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PubMed2005

Occurrence of organotin compounds in house dust in Berlin (Germany).

In a study in the year 2000 on the occurrence of hazardous environmental contaminants house dust samples from 28 Berlin apartments were measured for the presence and concentrations of six organotin compounds, monobutyltin (MBT), dibutyltin (DBT), tributyltin (TBT), monooctyltin (MOT), dioctyltin (DOT) and triphenyltin (TPT). The concentrations of MBT and DBT determined ranged considerably from 0.01 mg kg-1 to 1.5 mg kg-1 (median: 0.05 mg kg-1) and 0.01 to 5.6 mg kg-1 (median: 0.03 mg kg-1), respectively. Maximum levels of TBT and MOT were only 0.08 mg kg-1 and 0.04 mg kg-1. The maximum total value of the organotins was 7.2 mg kg-1 (median: 0.11 mg kg-1). MBT was found in 86% and DBT in 82% of the samples above the limit of quantification, TBT and MOT only in 50% and DOT in 43%. The focus of ecotoxicology is on the risks arising from organotin compounds (especially butyltins) when used as biocides in antifouling paints. TBT acts as an endocrine disrupter in animals, inducing masculinization (imposex) in female gastropods of different species by increasing testosterone levels. The most critical organ site in experimental animals is the cellular immune system, where lymphocyte depletion in the thymus and peripheral lymphoid tissues takes place. Our study does not provide data on the basis of which population exposure could be estimated; house dust containing harmful organotins could, however, under some conditions, become a relevant intake possibility for young children.

Berlin↗

PubMed2004

Organotin compounds promote adipocyte differentiation as agonists of the peroxisome proliferator-activated receptor gamma/retinoid X receptor pathway.

Nuclear receptors play important roles in the maintenance of the endocrine system, regulation of organ differentiation, and fetal development. Endocrine disruptors exert their adverse effects by disrupting the endocrine system via various mechanisms. To assess the effects of endocrine disruptors on nuclear receptors, we developed a high-throughput method for identifying activators of nuclear receptors. Using this system, we found that triphenyltin and tributyltin were activators of peroxisome proliferator-activated receptor (PPAR) gamma and retinoid X receptor. Because PPARgamma is a master regulator of adipocyte differentiation, we assessed the effect of organotin compounds on preadipocyte 3T3-L1 cells. We found that organotin compounds stimulated differentiation of 3T3-L1 cells as well as expression of adipocyte marker genes.

3T3 Cells↗

PubMed1991

Comparison of sulphur-mode and tin-mode flame photometric detectors for the gas chromatographic determination of organotin compounds.

A comparison of sulphur-mode (393 nm) and tin-mode (610 nm) flame photometric detectors for the gas chromatographic determination of butyl- and phenyltin compounds is described. The chromatographic peaks of the butyl- and phenyltin compounds were well separated, and high sensitivity was achieved in both modes; however, the tin-mode was more specific for tin compounds than the sulphur-mode. The absolute detection limits with the sulphur-mode and the tin-mode were 3.9-7.6 pg and 2.6-5.1 pg as tin, respectively. The application of the tin-mode gas chromatographic method to the determination of organotin compounds in fish is presented. For this application, organotins are extracted (as chloride) with hydrochloric acid and n-hexane-benzene (3:2, containing 0.05% tropolone) and the extracts are pentylated by a Grignard reagent prior to gas chromatography. The absolute recoveries of butyl- and phenyltin compounds added to fish samples ranged from 68.5 to 84.4% (the coefficients of variation were less than 6.6% for all substances, n = 8). Significant amounts of three organotin compounds (di- and tributyltin and triphenyltin) in fish samples were detected by this method. This technique may have application for other organotin compounds and the monitoring of butyl- and phenyltin compounds in the environment.

Animals↗

PubMed2005

Apoptosis of cerebellar granule cells induced by organotin compounds found in drinking water: involvement of MAP kinases.

