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PubMed2002

Butyltin compounds in Portuguese wines.

Butyltin compounds are widespread contaminants that have also been found in some wines. The purpose of the present work was to make a survey of butyltin compounds in Portuguese wines. Forty-three table wines and 14 Port wines were analyzed for butyltin contents by using solid-phase microextraction gas chromatography mass spectrometry (SPME-GC-MS). In 14% of the analyzed wine samples, measurable dibutyltin (DBT) was found at concentrations ranging between 0.05 and 0.15 microg/L as Sn. Monobutyltin (MBT) was also observed (0.05 microg/L as Sn) in just a single wine. A search for the possible sources of DBT residues found in the wines was carried out. Therefore, some plastics and oak wood used in the process of wine-making, which have been directly in contact with the musts or the wines, were studied to check their possible release of butyltins. The eventual presence of DBT was also tested directly along the vinification process, from the must to the finished product. The results suggest that high-density polyethylene containers used in the transfer of wine in an early stage of the vinification process may be the main sources of these contaminants. Therefore, it is recommendable that plastic materials to be used in wineries be previously tested for the release of butyltin compounds.

Food Contamination↗
PubMedDate not supplied

Cytotoxic activity of di-n-butyltin(IV)(X-A-B-Y) compounds related to salicylic acid against human tumour cells.

A series of di-n-butyltin(IV) compounds of the type di-n-butyltin(IV)(X-A-B-Y) with the (X-A-B-Y) being related to salicylic acid was tested in vitro for cytotoxic activity against tumour cells of the human A 204, MCF-7, T24, WiDr and IgR-37 cell lines using the PIT method. In each cell line the di-n-butyltin(IV) compounds displayed similar activity. As compared to cisplatin, the compounds were 4- to 10-fold more effective against A 204, MCF-7 and T24 tumour cells and slightly more effective against WiDr cells. The effectiveness against IgR-37 cells was similar for cisplatin and di-n-butyltin (IV) compounds.

Cell Survival↗
PubMed1990

The neurotoxicology and pathology of organomercury, organolead, and organotin.

The toxicities of many metals, such as mercury and lead, are known to man since the dawn of civilization. Organic compounds of some heavy metals are known to have a particular toxic impact on the central nervous system. Organomercury, particularly alkyl-mercuric compounds (e.g. methylmercury), has a selective effect on the granule cells of the cerebellum, the nerve cells of the calcarine cortex, and the sensory neurons in the dorsal root ganglia. The well known Minamata Bay disease is the result of a massive epidemic episode of human exposure to alkylmercury contaminated food sources. Mental retardation and other developmental defects are also known to be a consequence of exposure to this toxic metal. Organic lead compounds have been employed as gasoline additives and in other industrial purposes. Unlike its inorganic counterpart, organolead compounds have a more prominent impact on the central nervous system. Pathological changes of the brain stem neurons have been described. Organotin compounds have been used in plastic industries and as agricultural chemicals. Both trimethyl and triethyl tin compounds are found to be extremely neurotoxic. Despite the similarity of their chemical structures, trimethyl and triethyl tins have a diversely different toxic property and effects. While triethyl tin is myelinotoxic, producing edematous and vacuolar changes in the central myelin, trimethyl tin is neurotoxic, producing prominent toxic changes in the neurons of the limbic system (hippocampus, entorhinal cortex, etc.). The factors which determine the specificity and selectivity of the neurotoxic impacts by various organometals are still unknown. In view that most of the organometals are still widely employed by many countries for industrial and for agricultural purposes, caution must be made for their proper handling and disposure to avoid undesirable exposures to workers and environmental contamination of water sources and food-chain for the common public. Since organometals are difficult to eliminate from the central nervous system, injuries usually lead to permanent neurological deficits, such tragedies are frequently long lasting and create not only a medical problem, but also a social economical problem for the society.

Animals↗
PubMedDate not supplied

Differential effects of organometallic tin compounds on Na+/K+-ATPase activity.

