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PubMed1985

Acute and sublethal effects of organotin compounds on aquatic biota: an interpretative literature evaluation.

The objectives of this review were to: (1) collect, synthesize, and interpret acute and sublethal organotin toxicity data in both freshwater and estuarine-marine ecosystems; (2) present environmental water column and sediment concentrations of organotin compounds in both freshwater and estuarine-marine systems to facilitate interpretation of toxicity data; and (3) identify deficiencies in available data to recommend areas of future research for assessing ecological effects of organotin compounds in aquatic systems. The following recommendations are suggested: (1) evaluation of the bioavailability of organotin compounds in aquatic systems; (2) assessment of the relationship between physicochemical characteristics of organotin compounds and subsequent toxicity effects on aquatic organisms; (3) determination of organotin effects on food chains; (4) evaluation of the specific mechanisms and modes of toxicity for organotin compounds with aquatic biotia; (5) evaluations of the adaptive responses of aquatic biota to organotins; (6) measurement of organotin concentrations in testing chambers throughout toxicity tests using peer-reviewed analytical techniques (nominal concentrations can provide misleading data); (7) assessment of long-term "low level" exposures of organotin compounds on histological, histochemical, behavioral, and physiological responses of aquatic biota; and (8) toxicity assessment of plasticizer organotin compounds to aquatic biota.

Amphibians↗
PubMed1998

Electrostatic inhibition of hemolysis induced by organotin compounds.

The effect of cations on the kinetics of hemolysis caused by organotin compounds was studied. The ions used in the investigation diminish or totally inhibit hemolysis of red cells induced by organotin compounds. The degree of inhibition depends both on the kind of ion and the compounds that induce hemolysis. The ions Zn2+, Co2+, and Cd2+ present in the medium at 50 microM concentration totally protect the erythrocytes against hemolysis induced by the compound (C3H7)3SnCl. The study has also shown the monovalent ions K+ and trimethyldodecylammonium bromide are less potent inhibitors of hemolysis than divalent ions, which is not the case for two non-ionic organotin compounds only. The studies performed indicate that hemolysis induced by organotin compounds is inhibited due to electrostatic interaction between the cations selected and erythrocyte membrane.

Animals↗
PubMedDate not supplied

Screening for organotin compounds in European landfill leachates.

As industrial chemicals, organotin compounds are predominantly applied as polyvinyl chloride (PVC) stabilizers and biocides. They are widely encountered in environmental samples and may be introduced into landfills by disposal of municipal solid waste or sewage sludge. In the present study, leachate samples were obtained from several sanitary landfill sites in Sweden, Italy, and Germany. These samples were analyzed by means of a highly sensitive and species-selective method for methyltin, butyltin, and octyltin species. In total, twelve samples from eight different landfill sites at various ages were investigated. The findings of all target compounds range between less than the limit of detection at 0.1 microg/L and, at maximum, 4 microg/L. Only octyltin compounds can be attributed to PVC products with any certainty, whereas for methyltin and butyltin compounds alternative and less distinct sources exist. Organotin compounds are subject to microbial transformation, such as dealkylation and methylation processes. Consequently, caution should be exercised when attributing findings to potential sources and deriving any predicted environmental concentrations.

Biotransformation↗
PubMed2001

Antiproliferative activity and interactions with cell-cycle related proteins of the organotin compound triethyltin(IV)lupinylsulfide hydrochloride.

