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PubMed2004

Concentrations of organotin compounds and imposex in the gastropod Hexaplex trunculus from the Lagoon of Venice.

In four stations located close to the channels connecting the Lagoon of Venice with the Adriatic Sea (two inside the lagoon and two outside it), individuals of Hexaplex trunculus were collected in order to assess their contamination. Concentrations of some organotin compounds, i.e. tributyltin and triphenyltin with their di- and mono- substituted metabolites, were measured and endocrine disruption such as imposex (superimposition of male sexual characteristics on females of gonochoristic gastropods) was observed. Vas deferens sequence indexes (VDSI) of 4.1-4.9 were found in organisms from stations inside the lagoon, and 3.6-4.2 in the sea stations. Organotin derivatives were measured in both the visceral coil and the rest of the soft body of the organisms. Total concentrations of butyltin compounds ranged from 102 +/- 17 to 432 +/- 27 ng Sn g(-1) d.w. in the visceral coil, and from 96 +/- 24 to 297 +/- 107 ng Sn g(-1) d.w. in the rest of the soft body. Phenyltins were found at far lower concentrations, ranging from 8 +/- 1 to 41 +/- 3 ng Sn g(-1) d.w. (visceral coil) and from 0.25 to 32 +/- 22 ng Sn g(-1) d.w. (rest of soft body). The degree of imposex in female gastropods, evaluated from VDSI and penis lengths, was related to organotin contents in the soft body. In particular, female penis lengths were significantly correlated (r = 0.917 and r = 0.982, P<0.05) to tributyltin (TBT) contents and the sum of organotin compounds in organisms.

Animals↗
PubMed1976

Application of tributyltin chloride to the separation and column chromatography of thiols.

Tributyltin chloride (TBT) has the properties of a liquid anion exchanger with a special affinity for sulphydryl groups. Thiols such as cysteine can be separated by extraction from aqueous solution with organic solvents in the form of TBT mercaptides. The graphs of extraction coefficient verus pH have maxima whose positions depend on the nature of the thiols. Thiols can be separated from each other by using TBT on polyamide as the column packing and elution with buffers of gradually increasing or decreasing pH.

Chromatography, Affinity↗
PubMed1998

Field studies on imposex and organotin accumulation in the rock shell, Thais clavigera, from the Seto Inland Sea and the Sanriku region, Japan.

Field studies on imposex and organotin (butyltin and phenyltin) contamination in the Japanese molluscs (the rock shell, Thais clavigera, and the Pacific oyster, Crassostrea gigas) were conducted along the coast of both the Seto Inland Sea and the Sanriku region, Japan, during February-March 1996. The percentage occurrence of imposex in the rock shell, Thais clavigera, was still 100% at all sites surveyed (22 and seven sites in the Seto Inland Sea and the Sanriku regions, respectively). Observed values of the Relative Penis Length (RPL) index (%), defined as the ratio of mean penis length in females to that in males, exceeded 50 at many sites. Sterile individuals whose oviducts were blocked by vas deferens formation were also extensively observed. Tissue concentrations of organotin compounds in the rock shell and the Pacific oyster were higher than those from other areas of Japan. The degree of imposex (RPL index) was correlated with the sum of TBT and TPT concentrations in tissue of the rock shell. Less recovery from imposex in the rock shell and less amelioration of TBT pollution were observed, suggesting that organotin use in antifouling paints has still continued for vessels larger than 25 m in length and that it has influenced imposex symptoms in the rock shell.

Animals↗
PubMed2001

Organotins in zebra mussels (Dreissena polymorpha) and sediments of the Quebec City Harbour area of the St. Lawrence River.

Toxic antifouling agents such as tributyltin (TBT) and triphenyltin (TPT) have been released in aquatic ecosystems through the use of antifouling paint applied to ship hulls, pleasure crafts and fish nets and these compounds can bioaccumulate in aquatic organisms. The purpose of this study was 1) to assess the extent of the distribution of organotins from a contaminated marina to the St. Lawrence River system by measuring organotin concentrations in zebra mussels (Dreissena polymorpha) and in sediments collected from 9 sites along the St. Lawrence River near Quebec City in July 1998, and 2) to examine the histopathological condition of zebra mussel tissues from these sites. TBT concentrations in zebra mussels were between 37 and 1078 ng Sn g(-1) wet weight, with the highest value found in the Bassin Louise marina. Elevated concentrations were also found in two other marinas. The concentrations decreased sharply to background levels just outside the marinas. All butyltins were detected in all sediments analysed, with highest values found in the Bassin Louise marina. Phenyltins were detected in three of the nine sites in low concentrations (<55 ng Sn g(-1)) in zebra mussels. There was a significant correlation between TBT in sediments and mussels. Gonadal development of zebra mussels varied largely between sites, and was negatively associated to TBT levels in mussel tissue. This study shows that TBT contamination remains a problem in localised freshwater sectors of the St. Lawrence River.

