Residues on apples and pears from use of plictran miticide.
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Cyclohexanes↗
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Results for “Trialkyltin Compounds”
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Bioorganotin chemistry. Metabolism of organotin compounds in microsomal monooxygenase systems and in mammals.
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Animals↗
Modeling and experiment reveal an unexpected stereoelectronic effect on conformation and scalar couplings of alpha-aminoorganostannanes, with possible relevance to the tin-lithium exchange reaction.
The solution conformation of N-methyl-2-(tributylstannyl)piperidines has been determined through the use of vicinal 119Sn-13C coupling constants, revealing a conformational distortion caused by an unexpected stereoelectronic effect in some cases. Specifically, the "equatorial" conformer is distorted into a half-chair, in which the nitrogen lone pair eclipses the C-Sn bond. This distortion, which "costs" approximately 1 kcal/mol, correlates with a conformational dependence of geminal 119Sn-15N couplings and a possible correlation with reactivity in the tin-lithium exchange reaction.
Carbon Isotopes↗
Synthesis of spirocycles via ring closing metathesis of heterocycles carrying gem-diallyl substituents obtained via ring opening of (halomethyl)cyclopropanes with allyltributyltin.
In the presence of allyl tri-n-butyltin--AIBN, cyclopropylmethyl bromides/xanthates undergo ring-opening reaction with concomitant formation of geminal diallyl derivatives in good yields. The ring closing metathesis reactions on geminal diallyl derivatives with Grubbs' catalyst provided spirocyclopentenyl products. Combination of these two methodologies has been applied to the synthesis of mono-, bis-cyclopentyl-carbohydrates as well as spirocyclopentylproline derivatives.
Cyclopropanes↗
Organotin pollution in China.
A preliminary investigation of the occurrence of butyltin compounds was made in various environmental samples including water, sediment, sea products, and other commodities from China. Detection was carried out by the method of hydrogenation coupled with SPME or Grignard derivatization, followed by GC-FPD analysis. The results showed the universal existence of butyltin compounds in a wide range of tested samples, which was a potential danger for human health. Urgent control or management of organotin compounds is necessary to prevent the underlying hazard caused by this kind of pollutant.
Animals↗
Skin water content as a quantitative index of the vascular and histologic changes produced in rat skin by di-N-butyltin and tri-N-butyltin.
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Animals↗
Determination of butyltin metabolites in the mouse liver by flameless atomic absorption spectrophotometry.
A new analytical method for observation of the metabolic status of butyltin compounds in the mouse liver was devised by a combination of extraction, purification and separation followed by quantitative analysis of each butyltin compound. After the extraction of all tin compounds from liver homogenate with ethyl acetate, these compounds were purified by combination of the fractional extract with organic solvents and column chromatography. The purified fraction was also analyzed by thin-layer chromatography, identifying each tin compound from differences in mobility on a silica gel plate. The tin content in the each separated spot on the plates was measured by flameless atomic absorption spectrophotometry after extraction by acid treatment. About 90% of tin was recovered by this method from the liver of mice which had been administered tri- or dibutyltin compound orally. This method will be useful for quantification of each metabolic product formed from butyltin compounds in vivo.
Animals↗
Highly persistent butyltins in northern marine sediments: a long-term threat for the Saguenay Fjord (Canada).
An exhaustive study of the distribution of butyltin species was conducted in the sediment of the Saguenay Fjord (Canada), a semi-enclosed marine system with sediment permanently submitted to sub-Arctic cold conditions. Concentrations of total butyltins (tributyltin [TBT], dibutyltin, and monobutyltin) ranged from 6 to 288 ng Sn/g dry weight and were typical of those reported for contaminated coastal areas despite limited seasonal traffic of commercial vessels in the fjord. The distribution profiles of butyltin species in four sediment cores clearly indicated the high persistence of TBT that was dominating other species. The particular oceanographic conditions of the Saguenay Fjord (low seawater temperature, anoxic sediments, and low exchange rate of deep waters) combined with a high sediment/pore-water partition coefficient (Kdobs = 1.0 x 10(4) to 1.2 x 10(4) L/kg) and a low sediment/ water diffusive flux of TBT (J1 = 13 x 10(-8) mol/m2/year) are responsible for the burial and preservation of TBT in this marine ecosystem. The half-life of TBT in deep sediment was estimated to be approximately 87+/-17 years (+/-SEM), which implies a much slower degradation rate than any previously reported. Finally, a flood event that occurred five years before the sampling enabled us to calculate a very slow diffusive flux from the preflood to the postflood layer (J2 = 2 x 10(-8) mol/m2/year), indicating an almost permanent sequestration of TBT in the buried layers.
Canada↗
Bis(tributyltin) oxide toxicology.
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Animals↗
[Effects of tributyltin chloride (TBT) and triphenyltin chloride (TPT) on rat testicular Leydig cells].
