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PubMed2001

Synthesis and evaluation of diazine containing bioisosteres of (-)-ferruginine as ligands for nicotinic acetylcholine receptors.

In this structure-affinity relationship (SAFIR) study, the bioisosteric potential of diazines in the field of ferruginine-type nAChR ligands was investigated. Novel enantiopure analogues of (-)-Ferruginine (3) such as 6-8 were synthesized utilizing enantiomerically pure N-protected (+)-2-tropanone 9 from the 'chiral pool' as versatile chiral building block and a palladium-catalyzed Stille cross-coupling of the tributylstannyl diazines 12, 14 and 16 with the vinyl triflate 11 of (+)-2-tropanone 9. The structures of the novel diazine analogues 6-8 of (-)-ferruginine (3) were assigned on the basis of spectral data, that of ligand 7 being additionally verified by X-ray crystallography. The bioisosteric replacement of the acetyl moiety as structural part of the lead compound 3 with the pyridazine, pyrimidine and pyrazine nucleus resulted in ligands with high to moderate affinity for the central alpha4beta2 and remarkably low affinity for the alpha7* nAChR subtypes. Among the compounds synthesized and tested, 7 was the most active one with K(i)=3.7 nM (alpha4beta2). Compared with the lead 3, this value represents a 30-fold improvement in the affinity for the alpha4beta2 subtype combined with a substantially improved selectivity ratio between the alpha4beta2 and alpha7* subtypes.

Animals↗
PubMed2004

Antiproliferative effect of butyltin in MCF-7 cells.

Humans are exposed to tributyltin compounds primarily through the intake of marine food. Previous reports on toxic effects to humans are limited to a few in vitro studies giving conflicting results regarding their effects on the aromatase enzyme and androgen receptor (AR) responses. The present study evaluates the estrogenic potential of three butyltin compounds (mono-, di-, and tributyltin) in an in vitro system based on the E-Screen assay. None of the butyltin compounds tested was estrogenic in the concentration range assayed (0.01-1000 nM). However, both dibutyltin dichloride (DBT) (500 nM) and tributyltin chloride (TBT) (10 nM) inhibited 17beta-estradiol-induced cell proliferation. DBT (500 nM) and TBT (10 nM) also significantly reduced testosterone-induced cell proliferation, and the inhibition by TBT was rescued by increasing the concentration of testosterone. The present study did not confirm the inhibition of aromatase as the mechanism for an endocrine effect of butyltin compounds; moreover, the inhibition of cell proliferation by DBT and TBT occurred at concentrations at which no cytotoxicity was observed. The exact mechanism by which TBT and DBT inhibit cell proliferation remains unexplained, but it might be essentially independent of the estrogen receptor. Therefore, these compounds may not be termed classical endocrine disruptors, but rather as compounds that cause a functional anti-estrogenic response.

Aromatase↗
PubMed2006

In vitro metabolism of tributyltin and triphenyltin by human cytochrome P-450 isoforms.

The metabolic fate of tributyltin and triphenyltin may contribute to the toxicity of these chemicals. We used human hepatic cytochrome P-450 (CYP) systems to confirm the specific CYP(s) involved in the in vitro metabolism of tributyltin and triphenyltin. There were no significant sex differences in the metabolic pattern of tributyltin or triphenyltin, indicating that the CYP(s) responsible for the metabolism of these chemicals in humans is/are not sex-specific form(s). Six major drug-metabolizing isoforms of cDNA-expressed human CYPs and the CYP2C subfamily were tested to determine their metabolic capacities for tributyltin and triphenyltin. CYP2C9, 2C18, 2C19, and 3A4 significantly mediated both dealkylation and dearylation of these triorganotins. Furthermore, the metabolism of tributyltin and triphenyltin was significantly inhibited in vitro by pretreatment with selective inhibitors, azamulin for CYP3A4 and N-3-benzylnirvanol for CYP2C19. Since the CYP2C18 content of hepatic microsomes in humans is relatively low, CYP2C9, 2C19, and 3A4 might be the main isoforms of CYP that are responsible for tributyltin and triphenyltin metabolism in the human liver.

