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PubMed1991

Subchronic toxicity studies of tri-n-butyltin and triphenyltin acetates in rats.

The effects of a moderate but prolonged exposure of rats to tri-n-butyltin acetate (TBTA) and triphenyltin acetate (TPTA), as might be encountered as residues in yam peel diets, were investigated in rats. These subchronic toxicity studies (16, 8, or 4 mg TBTA/kg and 20, 10 or 5 mg TPTA/kg) showed histopathologic lesions in lungs, liver, intestine and kidney. The hematologic parameters in the groups treated with either compound fell within the normal range for the rats. However, there was a reduction in mean lymphocyte count for rats receiving 10 or 20 mg TPTA/kg, and a reduction in monocyte count in the 20 mg TPTA/kg group. These data indicate a need for further toxicologic studies and cautionary measures to avoid ingestion, inhalation or contamination of dietary materials by these fungicides.

Animals↗
PubMed1978

Atomic absorption spectrometric determination of cyhexatin in apples.

A rapid method using atomic absorption spectrometry has been developed for determining residues of cyhexatin in apples. Each analysis takes less than 30 min and the method is sensitive to less than 0.1 mg cyhexatin/kg. Recoveries varied from approximately 100% at 0.25 and 0.05 mg/kg to 70% at 5 mg/kg. No acid digestion or cleanup is required for the analysis.

Fruit↗
PubMed1981

Pathogenesis of trimethyltin neuronal toxicity. Ultrastructural and cytochemical observations.

The ultrastructural cytopathologic and cytochemical effects of trimethyltin (TMT) neurotoxicity were delineated in hippocampal and pyriform neurons of acutely intoxicated adult rats. TMT produced neuronal necrosis that preferentially involved hippocampal formation pyriform cortex. The first subcellular alterations were multifocal collection of dense-cored vesicles and tubules and membrane-delimited vacuoles in the cytoplasm of the perikaryon and proximal dendrite. Ultrastructural cytochemical examination revealed that the vesicles and tubules had acid phosphatase activity analagous to Golgi-associated endoplasmic reticulum (GERL). Shortly after the appearance of the GERL-like vesicles and tubules, autophagic vacuoles and polymorphic dense bodies accumulated in the neuronal cytoplasm. Some dense bodies appeared to arise from the dense-cored tubules. Neuronal necrosis was characterized by increased electron density of the cytoplasm and large, electron-dense intranuclear masses. Alterations of mitochondria and other organelles were not observed in the early stages of cell injury. No light- or electron-microscopic alterations were found in liver or kidney. Comparable subcellular alterations were observed in adult and neonatal rats chronically intoxicated with TMT. A series of other trialkyl and tricyclic tins and dimethyltin did not produce similar pathologic findings. The GERL-like accumulations are unique in neuronal cytopathology. These findings suggests that GERL and autophagy play an important role in the pathogenesis of TMT-induced neuronal injury.

Animals↗
PubMedDate not supplied

Comparative developmental toxicity of butyltin trichloride, dibutyltin dichloride and tributyltin chloride in rats.

Butyltin trichloride (BT), dibutyltin dichloride (DBT) and tributyltin chloride (TBT) were compared for their developmental toxicity including teratogenic potential following administration during the susceptible period for the teratogenesis of DBT. Pregnant rats were given either BT at a dose of 1000, 1500 or 2000 mg kg-1, DBT at a dose of 10 or 15 mg kg-1 or TBT at a dose of 40 or 80 mg kg-1 by gastric intubation on days 7 and 8 of pregnancy. Although maternal toxicity occurred, as evidenced by a significantly increased maternal lethality at 1500 and 2000 mg kg-1 and decreased maternal weight gain at 1000 and 1500 mg kg-1, no significant increase in the incidences of postimplantation loss and malformed fetuses were observed after treatment with BT. Treatment with DBT resulted in a significantly lower maternal weight gain, lower fetal weight and higher postimplantation embryolethality. A significantly and markedly increased incidence of fetuses with malformations, such as exencephaly, cleft jaw, cleft lip, ankyloglossia, club foot, deformity of the vertebral column in the cervical and thoracic regions and of the ribs and ano- or microphthalmia, was observed in both groups treated with DBT. While treatment with TBT at 40 and 80 mg kg-1 caused a significantly decreased maternal weight gain and increased postimplantation embryolethality, no significantly increased incidence of malformed fetuses occurred. It could be concluded that BT, DBT and TBT are different in the susceptibility and spectrum of developmental toxicity.

