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At least 613 records · Page 34Linked to original sources

PubMed2006

Triphenyltin and tributyltin, single and in combination, promote imposex in the gastropod Bolinus brandaris.

Specimens of Bolinus brandaris (neogastropod) were injected with a single dose of 500 ng/g body weight (b.w.) of tributyltin chloride (TBTCl) or triphenyltin chloride (TPTCl), or a mixture of both compounds (250 ng TBT/g b.w.+250 ng TPT/g b.w.), for a period of up to 31 days. At the end of 4 weeks, significant increases in the female penis size of those gastropods injected with TBT (P<0.05), TPT (P<0.05), or the mixture TBT+TPT (P<0.01) were recorded. In parallel, a group of animals was injected with the neuropeptide APGWamide but this compound failed to promote imposex, suggesting that APGWamide is not involved in imposex promotion in B. brandaris. Acetylcholinesterase activity, a biomarker of neurotoxicity, was determined in the neuroganglia at the end of the experiment, but no significant differences among treatments were found. Overall, these results support the hypothesis that TPT also acts as an endocrine disrupter in this neogastropod species. Our observations also highlight, for the first time, synergistic effects of organotin mixtures having imposex promotion as an endpoint.

Animals↗

PubMed1989

[Simultaneous determination of tributyltin and its metabolites, dibutyltin and monobutyltin, in biological materials by capillary gas chromatography].

Determination of tributyltin and its metabolites, dibutyltin and monobutyltin, in biological materials was made by capillary gas chromatography (C-GC) using a flame photometric detector (FPD). Butyltin compounds (BuTC) were extracted (as bromides) from tissue homogenates with hydrobromic acid and ethyl acetate. These compounds were converted to pentyl derivatives with pentyl Grignard reagent and then analysed by C-GC. The recoveries of each BuTC added to tissues were 96-99% for monobutyltin, 87-93% for dibutyltin and 90-93% for tributyltin. The detection limit of BuTC was 4-5 pg as tin. This method was applied to the analysis of BuTC in the liver and kidney of rats orally administered tributyltin chloride. Time course of three BuTC showed that the maximum value appeared 24 h after administration of the tin compound, which was followed by a rapid decrease. The order of the concentration of BuTC in both organs was dibutyltin greater than tributyltin greater than monobutyltin. The rate of dealkylation was more rapid in liver than in kidney.

Animals↗

PubMedDate not supplied

The acute toxicity and in vivo antitumour activity against L1210 leukemia of triphenyltin 3,5-diisopropylsalicylate, bis (di-n-butyl-(s)-2-pyrrolidone-5-carboxylato)tin oxide and di-n-butyltin bis(3-amino-4-methylbenzoate).

Triphenyltin 3,5-di-isopropylsalicylate, compound 1, is characterized by a maximum tolerated dose (MTD) of 20 mg/kg. Bis[di-n-butyl(2-pyrrolidone-5-carboxylato)tin] oxide, compound 2, and (di-n-butyltin bis(3-amino-4-methyl-benzoate), compound 3, exhibit similar acute toxicities (MTD = 8 mg/kg) despite their lower in vitro activity, as compared to compound 1, against the two human tumor cell lines MCF-7 and WiDr. All three are inactive in vivo against L1210 leukemia in mice.

Aminobenzoates↗

PubMed2005

Accumulation of butyl- and phenyltin compounds in starfish and bivalves from the coastal environment of Korea.

Triphenyltin (TPT) and tributyltin (TBT) concentrations were determined in two starfish species (Asteria pectinifera and Asterias amurensis), bivalves (Crassostrea gigas or Mytilus edulis), and seawater samples from sites around the coasts of Korea. Both TPT and TBT concentrations in starfish ranged from 8 to 1560 ng/g and from <2 to 797 ng/g as Sn on a dry weight basis, respectively. TPT concentration accounted for 75.4% and 86.4% of total phenyltin concentration in A. pectinifera and A. amurensis, respectively, while monobutyltin, a degradation product of TBT, accounted for 86.3% and 57.2% of total butyltin, respectively. Triphenyltin concentrations in A. pectinifera were significantly correlated to water and bivalve TPT concentrations, which implies that dietary uptake of TPT from contaminated prey as well as direct uptake from surrounding water contribute to TPT body residues in the starfish. Starfish could be target organisms for monitoring TPT compound in the marine environment, due to their high accumulation and low degradation capacity towards TPT.

Animals↗

PubMed2001

Tributyltin or triphenyltin inhibits aromatase activity in the human granulosa-like tumor cell line KGN.