Organotin compounds, particularly tri-organotin, have demonstrated cytotoxic properties against a number of tumor cell lines. On this basis, triethyltin(IV)lupinylsulfide hydrochloride (IST-FS 29), a quinolizidine derivative, was synthesized and developed as a potential antitumor agent. This tin-derived compound exhibited potent antiproliferative effects on three different human cancer cell lines: teratocarcinoma of the ovary (PA-1), colon carcinoma (HCT-8) and glioblastoma (A-172). Cytotoxic activity was assessed by MTT and cell count assays during time course experiments with cell recovery after compound withdrawal. Significant cell growth inhibition (up to 95% in HCT-8 after 72 h of exposure), which also persisted after drug-free medium change, was reported in all the cell lines by both assays. In addition, the cytocidal effects exerted by IST-FS 29 appeared more consistent with necrosis or delayed cell death, rather than apoptosis, as shown by morphologic observations under light microscope, DNA fragmentation analysis and flow cytometry. In the attempt to elucidate whether this compound might affect genes playing a role in G1/S phase transition, the expressions of p53, p21(WAF1), cyclin D1 and Rb, mainly involved in response to DNA-damaging stress, were analyzed by Western blot. Heterogeneous patterns of expression during exposure to IST-FS 29 were evidenced in the different cell lines suggesting that these cell-cycle-related genes are not likely the primary targets of this compound. Thus, the present data seem more indicative of a direct effect of IST-FS-29 on macromolecular synthesis and cellular homeostasis, as previously hypothesized for other organotin complexes.

Antineoplastic Agents↗
PubMed2002

Organotin compounds promote the formation of non-lamellar phases in phosphatidylethanolamine membranes.

Organotin compounds are important contaminants in the environment. They are membrane active molecules with broad biological toxicity. We have studied the interaction of tri-n-butyltin chloride and tri-n-phenyltin chloride with model membranes composed of different phosphatidylethanolamines using differential scanning calorimetry, X-ray diffraction, 31P-nuclear magnetic resonance and infrared spectroscopy. Organotin compounds laterally segregate in phosphatidylethanolamine membranes without affecting the shape and position of the lamellar gel to lamellar liquid-crystalline phase transition thermogram of the phospholipid. This is in contrast with their reported effect on phosphatidylcholine membranes [Chicano et al. (2001) Biochim. Biophys. Acta 1510, 330-341] and emphasises the importance of the nature of the lipid headgroup in determining how the behaviour of lipid molecules is affected by these toxicants. Interestingly, we have found that organotin compounds disrupt the pattern of hydrogen-bonding in the interfacial region of dielaidoylphosphatidylethanolamine membranes and have the ability to promote the formation of hexagonal H(II) structures in this system. These results open the possibility that some of the specific toxic effects of organotin compounds might be exerted through the alteration of membrane function produced by their interaction with the lipidic component of the membrane.

Calorimetry, Differential Scanning↗
PubMed2006

Magnetic isotope effect in the photolysis of organotin compounds.

Photolysis of organotin molecules RSnMe3 is shown to be a spin selective radical reaction accompanied by fractionation of magnetic, (117,119)Sn, and nonmagnetic, (118,120)Sn, isotopes between starting reagents and products. A primary photolysis process is a homolytic cleavage of the C-Sn bond and generation of a triplet radical pair as a spin-selective nanoreactor. Nuclear spin dependent triplet-singlet conversion of the pair results in the tin isotope fractionation. Experimentally detected isotope distribution unambiguously demonstrates that the classical, mass-dependent isotope effect is negligible in comparison with magnetic, spin-dependent isotope effect.

Free Radicals↗
PubMed1998

Comparative studies on the induction of muscle contracture in mouse diaphragm and Ca2+ release from sarcoplasmic reticulum vesicles by organotin compounds.

Effects of organotins, including triethyltin and tributyltin, on skeletal muscle were studied with diaphragm and isolated sarcoplasmic reticulum membrane vesicles. Triethyltin induced muscle contracture in mouse diaphragm while tributyltin had comparatively less potency and efficacy in inducing the muscle contracture. The contracture induced by tributyltin was inhibited when the diaphragm was pretreated with low Ca2+ medium or caffeine while the contracture induced by triethyltin persisted in the Ca2+-free medium but was inhibited by pretreatment of caffeine. Pretreatment of dithiothreitol blocked the contracture induced by tributyltin but not that by triethyltin. Triethyltin dose-dependently induced Ca2+ release from sarcoplasmic reticulum vesicles and inhibited the Ca2+-ATPase activity. These results suggested that triethyltin induced contracture in mouse diaphragm was mainly by induction of Ca2+ release and inhibition of Ca2+ uptake of the internal Ca2+ storage site the sarcoplasmic reticulum, while the tributyltin induced contracture might be due to enhancement of extracellular Ca2+ influx which further induce the release of internal Ca2+ through the Ca2+-induced Ca2+ release mechanism.