Abnormalities, Drug-Induced↗
PubMed2002

Metabolism of tributyltin and triphenyltin by rat, hamster and human hepatic microsomes.

Tributyltin and triphenyltin are metabolized by cytochrome P-450 system enzymes, and their metabolic fate may contribute to the toxicity of the chemicals. In the current study, the in vitro metabolism of tributyltin and triphenyltin by rat, hamster and human hepatic microsomes was investigated to elucidate the metabolic competence for these compounds in humans. The metabolic reaction using microsome-NADPH system that is usually conducted was not applicable to in vitro metabolism of organotins, especially triphenyltin. We therefore examined the effects of dithiothreitol (DTT), one of the antioxidants for sulfhydryl groups, to determine the in vitro metabolism of tributyltin and triphenyltin. As a result, the treatment with 0.1 mM DTT in vitro increased the activity of the microsomal monooxygenase system for metabolism of tributyltin as well as triphenyltin; the total yield of tributyltin and triphenyltin metabolites as tin increased, respectively, by approximately 1.8 and 8.9 times for rat, 2.1 and 1.2 times for hamster, and 1.6 and 1.5 times for human. It is suggested that the organotins directly inactivate cytochrome P-450 because of the interaction with critical sulfhydryl groups of the hemoprotein. We confirmed the utility of this in vitro metabolic system using DTT in the hepatic microsomes of phenobarbital (PB)-pretreated and untreated hamsters. Thus, the in vitro metabolic system described here was applied to a comparative study of the metabolism of organotins in rats, hamsters and humans. Tributyltin was metabolized more readily than triphenyltin in all the species. In humans, the in vitro metabolic pattern resembled that of hamsters, which were susceptible to in vivo triphenyltin toxicity because of incompetent metabolism. It is possible that the hamster is a qualitatively and quantitatively suitable animal model for exploring the influence of tributyltin and triphenyltin in humans.

Adult↗
PubMed2000

Accumulation of butyltin and phenyltin compounds in various fish species.

Concentrations of organotins (OTs) were measured in the muscle of 11 species of fishes from the Port of Osaka and Yodo River, Japan. Tributytin (TBT) and triphenyltin (TPT) compounds were detected in the range of 0.011-0.182 mg/kg wet weight and < 0.001-0.130 mg/kg wet weight, respectively. Concentrations of TBT were higher than those of TPT in the muscle of fish. Concentrations of OTs in fish from sea areas were higher than those from rivers, and the ratios of TBT to total butyltins (BTs) in fish from sea areas were also higher than those from rivers. A similar trend was found for TPT. Logarithm of bioconcentration factor (BCF) of TBT in fish was in the range of 2.7-3.9. No sex differences in TBT and TPT concentrations in Japanese sea perch were observed, and the concentrations of TBT and TPT were not related to total length of fish. No correlation was also observed between the concentration of TBT or TPT and lipid content. The concentrations of BTs and phenyltins (PTs) in organs and tissues of three fish species were determined. TBT was higher concentration in liver, brain, and muscle of white croaker and yellowtail. The ratios of TBT to the total BTs were 30-40%, and the ratios of TPT to total PTs in these fishes were greater than 50% of the total PT concentrations.

Animals↗
PubMed1998

Accumulation of tributyl- and triphenyltin compounds in Pacific oyster, Crassostrea gigas, from the Chinhae Bay System, Korea.

Butyl- and phenyltin residues were quantified in seawater and Pacific oyster (Crassostrea gigas) from the Chinhae Bay System, Korea. Butyltin compounds were detected in all the seawater and C. gigas samples, whereas phenyltin compounds were not detected in any seawater samples. Tributyltin (TBT) concentrations in seawater ranged <8-35 ng Sn L-1. TBT and triphenyltin (TPhT) concentrations in oysters ranged 95-885 and 155-678 ng Sn g-1, respectively. Spatial distribution of TBT was closely related to boating and dry-docking activities. However, spatial distribution of TPhT was not consistent with that of TBT. The estimated biological concentration factor (BCF) for TBT in C. gigas was about 25,000. Furthermore, 19 and 28% of total body burdens of TBT and TPhT were found in gonadal mass of C. gigas just prior to the spawning period, indicating that a proportional amount of TBT and TPhT would be released with a following reproductive process.

