. However, they can be explained on the basis of three actions: inhibition of the phosphorylation reactions, uncoupling and direct inhibition of electron transport. 5. The inhibition of cyclic photophosphorylation in the presence of phenazine methosulphate by diphenyleneiodonium sulphate shows that it inhibits in the region of photosystem 1.

Adenosine Diphosphate↗
PubMed1984

Determination of trialkyltin, dialkyltin, and triphenyltin compounds in environmental water and sediments.

An analytical procedure for the determination of trialkyltin (tributyltin, tripropyltin), triphenyltin and dialkyltin (dibutyltin) compounds in environmental water and sediment was studied. Water samples were extracted into benzene with hydrochloric acid and sodium chloride. Sediment samples were extracted into methanolic hydrochloric acid and converted into benzene. Silica gel, which was impregnated with hydrochloric acid and activated, was used for clean-up of these compounds. These extracts of organotin chlorides were hydrogenated with an ethanol solution of sodium borohydride. Organotin hydrides were measured by gas chromatography with electron-capture detection. Recoveries of these compounds were ca. 70-95% from river water and sediment samples. The detection limits were 0.4-0.8 micrograms/l in water and 0.02-0.04 micrograms/g in sediment samples.

Chromatography, Gas↗
PubMed1979

Effect of organotin compounds and hexachlorophene on brain adenosine cyclic 3',5'-monophosphate metabolism.

The effect of triethyltin (TET), triphenyltin (TPT), hexachlorophene (HCP) and cuprizone on adenosine cyclic 3',5'-monophosphate (cyclic AMP) production in rat brain was examined both in vitro and in vivo. TET and TPT inhibited basal adenylate cyclase activity of brain homogenate at a concentration as low as 1 microM in vitro but these compounds had no effect on norepinephrine (NE) and dopamine(DA)-stimluated enzyme activity. HCP and cuprizone failed to inhibit adenylate cyclase activity. In vivo TET given intravenously at a dose rate of 10 mg/kg decreased the cyclic AMP content of cerebrum, but not of medulla. TPT and HCP give intravenously and intraperitoneally respectively failed to decrease the cyclic AMP content of the cerebrum. In the case of TET the reduction in cyclic AMP content of the cerebrum was prevented by maintaining the rats normothermic after treatment. On the basis of these results the inhibition of adenylate cyclase produced by TET in brain homogenates in vitro would not appear to be involved in the development of nervous changes associated with acute TET toxicity, or in the production of progressive brain oedema caused by TET, HCP and cuprizone.

Adenylyl Cyclases↗
PubMed1991

Analysis of organotin uptake in Escherichia coli K-12.

The effect of tributyltin chloride (TBT) was potentiated by the presence of Tris ions in the growth medium compared with phosphate ions. The growth of Escherichia coli in the presence of Tris ions was inhibited completely at a concentration of 25 microM TBT whereas 79% growth was recorded in the presence of phosphate ions. Tris ions caused more protein to be released into the medium than phosphate ions. However, apart from protein release the rate of organotin uptake was less in Tris than in phosphate ions. Phosphate ions may play a positive role in the active accumulation of organotin into E. coli cells by providing cellular energy.

Bacterial Proteins↗
PubMed1993

Organotins are co-clastogens in a whole mammalian system.

The frequency of micronuclei induced by mitomycin C (MMC) in mouse peripheral reticulocytes was enhanced by treatment with organotins: bis(tri-n-butyltin) oxide (TBTO) and triphenyltin chloride (TPTC). TBTO and TPTC did not themselves induce micronucleated reticulocytes (MNRETs) in mouse peripheral blood. When 50 mg/kg TBTO or 100 mg/kg TPTC was given orally to mice simultaneously with an intraperitoneal (i.p.) administration of 1 mg/kg MMC, however, TBTO and TPTC caused about 55% and 51% increases, respectively, in MMC-induced a synergistic MNRET frequency. Organotin administration 3 or 6 h before and 3 h after MMC injection also caused enhancement of MNRET frequency. These results demonstrate that TBTO and TPTC act as co-clastogens in a whole mammalian system.

Animals↗
PubMed1988

Metal-induced alteration of the cell membrane/cytoplasm complex studied by flow cytometry and detergent lysis.

Flow cytometric analysis of the cell cycle is most effectively accomplished with membrane-/cytoplasm-free ("clean") nuclei. Non-ionic detergents (e.g. NP40 or Triton X-100) commonly are employed to solubilize cell membranes/cytoplasm to produce "clean" nuclei. Treatment of murine erythroleukemic cells (MELC) with tri-n-butyltin methoxide, cadmium acetate, zinc sulfate, or lead acetate alters the properties of the cell membrane/cytoplasm complex making it resistant to NP40 dissolution. On a molar basis, the organotin compound was more effective in inducing resistance to detergent-mediated dissolution than the inorganic metal compounds. Resistance to NP40-mediated dissolution was manifested as an increase in the flow cytometric parameters 90 degrees scatter and fluorescein isothiocyanate (FITC) fluorescence and was confirmed by light microscopy.

Acetates↗
PubMed1989

Toxicity of dibutyltin, tributyltin and other organotin compounds to humans and to experimental animals.