Biotransformation↗
PubMed1982

Comparative toxicity of alkyltin and estertin stabilizers.

In a 2-wk feeding study the oral toxicities of the estertin compounds bis-(beta-carbobutoxyethyl)-tin dichloride (CBETC) and bis-(beta-carbomethoxyethyl)tin dichloride (CMETC) and their hydrolysis products bis-(beta-carboxyethyl)tin dichloride (CETC) were compared with those of the dialkyltin compounds di-n-octyltin dichloride (DOTC) and di-n-butyltin dichloride (DBTC). At a dietary level of 450 ppm the estertins did not affect weights, but at the relatively high level of 1350 ppm both caused growth retardation and a statistically significant decrease in the relative weight of the liver, while CBETC also reduced the relative weights of the thymus and spleen. A diminished amount of liver glycogen was the only treatment-related histopathological change observed in these organs. CETC caused no signs of toxicity up to a level of 1350 ppm. Slightly decreased body-weight gains were recorded in rats fed 50 ppm DBTC or 150 ppm DBTC or DOTC, but the main effect in dialkyltin-fed rats was a decrease in lymphoid-organ weights. In rats fed 150 ppm DBTC or DOTC for 2 wk, the relative thymus weight was decreased by more than 70% compared with the control value and there was lymphocyte depletion in the thymus, especially the thymic cortex, and in thymus-dependent lymphoid areas of the spleen. Parenteral exposure demonstrated a similar difference in toxicity between these groups; a single ip or iv injection of 2.5 mg DBTC/kg body weight caused a slight reduction in body-weight gain and severe thymic atrophy, whereas CBETC and CETC had no such effects even at 10 mg/kg. However, in vitro the activities of the esterins were similar to those of the dialkyltins. In lymphocyte metabolism studies, all these compounds induced a dose-dependent stimulation of glucose consumption, with maximum stimulation occurring at a level of 5 microM with DBTC and CBETC and at 120 microM with DOTC and CMETC. At higher exposure levels, glucose consumption fell sharply, oxygen consumption was reduced and lymphocyte viability was impaired. Since the dicarboxyltin compound CETC induced no signs of lymphocytotoxicity in the in vitro cell-metabolism, cell-viability or blast-transformation studies, hydrolysis of CBETC and CMETC to CETC in the rat is suggested as a possible explanation for the discrepancy between the lymphocytotoxic activity of the estertin compounds in vitro and the absence of lymphoid atrophy following in vivo exposure, and for the finding that in the rat CMETC and CBETC are much less toxic than the dialkyltin compounds DBTC and DOTC, which induce lymphocytotoxicity both in vitro and in vivo.

Animals↗
PubMedDate not supplied

Effect of organic tin compounds on electric properties of model membranes.

The objective of the present work was to investigate the effect of selected organic tin compounds and potassium chloride (used as a reference substance) on the trans-membrane electric voltage and electric resistance of model membranes, the latter being nitrocellulose filters impregnated with butylene ester of lauric acid. The increasing KCl concentration (in the measurement chambers) caused a rapid rise of the negative trans-membrane voltage, whose value stabilized afterwards. In the case of (C3H7)3SnCl an abrupt maximum of the negative voltage was observed followed by a monotonic drop to zero. In the case of highest concentrations of this compound the voltages, after having reached zero, changed their polarization to the opposite. Within the range of small concentrations two slight voltage maxima were observed. Non-ionic tin compounds like (CH3)4Sn and (C2H5)4Sn had an insignificant influence on the electric properties of the studied membranes.

Electrochemistry↗
PubMed2000

Phenyltin inhibition of the cytotoxic function of human natural killer cells.