Animals↗
PubMed1993

Tri-n-butyltin chloride promotes morphological transformation and induces proliferin expression in C3H10T1/2 cells.

Transcripts from the murine gene family proliferin, which are increased by a wide assortment of chemical promoters of C3H10T1/2 cell morphological transformation, were shown to be induced by tri-n-butyltin chloride at concentrations above 50 nM. Two-stage transformation assays, with 3-methylcholanthrene as inducer and tri-n-butyltin chloride as promoter, were performed to determine if promotion of morphological transformation and proliferin induction were properties shared by this compound. Tri-n-butyltin chloride synergistically enhanced focus formation at concentrations ranging from 20 to 75 nM. Di-n-butyltin dichloride, n-butyltin trichloride and tin (II) chloride, but not tin (IV) chloride, were also effective inducers of proliferin. Changes in patterns of TPA-inducible, secreted proteins, including those likely to be proliferin, were detected following organotin treatment of confluent monolayers. Tri-n-butyltin chloride resembles other agents active as promoters in C3H10T1/2 two-stage transformation assays by possessing an ability to induce proliferin expression.

Animals↗
PubMed1995

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

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

Electrophoresis, Capillary↗
PubMed2006

TBT and TPhT persistence in a sludged soil.

The persistence of tributyltin (TBT) and triphenyltin (TPhT) in soils was studied, taking into consideration the quantity of sewage sludge, TBT and TPhT concentrations in soil as well as the soil pH. The organotin compounds (OTC) were introduced into the soil via a spiked urban sludge, simulating agricultural practise. OTC speciation was achieved after acidic extraction of soil samples followed by gas chromatography-pulsed flame photometric analysis (GC-PFPD). Leaching tests conducted on a spiked sludge showed that more than 98% of TBT are sorbed on the sludge. TBT persistence in soil appeared to depend on its initial concentration in sludge. Thus, it was more important when concentration is over 1000 microg(Sn) kg(-1) of sludge. More than 50% of the initial TBT added into the soil were still present after 2 months, whatever the experimental conditions. The main degradation product appeared to be dibutyltin. About 90% of TPhT were initially sorbed on sludge, whatever the spiking concentration in sludge was. However, TPhT seemed to be quantitatively exchangeable at the solid/liquid interface, according to the leaching tests. It was also significantly degraded in sludged soil as only about 20% of TPhT remain present after 2 months, the monophenyltin being the main degradation product. pH had a significant positive effect on TBT and particularly TPhT persistence, according to the initial amounts introduced into the soil. Thus, at pH over 7 and triorganotin concentration over 100 microg(Sn) kg(-1), less than 10% of TBT but about 60% of TPhT were degraded. When the sludge was moderately contaminated by triorganotins (typically 50 microg(Sn) kg(-1) in our conditions) the pH had no effect on TBT and TPhT persistence.

Organotin Compounds↗
PubMed1998

Liquid chromatography with fluorimetric detection of triorganotin compounds in marine biological materials.

Several extraction methods have been evaluated for marine biological materials with regard to tributyltin and triphenyltin determination by liquid chromatography with post-column fluorimetric detection using fisetin as a fluorogenic reagent. Extraction with ethyl acetate in a hydrochloric acid medium has been shown to be the most appropriate extraction method and it has been successfully applied to fish (sea bass) reference material from the National Institute for Environmental Studies (NIES-11) and to a candidate reference material.

Animals↗
PubMed2001

Stir bar sorptive extraction for the determination of ppq-level traces of organotin compounds in environmental samples with thermal desorption-capillary gas chromatography--ICP mass spectrometry.

