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PubMed1981

The acute toxicity of some organolead and organotin compounds in the rat, with particular reference to a gastric lesion.

The acute toxicity of triphenyl, tributyl and dibutyllead in the rat appears to result from their irritating properties to membranes regardless of their route of administration. A more detailed examination of their oral toxicity has shown that a single dose inhibits gastric emptying with resulting fluid distension. A similar effect was observed with a number of other organolead and organotin compounds. Analysis of gastric fluid from pyloric ligated rats following an oral organolead dose showed increased concentrations of Na+ and glucose and decreased concentrations of H+ and K+. Dilation of the gastric mucosal microcirculation was also observed along with desquamation of surface mucous cells which resulted in shallow erosions of the upper portions of the gastric glands. It is suggested that oral dosing with a number of organoleads and, possibly, organotins has an effect on mucosal membranes that results in erosion of the gastric mucosa and increases permeability of the mucosal microcirculation. This would allow leakage of plasma constituents into interstitial fluid and ultimately the gastric lumen with back-diffusion of H+ into the gastric mucosa. Such a lesion would impair gastric function and reduce normal food and water consumption. The starvation and dehydration may then be the important factors for death that follows oral dosing with organolead and organotin compounds.

Animals↗
PubMed2002

Fine-tuned characterization at the solid/solution interface of organotin compounds grafted onto cross-linked polystyrene by using high-resolution MAS NMR spectroscopy.

The structural characterization of organotin compounds that are grafted onto insoluble cross-linked polymers has necessarily been limited to elemental analysis, infrared spectroscopy, and in a few instances, solid-state NMR spectroscopy. This important bottleneck in the development of such grafted systems has been addressed by using high-resolution magic angle spinning (hr-MAS) NMR spectroscopy. The great potential of this technique is demonstrated through the structural characterization of diphenylbutyl-(3,4) and dichlorobutylstannanes (5,6), grafted onto divinylbenzene cross-linked polystyrene by means of a suitable linker (1, 2). First, conditions suitable for the application of hr-MAS NMR spectroscopy were identified by characterizing the (1)H resonance line widths of the grafted organotin moiety following swelling of the functionalized beads in eight representative solvents. The presence of clearly identifiable tin coupling patterns in both the 1D (13)C and 2D (1)H-(13)C HSQC spectra, and the incorporation of (119)Sn chemical shift and connectivity information from hr-MAS 1D (119)Sn and 2D (1)H-(119)Sn HMQC spectra, provide an unprecedented level of characterization of grafted organotins directly at the solid/liquid interface. In addition, the use of hr-MAS (119)Sn NMR for reaction monitoring, impurity detection, and quantification and assessment of the extent of coordination reveals its promise as a novel tool for the investigation of polymer-grafted organotin compounds. The approach described here should be sufficiently general for extension to a variety of other nuclei of interest in polymer-supported organometallic chemistry.

Magnetic Resonance Spectroscopy↗
PubMedDate not supplied

Application of gas chromatographic determination of organotin compounds to basic research on the metabolism of triphenyltin chloride in rats.

This paper describes the application of gas chromatographic determination of organotin compounds to basic research on the metabolism of triphenyltin chloride in rats. Phenyltin compounds were extracted (as chloride) from rat-liver homogenates and subcellular fractions with hydrochloric acid and n-hexane-benzene (3:2, containing 0.05% tropolone). These organotin compounds were pentylated with a Grignard reagent prior to capillary gas chromatography. The absolute detection limits were in the range of 3.6 to 4.4 pg as tin. The absolute recoveries of phenyltin compounds added to homogenized whole liver and each subcellular fraction sample ranged from 73.9 to 97.4%. The intracellular distribution of triphenyltin and its metabolites in the liver was observed for 72 h after a single oral dose of triphenyltin chloride was given to rats. The tri-, di-, and monophenyltin compounds in the fractions reached maximal amounts about 6, 48, and 72 h after administration, respectively. Also, the concentrations of monophenyltin compounds in the liver were typically lower than to those of di- and triphenyltin compounds. The highest contents of di- and triphenyltin compounds per protein were found in the microsomal fractions.