The superimposition of male sex organs (penis and vas deferens) in a female gastropod, called imposex, is widely attributed to the exposure to tributyltin (TBT) compounds, used world-wide in antifouling paints for ships. It has been hypothesized that the TBT-induced imposex is mediated by an increasing androgen level relative to the estrogen level, namely a decreased conversion of androgens to estrogens (i.e., aromatization). In the present study, we tested this hypothesis by examining the effects of TBT or triphenyltin (TPT) on the aromatase activity in a cultured human granulosa-like tumor cell line, KGN, which was recently established by our group. Treatment with more than 1000 ng/ml TBT compounds was very toxic to the cells and caused immediate cell death within 24 h, while 200 ng/ml was found to cause apoptosis of the cells. Treatment of the KGN cells for more than 48 h with 20 ng/ml TBT or TPT, which is a concentration level reported to cause imposex in marine species, did not affect cell proliferation but significantly suppressed the aromatase activity determined by a [(3)H]H(2)O release assay. Treatment with 20 ng/ml TBT compounds for 7 days also resulted in a reduction of the E2 production from Delta 4-androstenedione stimulated by db-cAMP. The changes in the aromatase activity by TBT compounds were associated with comparable changes in P450arom mRNA assessed by RT-PCR. The luciferase activity of the P450arom promoter II (1 kb) decreased after the addition of 20 ng/ml TBT compounds in transfected KGN cells either in a basic state or in states stimulated by db-cAMP. The Ad4BP-dependent increase in the luciferase activity of P450arom promoter II was also downregulated by such treatments. These results indicate that TBT compounds inhibited the aromatase activity and also decreased the P450arom mRNA level at the transcriptional level in KGN cells. The direct inhibitory effect of TBT compounds on the aromatase activity may therefore partly explain the induction of imposex by these compounds in female species.

Androstenedione↗

PubMed2003

Characterisation of gene expression patterns in 22RV1 cells for determination of environmental androgenic/antiandrogenic compounds.

Alteration of androgen receptor function due to hormonally active compounds in the environment, may be responsible for impaired reproductive function in aquatic wildlife. Based on human prostate carcinoma 22RV1 cells, a cell culture expression system was established to test effects of putative androgenic/antiandrogenic compounds on endogenous gene expression. 22RV1 cells were shown to express human androgen receptor, but not human progestin (hPR) or human oestrogen receptor (hER) alpha and beta. Six androgen-regulated genes (ARGs) were chosen to determine androgenic/antiandrogenic action using highly sensitive real-time RT-PCR. Results showed that gene expression is altered in a time-dependent manner. After stimulation of cells by DHT (10nM), synthetic androgen R1881 (1 nM), or organic pesticides (difenoconazole, fentinacetate, tetramethrin) TMPRSS2 mRNA expression was down-regulated by the factor 0.6 after 24h of DHT treatment. Similar results were obtained when cells were assayed for mRNA expression of PSA after fentinacetate and R1881 stimulation. In contrast, TMPRSS2 expression was up-regulated by the factor 0.9 when cells were stimulated by tetramethrin. Final goal of the work is a sensitive determination of differential gene expression by different compounds under study, achievement of substance-specific expression patterns and function related analysis of potential androgens/antiandrogens.

Androgen Antagonists↗

PubMed2005

Study of the accumulation of tributyltin and triphenyltin compounds and their main metabolites in the sea bass, Dicentrachus labrax, under laboratory conditions.

Accumulation of two triorganotins, tributyltin (TBT) and triphenyltin (TPhT), has been studied by exposing the sea bass, Dicentrachus labrax, to different concentrations of both compounds, under controlled laboratory conditions. D. labrax juvenile fish were acclimatized in a laboratory and isolated to four groups. One group was used as control (first group), while the other three were exposed, during 28 days, in tanks with seawater containing simultaneously 2.5 microg/l TBT and 2.5 microg/l (second group), 5 microg/l TBT and 5 microg/l (third group) and 15 microg/l TBT and 15 microg/l (fourth group), respectively. The higher exposure dose caused mortality to all animals after 48 h. In the other two groups, quantitative analysis of TBT and TPhT was carried out, weekly, on the target organs (muscle and liver). Also, the main metabolites of TBT, monobutyltin (MBT) and dibutyltin (DBT), and TPhT, monophenyltin (MPhT) and diphenyltin (DPhT) were monitored. Gas chromatography (GC) coupled to mass spectrometry in tandem (MS/MS) mode was used for their identification. The results of analysis of TBT and TPhT showed that D. labrax accumulated the compounds from the first week, although the levels depended on medium concentration exposure. Liver was found to accumulate higher concentrations of TBT and TPhT than muscle.