Animals↗
PubMed2003

[Determination of organotin compounds in polyvinyl chloride toys].

Organotin compounds in polyvinyl chloride toys were determined by GC/MS after ethyl derivatization with sodium tetraethylborate. The samples were 12 balls, 12 soft toys, 10 food toys and 13 face masks for children. Monooctyltin, dioctyltin and trioctyltin compounds were found in all face masks at the levels of 74.8-917 micrograms/g. 474-3,960 micrograms/g and 1.0-213 micrograms/g, respectively. They also were detected in 6 balls, 4 soft toys and 1 food toy. Monomethyltin and dimethyltin compounds were found in 8 face masks at the levels of 40.9-227 micrograms/g and 222-1,450 micrograms/g, respectively. Monobutyltin and dibutyltin (DBT) compounds were found in 1 ball, 3 food toys and 5 face masks. In particular, 1 ball and 4 face masks contained toxic DBT at the levels of 527-999 micrograms/g.

Borates↗
PubMed1999

Chemical species of organotin compounds in sediment at a marina.

A bottom sediment collected in a marina was analyzed for organotin species, and >20 organotin compounds including biodegraded ones were confirmed by comparison with the synthesized standards using gas chromatography (GC)/mass spectrometry and a GC/atomic emission detection system. Their structures were also determined in comparison with those in a technical grade of tri-n-butyltin chloride (TBTC). Eleven organotin compounds were found in the technical TBTC. Among them, unexpected organotin compounds, such as di-n-butyl(2-ethylhexyl)tin chloride and di-n-butyloctyltin chloride, were identified, although the levels were low. These compounds were also found in the sediment sample. The relationship between organotin compounds in the technical TBTC and those in marine products was also discussed.

Chromatography, Gas↗
PubMed1996

Differential effects of organotin compounds on voltage-gated potassium currents in lymphocytes and neuroblastoma cells.

Effects of organotin compounds were studied on voltage-gated K+ current in whole-cell voltage clamped lymphocytes and in N1E-115 neuroblastoma cells. In human peripheral blood lymphocytes the immunotoxic compounds dibutyltinchloride (DBT, 2.5 microM) and triphenyltinchloride (TPhT, 2.5 microM) decrease the peak amplitude of the K+ current and prolong time to peak. Tributyltinchloride (TBT, 2.5 microM) decreases the K+ current to a greater extent than DBT and TPhT, without affecting the time to peak. The neurotoxic organotin compound trimethyltinchloride (TMT, 2.5 microM) does not affect the voltage-gated K+ current in lymphocytes. Similar effects of DBT were observed in freshly isolated and PHA-activated human lymphocytes and with rat thymocytes. On the other hand, in mouse N1E-115 neuroblastoma cells, none of the organotin compounds altered the voltage-dependent K+ current. In human lymphocytes DBT affects both the peak amplitude and the time to peak of the K+ current in a concentration-dependent manner. At the maximum concentration of 10 microM tested, the peak amplitude of the K+ current was reduced to 22 +/- 4% of the control current. The IC50 and slope factor for block of the peak outward current by DBT amounts to 6.7 +/- 0.4 microM, and 2.7 +/- 0.4, respectively. The delay in K+ current activation does not saturate. At 10 microM DMT increases the time to peak to 332 +/- 12% of the control value. The present results suggest that the effects by DBT originate from two separate interactions with the voltage-gated K+ channel at the extracellular site of the membrane: a direct effect on the closed K+ channel causing a delay in current activation and a membrane-related effect causing inhibition of the K+ current. The differential effects of the organotin compounds may relate to their differential toxicological action.