Mono- and dialkyl organotin compounds are used primarily as heat stabilizers in polyvinyl chloride (PVC) plastics. Recently, monomethyltin (MMT), dimethyltin (DMT), monobutyltin (MBT), and dibutyltin (DBT) have been detected in water from homes and businesses served by PVC pipes. While trialkyl organotins such as trimethyltin (TMT) and triethyltin (TET) are well known neurotoxicants, the toxicity of the mono- and dialkyl organotins is not well described. The present study compared the cytotoxicity of organotins found in drinking water with the known neurotoxicant TMT in primary cultures of cerebellar granule cells, and examined the role of MAP kinase signaling in organotin-induced cell death. Twenty-four hour exposure to TMT resulted in a concentration-dependent decrease in cell viability with an EC(50) of 3 microM. Exposure to MMT, DMT, and MBT at concentrations up to 10 microM had no effect. DBT, however, was very potent, and decreased cell viability with an EC(50) of 0.3 microM. Staining of organotin-treated cerebellar granule cells with the nuclear dye Syto-13 revealed that TMT and DBT, but not MMT, DMT, or MBT, produced condensation and fragmentation of chromatin characteristic of apoptosis. TMT- and DBT-induced apoptosis was confirmed using TUNEL staining and measurement of PARP cleavage. Activation of MAP kinase pathways was examined after 6 h of exposure to the organotins which induced apoptosis. Both TMT and DBT activated ERK1/2, but only TMT activated the JNK/c-Jun and p38 pathways. Pharmacologic blockade of JNK/c-Jun and p38 activation significantly decreased apoptosis produced by TMT, but not by DBT. These results show that DBT is a potent neurotoxicant in vitro, but unlike TMT, does not induce cell death via activation of MAP kinase signaling.

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↗

PubMed1984

Inhibition of carrageenan edema formation by organotin compounds.

The effects of a single p.o. dose of 0.3-10 mg/kg of organotin compounds such as dibutyltin dichloride (Bu2SnCl2) and triphenyltin chloride (Ph3SnCl) on the development of edema after subplantar injection of 0.5 mg of carrageenan in 0.05 ml of pyrogen-free saline were examined as compared with those of hydrocortisone. Bu2SnCl2, Ph3SnCl and hydrocortisone did not significantly inhibit the development of the first phase of edema at any dose level, but produced more than 90, 70 and 90% inhibition of the second phase, respectively, at a dose of 10 mg/kg 1 hr before the irritant. Moreover, these inhibitions of the second phase were dose-dependent.

Animals↗

PubMed1999

Organotin compounds decrease in vitro survival, proliferation and differentiation of normal human B lymphocytes.

Organotin compounds (OTC) are organometallic compounds with vast industrial and agriculture applications that give rise to ubiquitous environmental contamination. OTC are immunotoxic, but most studies have been performed in rodents and almost exclusively focused on T cell immunity. Humans can be exposed to OTC by inhalation, absorption, and consumption of contaminated food and water. To analyse the effects of OTC in human immune tissue, we isolated B cells from tonsils and exposed them to five OTC at various concentrations, during in vitro culture. Non-stimulated B cells were killed by 100 nM of all tested OTC after 8 h in vitro culture, under sub-optimal conditions, except TET. OTC also decreased the proliferation of tonsillar B lymphocytes stimulated with Staphylococcus aureus Cowan 1 (SAC) and IL-2, when present at 100 nM and higher concentrations. IgM secretion was reduced in stimulated cell cultures exposed to 100 nM dibutyltin chloride (DBT). Accordingly, increased phosphatidylserine exposure demonstrated that 100 nM TPT and DBT induced B cells to die by apoptosis. These data indicate that human B cells are diminished in their capacity to survive, proliferate and differentiate in the presence of OTC in vitro.

Apoptosis↗

PubMed2000

Monitoring of organotin compounds in seawater using semipermeable membrane devices (SPMDs)--tentative results.

The impact of anthropogenic pollutants on the marine ecosystem is related to the concentrations experienced by the biota in the seawater and the resulting concentration in the organism. Results from monitoring of pollutants in water samples provide snapshots that can be high or low depending on a wide range of variables. To provide more integrated information, semipermeable membrane devices, SPMDs, have been used to monitor different organic pollutants. In this survey, SPMDs were used to monitor organotin compounds in the marine environment. Time-integrated sampling using SPMDs and direct water sampling was carried out at six stations in the inner Oslofjord, Norway. The sample work-up procedure for both water and SPMDs was based on direct derivatisation using NaBEt4 and simultaneous extraction with an organic solvent. Analysis was performed using a gas chromatograph equipped with an atomic emission detector. The results show that SPMDs do accumulate organotin compounds from the water phase. Both tributyl- (TBT) and dibutyltin were detected in all of the analysed membranes while no monobutyltin was found. Levels found in SPMDs range from < 1 to 220 ng Sn SPMD(-1). Water concentrations range from 0.4 to 10 ng Sn L(-1). An investigation of relative levels of TBT showed a similar concentration gradient in the inner Oslofjord using either direct water sampling or passive sampling by SPMDs. As the membranes are able to accumulate the organotins from the water it will be possible to locate lower concentrations than with direct analyses of water samples.

