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PubMed1998

Trace analysis of tributyltin and triphenyltin compounds in sea water by gas chromatography-negative ion chemical ionization mass spectrometry.

An analytical gas chromatography-mass spectrometry (GC-MS) method using negative ion chemical ionization (NICI) has been investigated for the determination of trace tributyltin (TBT) and triphenyltin (TPhT) compounds in sea water. TBT and TPhT were extracted from samples as chloride under the acidic condition of HCl. Doping of the GC system with a dilute HBr-methanolic solution resulted in direct detection of the chlorides of TBT, TPhT and tripentyltin (TPenT, internal standard). As the result of HBr doping, a sharp peak of the respective organotin bromides appeared: during GC analysis, halogen exchange from the chloride to the bromide occurred. NICI-MS was highly selective and sensitive for the detection of TBT. TPhT and TPenT bromides. In the selected ion monitoring mode of NICI-MS, the minimum detectable amounts defined as the signal equal to three times the standard deviation (3 sigma) of the baseline noise were 20 and 25 pg ml-1 for TBT and TPhT, respectively. These amounts are approximately 250-400 times better than those in electron impact mode. The combination of GC using an apolar capillary column doped with a dilute HBr-methanolic solution and NICI-MS made it possible to determine TBT and TPhT at less than the ng l-1 level in sea water.

Gas Chromatography-Mass Spectrometry↗

PubMed2002

Structure, properties and in vitro cytotoxic activity of hexakis(2-cyanoethyl)ditin(III).

The structure of the tin(III) complex [Sn(2)(CH(2)CH(2)CN)(6)] has been determined. There are two independent molecules in the crystal, both adopt distorted eclipsed conformation. The molecular and electronic structures of this compound have been studied both at the semiempirical level and with the use of non-empirical ab initio methods. The calculated Sn-Sn distances agree well with those found crystallographically. The results of calculations showed that the eclipsed conformation of complex is more stable as compared with staggered conformation. The compound show modest cytotoxic activity against A549 and HSMC cells.

Antineoplastic Agents↗

PubMed1984

Mechanisms of dialkyltin induced immunopathology.

In this report the immunotoxic effects of dialkyltin compounds are reviewed. In rats they induce lymphocyte depletion in the thymus and the thymus dependent areas of the peripheral lymphoid organs, without signs of a generalized toxicity. As a consequence of their selective lymphocytotoxic action they cause immunosuppression, especially of the cell mediated immunity. Various mechanisms are discussed that may be involved in the selective effect on the thymus, indirectly through changes in endocrine control or the reticular epithelial cells, and directly on the intrathymic rapidly dividing cells. It is suggested that the immunotoxicity of dialkyltin compounds is related to their affinity for dithiol groups, resulting in a disturbance of cell energetics as well as in cell proliferation.

Animals↗

PubMed1995

Role of cytochrome P450 in hepatotoxicity induced by di- and tributyltin compounds in mice.

The role of cytochrome P450 in the induction of hepatotoxicity by butyltin compounds such as tributyltin chloride (TBTC) and dibutyltin dichloride (DBTC) was investigated in vivo. The pretreatment of mice with SKF-525A, which decreased hepatic levels of cytochrome P450, suppressed TBTC-induced hepatotoxicity, as estimated by serum ornithine carbamyl transferase activity, whereas pretreatment with phenobarbital (PB), which increased the levels of cytochrome P450, enhanced the hepatotoxicity of TBTC. In the case of DBTC, PB pretreatment enhanced hepatotoxicity, while SKF-525A had no effect. Under these experimental conditions only PB pretreatment was found to increase hepatic levels of tin in mice treated with TBTC. These results suggest that hepatic metabolism of butyltin compounds by cytochrome P450 is more closely related to the induction of hepatotoxicity by TBTC than by DBTC. The active tin compounds formed during hepatic metabolism, which are responsible for induction of hepatotoxicity, will be discussed.

Animals↗

PubMed1993

Tri-n-butyltin chloride promotes morphological transformation and induces proliferin expression in C3H10T1/2 cells.