Animals↗
PubMed2001

Occurrence of butyltin compounds in the waters of selected lakes, rivers and coastal environments from China.

The presence of butyltin compounds was investigated for the first time in selected lakes, rivers and coastal environments of China. Aqueous samples were pretreated by the technique of headspace solid phase micro-extraction after hydride generation with sodium tetrahydroborate (NaBH4). Quantitative measurement of tributyltin (TBT), dibutyltin (DBT) and monobutyltin (MBT) concentrations were accomplished by capillary gas chromatography with flame photometric detector using quartz surface-induced luminescence. Experimental data demonstrated the widespread occurrence of butyltin compounds in the Chinese aquatic environment. In some locations, the concentrations of TBT were higher than the acute and chronic toxicity threshold of sensitive fresh water or marine organisms. Although DBT and MBT (which mainly come from the degradation of TBT), are less toxic, their occurrence can still affect the ecosystem over a long time frame.

China↗
PubMed2006

Trophic magnification of triphenyltin in a marine food web of Bohai Bay, North China: comparison to tributyltin.

Organotins, especially tributyltin (TBT) and triphenyltin (TPT), are of particular concern due to their ubiquity in the aquatic environment and theirtoxicityto aquatic organisms. This study reports field studies on trophic magnification factors (TMF) of TBT and TPT in a marine food web. TBT, TPT, and their metabolites in plankton, five benthic invertebrate species, and six fish species collected from Bohai Bay, North China were determined, and it was found that the concentrations of TPT in marine fish were unexpectedly higherthan those of TBT. A positive relationship was found between trophic levels and concentrations of TPT, indicating trophic magnification of TPT in this food web. The TMF of TPT was calculated to be 3.70. On the other hand, concentrations of TBT, dibutyltin (DBT) and monobutyltin (MBT) did not exhibit statistically significant trends with trophic levels, and the TMF of TBT was 0.59. Analysis of organotins in the water and surface sediment from Bohai Bay revealed low inputs of TPT to the environment, which indicated that the high concentrations of TPT found in fish from Bohai Bay were due to the food web magnification of TPT.

Animals↗
PubMed2005

Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: access to enantiomerically enriched all-carbon quaternary centers.

The catalytic asymmetric alpha-alkylation of tributyltin enolates with a range of primary alkyl halides is catalyzed by a chiral Cr(salen) complex. The reaction constitutes the first transition-metal-catalyzed system for alpha-alkylation of carbonyl substrates with this important class of electrophiles, providing access to five-, six-, and seven-membered ring ketone products bearing alpha-quaternary stereocenters in high enantioselectivity and synthetically useful yields.

Alkenes↗
PubMed2006

Radical-induced cyclopentannulation of Henry (nitroaldol)-derived intermediates.

Tributyltin hydride-mediated cyclizations of 1-nitro-2-acetoxy-5-hexenes 7a-g having multiple substitutions on carbons 1 and 6 result in 2,3-substituted-1-acetoxycyclopentanes 1a-g. The substrates were prepared by nitroaldol reactions of silyloxyaldehydes followed by acetylation, desilylation, and oxidation to the acetoxynitroaldehydes 6a-e. Wittig olefination of aldehydes 6a-e then afforded substrates for the radical cyclizations. The overall scheme gave a diverse array of cyclopentanes, including gem-disubstituted cyclopentanes having substitution on three contiguous carbons.

Alkenes↗
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↗
PubMed2005

Determination of metal and organometal trophic bioaccumulation in the benthic macrofauna of the Adour estuary coastal zone (SW France, Bay of Biscay).