Environmental Monitoring↗

PubMed1991

Comparative toxicity of organotin compounds to rainbow trout (Oncorhynchus mykiss) yolk sac fry.

The comparative toxicity of various organotin compounds was investigated in early life stages of the rainbow trout. Beginning with yolk sac fry, trout were continuously exposed for 110 days to tributyl- (TBTC), triphenyl- (TPhTC) or tricyclohexyltin chloride (TCHTC) at concentrations of 0.12-15 nM, to trimethyltin chloride (TMTC) at concentrations of 3-75 nM or to dibutyl- (DBTC) or diphenyltin chloride (DPhTC) at 160-4000 nM. The diorganotin compounds DBTC and DPhTC were about three orders of magnitude less toxic than the triorganotin homologs TBTC and TPhTC. Both for DBTC and DPhTC, a no-observable-effect concentration (NOEC) of 160 nM was established, corresponding to 40 and 60 ppb, respectively. Of the triorganotin compounds, TCHTC appeared to be the most toxic, inducing 100% mortality within 1 week at a concentration of 3 nM. Only a few trout survived exposure to 0.6 nM TCHTC for 110 days. TBTC and TPhTC caused acute mortality at a concentration of 15 nM. For both TBTC and TPhTC a NOEC of 0.12 nM was established, corresponding to water concentrations of 40 and 50 ppt, respectively. Histopathological examination revealed depletion of glycogen in liver cells of both di- and triorganotin exposed fish, except in the case of TMTC. No signs of toxicity were observed in fish exposed to up to 75 nM TMTC, the highest concentration tested. Atrophy of the thymus, the most prominent sign of toxicity of di- and tributyltin compounds in mammalian species, was not observed in early life stages of rainbow trout. Tail melanization was observed in the groups exposed to 3 nM TPhTC, 3 nM TBTC, 800 nM DBTC and 800 nM DPhTC. At the end of the exposure period, resistance to infection was examined by an intraperitoneal challenge with Aeromonas hydrophila, a secondary pathogenic bacterium to fish. Resistance of bacterial challenge was found to be decreased even at the lowest-effect concentration of both di- and triorganotin compounds.

Aeromonas↗

PubMed1993

In vitro assessment of teratogenic potential of organotin compounds using rat embryo limb bud cell cultures.

Assessment of the relative teratogenic potential of bis(tri-n-butyltin)oxide (TBTO), tri-n-butyltin chloride (TBT), and its metabolites, i.e., (3-OH)hydroxybutyl dibutyltin chloride ((3-OH-Bu)DBT), di-n-butyltin dichloride (DBT), and butyltin trichloride (MBT) have been conducted using rat embryo limb bud cell cultures (LBC) to gain some knowledge of TBT embryotoxicity and DBT teratogenicity. Triphenyltin chloride (TPT), trimethyltin chloride (TMT), and triethyltin bromide (TET) have also been tested to obtain data for validation of LBC as a teratogen prescreening for organotin compounds. Fifty percent inhibition concentration for cell proliferation (IP50), and for cell differentiation (ID50), and the ratio of the former to the latter (P/D ratio) were obtained. The ID50 values in increasing order were as follows; TPT, DBT < TBT, TBTO < (3-OH-Bu)DBT < TET < TMT << MBT. With the exception of MBT, organotin compounds tested were very strong inhibitors of cell differentiation (ID50; 0.13-1.71 microM) and cell proliferation (IP50; 0.12-2.81 microM). P/D ratios for TBT, (3-OH-Bu)DBT, DBT and MBT were 1.0, 1.43, 1.32 and 1.08, respectively. These results suggest that the proximal toxin of DBT teratogenicity is DBT itself, and TBT is rather embryocidal than teratogenic so that TBT might mask the teratogenic and/or fetotoxic effects of its metabolites.

Abnormalities, Drug-Induced↗

PubMed2006

Certification of butyltins and phenyltins in marine sediment certified reference material by species-specific isotope-dilution mass spectrometric analysis using synthesized 118Sn-enriched organotin compounds.