Transcripts from the murine gene family proliferin, which are increased by a wide assortment of chemical promoters of C3H10T1/2 cell morphological transformation, were shown to be induced by tri-n-butyltin chloride at concentrations above 50 nM. Two-stage transformation assays, with 3-methylcholanthrene as inducer and tri-n-butyltin chloride as promoter, were performed to determine if promotion of morphological transformation and proliferin induction were properties shared by this compound. Tri-n-butyltin chloride synergistically enhanced focus formation at concentrations ranging from 20 to 75 nM. Di-n-butyltin dichloride, n-butyltin trichloride and tin (II) chloride, but not tin (IV) chloride, were also effective inducers of proliferin. Changes in patterns of TPA-inducible, secreted proteins, including those likely to be proliferin, were detected following organotin treatment of confluent monolayers. Tri-n-butyltin chloride resembles other agents active as promoters in C3H10T1/2 two-stage transformation assays by possessing an ability to induce proliferin expression.

Animals↗

PubMedDate not supplied

[Preparation and spectroscopic studies of diorganotin(IV) complexes with adenosine and related compounds].

Nine complexes of adenosine and related compounds (adenosine-5'-monophosphate, adenosine-5'-triphosphate, 1-methyl-adenosine, pyridoxal-5-phosphate and beta-nicotinamide-adenine-dinucleotide-phosphoric acid) with di-n-butyltin(IV) oxide and/or di-n-butytin(IV) dichloride were prepared in the solid state. The compositions of the complexes were determined by standard analytical methods. It was found that the complexes contain organotin(IV) moiety and the ligand in a ratio of 1:1 or 2:1. The FTIR spectra demonstrated that di-n-butyltin(IV) oxide reacts with the D-ribose moiety of the ligands, while di-n-butyltin(IV) dichloride is co-ordinated to the deprotonated phosphate group. The basic part of the ligands does not participate directly in complex formation. Comparison of the experimental Mössbauer delta E values with those calculated on the basis of the PQS concept revealed that the organotin(IV) moiety has trigonal-bipyramidal, octahedral and in some cases tetrahedral geometry also. Some of the complexes contain the organotin(IV) cation in two different surroundings.

Adenosine↗

PubMed1984

Methyltin intoxication in six men; toxicologic and clinical aspects.

Neurologic and psychiatric symptoms such as headache, tinnitus, defective hearing, changing desorientation and aggressiveness are initial symptoms of methyltin chloride intoxication. Some patients also developed epileptic equivalents, such as dreamy attacks and central ventilation transaminases. Laboratory findings included low levels of serum potassium, leucocytosis and elevated transaminases. The excretion rate of tin in the urine correlated with the severity of the intoxication. There was no measurable effect of plasma separation or d-penicillamine therapy on tin excretion in the urine or on the clinical picture. The long-term prognosis of severely intoxicated persons is poor. Neurohistopathologic findings confirm the animal studies by Brown et al and the severe damage and cell necrosis in the hippocampus area. To prevent such events workers need to be warned of the risk and dangers of working with organo-metallic compounds. The effectiveness of protective clothes and gas masks should be checked. In exposed workers regular testing is advised of tin concentrations in the urine.

Accidents, Occupational↗

PubMed2004

Applicability of solid-phase microextraction combined with gas chromatography atomic emission detection (GC-MIP AED) for the determination of butyltin compounds in sediment samples.

The performance of solid-phase microextraction (SPME) applied to the determination of butyltin compounds in sediment samples is systematically evaluated. Matrix effects and influence of blank signals on the detection limits of the method are studied in detail. The interval of linear response is also evaluated in order to assess the applicability of the method to sediments polluted with butyltin compounds over a large range of concentrations. Advantages and drawbacks of including an SPME step, instead of the classic liquid-liquid extraction of the derivatized analytes, in the determination of butyltin compounds in sediment samples are considered in terms of achieved detection limits and experimental effort. Analytes were extracted from the samples by sonication using glacial acetic acid. An aliquot of the centrifuged extract was placed on a vial where compounds were ethylated and concentrated on a PDMS fiber using the headspace mode. Determinations were carried out using GC-MIP AED.

Acetic Acid↗

PubMed1999

A new mussel certified reference material (CRM 477) for the quality control of butyltin determination in the marine environment.