Animals↗
PubMed2002

Organochlorine and organotin compounds in Caspian seals (Phoca caspica) collected during an unusual mortality event in the Caspian Sea in 2000.

Polychlorinated biphenyls (PCBs), organochlorine pesticides and organotin compounds were determined in the blubber and liver of Caspian seals (Phoca caspica) found stranded on the coast of the Caspian Sea during an outbreak of canine distemper virus (CDV) in 2000. Among organochlorines analyzed, DDTs were the most dominant contaminants with concentrations ranging from 6.3 to 470 microg/g on a lipid-weight basis. Caspian seals collected in 2000 during the epizootic had higher concentrations of organochlorines than healthy individuals sampled in 1998. However, the blubber layer was generally thinner in the seals collected in 2000 than those in the previous surveys. Although compositions of organochlorine pesticides in seals suggested that the contamination status in the Caspian Sea is improving, the levels found in Caspian seals in 2000 were comparable to those in other marine mammals that have suffered from epizootics. This implies that the present status of contamination found in Caspian seals poses a risk of immunosuppression. Concentrations of butyltin compounds in livers of seals ranged from 0.49 to 17 ng/g on a wet-weight basis and octyltin compounds were below limit of detection in all the samples analyzed, suggesting less contamination by organotin compounds in the Caspian Sea.

Algorithms↗
PubMed2001

Use of imposex (pseudohermaphroditism) as indicator of the occurrence of organotin compounds in Portuguese coastal waters--Sado and Mira estuaries.

Organotin compounds, including tributyltin (TBT), are a class of the most toxic xenobiotics occurring in aquatic systems. High concentration levels in waters and sediments are mainly due to their extensive use as biocides and high persistence when present in sediments under anaerobic conditions. Toxicity studies have revealed the acute effects of TBT for aquatic organisms at concentrations as low as 1 microgram/L, and the induction of imposex at levels below 0.5 ng/L TBT (as Sn). At 20 ng/L TBT (as Sn) causes sterility and is followed with the disappearance of the most sensitive neogastropods on a given shore. Imposex is the most sensitive response of all known pathological conditions for nontarget organisms following an exposure to tributyltin. In this study results are discussed that were obtained from two monitoring sites with different anthropogenic background using imposex monitoring as an indicator of TBT concentrations, as well as chemical analysis of tissue of Hinia (= Nassarius) reticulata (L.) (Gastropoda).

Animals↗
PubMed2004

Biogeochemistry of organotin compounds and tin in a forested catchment in Germany.

Organotin compounds (OTC) are highly toxic pollutants that have been shown to affect many aquatic ecosystems. Little is known about the input and fate of OTC in terrestrial ecosystems. Here, soil pools, concentrations and fluxes in bulk precipitation, throughfall, fog, litterfall and runoff of OTC and Sntotal were investigated in a forested ecosystem (Picea abies, Karst.) in NE Bavaria, Germany. The concentrations of OTC and Sntotal were generally in the order fog>throughfall>bulk precipitation. Average concentrations of OTCtotal ranged from 57 ng Sn l(-1) in fog to 5.8 ng Sn l(-1) in bulk precipitation. Concentrations of Sntotal were in the same order but between 490 ng Sn l(-1) in fog and 140 ng Sn l(-1) in bulk precipitation, on average. Average OTCtotal concentrations in litterfall were 12.9 ng Sn g(-1) and those of Sntotal in litterfall 38 ng Sn g(-1). All OTC concentrations in runoff were lower than in bulk precipitation, while those of Sntotal were similar to the concentrations in bulk precipitation. Monobutyltin was the dominating OTC in bulk precipitation, throughfall, fog and litterfall, but was seldom detected in the runoff. The annual total deposition of OTCtotal (calculated as throughfall + litterfall) was 172 mg Sn ha(-1) year(-1), with 45 mg Sn ha(-1) year(-1) represented by litterfall. The annual runoff from the catchment of OTCtotal amounted to 25 mg Sn ha(-1) year(-1). The total deposition of Sntotal was 4.9 g Sn ha(-1) year(-1), of which 0.2 g Sn ha(-1) year(-1) was litterfall. The annual runoff of Sntotal was 2.4 g Sn ha(-1) year(-1). The mass balance showed a high retention of OTC and Sntotal in the catchment. The forest soils act as a strong sink for OTC and Sntotal. Only small amounts of deposited OTC are released to runoff. The ratio of soil pools to annual accumulation for total OTC (46 years) indicates that OTC inputs have been occurring already for many decades or have been substantially higher in the past than today.