Alkyltin compounds are used as stabilizers and antifouling agents. Food chain accumulation and bioconcentration have been demonstrated in crabs, oysters and salmon exposed to tributyltin oxide. In mammalian species, tributyltin compounds may be metabolized to dibutyltin derivatives and related metabolites. Di- and tributyltins appear to be less potent neurotoxicants than trimethyltins and triethyltins. Dibutyltins and tributyltins produced bile duct damage in rats, mice and hamsters. Tributyltin oxide and dibutyltin and dioctyltin compounds are potent thymolytic and immunotoxic agents in rats. Tributyltin oxide at 5 ppm in the rat diet produced immunotoxicity in a 2-year feeding study, and at 50 ppm increased the incidence of tumors of endocrine origin. In preliminary reports, 5 ppm tributyltin produced no detectable increase in tumor incidence, and 0.5 ppm produced no detectable immunotoxicity in long-term studies. Tributyltin oxide and dibutyltin acetate did not appear to be mutagenic in a large battery of mutagenicity assays but produced base-pair substitutions in one of the bacterial strains tested. Tributyltin oxide produced mutations in Chinese hamster ovary cells, increased the incidence of micronuclei in the erythrocytes of exposed male BALB/c mice, and was highly embryotoxic in vitro. Embryotoxic and teratogenic effects in mice exposed to tributyltin oxide in vivo may have been due either to direct tributyltin oxide action or responses secondary to maternal toxicity. More information is needed to determine the applicability to human risk assessments of the immunotoxicity data derived from rat studies and to establish a definitive tolerable daily intake for tributyltin oxide.

Animals↗
PubMed2006

Sources and fate of butyltins in the St. Lawrence Estuary ecosystem.

Butyltins (BTs) were determined in sediment, zooplankton, benthic fish and invertebrates in the St. Lawrence Estuary and its mixing zone with the Gulf of St. Lawrence (Canada) in an attempt to assess sources and fate of these compounds in a large ecosystem before the enforcement of the world-wide ban of TBT-based antifouling paints. All BTs (MBT, DBT and TBT) were found along the studied area (450 km) where the traffic of large vessels occurs around the year. Concentrations of total butyltins (BTs) in surface sediment were below 6 ng Sn g(-1) d.w. Total BTs concentrations found in zooplankton samples at the mouth of the Saguenay Fjord were the highest (793 ng Sn g(-1) d.w.), indicating the influence of the Fjord on the St. Lawrence contamination. Although a relatively low contamination level was measured in sediment, total BTs concentrations ranged from 9 to 489 ng Sn g(-1) d.w. for benthic organisms. Biota-sediment accumulation factors (BSAFs), calculated on the basis of the organic carbon content in the sediment (concentrations normalized to 1% Corg), ranged from 0.9 to 98.3, and are an indicator of an important source of BTs from the Saguenay Fjord particulate matter. This may be explained by the fact that when TBT is released in a large and deep well stratified coastal environment, it could bind to the suspended particulate matter and then be taken in charge by water column organisms and may be mostly metabolised before it reaches bottom sediment. Sediment is not considered as the main contributor to the contamination of fish and invertebrates. It is expected that any reduction of direct inputs of TBT from ship hulls in a near future should result in a rapid reduction of butyltins in the St. Lawrence ecosystem.

Animals↗
PubMed2005

Imposex occurrence in marine whelks at a military facility in the high Arctic.

Imposex was found in the Arctic whelk Buccinum finmarkianum at several marine stations off Thule Air Base, an US military facility in Northwest Greenland. This indicates a widespread contamination with the antifouling agents, tributyltin (TBT) or triphenyltin (TPhT) in the area, but such contamination was not supported by the organotin analyses in sediments, whelks and clams, which in general was below the analytical detection limit. Organotin concentrations above the detection limit were found only at one station close to a quay, where the highest frequency of imposex also occurred. This suggests that imposex in B. finmarkianum is a biomarker of TBT more sensitive than the detection limits, which the analytical chemistry could achieve in this study.

Animals↗
PubMed2005

Imposex and surface sediment speciation: a combined approach to evaluate organotin contamination in Guanabara Bay, Rio de Janeiro, Brazil.

An integrated biological-chemical survey of organotin compounds was carried out in Guanabara Bay, the second most important Brazilian harbor complex. The biological survey revealed high levels of imposex in Stramonita haemastoma populations. Inside the bay values of relative penis length index from 42.7 to 107.6 and vas deferens sequence index from III to VI were found, while organisms collected outside the bay had values ranging from <0.1 to 35.2 and from 0 to II. None of the females sampled inside the bay were normal and imposex was found in all stations. Surface sediments in the bay are contaminated by tributyltin (10-522 ng/g d.w.) and triphenyltin (<3.9-39.4 ng/g d.w.) with greater concentrations close to shipyards and marinas. The observed predominance of parent compounds (TBT and TPT) is commonly found when recent inputs occur, but may also indicate slow degradation processes in the anoxic conditions of these sediments. To our knowledge, this is the first report of a combined imposex-sediment approach to evaluate organotin contamination in marine environments of South America, and also the first report of TPT detection in environmental matrices in this region.

Animals↗