The analytical techniques used for the determination of butyltin compounds in biological tissues are generally based on a succession of steps (e.g., extraction, derivatization, separation, detection) which are all prone to systematic errors. An interlaboratory programme performed at the EU level and based on a stepwise approach has enabled one to identify and remove most of these errors and to improve considerably the state of the art so that certification of a mussel reference material has been made possible. This paper describes the preparation of this mussel reference material containing monobutyltin (MBT), dibutyltin (DBT) and tributyltin (TBT), the homogeneity and stability studies and the analytical work performed for the certification of the contents of MBT [Sn(C4H9)3+], DBT [Sn(C4H9)2(2+)] and TBT [Sn(C4H9)3+]. The results obtained by a group of expert EU laboratories are discussed along with the methods used to certify the mass fractions (based on dry mass) of monobutyltin (1.50 +/- 0.28 mg kg-1 as MBT cations), dibutyltin (1.54 +/- 0.12 mg kg-1 as DBT cations) and tributyltin (2.20 +/- 0.19 mg kg-1 as TBT cations). The paper also describes an attempt to certify the content of triphenyltin in this material which, although reasonable agreement was found among the participants' results, failed owing to the instability of this compound. This new material will be of great support to ensure the quality control of butyltin determination in shellfish, as carried out in environmental monitoring programmes.

Animals↗

PubMed2004

Contamination of butyltin compounds in Malaysian marine environments.

Concentration of butyltin compounds (BTs), including tributyltin (TBT), dibutyltin (DBT) and monobutyltin (MBT) and total tin (SigmaSn) were determined in green mussel (Perna viridis), 10 species of muscle fish and sediment from coastal waters of Malaysia. BTs were detected in all these samples ranging from 3.6 to 900 ng/g wet wt., 3.6 to 210 ng/g wet wt., and 18 to 1400 ng/g dry wt. for mussels, fish and sediments, respectively. The concentrations of BTs in several locations of this study were comparable with the reported values from some developed countries and highest among Asian developing nations. Considerable concentration of BTs in several locations might have ecotoxicological consequences and may cause concern to human health. The parent compound TBT was found to be highest than those of its degradation compounds, DBT and MBT, suggesting recent input of TBT to the Malaysian marine environment. Significant positive correlation (Spearman rank correlation: r2=0.82, P<0.0001) was found between BTs and SigmaSn, implying considerable anthropogenic input of butyltin compounds to total tin contamination levels. Enormous boating activities may be a major source of BTs in this country, although aquaculture activities may not be ignored.

Animals↗

PubMed1983

Di-n-butyltindichloride uncouples oxidative phosphorylation in rat liver mitochondria.

In this study di-n-butyltindichloride (DBTC) was found to inhibit alpha-ketoacid-stimulated response of rat liver mitochondria to the addition of ADP and the uncoupler carbonyl cyanide p-trifluoromethoxyphenyl hydrazone (FCCP). The alpha-ketoglutarate oxidation was already inhibited at a level of 0.8 nmol DBTC/mg protein. When succinate was used as substrate together with rotenone, the State 3 and FCCP stimulated oxidation were not inhibited by DBTC. But from a level of 8.3 nmol DBTC/mg protein, the State 4 respiration was increased. It is concluded that in low amounts DBTC specifically blocks alpha-ketoacid dehydrogenases, but higher concentrations of this compound uncouples oxidative phosphorylation. However, this uncoupling will be masked when the NADH production from substrate oxidation is decreased by DBTC as will be in case of alpha-ketoacids.

Adenosine Diphosphate↗

PubMed1996

Comparative study of the metabolism of triphenyltin in hamsters and rats after a single oral treatment with triphenyltin chloride.

Our previous work has shown that triphenyltin compound induces the diabetogenic effects, such as hyperglycemia and hypertriglyceridemia, on hamsters, but not on rats. In the present study, it is examined whether the species differences in the metabolic fate of triphenyltin exist for susceptibility between hamsters and rats. Triphenyltin chloride was orally dosed to hamsters and rats, and triphenyltin and its metabolites, mono- and diphenyltin, and inorganic tin, in liver, kidney, pancreas, brain, and blood were determined by gas chromatography periodically for 96 h after the treatment. Triphenyltin levels in the tissues of both species were almost maxima within 24 h after treatment. Although there were relatively high levels of triphenyltin in the tissues of hamsters dosed with triphenyltin chloride, compared with those in the rats, the proportion of metabolites to triphenyltin were lower than those in the rats. In particular, hamsters were more susceptible than rats to the pancreatic accumulations of triphenyltin and good correlation exists between the tin concentrations in the pancreas and the plasma glucose levels in triphenyltin-treated hamsters. These findings suggest that the dearylation of absorbed triphenyltin in hamsters is slower than that in rats and that triphenyltin-induced hyperglycemic action depends upon the amount of tin compounds absorbed into the pancreas. Furthermore, most of the tin compounds in the brains of both species were triphenyltin. This result shows that the metabolism of triphenyltin in the brains of both species was different from that in other tissues.