OBJECTIVE: To investigate the effects of tributyltin chloride (TBT) and triphenyltin chloride (TPT) on rat testicular Leydig cells. METHODS: The rat Leydig cells (LC-540) were incubated with 0 to 80 nmol/L TBT and TPT for 24 to approximately 96 h, and then the cell viability was determined by MTT. DNA fragmentation ladder formation of cell apoptosis was examined by agarose electrophoresis. Effects of chelator of intracellular Ca2+ (BAPTA) and the inhibitors of PKA, PKC and TPK on cell apoptosis induced by TBT were observed. Effects of TBT on testosterone production in primary cultured rat Leydig cells treated with or without hCG were detected. RESULTS: TBT and TPT suppressed Leydig cell survival in a time- and dose-dependent manner. The suppressive effects of TBT and TPT on the cell survival was caused by apoptosis which was determined by DNA ladder formation. The apoptotic effect of TBT was possibly mediated by the rise in intracellular Ca2+ because it could be blocked by BAPTA, the chelator of intracellular Ca2+; PKA, PKC and TPK inhibitors did not prevent the apoptotic effects induced by TBT. TBT markedly suppressed testosterone production of primary cultured rat Leydig cells with or without hCG stimulation. CONCLUSION: TBT and TPT induced apoptosis in rat testicular Leydig cells possibly through increasing intracellular Ca2+. TBT reduced the testosterone production of rat Leydig cells.
Animals↗
Mechanism of energization of uptake of the fluorescent dye 2-(4-dimethylaminostyryl)-1-ethylpyridinium cation [DMP+] into an acrA strain of Escherichia coli.
The mechanism of uptake of the fluorescent dye 2-(4-dimethylaminostyryl)-1-ethylpyridinium cation (DMP+) into cells and vesicles of the acrA strain AS-1 of Escherichia coli was examined. Uptake was energized by substrate oxidation and discharged by uncouplers. Uptake was enhanced by the presence of tetraphenylphosphonium cation, tetraphenylboron anion and tributyltin chloride, which may inhibit the efflux system for DMP+. Uptake was inhibited by 5-methoxyindole-2-carboxylic acid (MIC). By the use of ionophores with right-side-out vesicles loaded with monovalent cations it was shown that DMP+ uptake could be driven both by the establishment of a membrane potential across the vesicle membrane and by a H+/DMP+ antiport system. Attempts to demonstrate the latter mechanism in everted membrane vesicles were unsuccessful.
Animals↗
Bioorganotin chemistry: a commentary on the reactions of organotin compounds with a cytochrome P-450 dependent monooxygenase enzyme system.
The biological oxidation of several tributyltin derivatives, by a cytochrome P-450 dependent monooxygenase enzyme system with reduced nicotinamideadeninedinucleotidephosphate as the essential cofactor, produced carbon-hydroxylated compounds identified as alpha-, beta-, gamma- and delta-hydroxybutyldibutyltin derivatives. The hydroxylation pattern and the lack of oxidative cleavage of tin-carbon bonds strongly suggest a free radical rather than an oxenoid mechanism, while the predominance of beta-carbon-hydroxylation further implies some role of the tin-carbon sigma electrons in directing the site of hydroxylation.
Animals↗
Daily intakes of tributyltin and triphenyltin compounds from meals.
Daily intakes of tributyltin (TBT) and triphenyltin (TPT) compounds from meals in Shiga Prefecture, Japan, were investigated by 2 methods. Daily intakes of TBT and TPT by the duplicate portion method were, respectively, 4.7 and 0.7 microgram in 1991 and 2.2 and 0.7 microgram in 1992. Those by the market basket method were, respectively, 6.9 and 5.4 micrograms in 1991 and 6.7 and 1.3 micrograms in 1992. Daily intakes of TBT and TPT by the market basket method were higher than those by the duplicate portion method. These values were considerably lower than acceptable daily intakes of 80 micrograms/50 kg body weight specified by the Welfare Ministry of Japan for bis(tri-n-butyltin)oxide and of 25 micrograms/50 kg body weight specified by the Food and Agriculture Organization/World Health Organization for TPT.
Adult↗
The decrease of mitochondrial substrate uptake caused by trialkyltin and trialkyl-lead compounds in chloride media and its relevance to inhibition of oxidative phosphorylation.
1. In a 100 mM-KCl medium (pH 6.8) containing ATP, triethyltin (1 muM) causes a decrease in the uptake of pyruvate, malate, citrate or beta-hydroxybutyrate by rat liver mitochondria, but no decrease is observed in a 100 mM-KNO3 medium. This response is not modified by the presence of rotenone in the incubation medium. 2. In the KCl medium at least 1 muM-triethyltin is required to cause maximum inhibition of pyruvate uptake. 3. Trimethyltin, tributyltin and the trialkyl-lead analogues at 1 muM, to varying degrees, also cause a decrease in pyruvate uptake by mitochondria only in the KCl medium. 4. Triethyltin stimulates resting respiration of mitochondria with all the substrates tested in the KCl medium but not in the KNO3 medium, yet this stimulation of O2 uptake occurs under conditions when substrate uptake is decreased. 5. In contrast, both O2 uptake during state 3 respiration and ATP synthesis when linked to the oxidation of pyruvate, malate or citrate are strongly inhibited by 1 muM-triethyltin in a KCl medium, but O2 uptake and ATP synthesis during the oxidation of beta-hydroxybutyrate are only slightly affected. In a KNO3 medium O2 uptake and ATP synthesis linked to the oxidation of all substrates are only slightly affected. 6. The relevance of the decrease in substrate uptake by mitochondria caused by triethyltin in a KCl medium to the greater sensitivity of various mitochondrial functions observed in vitro is discussed. It is concluded that decrease of matrix substrate content is probably not the major cause of the greater sensitivity of oxidative phosphorylation to triethyltin in a KCl medium observed previously.