Air Pollutants↗
PubMed2001

Speciation of organotin compounds in marine sediments by capillary column gas chromatography-atomic absorption spectrometry coupled with hydride generation.

A method for speciation of organotin compounds in marine sediments by solvent extraction combined with hydride generation gas chromatography-atomic absorption spectrometry has been developed. Sediment samples spiked with tributyltin and triphenyltin chlorides were homogenized in hydrochloric acid. The chlorides were extracted twice into toluene. Recoveries of the organotin compounds from the spiked sediment samples were improved by the addition of 8-quinolinol. Tributyltin and triphenyltin chlorides form ion-associates with 8-quinolinol in aqueous hydrochloric acid. The method was optimized with respect to derivatization reactions and extraction conditions. Interferences from Sn(II/IV) and additional 13 ions were investigated. Recoveries of 84-100% for tributyltin and 86-100% for triphenyltin were achieved using this method. The detection limits obtained for tributyltin and triphenyltin chlorides were 95 and 145 pg, respectively, corresponding to a relative detection limit of 95 and 145 ng kg(-1) in the sediment.

Chromatography, Gas↗
PubMed2002

Inhibitory effects of organotin compounds on voltage-dependent, tetrodotoxin-resistant Na+ channel current in guinea pig dorsal root ganglion cells.

The effects of organotin compounds on voltage-dependent, tetrodotoxin (TTX)-resistant Na+ channel current (I(Na)) in single cells isolated from guinea pig dorsal root ganglion were investigated using a whole cell patch clamp technique. Extracellular application of tributyltin (TBT) inhibited I(Na) in a concentration-dependent manner with an IC50 of 7.2 microM. TBT (100 microM), when applied intracellularly, was without effect. Triphenyltin (TPT, 100 microM) and dibutyltin (DBT, 100 microM), applied extracellularly, inhibited I(Na) with an efficacy ranking of TBT>TPT>DBT. Monobutyltin (100 microM), whether applied externally or internally, had little effect on I(Na). TBT (30 microM) significantly prolonged both time to peak and half-decay time of I(Na) and shifted the activation curve of I(Na) in the positive direction without changing the slope. No such effect was produced by TPT (100 microM). The results indicate that organotin compounds inhibit voltage-dependent, TTX-resistant Na+ channel activity and suggest that the inhibitory action may account, at least in part, for their neurotoxic effects.

Animals↗
PubMed1985

Organotin compounds and international treaties on the pollution of water by dangerous substances: black or grey list substances?

A brief review is given of international agreements governing water pollution by hazardous organotin compounds. Emphasis is placed on the Rhine Chemical Convention (1976) and the Dangerous Substances Directive 76/464/EEC. Organotin pesticides first appeared in 1974 on the grey list. In 1976, however, the whole group of organotin compounds was placed on the black list. Although priorities have recently been set for the Rhine and the European Community (EC), no scientific arguments have apparently been put forward to date either in support of these priorities or to explain the need to move this group of substances to the black list.