Administration, Oral↗

PubMed2002

[Study of the interactions between diorganotin (IV) complexes of 1,3-dimethyl-4-acetyl-5-pyrazolone and mononucleotides and DNA].

AIM: The interactions between diorganotin (IV) complexes of 1,3-dimethyl-4-acetyl-5-pyrazolone (HL1) and mono-nucleotides together with DNA near physiological condition were investigated. METHODS: The mode of action of the diorganotin (IV) complexes with mononucleotides and DNA under different conditions and different times were investigated by high resolution NMR technology and UV spectra. RESULTS: The interaction of [(L1)2SnEt2] with AMP was shown to result in significant change of chemical shift of H(8), H(2) and 31P of AMP. Hyperchromic effect of DNA could be observed due to the interaction of; [(L1)2SnEt2] with DNA, while interaction of [(L1)2SnMe2] with AMP and DNA could only cause obvious change of chemical shift of 31P and lead to hypochromic effect of DNA. CONCLUSION: The results indicate that [(L1)2SnEt2] can selectively bind to the N1 atom of the base and the phosphate oxygen atom of AMP and may further destroy the helical structure of DNA, while the dimethyltin (IV) compound of 1,3-dimethyl-4-acetyl-5-pyrazolone [(L1)2SnMe2] merely binds to the the phosphate oxygen atom of AMP and causes the contraction of DNA helical structure.

Antineoplastic Agents↗

PubMed2000

Induction of aberrant mitosis with PCBs: particular efficiency of 2, 3,3',4,4'-pentachlorobiphenyl and synergism with triphenyltin.

The polychlorinated biphenyls 2,2',5,5'- and 3,3',4, 4'-tetrachlorobiphenyl, 2,3,3',4,4'- and 3,3',4,4', 5-pentachlorobiphenyl and 2,2',4,4',5,5'-hexachlorobiphenyl were tested for spindle-disturbing activity in V79 Chinese hamster cells. Clones lacking endogenous cytochrome P450 activity or expressing rat CYP1A1 or CYP2B1 were used. Induction of abnormal chromosomal arrangements in mitosis were found to be favoured by o-chlorine substitutions, but not by co-planarity giving affinity, for example, for the Ah receptor and CYP1A isoenzymes. Only 2,2',5, 5'-tetrachloro- and 2,3,3',4,4'-pentachlorobiphenyl gave dose-response curves similar to many other compounds tested in vitro, showing an increase from the background level of 10 to 100% disturbed mitoses with nominal concentrations >10(-6) M, i.e. concentrations far above the total PCB concentrations found in human blood. Cells transfected with rat CYP2B1 were more sensitive to the most active congener, 2,3,3',4,4'-pentachlorobiphenyl, than cells lacking P450 activity or expressing CYP1A1. Induction of abnormal mitosis by PCB metabolites formed by P450 enzymes cannot be excluded, but does not seem likely because of the short treatment time and the reportedly slow metabolism of PCBs. 2,3,3',4, 4'-Pentachlorobiphenyl showed synergistic activity with the potent spindle poison triphenyltin. Inactive concentrations of both agents (10 and 50 nM, respectively) caused abnormal configurations when combined. This is an important finding since exposure to mixtures of compounds is common and it motivates further studies of subthreshold activities of highly lipophilic environmental contaminants.

Animals↗

PubMed1999

Butyltin compounds in river otters (Lutra canadensis) from the northwestern United States.