Animals↗

PubMed2006

Synthesis, characterization and in vitro cytotoxicity of pentacoordinated Tin(IV) complexes derived from aminoalcohols.

The synthesis of pentacoordinated Tin(IV) compounds derived from aminoalcohols is described. The compounds were characterized by IR, 1H-, 13C-, and 119Sn-NMR, the mass spectrometry exhibits molecular ions corresponding to monomeric species. All compounds were evaluated for in vitro cytotoxic activities against five human tumor cell lines, U251 (human glioblastoma), PC-3 (human prostatic adenocarcinoma), K-562 (human chronic myelogenous leukemia), HCT-15 (human colorectal adenocarcinoma), MCF-7 (human mammary adenocarcinoma). The cytotoxic evaluation revealed that all compounds possess higher cytotoxic potency than that of the cisplatin, which was used as reference. Additionally, MT2 cells (human T-lymphocytes) were also evaluated.

Amino Alcohols↗

PubMedDate not supplied

Determination of tri-n-butyltin and di-n-butyltin compounds in fish by gas chromatography with flame photometric detection.

An analytical method is described for the simultaneous quantitative determination of tri-n-butyltin and di-n-butyltin compounds in fish. The sample was extracted with 0.5N HCl-methanol, and the methanol solution was extracted with hexane. The extract was purified by gel permeation chromatography and treated with Grignard reagent to yield the methyl derivatives, which were determined by gas chromatography with flame photometric detection operated in the tin mode (610 nm). Recoveries of tri-n-butyltin chloride (Bu3SnCl) and di-n-butyltin dichloride (Bu2SnCl2) spiked to fish at the levels of 0.2 and 1.0 ppm ranged from 80 to 105%. Detection limits were 0.02 micrograms/g for both compounds. Tri-n-butyltin compounds equivalent to Bu3SnCl levels of 0.07-2.0 ppm and di-n-butyltin compounds equivalent to Bu2SnCl2 levels of 0.02-0.11 ppm were found in reared yellowtails, and these values showed good agreement with the results from gas chromatographic-mass spectrometric analysis.

Animals↗

PubMed1994

[Subacute toxicity of triphenyltin acetate (TPTA) in the rabbit: clinical observations and hematologic, hematochemical and enzymatic changes].

Twenty-eight immature male rabbits were divided into four experimental groups and administered a standard diet containing respectively 0, 15, 75 and 150 ppm of triphenyltin acetate (TPTA) for 70 days. The highest dose group showed a decrease in erythrocyte count, haemoglobin content and packed cell volume. As early as on day 35, leucopenia and lymphopenia were recorded in all treated groups, thereby confirming the well-known immunosuppressive activity of organo-tin compounds. Both total serum protein and albumin levels apparently altered by TPTA treatment. Conversely, there was a dose-dependent increase for both alpha 2-globulin fraction and blood urea nitrogen serum levels, suggesting a possible renal involvement.

Animals↗

PubMed2005

Bioassays and selected chemical analysis of biocide-free antifouling coatings.

Over the years several types of biocide-free antifouling paints have entered the market. The prohibition of biocidal antifouling paints in special areas of some European countries such as Sweden, Denmark and Germany has favoured the introduction of these paints to the market. Several types of biocide-free antifouling paints were subjected to bioassays and selected chemical analysis of leachate and incorporated substances. Both non-eroding coatings (silicones, fibre coats, epoxies, polyurethane, polyvinyl) and eroding coatings (SPCs, ablative) were tested to exclude the presence of active biocides and dangerous compounds. The paints were subjected to the luminescent bacteria test and the cypris larvae settlement assay, the latter delivering information on toxicity as well as on efficacy. The following chemical analyses of selected compounds of dry-film were performed: The results of the bioassays indicated that none of the coatings analysed contained leachable biocides. Nevertheless, some products contained or leached dangerous compounds. The analyses revealed leaching of nonylphenol (up to 74.7 ng/cm2/d after 48 h) and bisphenol A (up to 2.77 ng/cm2/d after 24 h) from epoxy resins used as substitutes for antifouling paints. The heavy metal, zinc, was measured in dry paint film in quantities up to 576,000 ppm in erodable coatings, not incorporated as a biocide but to control the rate of erosion. Values for TBT in silicone elutriates were mostly below the detection limit of 0.005 mg/kg. Values for DBT ranged between <0.005 and 6.28 mg/kg, deriving from catalysts used as curing agents. Some biocide-free paints contained leachable, toxic and dangerous compounds in the dry film, some of which may act as substitutes for biocides or are incorporated as plasticizers or catalysts. Implications to environmental requirements and legislation are discussed.