Animals↗
PubMed1996

Pilot study on the contamination of drinking water by organotin compounds from PVC materials.

Raw and treated water samples and tap water samples from four to six houses located on distribution lines where PVC pipe/tubing had been recently installed were collected in five Canadian municipalities for the analysis of organotin compounds. After derivatisation with sodium tetraethylborate the ethylated organotin compounds were extracted with hexane and analysed by gas chromatography-microwave induced plasma atomic emission spectrometry using a wavelength (326.234 nm) specific for tin. Organotin compounds, mainly methyltin and dimethyltin at concentrations ranging respectively from 0.5 to 257 ng Sn/L and from 0.5 to 6.5 ng Sn/L, were detected in samples from ten of the twenty-two houses. No organotin compounds were detected in raw water or treated water leaving the treatment plant, indicating that the organotin compounds were leaching into the water from some component of the distribution system.

Borates↗
PubMed2000

Simple and effective gas chromatographic mass spectrometric procedure for the speciation analysis of organotin compounds in specimens of marine mussels. An evaluation of the organotin pollution of the lagoon of venice.

This paper describes a simple, effective analytical procedure, based on a gas chromatographic mass spectrometric technique, for the speciation analysis of organotin compounds (OTC) in mussel samples. The direct alkylation reaction of the organotin chlorides in the aqueous digestion solution by NaBEt(4) allowed a short analysis time and a good recovery. The evaluation of the yield of each step constituting the analytical procedure indicated that the alkylation step is the most critical one. The proposed method was advantageously utilised to monitor the level of OTC pollution of the Lagoon of Venice. All the sites examined, both near to and far from anthropogenic activities, revealed significant levels of OTC pollution.

Animals↗
PubMed2002

Antiproliferative and cytotoxic effect of a novel organotin compound on mammalian cells both in vitro and in vivo.

Organotin compounds are organometallic compounds showing various toxicological properties. Several organotin compounds also showed an antineoplastic effect. However, their relative mutagenic potential is not well established. In this study Et(2)SnCl(2).L [L=N-(2-pyridylmethylene)-4-toluidine] (OTC) has been subjected to investigation for its cytotoxic effect in mouse bone marrow cells (BMCs) and human peripheral blood lymphocyte cells (HPBLs). The Sn [bond] N bond in OTC is 2.46A which is greater than 2.39A and therefore, a better formation of tin-DNA complex can be expected. The present data indicate that OTC induced significant delay in cell kinetics and sister chromatid exchanges (SCEs) in both BMCs and HPBLs, whereas, induction of chromosome aberrations was found only in HPBLs. The presence of buthionine sulfoximine (BSO) modulated cellular sensitivity towards OTC in both cell systems. It may be inferred that the OTC could bind on DNA more easily owing to its structural advantage and this may explain the induction of DNA damage and the delay in cell proliferation. Since the cytotoxic effect of OTC is more in glutathione depleted cells, the concentration of OTC may be reduced to get an antitumour effect in GSH-depleted cells and thus minimizes its toxic side effect.

Animals↗
PubMed1993

The mutagenicity of organotin compounds as environmental pollutants.

The mutagenicity of 14 organotin compounds which have been reported to be environmental pollutants, their environmental metabolites and inorganic tin (SnCl4) was studied. The experiments were carried out by a modification of the conventional Salmonella assay. Each tested chemical was removed by washing the tested strain with phosphate buffer, before the strain with top agar was poured onto minimal glucose agar. By this method, we were able to estimate the mutagenicity of organotin compounds which had antibacterial activity. It was apparent that mono-n-butyltin oxide, n-butyltin trichloride, di-n-butyltin dichloride, tri-n-butyltin chloride, bis-(tri-n-butyltin)-oxide and dimethyltin dichloride were mutagens on Salmonella typhimurium TA100 and bis-(tri-n-butyltin)-oxide showed the highest mutagenicity. With S. typhimurium TA98, di-n-butyltin dichloride was found to be a mutagen.