Phenyltin (PT) contamination has been reported in water, sediment, and fish. However, the role of PT in weakening human immune function mediated through natural killer (NK) lymphocytes has not been elucidated. In this study, we report the effects of in vitro exposure to triphenyltin (TPT), diphenyltin (DPT), and monophenyltin (MPT) on the function of human NK cells. Exposure to TPT (1 microM, for 1 h) inhibited the tumor killing capacity of NK cells by 85%. Exposure of NK cells to DPT for 1 h (5 microM) and 24h (1.5 microM) reduced tumor lysis by greater than 90%. A 24-h exposure of NK cells to 5 microM MPT reduced tumor lysis by greater than 80%. Assays assessing the ability of NK cells to bind to tumor cells showed that a 24-h pretreatment with TPT, DPT, or MPT reduced NK cell binding to tumor cells by greater than 50%. The toxic potential of the PTs followed the order TPT > DPT > MPT. In comparison with butyltins (BTs), in vitro effects of PTs revealed that these compounds are relatively less toxic to NK cells than BTs. The results of this study provide evidence that phenyltin compounds are immunotoxic to human NK cells under in vitro experimental conditions.

Cell Adhesion↗
PubMed2005

Interpretation of butyltin mass spectra using isotope pattern reconstruction for the accurate measurement of isotope ratios from molecular clusters.

The fragmentation patterns of butyltin compounds (mono-, di-, and tributyltin) in an electron impact ion source were studied using an isotope pattern reconstruction algorithm with emphasis on isotope ratio measurements from molecular clusters. For this purpose, standards of natural tin isotope abundance and a (119)Sn-enriched mixture of the three compounds were both ethylated and propylated using sodium tetraalkylborates. The corresponding mass spectra of the various tetraalkyltin compounds prepared were obtained by GC/MS after their extraction with hexane. The results showed that pure interference-free molecular clusters were obtained only for certain R(3)Sn(+) ions where no isobaric overlap with R(2)SnH(+) ions occurred (e.g. BuEt(2)Sn(+) overlaps with Bu(2)SnH(+)). These ions are ideal candidates for accurate Sn isotope ratio measurements, while isotope pattern perturbing interferences are observed for other molecular fragments down to Sn(.)(+). Isotope pattern reconstruction algorithm thus can be used as an analytical tool to ensure the absence of molecular interferences--a requirement for accurate isotope ratio measurements from molecular clusters. The relevance of these studies for the determination of butyltin compounds in environmental samples by isotope dilution GC/MS is also discussed.

Environmental Monitoring↗
PubMed2001

Accumulation of organochlorine pesticides and polychlorinated biphenyls in sediments, aquatic organisms, birds, bird eggs and bat collected from south India.

Concentrations of polychlorinated biphenyls (PCBs), DDT and its metabolites (DDTs), HCH isomers (HCHs), chlordane compounds (CHLs) and hexachlorobenzene (HCB) were determined in sediment, soil, whole body homogenates of resident and migratory birds and their prey items (including fish, green mussel, snail, earthworm, crabs, prawn, lizard and frogs), bird eggs and bats collected from southern India during 1995 and 1998. Accumulation pattern of organochlorines (OCs) in biota was, in general, in the order, HCHs > DDTs > PCBs > CHLs = HCB. Magnitude of OC concentrations increased in the order of sediments < green mussel < earthworm < from < lizard < fish < bird egg < bats < birds tissues. Biomagnification features of OCs were examined in resident and migrant birds to evaluate the exposure levels of these chemicals in wintering grounds of migrant birds. Accumulation of DDTs in migratory birds during wintering in India may be of concern due to the great biomagnification potential of DDTs. Eggs of some resident species contained noticeable concentrations of OCs. Concentrations of OCs in three species of bats analyzed in this study were lower than that found in passerine birds. In addition to OCs, butyltin compounds were also detected at low concentrations in bats.

Animals↗
PubMedDate not supplied

A method for the analysis of butyltin chlorides in air by gas chromatography with atomic emission detection.