A new marine sediment certified reference material, NMIJ CRM 7306-a, for butyltin and phenyltin analysis has been prepared and certified by the National Metrological Institute of Japan at the National Institute of Advanced Industrial Science and Technology (NMIJ/AIST). Candidate sediment material was collected at a bay near industrial activity in Japan. After air-drying, sieving, and mixing the material was sterilized with gamma-ray irradiation. The material was re-mixed and packaged into 250 glass bottles (15 g each) and these were stored in a freezer at -30 degrees C. Certification was performed by use of three different types of species-specific isotope-dilution mass spectrometry (SSID-MS)-SSID-GC-ICP-MS, SSID-GC-MS, and SSID-LC-ICP-MS, with 118Sn-enriched organotin compounds synthesized from 118Sn-enriched metal used as a spike. The 118Sn-enriched mono-butyltin (MBT), dibutyltin (DBT), and tributyltin (TBT) were synthesized as a mixture whereas the 118Sn-enriched di-phenyltin (DPhT) and triphenyltin (TPhT) were synthesized individually. Four different extraction methods, mechanical shaking, ultrasonic, microwave-assisted, and pressurized liquid extraction, were adopted to avoid possible analytical bias caused by non-quantitative extraction and degradation or inter-conversion of analytes in sample preparations. Tropolone was used as chelating agent in all the extraction methods. Certified values are given for TBT 44+/-3 microg kg(-1) as Sn, DBT 51 +/- 2 microg kg(-1) as Sn, MBT 67 +/- 3 microg kg(-1) as Sn, TPhT 6.9 +/- 1.2 microg kg(-1) as Sn, and DPhT 3.4 +/- 1.2 microg kg(-1) as Sn. These levels are lower than in other sediment CRMs currently available for analysis of organotin compounds.

Chemistry Techniques, Analytical↗

PubMed1998

Immunotoxic effects of organotin compounds in Tapes philippinarum.

One of the most harmful groups of coastal pollutants is the organotin compounds (OTCs) which have severe effects on both aquatic organisms and mammals including humans. The immunotoxic effects of OTCs were studied in the cultivated clam Tapes philippinarum by determining the immunosuppressant role on in vitro yeast phagocytosis at low doses (0.01, 0.05, 0.1 microM). The phagocytic index was significantly reduced in an irreversible non-lethal manner depending on concentration and lipophilic affinity. The order of inhibition was TBT > or = DBT > MBT for butyltins and TPTC > TPTA > or = TPTH for triphenyltins.

Animals↗

PubMed2005

Automated headspace-solid-phase micro extraction-retention time locked-isotope dilution gas chromatography-mass spectrometry for the analysis of organotin compounds in water and sediment samples.

An automated method for the simultaneous determination of six important organotin compounds namely monobutyltin (MBT), dibutyltin (DBT), tributyltin (TBT), monophenyltin (MPhT), diphenyltin (DPhT) and triphenyltin (TPhT) in water and sediment samples is described. The method is based on derivatization with sodium tetraethylborate followed by automated headspace-solid-phase micro extraction (SPME) combined with GC-MS under retention time locked (RTL) conditions. Home-synthesized deuterated organotin analogues were used as internal standards. Two high abundant fragment ions corresponding to the main tin isotopes Sn118 and Sn120 were chosen; one for quantification and one as qualifier ion. The method was validated and excellent figures of merit were obtained. Limits of quantification (LOQs) are from 1.3 to 15 ng l(-1) (ppt) for water samples and from 1.0 to 6.3 microg kg(-1) (ppb) for sediment samples. Accuracy for sediment samples was tested on spiked real-life sediment samples and on a reference PACS-2 marine harbor sediment. The developed method was used in a case-study at the harbor of Antwerp where sediment samples in different areas were taken and subsequently screened for TBT contamination. Concentrations ranged from 15 microg kg(-1) in the port of Antwerp up to 43 mg kg(-1) near a ship repair unit.

Automation↗

PubMed1997

Effect of organotin compounds on trout hemoglobins.

The stability of trout hemoglobin was examined in the presence of some organotin compounds. Tributyltin chloride (TBTC) and triphenyltin chloride (TPTC) protect HbI most efficently from the oxidation. On the other hand, the same compounds accelerate the precipitation process in HbIV to a great extent. Parahydroxymercuribenzoate (PMB), an agent blocking free SH-groups of the protein, abolished the ability of TPTC to decrease the oxidation rate of HbI.