A multidisciplinary approach has been adopted in order to investigate the bioaccumulation of metals and organometals in macrobenthic populations. A complete method coupling a sampling strategy and classification of benthic organisms with a performant analytical procedure for the analysis of both metals and organometals has been developed. A single sample preparation method using a TMAH extraction and species specific isotope dilution makes it possible to analyse metals and organometals in the same extract, which is especially interesting for situations where only a limited amount of sample is available. Low detection limits have been obtained in the range of 12-250 pg g(-1) for mercury and butyltin compounds and 0.4-50 ng g(-1) for metals with good precision (1-10% RSD) even for a very low mass of sample (0.02 g). This method has been applied for monitoring contamination and bioaccumulation of metals and organometals as well as the biodiversity and trophic structure of the macrobenthic population of the Adour Estuary (South-West, France). The benthic macrofauna diversity indicates that inner estuarine stations are moderately polluted whereas outer estuarine stations are less impacted. However, metals concentrations in both sediment and benthic biomass do not change drastically between stations. Moreover, the bioaccumulation has been determined in relation to the feeding guild of benthic organisms. The results demonstrate that higher bioaccumulation is generally observed for deposit feeders directly impacted by sediment contamination compared to suspensive feeders and predators. Biomagnification along the trophic levels was highlighted for MMHg but no significant trend was observed for the other metallic compounds.

Animals↗
PubMed2004

Survey of butyltin compounds in 12 types of foods collected in China.

Twelve representative food types including beans, fruit, vegetables, fish, meat, potatoes, sugar, beverages, alcohol, eggs, milk and corn were collected from four districts in China for the analysis of butyltin compounds. The hyphenated system of capillary gas chromatography-flame photometric detector using quartz surface-induced tin emission was used to measure proyylated butyltins in various samples. Low levels (ng g(-1)) of butyltin compounds were found in some samples and possible sources of contamination and their significance are discussed.

China↗
PubMed2004

Removal of organotins during sewage treatment: a case study.

Discharge consents for tributyltin (TBT) from wastewater treatment works in the UK are set by the Environment Agency. These values are normally derived from the Environmental Quality Standards for concentrations of TBT in the receiving water, based on the volume of effluent discharged and subsequent dilution within the environment. In this study, a sampling program was designed to monitor concentrations of TBT (and other organotins) in the influent and effluent at each stage of treatment. Sampling was undertaken at 3 hourly intervals, over 24 hours, at 8 locations throughout the works for five days. Organotin concentrations were determined using capillary gas chromatography with flame photometric detection. The results demonstrated that TBT was consistently present in the influent at concentrations of approximately 0.1 microg l(-1). However, a "pulse" of TBT and monobutyltin (MBT) was observed on the third day when the concentration of TBT and MBT in the influent increased to 14 microg l(-1). This "pulse" of TBT and MBT was also observed as the wastewater passed through the unit treatment processes. Concentrations of both compounds were much reduced in the final effluent (TBT 2.5 microg l(-1) and MBT 6.9 microg l(-1)). Over the entire period, the average removal of TBT during primary treatment was 81%, and during secondary biological treatment was 71%. The overall removal efficiency of the plant, taking into account the recycling of returned liquors was 86% between influent and effluent for TBT. Removal efficiency of TBT was correlated to that of suspended solids, and it was demonstrated that on days when suspended solids removal was low, TBT removal was also reduced. The mass flow of organotins through the plant indicated that the majority of TBT was concentrated into the sewage sludge. Concentrations of TBT in sludge at the plant were approximately 18 microg kg(-1) (dry weight).

Organotin Compounds↗
PubMed2000

Alkyltins in farmed fish and shellfish.

A study to update dibutyltin (DBT) and tributyltin (TBT) residues in farmed fish and shellfish (Mytilus edulis) was carried out 4 years after the adopting of the restricting regulation of the antifouling uses of organotins in Italy. DBT and TBT were simultaneously extracted from farmed fish and shellfish (M. edulis) and from free living specimens, used as control, purchased from retail stores or fishermen in the province of Naples (Italy), and detected using a capillary gas chromatograph equipped with a flame photometric detector (GC-FPD). Dosable amounts of DBT were found in the 10% of the farmed fish analyzed, ranging from 1 to 26 micrograms kg-1 wet wt (mean 10 micrograms kg-1) and in the 23% of the free living fish at an average level of 2 micrograms kg-1 wet wt (range 1-4 micrograms kg-1 wet wt). TBT was detected in 85% of the farmed fish, in concentrations varying from 2 to 260 micrograms kg-1 wet wt (mean 28 micrograms kg-1 wet wt) and in 46% of the free living specimens (mean 39 micrograms kg-1 wet wt; range 1-93 micrograms kg-1). All the mussel samples analyzed were polluted by both DBT and TBT. In the farmed mussels the average amounts of DBT and TBT were, respectively, 4 and 2 micrograms kg-1 wet wt; in the free living they were 4 and 5 micrograms kg-1 wet wt, respectively. The results indicate that the DBT and TBT contamination is as highly diffuse in farmed as in free living fish and mussels on sale in retail markets in Naples province even if the levels of the contamination are meanly quite low.