The extraction and preconcentration capabilities of a new extraction technique, stir bar sorptive extraction, were combined with the separation power of capillary gas chromatography (CGC) and the low limits of detection (LODs) of inductively coupled plasma mass spectrometry (ICPMS) for the determination of the organotin compounds tributyltin (TBuT) and triphenyltin (TPhT) in aqueous standard solutions, harbor water, and mussels (after digestion with tetramethylammonium hydroxide). Throughout, tripropyltin for TBuT and tricyclohexyltin for TPhT were used as internal standards to correct for variations in the derivatization and extraction efficiency. Calibration was accomplished by means of single standard addition. Derivatization to transform the trisubstituted compounds into sufficiently volatile compounds was carried out with sodium tetraethylborate. The compounds were extracted from their aqueous matrix using a stir bar of 1-cm length, coated with 55 microL of poly(dimethylsiloxane) (PDMS). After 15 min of extraction, the stir bar was desorbed in a thermal desorption unit at 290 degrees C for 15 min, during which the compounds were cold-trapped on a precolumn at -40 degrees C. Flash heating was used to rapidly transfer the compounds to the GC where they were separated on a capillary column with a PDMS coating. After separation, the compounds were transported to the ICP by means of a homemade heated (270 degrees C) transfer line. Monitoring of the 120Sn+ signal by ICPMS during the run of the GC provided extremely low LODs for TPhT in water: 0.1 pg L(-1) (procedure) and 10 fg L(-1) (instrumental) and a repeatability of 12% RSD (n = 10). In harbor water, concentrations of 200 pg L(-1) for TBuT and 22 pg L(-1) for TPhT were found. In fresh mussels, a concentration of 7.2 ng g(-1) (dry weight) TPhT was found. The accuracy of the method was checked by the determination of TPhT in CRM477 (mussel tissue) and comparison of the result to that of an analysis of the same material with a classical liquid/liquid extraction with isooctane.

Animals↗
PubMed2002

Determination of methylmercury and butyltin compounds in marine biota and sediments using microwave-assisted acid extraction, solid-phase microextraction, and gas chromatography with microwave-induced plasma atomic emission spectrometric detection.

A method is described for the determination of methylmercury and butyltin compounds in marine sediment and tissue using microwave-assisted acid extraction or digestion and solid-phase microextraction (SPME) followed by analysis using gas chromatography with microwave-induced plasma atomic emission spectrometric detection (GC-MIP-AES). Using the SPME-GC-MIP-AES method, enrichment factors for methylmercury and butyltin compounds of 50-100 were achieved, as compared to the typical hexane extraction, and measurements in marine tissue and sediment matrixes were possible at 1-2 microg/kg (methylmercury) and 10-100 ng/kg (butyltins). The SPME-GC-MIP-AES method was validated using several marine sediment and tissue matrix certified reference materials (CRMs) with certified values for methylmercury and butyltin compounds. The SPME-GC-MIP-AES method was used to measure methylmercury in four marine tissue CRMs ranging from oyster tissue at 13.0 +/- 1.0 microg/kg to fish tissue at 397 +/- 13 microg/kg (as Hg dry mass). Results from the SPME-GC-MIP-AES method were used in conjunction with results from other techniques to assign certified values for methylmercury in oyster, mussel, and fish tissue CRMs. Mono-, di-, and tributyltin were measured in three sediment CRMs at concentration levels of (0.08 +/- 0.03)-(0.35 +/- 0.05) mg/kg (as Sn dry mass).

Animals↗
PubMed2004

Involvement of the retinoid X receptor in the development of imposex caused by organotins in gastropods.

Organotin compounds released from antifouling paints, such as tributyltin (TBT) and triphenyltin (TPT), are potent inducers of imposex (a superimposition of male genital tracts, such as penis and vas deferens, on females) in marine gastropods. Little is known about the induction mechanism of gastropod imposex. Here, we show that organotins bind the human retinoid X receptors (hRXRs) with high affinity and that injection of 9-cis retinoic acid (RA), the natural ligand of hRXRs, into females of the rock shell (Thais clavigera) induces the development of imposex. Cloning of the RXR homologue from T. clavigera revealed that the ligand-binding domain of rock shell RXR was very similar to vertebrate RXR and bound to both 9-cis RA and to organotins. These suggest that RXR plays an important role in inducing the development of imposex, namely, the differentiation and growth of male genital tracts in female gastropods.