Europe↗
PubMed1996

Effect of organotin compounds on the growth of the freshwater alga Scenedesmus quadricauda.

Organotin compounds (OTCs) are extensively used in a variety of industrial processes and their increasing discharge into the environment is a topic of current concern. Many OTCs are toxic to various organisms and they are used to a limited but significant extent as biocidal agents in agriculture and technology. The concentration and form in which tin (Sn) is present in the environment determines its toxicological effects. The present study was conducted to determine the inhibitory effect of 12 OTCs [A, dibutyl tin bis-N,N-diethyldithiocarbamate; B, dimethyltin bis(N, N-diethyldithiocarbamate); C, triphenyltin chloride; D, triphenyltin acetate; E, triphenyltin N,N-diethyldithiocarbamate; F, tribenzyltin bis(N,N-diethyldithiocarbamate); G, tribenzyltin chloride; H, bis (tributyltin)-3,4,5,6-tetrachlor phthalate; I, tributyltin sulfaminate; J, tributyltin N,N-diethyldithiocarbamate; K, tributyltin naphthenate; and L, tributyltin oxide (TBTO)] in four concentrations (0.001, 0.01, 0.1, and 1.0 mg/liter) on the growth of freshwater alga Scenedesmus quadricauda under standardized conditions. The inhibitory effect of OTCs after 12 days cultivation in percentages for each concentration used was determined and individual growth curves of S. quadricauda for tested concentrations of OTCs and for control were plotted. On the basis of the percentage of control growth the rank order of inhibition after 12 days application of OTCs in concentration 1.0 mg/liter was made: L = H = F = C > E > D > J = K > I > G > A > B. From this rank order, it is evident that the least inhibitive effects on algal growth were from the diorganotin compounds A and B, especially compound B with a methyl group in the n-alkyl chain. The most toxic was compound L (TBTO) with a butyl group in side chain.

Dose-Response Relationship, Drug↗
PubMed1976

[Separation and quantitative "in situ"-determination of organotin compounds on thin layer plates].

Residues of organotin compounds in feed and food are extracted with isopropanol. Clean up by means of a Sephadex LH-20 column and separation of the compounds of Kieselgel-G thin layer plates by 4-methyl-pentanone (2)/pyridine/acetic acid (97.5 + 1.5 +1) is achieved. Triphenyl- and tricyclohexyltin fungicides are quantitatively determined by direct scanning the thin layer plates using a chromatogram spectralphotometer.

Animal Feed↗
PubMed2001

Sorption and desorption behavior of organotin compounds in sediment-pore water systems.

Sediments contaminated with organotin compounds (OTs), in particular triorganotins (TOTs), are abundant in areas with high shipping activities. To assess the possible remobilization of these highly toxic compounds from such sediments, a profound understanding of their sorption/desorption behavior is necessary. In this work the extent and reversibility of sorption of OTs to sediments has been investigated using contaminated freshwater harbor sediments and two certified OT containing marine sediments. Experiments conducted with perdeuterated OTs showed that sorption of OTs to sediments is a fast and reversible process involving primarily particulate organic matter (POM) constituents as sorbents. The organic carbon-normalized sediment-water distribution ratios (DOC, expressed in L/kgOC) determined in the laboratory were consistent with in-situ DOCs obtained from OT concentrations measured in sediment and pore water samples from two dated sediment cores. For both butyl- and phenyltin compounds the log DOC values were in the range of 4.7-6.1, and the following sequence was observed: DOC (tri-OT) > or = DOC (di-OT) > or = DOC (mono-OT). However, the differences were much less pronounced than would have been expected for hydrophobic partitioning of the corresponding compounds into POM. These results support our hypothesis from earlier work with dissolved humic acids that OT sorption to sediments occurs primarily by reversible formation of (innerspere) complexes between the tin atom and carboxylate and phenolate ligands present in POM. Because of the high DOC values (i.e. log DOC > or = 4) the diffusion of OTs from deeper sediments to the surface will be rather slow, and thus a major release from undisturbed sediments is not expected. However, because OTs readily desorb, any resuspension of contaminated sediments (e.g., by the tide, storms or dredging activities) will lead to enhanced OT concentrations in the overlaying water column. Furthermore, in contrastto polycyclic aromatic hydrocarbons (PAH) where large fractions may be tightly bound (in)to soot or other carbonaceous materials, OTs will be more readily bioavailable due to the fast and reversible sorption/desorption behavior.