Adenosine Triphosphate↗
Effects of in vitro exposure to low levels of organotin and carbamate pesticides on human natural killer cell cytotoxic function.
Human natural killer (NK) lymphocytes play a central role in immune system defense against viral infection and against the formation of primary tumors. Organotin (OT) pesticides have been used in industrial and agricultural applications, and OT contamination has been reported in water, sediment, and fish. Carbamate pesticides are currently used in agricultural chemicals. Two specific carbamates used in agriculture are ziram and maneb; ziram also is used as an additive in rubber products including latex gloves. In previous studies we demonstrated that at concentrations in the 150-200 nM range, the OTs tributyltin (TBT) and triphenyltin (TPT) were capable of disrupting the function of human NK cells after incubations to as short as 24 h. Previously, we also examined the effects of ziram and maneb at higher concentrations on the cytotoxic function of human NK cells. The current study examined the effects of exposure of up to 6 days to lower concentrations of each of these compounds on the cytotoxic function of NK cells. The OTs were studied at concentrations ranging from 200 to 10 nM; ziram was studied at concentrations of 2.5 microM-125 nM and maneb at concentrations of 10-1 microM. These conditions were studied both in highly purified NK cells and in a mixture of lymphocytes containing both T and NK cells. As little as 25 nM TBT decreased the function of purified NK cells after 24 and 48 h, whereas 10 nM TBT was effective after 6 days. The lowest level of TPT that was effective at 24 h was 50 nM whereas the results after 48 h and 6 days were similar to those seen with TBT. The presence of T lymphocytes diminished the effects of both TBT and TPT on NK cytotoxic function. A concentration of ziram as low as 125 nM produced significant loss of cytotoxic function in highly purified NK cells (65% decrease in function after 6 days). The toxicity of each of the compounds studied increased very significantly with length of exposure.
Cell Culture Techniques↗
Toxicity of organotin compounds on embryos of a marine invertebrate (Styela plicata; tunicata).
In order to clarify the interaction mechanism between organotin compounds and organisms, the effects of these compounds on the development of a benthonic filter-feeding invertebrate were studied. Embryos of the ascidian Styela plicata were obtained in laboratory by cross-fertilization and their development was followed in vivo after incubation with 0.1, 1, and 10 microM organotin compounds for various exposure times. Moreover, embryos selected at opportune stages after incubation with 10 microM tributyltin (TBT) or triphenyltin (TPT) for 1 hr were observed at the electron microscope to recognize cell alterations. Results indicate that organotins significantly affect all stages of ascidian development in a dose- and time-dependent manner and the most sensitive stages are gastrula and neurula. These compounds are able to block development, giving rise to anomalous embryos with irreversible effects. The order of inhibition appears to be strongly dependent on the organotin liposolubility: TBT > dibutyltin (DBT) > monobutyltin (MBT) and TPT > tricyclohexyltin (TCHT). The mitosis block of blastomeres in the early stages may be related to an inhibition of the microtubule polymerization. Observations with light and electron microscopes reveal globeshaped blastomeres with large intercellular spaces in the morula and gastrula stages, suggesting a toxic damage with alteration of the cytoskeleton. Moreover, the occurrence of electron-dense precipitates of organotins in the inner membrane of mitochondria and morphological changes of their cristae suggest an inhibitory effect on oxidative phosphorylation which is conspicuous in the gastrula stage. In this stage, the size of the electron-dense aggregates grow from 50-70 to 110-170 nm, while at the same time the alteration of the cristae increases.
Animals↗
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↗
Dibutylchloromethyltin chloride, a potent inhibitor of electron transport in plant mitochondria.
Dibutylchloromethyl tin chloride (DBCT) inhibits coupled and uncoupled respiration of mitochondria from potato tubers, cauliflower florets and etiolated mung bean hypocotyls with succinate and L-malate but not with external NADH or TMPD/ascorbate as substrates. Using potato and cauliflower mitochondria. DBCT at 200 pmole/mg of protein gives complete inhibition only in KCl-based media and at pH 6.8. DBCT has no effect on the internal pH of mung bean mitochondria, but does cause a decrease in the membrane potential. Electron transport through the alternative oxidase is not inhibited, neither is the ATP-synthase system. DBCT appears to interact with the functionally-distinct pool of ubiquinone associated with the oxidation of succinate and L-malate.
Electron Transport↗