Animals↗
PubMed1979

Organotin-mediated exchange diffusion of anions in human red cells.

Organotin cations (R3Sn+) form electrically neutral ion pairs with monovalent anions. It is demonstrated that the tin derivatives induce exchange diffusion of chloride in red cells and resealed ghosts, without any detectable increase of membrane permeability to net movements of chloride ions. The obligatory anion exchange is believed to be due to the permeation of electroneural ion pairs, whereas the organic cation (R3Sn+) has an extremely low membrane permeability. Exchange fluxes of chloride increased with the lipophilicity of the substituting group (R3). At the same molar concentration of organotin, the relative potencies of the tin derivatives as anion carriers (with trimethyltin as a reference) were: methyl 1, ethyl 30, propyl = phenyl 1,00, and butyl 10,000. Tributyltin-mediated anion exchange was studied in detail. The organotin-induced anion transport increased through the sequence: F- less than Cl- less than Br- less than I- = SCN- less than OH-. Partitioning of tributyltin into red cell membranes was greater in iodide than in chloride media (partition coefficients 6.6 and 1.7 x 10(-3) cm, respectively). Bicarbonate, fluoride, nitrate, phosphate, and sulphate did not exchange with chloride in the presence of tributyltin. Chloride exchange fluxes increased linearly with tributylin concentrations up to 10(-5) M, and with chloride concentrations up to at least 0.9 M. The apparent turnover number for tributyltin-mediated chloride exchange increased from 15 to 1,350 s-1 between 0 and 38 degrees C. These figures are minimum turnover numbers, because it is not known what fraction of the organotin in the membrane exists as chloride ion pairs.

Adsorption↗
PubMed1993

Stimulatory effect of cooling tower biocides on amoebae.

Two species of amoebae were isolated from the cooling tower of an air-conditioning system and examined for effects of exposure to four cooling tower biocides, a thiocarbamate compound, tributyltin neodecanoate mixed with quaternary ammonium compounds, another quaternary ammonium compound alone, and an isothiazolin derivative. The amoebae isolated were Acanthamoeba hatchetti and a Cochliopodium species. Two other amoeba cultures, an A. hatchetti culture and Cochliopodium bilimbosum, were obtained from the American Type Culture Collection (ATCC) and were also tested. The cooling tower isolates were more resistant to most of the biocides than the ATCC isolates were. The isothiazolin derivative was the least inhibitory to all four amoeba isolates, and tributyltin neodecanoate mixed with quaternary ammonium compounds was the most inhibitory to three of the four isolates. After exposure to lower concentrations of the biocides, including for one strain the manufacturer's recommended concentration of one biocide, the cooling tower amoeba populations increased significantly compared with unexposed controls, whereas the ATCC isolates were not stimulated at any of the concentrations tested. In some cases, concentrations which stimulated cooling tower amoebae inhibited the growth of the ATCC isolates. These results suggest that cooling tower amoebae may adapt to biocides, underscoring the need to use freshly isolated cooling tower organisms rather than organisms from culture collections for testing the efficacy of such biocides. The stimulatory effect of biocides on amoeba populations is an alarming observation, since these organisms may be reservoirs for legionellae. Biocides used to control microbial growth may actually enhance populations of host organisms for pathogenic bacteria.

Acanthamoeba↗
PubMed1982

Effect of silver ions on transport and retention of phosphate by Escherichia coli.

Silver ions inhibited phosphate uptake and exchange in Escherichia coli and caused efflux of accumulated phosphate as well as of mannitol, succinate, glutamine, and proline. The effects of Ag+ were reversed by thiols and, to a lesser extent, by bromide. In the presence of N-ethylmaleimide and several uncouplers, Ag+ failed to cause phosphate efflux, but still inhibited exchange of intracellular and extracellular phosphate, indicating an interaction at more than one site. It is unlikely that Ag+ caused metabolite efflux by acting solely as an uncoupler, as an inhibitor of the respiratory chain, or as a thiol reagent.

Biological Transport↗
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↗