Absorption↗
PubMed2002

Analysis of organotin compounds by grignard derivatization and gas chromatography-ion trap tandem mass spectrometry.

The determination of organotin compounds in water using gas chromatography-tandem mass spectrometry (GC-MS-MS) is described. Several organotin derivatives were synthesized by the reaction of organotin chlorides with Grignard reagents such as methyl-, propyl- and pentylmagnesium halides. After the optimization of the GC-MS-MS conditions, several derivatizations with the Grignard reagents were compared by evaluating the molar responses and volatilities of the derivatives and derivatization yields. As a result, the derivatizing reagent of choice is pentylmagnesium bromide. Calibration curves for the mono-, di- and tributyltins and mono-, di- and triphenyltins with pentylmagnesium bromide were linear in the range of 0.5-100 pg of Sn. The instrumental detection limits of six organotins ranged from 0.20 to 0.35 pg of Sn. The recovery tests from water samples (500 ml) were performed by using sodium diethyldithiocarbamate (DDTC) as a complexing reagent. Except for monophenyltin, the absolute recoveries of organotins from pure water at 200 ng of Sn/l were satisfactory. The recoveries calibrated by surrogate compounds (perdeuterated organotin chlorides) ranged from 71 to 109%. The method detection limits ranged from 0.26 to 0.84 pg of Sn (500-ml sample). This method was applied to the recovery of organotins from river water and seawater. The calibrated recoveries were between 90 and 122%.

Calibration↗
PubMed1997

Effects of triphenyltin chloride and five other organotin compounds on the development of imposex in the rock shell, Thais clavigera.

The imposex promotion activities of six organotin compounds--tributyltin (TBT), dibutyltin (DBT), monobutyltin (MBT), triphenyltin (TPT), diphenyltin (DPT) and monophenyltin (MPT)--were examined by injection experiments with the rock shell, Thais clavigera (Prosobranchia; Muricidae). TPT and TBT had strong effects on the development of imposex in the rock shell (p<0.001). The other organotin compounds (DBT, MBT, DPT and MPT) had no or less effects on the development of imposex in T. clavigera. The difference between the effects of TPT and TBT was statistically insignificant (p>0.01). The effects of these compounds are estimated, from the relationships between TBT or TPT concentration in tissue and mean penis length of females after injections, to be approximately the same.

Journal Article↗
PubMed2004

Speciation of organotin compounds by capillary electrophoresis: comparison of aqueous and mixed organic-aqueous systems.

A capillary electrophoresis method with direct ultraviolet detection was developed for the analysis of organotin species. Despite the fact that direct detection of organotin compounds by ultraviolet absorption is difficult because most organotins possess poor chromophoric properties, the application of low wavelength (lambda = 200 nm) and mixed organic-aqueous media enabled a significant enhancement in sensitivity. A mixed organic-aqueous system (10% methanol/40% acetonitrile/50% H2O) containing acetic acid and tetrabutylammonium perchlorate formed the basis for rapid, efficient and sensitive determinations of organotin cations such as tripropyltin, tributyltin, triphenyltin and diphenyltin. The concentration limits of detection (LOD) for the four organotin compounds were in the range of 0.4-14 microM, comparable to that obtained with the most sensitive indirect UV method reported until now, and took advantage of a stable baseline, a symmetric peak shape and an absence of disturbing system peaks. The relative standard deviations (n = 7) for the relative peak time and peak area were 0.44-0.77 and 4.8-5.8%, respectively. In addition to sensitivity enhancements, the use of organic-aqueous systems instead of pure aqueous media resulted in improved selectivity and efficiency of separations.