Animals↗

PubMed1997

The effects of organotin compounds on growth, respiration rate, and chlorophyll a content of Scenedesmus quadricauda.

The inhibitory effect of 12 organotins in a four concentrations (0.001, 0.01, 0.1, and 1.0 mg/liter) of a 12-day growth and on the respiration rate and chlorophyll a content in 9-day tests were determined for the freshwater algae Scenedesmus quadricauda. Tested organotin compounds belonged to di-R2SnX2 (R:methyl, butyl) and triorganotins R3SnX (R:phenyl, benzyl, butyl).

Chlorophyll↗

PubMedDate not supplied

Occurrence of imposex in Thais haemastoma: possible evidence of environmental contamination derived from organotin compounds in Rio de Janeiro and Fortaleza, Brazil.

There are indications that the widespread use of organotin compounds (TBT and TPT) as antifoulings, as stabilizers in plastic and as pesticides, has severely affected several species of marine organisms. The most striking effect of TBT and TPT as hormonal disruptors is the development of male organs in females of gastropods, currently denominated imposex. This syndrome can lead to the sterilization and death of affected organisms. The present work gives an overview of the present state of knowledge on imposex occurrence and reports results of a survey conducted in Guanabara Bay, Rio de Janeiro and in several sites along the coast of Fortaleza, Ceará State. Different stages of imposex development were verified in this survey, however, the most prominent levels appeared associated to known spot sources of TBT and TPT.

Animals↗

PubMed2002

Antitumor activity of a new orally active organotin compound: a preliminary study in murine tumor models.

The toxicity and antitumor activity of the novel organotin compound triethyltin(IV)lupinylsulfide hydrochloride (IST-FS 29), administered by the oral route, have been evaluated against three transplantable murine tumor models: P388 lymphocytic leukemia, B16F10 melanoma and 3LL Lewis lung carcinoma. Mild and reversible signs of acute toxicity such as behavioral symptoms, weight loss and histological alterations were mainly reported at the highest single dose of 28 mg/kg. Conversely, lower concentrations of compound ranging from 7 to 21 mg/kg did not result in major toxic effects, even after repeated dosing. The antitumor activity studies showed that fractionation dosing, rather than single bolus administration, over 1 week, might prove more active and better tolerated by allowing the achievement of the highest therapeutic total dose of IST-FS 29 (42 mg/kg). Indeed, repeated administrations of IST-FS 29 resulted in marked significant improvement of antitumor activity against B16F10 (50% of tumor volume inhibition, p = 0.0003) and, to a greater extent, 3LL (90% of tumor volume inhibition, p = 0.0001) tumors. These results indicate that IST-FS 29 might be a suitable candidate as an orally administrable anticancer drug and support its further development in human tumor xenografts.

Animals↗

PubMed2001

Toxicity of organotin compounds in primary cultures of rat cortical astrocytes.

The neurotoxic organotin compounds trimethyl (TMT) and triethyltin (TET) are known to induce astrogliosis in vivo, which is indicated by an increased synthesis of glial fibrillary acidic protein (GFAP) in astrocytes. In contrast, tributyltin (TBT) does not induce astrogliosis. The aim of this study was to investigate whether trialkyltin derivatives can induce an increased GFAP synthesis in astrocyte cultures in the absence of neurons and whether differences between the action of TMT, TET, and TBT can be detected. Primary cultures of rat cortical astrocytes from 2-day-old rats were grown in 96-well plates until confluency and then exposed to various concentrations of TMT, TET, and TBT for 40 h. Effects on basal cell functions were measured by colorimetric determination of cell protein contents and by assessment of viability by means of the MTT assay. An indirect sandwich ELISA for 96-well plates was used for quantitative measurements of the GFAP content of the cells. All three compounds induced a concentration-dependent cytotoxicity indicated by parallel decreases of protein contents and MTT reduction. Half-maximum cytotoxic concentrations were 3 micromol/L (TBT), 30 micromol/L (TET), and 800 micromol/L (TMT). Cellular GFAP contents were reduced in parallel to cytotoxic action but no increase in GFAP expression at subcytotoxic concentrations could be observed. Thus, the astrocytes were not able to respond to TMT or TET exposure by an increased synthesis of GFAP in the absence of neuronal signals.

Animals↗