Animals↗
PubMed1989

Inhibition of trout gill and soybean lipoxygenases by organotin compounds.

Activity of trout gill and soybean lipoxygenase was inhibited by various low concentrations of tri-n-butyltin, di-n-butyltin and n-butyltin chlorides at pH 7.8. Tri-n-butyltin (0.044-0.19 mM; 8-100% inhibition) was significantly more inhibitory against trout gill lipoxygenase than di-n-butyltin (0.1-0.27 mM; 17-39% inhibition) or n-butyltin (1.2-3.6 mM; 26-43% inhibition). Soybean lipoxygenase displayed a similar sensitivity to the inhibitory effects of organotin compounds at pH 7.8. Although tri-n-butyltin (0.067-0.2 mM; 13-68% inhibition) was less inhibitory to soybean lipoxygenase, di-n-butyltin (0.134-0.537 mM; 51-75% inhibition) and n-butyltin (0.41-1.23 mM; 33-75% inhibition) were more inhibitory towards soybean lipoxygenase compared with trout gill lipoxygenase. Concentrations of butyltins required to provide substantial inhibition of trout gill lipoxygenase were of the order of magnitude of those reported for lethal water exposure concentrations of these compounds for trout and other fishes when bioaccumulation factors are considered. Thus, it is proposed that inhibition of lipoxygenase likely contributes to the biocidal activity of organotin compounds.

Animals↗
PubMed1988

Chloride-dependent uncoupling of oxidative phosphorylation by triethyllead and triethyltin increases cytosolic free calcium in guinea pig cerebral cortical synaptosomes.

Metabolically competent isolated cerebral cortical nerve terminals were used to determine the effects of triethyllead (TEL) and triethyltin (TET) on cytosolic free calcium ([Ca2+]c), on plasma and mitochondrial membrane potentials, and on oxidative metabolism. In the presence of physiological concentrations of extracellular ions, 20 microM TEL and 20 microM TET increase [Ca2+]c from 185 nM to 390 and 340 nM, respectively. A simultaneous depolarization of plasma membrane potential (delta psi p) by only 3-4 mV occurs, a drop which is insufficient to open the voltage-sensitive Ca2+ channels. In contrast, an instant and substantial depolarization of mitochondrial membrane potential (delta psi m) upon addition of TEL and TET is evident, as monitored with safranine O fluorescence. At the same concentration, TEL and TET stimulate basal respiration of synaptosomes by 45%, induce oxidation of endogenous NAD(P)H, and reduce the terminal ATP/ADP ratio by 45%. Thus, TEL and TET inhibit ATP production of intrasynaptosomal mitochondria by a mechanism consistent with uncoupling of oxidative phosphorylation. This bioenergetic effect by TEL and TET can be prevented by omitting external chloride, and a concomitant reduction of the increase in [Ca2+]c by about 60% is observed. Uncoupling of mitochondrial ATP synthesis from oxidation by TEL and TET, [corrected] a process that is dependent on external chloride, is the main mechanism by which they [corrected] increase [Ca2+]c.

Adenosine Diphosphate↗
PubMed1990

[Ca2+]i modulation of Cl- content controls cell volume in single salivary acinar cells during fluid secretion.

Differential interference contrast microscopy and low-light-level digital imaging of the fluorescent chloride indicator dye 6-methyl-1-(3-sulfonatopropyl)quinolinium (SPQ) were performed simultaneously in single mammalian salivary gland acinar cells to examine the relationship between cytoplasmic chloride concentration [( Cl-]i) and cell volume during stimulus-secretion coupling. Agonist stimulation of Cl(-)-driven fluid secretion is associated with rapid, Ca2(+)-dependent changes of cell volume, which are temporally coupled to changes of [Cl-]i. The agonist-induced changes in [Cl-]i, if accompanied by cations and water, quantitatively account for the cell volume changes, demonstrating in a single cell that cell volume is determined by cell solute content. Agonist-induced modulation of cell volume appears to be a consequence of the requirement to develop appropriate ion gradients necessary for vectorial salt (and fluid) transport.

Animals↗