Journal Article↗
PubMed2003

Rapid determination of organotin compounds by headspace solid-phase microextraction.

Headspace solid-phase microextraction (SPME) followed by gas chromatography (GC) coupled to pulsed flame photometric detection have been investigated for the simultaneous speciation analysis of 14 organotin compounds, including methyl-, butyl-, phenyl-, and octyltins compounds. The analytical process (sorption on SPME fibre and thermal desorption in GC injection port) has been optimised using experimental designs. Six operating factors were considered in order to evaluate their influence on the performances of a SPME-based procedure. The evaluation of accuracy, precision and limits of detection (LODs) according to ISO standards and IUPAC recommendations has allowed the method to be validated. The LODs obtained for the 14 studied organotins compounds are widely sub-ng(Sn) l(-1). The precision evaluated using relative standard deviation ranges between 9 and 25% from five determinations of the analytes at 0.25-125 ng(Sn) l(-1) concentrations. The accuracy was studied throughout the analysis of spiked environmental samples. These first results show that headspace SPME appears really as attractive for organotins determination in the environment and the monitoring of their biogeochemical cycle.

Chromatography, Gas↗
PubMed1989

Actions of orally administered organotin compounds on heme metabolism and cytochrome P-450 content and function in intestinal epithelium.

The gastrointestinal tract is a major route by which humans are exposed to environmental chemicals. We have examined in these studies the effects of oral administration of organotin compounds in the small intestinal epithelium, an organ which exhibits highly active drug and other chemical metabolism. A series of n-butyltin compounds was administered by gavage to male Sprague-Dawley rats (225-275 g) in single doses up to 250 mumol/kg body weight. Bis(tri-n-butyltin)oxide (TBTO) produced dose- and time-dependent decreases in the content and functional activity of intestinal cytochrome P-450, together with an elevation (3-fold) in the activity of microsomal heme oxygenase. The effects of di-n-butyltin dichloride on heme oxygenase and cytochrome P-450 were pronounced in the small intestine and extended to the liver and kidneys within 21 hr after oral-exposure, whereas TBTO did not affect the liver until much later (6 days), when cytochrome P-450 content was reduced markedly (30%). Furthermore, the effects produced by tetra-n-butyltin on cytochrome P-450 at 24 hr were localized in the intestinal epithelium. These studies indicate important pharmacological effects of organotin compounds in the gut, and raise the possibility that concurrent oral ingestion of organotins with other environmental pollutants may alter the cytochrome P-450-dependent metabolism of xenobiotics and natural substrates of this monooxygenase system in the small intestine.

Administration, Oral↗
PubMedDate not supplied

Cytotoxicity in vitro and preliminary antitumor activity in vivo of a novel organotin compound.

The cytotoxic effect and antitumor activity induced by the novel organotin compound triethyltin(IV)lupinyisulfide hydrochloride, have been investigated. Different patterns of antiproliferative effects have been observed in a panel of human tumor cell lines in vitro. Toxicity studies in mice reported acute toxicity at the doses of 21 and 17.5 mg/kg which progressively disappeared at lower concentrations. On this basis, the doses of 3.5, 7 and 14 mg/kg were selected to assess the antitumor activity in vivo against the P388 leukemic cells xenografted in mice. This compound was able to induce a dose-dependent significant reduction of tumor volume, up to 46%, at the highest concentration (p = 0.0062) without important toxicity, as also confirmed by histological analysis of the main organ tissues. This preliminary study seems to hold interest for further investigations in different tumor models as well as for the evaluation of optimal drug route and schedule.

Animals↗