Environmental Pollutants↗
PubMed2006

Organotin compounds and selected metals in the marine environment of Northern Adriatic sea.

The extent of pollution with organotin compounds and Cd, Pb, Ni, Cu, Zn, Cr, Mn, V, Co and Al was investigated in sediments and mussels (Mytilus galloprovincialis) from the Slovenian costal area of the Northern Adriatic Sea. Sampling was performed in Marina Portoroz, Dockyard Izola, non exposed area of the Bay of Mesecev zaliv and in Mariculture Secovlje. Mussels were taken in the summer and winter time, while sediments were collected during the winter sampling. Organotin compounds were determined by gas chromatography-mass spectrometry and metals by flame or electrothermal atomic absorption spectrometry. The accuracies of the analytical procedures were checked by the analysis of standard reference materials CRM 477 mussel tissue and PACS 2 marine sediment (organotin compounds) and SRM 2976 mussel tissue and CRM 320 river sediment (metals). Good agreements between certified and determined values were obtained. Normalization procedure to Al was applied to estimate the anthropogenic inputs of metals in sediments. The analyses of sediments demonstrated moderate pollution with organotin compounds in Marina Portoroz and in Dockyard Izola. Concentrations of tributyltin species were higher than those of dibutyltin and monobutyltin. In mussels substantial contamination with tributyltin was observed in Marina Porotroz and Dockyard Izola. The extent of pollution was higher in the winter time. The analysis of metals in sediments exhibited elevated concentrations in Marina Portoroz and Dockyard Izola. Data from the normalization procedure indicated the anthropogenic inputs of Cu, Zn and Cr in Marina Portoroz and Mn in Bay of Mesecev zaliv and Dockyard Izola. Mussels, as accumulators of pollutants, in general contained higher metal concentrations during winter time in Dockyard Izola.

Animals↗
PubMed1987

Biological activity of organotin compounds--an overview.

As a consequence of the rapid expansion of the uses and applications of the organotin compounds, the concern about their environmental and health effects is increasing. The main subject of this overview is the current understanding of the mammalian toxicity of the organotin compounds. Four different types of target organ toxicity, namely neurotoxicity, hepatoxicity, immunotoxicity, and cutaneous toxicity, are discussed in more detail. The effects of the organotin compounds on the mitochondrial and cellular level are summarized and discussed in relation to the mode of action of these compounds on the central nervous system, the liver and bile duct, the immune system, and the skin.

Animals↗
PubMed1992

Synthesis, structure, antimicrobial, and genotoxic activities of organotin compounds with 2,6-diacetylpyridine nicotinoyl- and isonicotinoylhydrazones.

A series of organotin compounds obtained from the reaction of 2,6-diacetylpyridine nicotinoyl- and isonicotinoylhydrazones with tri- and diorganotin chlorides was investigated. The IR and 119Sn NMR spectroscopic characterization of all the compounds is reported, together with the x-ray crystal structure of [SnEt2(H2dapin')]2[SnEt2Cl3]Cl3.2H2O (H2dapin' = 2,6-diacetylpyridine bis(isonicotinoylhydrazone)). The main feature in this compound is the presence of a tin atom in both the complex ionic units. The coordination polyhedron is a pentagonal bipyramid in the cation and a trigonal bipyramid in the anion. Results are discussed concerning the in vitro evaluation of antimicrobial properties and genotoxic potential of the compounds described. In all cases the complexes show a reduced antimicrobial activity as compared to that of the corresponding organotin compound. Genotoxic properties of the ligands, detected in the Ames test, disappear in the complexes.

Bacteria↗