Aliivibrio fischeri↗

PubMed1996

Radioiododestannylation: preparation of radioiodinated vinyl alcohols and selected evaluation in rats.

Radioiododestannylation has been employed to prepare a series of radioiodinated vinyl alcohols, two of which were evaluated for their tissue distribution in rats. The radioiodination method utilized tri-alkylstannylvinyl intermediates that can be prepared in good yields from 1,2-bis(tributylstannyl) ethylene and the appropriate ketones or by hydrostannation of the corresponding ethynyl alcohols. The radiolabeling proceeded at the no-carrier-added level to give, after HPLC separation, the desired products in 85-95% isolated yields. Tissue distribution studies in the rat indicated that the agents were rapidly extracted by the brain and then quickly cleared. No retention of activity was observed in the nonmetabolizing or nonexcretory organs. Chemically, the use of the E-tributylstannylvinyl lithium followed by radioiodination controlled stereochemistry and eliminated the separation of E- and Z-iodovinyl isomers. Biologically, the compounds behaved as neutral, diffusible and nonmetabolized radiotracers that may be used for the evaluation of cerebral blood flow, potentially with the short-lived radionuclide I-122 or other short-lived radiohalogens.

Alcohols↗

PubMed2001

Novel seven coordination geometry of Sn(IV): crystal structures of phthalocyaninato bis(undecylcarboxylato)Sn(IV), its Si(IV) analogue, and phthalocyaninato bis(chloro)silicon(IV). The electrochemistry of the Si(IV) analogue and related compounds.

Three newly elucidated crystal structures of group IV phthalocyaninato complexes are reported, along with data for two further SiPc carboxylate complexes. In one of these crystal structures, bis(undecylcarboxylate)Sn(IV) phthalocyanine, the tin ion is seven coordinate, which is a unique finding for this atom in phthalocyanine ring coordination. Comparison of these structures with other group IV phthalocyaninato and related structures reveals differences, illustrating features significant in the chemistries of Si(IV) and Sn(IV) ions. These differences are thought to originate from their differing sizes and polarizabilities. The structures show that the Sn(IV) ion can only occupy an in-plane location in the phthalocyaninato ring where it elongates toward the two axial ligands. When the axial ligands do not facilitate this elongation cis coordination is preferred and the Sn(IV) ion sits above the phthalocyaninato ring plane. In contrast, the Si(IV) structures, with smaller, harder (i.e., less polarizable) Si(IV) ions, are six coordinate with the Si(IV) ion in the phthalocyaninato ring plane in a distorted octahedral symmetry. The electronic spectra and cyclic voltammetry of some of the Si compounds indicate that on the electrode the oxidized/reduced species behave as though they are in a solid film, rather than a soluble freely diffusing species.

Crystallography, X-Ray↗

PubMedDate not supplied

Influence of dodecyltrimethylammonium halides on interaction of phenyltin compounds with model membranes.

The effects were studied of dodecyltrimethylammonium chloride (DTAC), dodecyltrimethylammonium bromide (DTAB) and dodecyltrimethylammonium iodide (DTAI) on thermotropic phase behaviour of phosphatidylcholine bilayers, as well as on 1H NMR and 31P NMR spectra, in the presence of diphenyltin dichloride (DPhT) and triphenyltin chloride (TPhT). The obtained results indicate that in the presence of the surfactant studied the interaction of phenyltin compounds with model membranes was changed and the changes depended on the kind of the counterion. The surfactants studied (especially DTAC) decrease the ability of phenyltin compounds to induce structural changes in the bilayer. It is suggested that DTAB, and especially DTAC, prevent DPhT induced interdigitated phase formation as well as formation of an inverted hexagonal phase (H(II)) in the case of TPhT/DPPC liposomes.

1,2-Dipalmitoylphosphatidylcholine↗

PubMed1984

The toxic effects of triorganotin(IV) compounds on the culicine mosquito, Aedes aegypti (L).

The structure-activity relationships of 25 triorganotin(IV) compounds were studied using the 4th instar A. aegypti larvae of the susceptible Liverpool Red-eye strain. The LC50 values of these compounds were compared with those of Malathion, DDT and Temephos. Maximal activities were obtained with tritolyltin chloride and its complexes with triphenyl-phosphine oxide and pyridine N-oxide, dimethyloctyltin- and diethyloctyltin acetates and tributyltin sucrose phthalate. A limited number of the triorganotin compounds was also tested with observed high activity against the 4th instar larvae of a local DDT-tolerant strain and against the 2nd instar larvae and adults of the susceptible strain. Delayed effect studies with both 2nd and 4th instar larvae showed high post-treatment mortality for the latter and, among the range of active compounds, the methyl- and aryltin compounds, in particular, were also found to exhibit high residual activities (100% kill) in laboratory tests conducted up to 10 weeks.