Butyltin compounds, including mono-, di-, and tributyltin (MBT, DBT, and TBT) were measured in livers of 40 adult river otters (Lutra canadensis) collected from rivers and coastal bays in Washington and Oregon, USA. Butyltins were found in all the river otters, at a concentration range of 8.5-2,610 ng/g, WW. The greatest concentration of total butyltins of 2,610 ng/g, WW, was found in a river otter collected in Puget Sound from Fort Ward, Washington. River otters collected near areas with major shipping activities, such as the Puget Sound, contained significantly greater concentrations (geometric mean: 367 ng/g, WW) of butyltins than those from rivers. Among butyltin compounds, MBT and DBT predominated in livers. The concentrations of butyltins in river otters ranged from comparable (Puget Sound) to less (rivers) than what was found in coastal cetaceans.

Animals↗

PubMed1986

Inhibition of arm regeneration by Ophioderma brevispina (Echinodermata, Ophiuroidea) by tributyltin oxide and triphenyltin oxide.

Effects of water-bourne toxicants on regeneration of arms by the brittle star, Ophioderma brevispina, are described. Regeneration was inhibited by 0.1 micrograms liter-1 bis(tri-n-butyltin)oxide and bis(triphenyltin)oxide. Both substances are known to act upon the nervous system, and it is suggested that inhibition was caused by neurotoxicological action of the tin compounds or by their direct effect upon tissue at the breakage point. The former is most likely because regeneration is mediated by the radial nerves of brittle stars.

Animals↗

PubMed1993

Teratogenic effects of various di-n-butyltins with different anions and butyl(3-hydroxybutyl)tin dilaurate in rats.

In our previous study, di-n-butyltin diacetate has been shown to cause malformations such as cleft mandible, ankyloglossia, fused ribs, etc. in rat fetuses after oral treatment of maternal rats on day 8 of gestation. In this study, teratogenic effects of five di-n-butyltin compounds with different anions and also butyl(3-hydroxybutyl)tin dilaurate (3-OHDBTL) were examined in Wistar rats. Anion groups of these compounds were as follows: diacetate (DBTA), dichloride (DBTC), maleate (DBTM), oxide (DBTO) and dilaurate (DBTL). On day 8 of gestation, pregnant rats were treated orally with these compounds at 80 mumol/kg, or with 3-OHDBTL at 80 or 160 mumol/kg. Cesarean sections were performed on day 20 of gestation and fetuses were examined for their external and skeletal anomalies. Types of the observed malformations were similar to those in the previous study with DBTA except 3-OHDBTL, though the incidence of fetuses with malformations was different. In the DBTC-treated group, skeletal anomalies were predominant to external ones, especially with the higher incidence of fused ribs than in the other groups. In the 3-OHDBTL-treated group, no external and skeletal anomalies were observed at 80 mumol/kg and cleft lower lip and ankyloglossia were observed in only one fetus, but peaked mandible (the tip of lower jaw with acute angle) was specific at 160 mumol/kg. From these results, the di-n-butyl group rather than anionic group was found to be important in the teratogenicity of di-n-butyltin compounds as well as in the other kinds of toxicities and 3-OHDBTL, one of the main metabolites of DBTL, is not the critical substance of teratogenicity because of a very low teratogenic potency.

Animals↗

PubMed2000

Determination of butyltin species in water and sediment by solid-phase microextraction-gas chromatography-flame ionization detection.

A procedure for determination of tetraethyltin (TeET) and tetrabutyltin (TeBT) in water by solid-phase microextraction (SPME) using the headspace approach has been developed. The method has been adapted for the simultaneous determination of mono-, di- and tributyltin species (MBT, DBT and TBT) after derivatization with sodium tetraethylborate in water and sediment samples. The analytical procedures were optimized with respect to stirring conditions, extraction time and extraction temperature. The pH and the amount of derivatizing reagent were also considered in derivatization reaction procedures. The analysis was carried out using gas chromatography equipped with flame ionization detection. The detection limits obtained for TeET and TeBT, in equilibrium conditions (room temperature for TeET and 40 degrees C for TeBT) were 28 and 20 ng/l (as Sn), respectively. The detection limit for butyltin species in water, which was limited by signals which are non-specific for the tin compounds and the sensitivity of the FID system, was found ca. 1 microg/l (as Sn). The SPME method was validated for analysis of sediments by analyzing the certified reference material PACS-2 finding a good agreement with the certified values.

Calibration↗