In vitro effects of six dibenzyltin dichloride (A-series) and another six dibenzyltin diisothiocyanate (B-series) complexes on Na+/K+-ATPase were studied. The rat brain synaptic membranes were prepared and significant ATPase inhibition was observed with all the complexes in a dose-dependent manner. The order of potency on Na+/K+-ATPase activity of the chloride complexes was found to be higher than that of the isothiocyanate complexes. The IC50 values range from 64 microM to 252 microM for the chloride complexes and from 132 microM to 399 microM for the isothiocyanate complexes. A structure-activity relationship could be derived for the chloride complexes.

Animals↗
PubMed1995

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↗
PubMedDate not supplied

Cytotoxic activity against a series of human tumour cell lines of some diorganotin(iv) 1,2-ethylenediamine N,N'-diacetates, N-(2-hydroxyethyl)- and N-(carbamoylmethyl)-iminodiacetates, and ortho-aminobenzoates.

The di-n-butyltin(IV) derivatives of N-(2-hydroxyethyl)- and N-(carbamoylmethyl)- iminodiacetic acid, compounds 1 and 2, the di-n-butyltin-, di-n-octyltin and dimethyltin-(IV) derivatives of 1,2-ethylene diamine N,N'-diacetic acid, compounds 3, 4 and 5, and di-n-butyltin bis-o-aminobenzoate, compound 6, were tested in vitro at the National Cancer Institute, Bethesda, Maryland, USA, for cytotoxic activity against a series of human tumor cell lines. Compounds 1 and 2 score globally satisfactorily since four of the five relevant selectivity or sensitivity parameters [DGI50, DTGI or DLC50 greater than 50, DH and MGDH greater than 75)] are statistically significant; compounds 4 and 6 score satisfactorily for only three of these parameters and compound 3, for only two. Compound 5, the dimethyltin derivative, is inactive.

Aminobenzoates↗
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↗
PubMed1988

Structure-activity relationships for diorganotins, chlorinated benzenes, and chlorinated anilines established with bluegill sunfish BF-2 cells.

The bluegill sunfish (Lepomis macrochirus) BF-2 cell line, propagated at 34 degrees C, served as target for evaluation of the acute toxicities of various classes of aquatic pollutants, using the neutral red cytotoxicity assay. For a series of chlorinated benzenes and anilines, the sequence of cytotoxicity was dependent on the degree of chlorination and on their hydrophobicity, as described by their logarithmic octanol/water partition coefficients (log P values). With increasing numbers of chlorine atoms in the ring structure or with increasing log P values, greater cytotoxicity was observed. For a series of diorganotins, the sequence of cytotoxicity was dependent on the length of the carbon chain and upon their hydrophobicity, as described by Hansch pi parameters. Thus, increasing the chain length or increasing the Hansch pi parameter resulted in greater cytotoxicity. Similar structure-activity relationships for these classes of test agents have been previously established using acute toxicity LC50 assays with aquatic species. The ability of the neutral red in vitro cytotoxicity assay, with cultured fish cells as the bioindicators, to mimic the acute toxicity data obtained from the LC50 assays suggests its utility as a tool for preliminary screening (tier I testing) of aquatic pollutants.

Aniline Compounds↗
PubMed1998

Photophysical properties of tin ethyl etiopurpurin I (SnET2) and tin octaethylbenzochlorin (SnOEBC) in solution and bound to albumin.

The photophysical characteristics of two second-generation PDT photosensitizers, tin ethyl etiopurpurin I (SnET2) and tin octaethylbenzochlorin (SnOEBC), have been measured in homogeneous solution and when bound to bovine serum albumin (BSA). The ground state and triplet state absorption spectra have been characterized, as have triplet lifetimes and quantum yields for intersystem crossing, singlet oxygen formation and photobleaching. In total, these parameters provide a complete set of data that can be used to quantitatively compare the photosensitizing efficiencies of these molecules. The photo-bleaching quantum yield of SnET2 is increased dramatically when it is bound to BSA, thus limiting the production of singlet oxygen at incident fluences above 1 J/cm2. In contrast, the quantum yield of photobleaching of SnOEBC is at least an order of magnitude lower than that of SnET2 under these conditions and does not significantly limit the photosensitization process for typical in vivo or in vitro fluences. This difference is expected to play a significant role in determining the relative photo-sensitizing ability of these compounds in vivo.

Animals↗