Aedes↗

PubMed2004

Distribution of tributyltin, dibutyltin and monobutyltin in the liver, brain and fat of rats: two-generation toxicity study of tributyltin chloride.

The distribution of tributyltin (TBT) and its metabolites, dibutyltin (DBT) and monobutyltin (MBT), was examined in the liver, brain and fat tissues in a two-generation reproductive toxicity study of tributyltin chloride (TBTCl) in rats using dietary supplementation at concentrations of 5, 25 and 125 ppm. In the liver, irrespective of TBTCl dietary concentration, gender or generation, the highest concentration of metabolite was consistently MBT, followed by DBT, and then TBT. In contrast, TBT was consistently present at the highest concentration in the brain, nearly always followed by DBT and MBT. In fat tissues, the concentrations of the three butyltin compounds showed similar relationships to those observed in the brain, although the concentrations were much lower. In the liver, the concentration of TBT was higher in females, and those of DBT and MBT were higher in males. Factorial ANOVA also suggested the effect of gender on the concentrations of the three butyltin compounds in the liver. The results of this study suggest tissue-dependent distribution of TBT, DBT and MBT and gender-dependent distribution of the three metabolites in the liver of rats.

Adipose Tissue↗

PubMed2006

Butyltin compounds in sediments of the Bahía Blanca estuary, Argentina.

Systematic measurements of both Tributyltin (TBT) and Dibutyltin (DBT) in sediments along different locations in the inner zone of Bahía Blanca estuary were done. Two samples were taken near the main dry dock facility, at Puerto Belgrano naval base, in Argentina. TBT concentrations from non-detected to 170.3 ng Sn g(-1) were measured in the inner region of the estuary, and higher one of 3,288 ng Sn g(-1) near the dry dock at Puerto Belgrano. DBT values ranging between non-detected and 75.2 ng Sn g(-1) were obtained along the principal channel, but extreme concentration of 1,645 ng Sn g(-1) was measured at Puerto Belgrano. These values show that this estuary is affected by organotin pollution, mainly in areas of heavy shipyard activities.

Argentina↗

PubMed2002

Evaluation of mitogen-induced responses in marine mammal and human lymphocytes by in-vitro exposure of butyltins and non-ortho coplanar PCBs.

The effects of exposure to butyltin compounds (BTs: tributyltin; TBT, dibutyltin; DBT and monobutyltin; MBT) and non-ortho coplanar PCBs (IUPAC 77, 126 and 169) on marine mammals and human lymphocyte were evaluated. Peripheral blood mononuclear cells (PBMCs) isolated from Dall's porpoises (Phocoenoides dalli), bottlenose dolphins (Tursiops truncatus), a California sealion (Zalophus californianus), a larga seal (Phocoa largha) and humans (Homo sapiens) were exposed at varying concentrations of BTs and coplanar PCBs. Concanavalin A (Con A)-stimulated mitogenesis found significantly suppressed (P<0.01) when the cells were exposed at 300 nM (89 ng/ml) of TBT and 330 nM of DBT (77 ng/ml), while MBT showed little cytotoxicity at treatment levels of up to 3,600 nM (620 ng/ml). BTs concentrations in the liver of Dall's porpoises from Japanese coastal waters ranged between 81-450 ng/g for TBT and 200-1,100 ng/g (wet wt.) for DBTs, which is greater than the cytotoxic levels registered in this study. In contrast, non-ortho coplanar PCBs did not suppress cell proliferation at concentrations of up to 30 nM (10 ng/ml). The residue levels of coplanar PCBs in the blubber of Dall's porpoises were 0.12-1.3 ng/g, which were one order of lower than those levels that do cell proliferation. When cells were exposed to a mixture of TBT/DBTand coplanar PCBs, the proliferation was significantly reduced to 33 nM DBT plus 34 nM CB-77 and 33 nM DBT plus 28 nM CB-169 mixtures, respectively. The investigations relating the contaminant-induced immunosuppression in marine mammals have been focused on persistent organochlorines such as PCBs. pesticides and dioxin compounds. However, this study suggested the possibility of BTs could also pose a serious threat to the immune functions in free-ranging marine mammals and humans.

Animals↗