An initial screening test compared the use of tropolone (2-hydroxy-2,4-6-cycloheptatrienone) in acetic acid with sodium diethyldithiocarbamate (NaDDC) as chelating agents for the extraction of butyltin chlorides from glass fiber filters and XAD-2 resin tube. NaDDC was chosen for subsequent analyses. Mono-, di-, and tributyltin chloride were spiked onto glass fiber filters and XAD-2 resin, extracted in toluene with NaDDC and derivatized with pentylmagnesium bromide. Derivatized butyltin species were determined by gas chromatography with plasma atomic emission detection. Glass fiber filters and XAD-2 resin were found to provide high retention of butyltin compounds during sampling and efficient recovery of butyltin compounds by extraction with NaDDC.

Air Pollutants, Occupational↗
PubMed2004

Survey of butyltin compounds in 12 types of foods collected in China.

Twelve representative food types including beans, fruit, vegetables, fish, meat, potatoes, sugar, beverages, alcohol, eggs, milk and corn were collected from four districts in China for the analysis of butyltin compounds. The hyphenated system of capillary gas chromatography-flame photometric detector using quartz surface-induced tin emission was used to measure proyylated butyltins in various samples. Low levels (ng g(-1)) of butyltin compounds were found in some samples and possible sources of contamination and their significance are discussed.

China↗
PubMed1982

Synthesis and antimicrobial activity of triorganotin 5-nitro-2-furoates.

Five triorganotin 5-nitro-2-furoates were synthesized by reacting 5-nitro-2-furoic acid with either the corresponding bis(triorganotin) oxide or the corresponding triorganotin hydroxide. The IR spectrum of each compound was obtained over the 4000--200-cm-1 range, and some of the bands were assigned. One compound, tri-n-butyltin 5-nitro-2-furoate, was an excellent antifungal agent, completely inhibiting the growth of six of ten test fungi at a concentration of 1 microgram/ml. The new compounds were also investigated for antibacterial activity and were especially inhibitory toward Gram-positive species. Two of the compounds completely inhibited the Gram-negative bacterium Escherichia coli at a concentration of 100 microgram/ml.

Bacteria↗
PubMed1999

Immunotoxicity of environmentally relevant concentrations of butyltins on human natural killer cells in vitro.

The widespread environmental contamination, bio-accumulation, and toxic effects of butyltins (BTs) in wildlife is well documented, but the role of BTs in debilitating human immune function mediated through natural killer (NK) lymphocytes (a primary immune defense against tumor and virally infected cells) has not been described. In this study, we assessed the effects of in vitro exposure to a range of concentrations (encompassing environmentally relevant concentrations) of MBT, DBT, and TBT on human natural killer lymphocytes obtained from adult male and female donors. TBT inhibited the tumor-killing capacity of NK cells when the NK cells were pretreated in vitro at 200 nM for as little as 1 h. Inhibition of NK cytotoxic function ranged from 40 to greater than 90%. The toxic potential of butyltins followed the order of TBT > DBT > MBT. Conjugation assays revealed that after a 24-h exposure to TBT, there was about a 50% decrease in NK cell binding to tumor cells, indicating alteration of the NK cell receptors for tumor cells. Analysis of whole-blood samples for BTs revealed the presence of detectable concentrations of MBT, DBT, and TBT in all of the donors, indicating possible exposure of NK cells to BTs in the blood. The results of this study provide evidence that butyltin compounds significantly inhibit NK cell function and possible NK cell-mediated immunotoxic potential in humans.

Adult↗
PubMedDate not supplied

Determination of butyltin, cyclohexyltin and phenyltin compounds in beers and wines.

Butyl- cyclohexyl- and phenyltin compounds were extracted from enzymically-hydrolysed wine and beer samples with 0.05% tropolone in pentane. Methyl derivatives were made by Grignard reaction for determination by gas chromatography-atomic absorption spectrometry. Wine and beer samples contained less than 0.1 to 160 nl/ml of butyltins from an undetermined source of contamination. GC-MS confirmation of butyltins also detected phenyltin, and di- and tricyclohexyltin compounds at levels less than the GC-AAS based method detection limits of 0.05-0.13 ng Sn/mL.

Beer↗
PubMed2005

Antioxidative effect of kaempferol and its equimolar mixture with phenyltin compounds on UV-irradiated liposome membranes.

The work investigates the possibility of the protective action of kaempferol on phosphatidylcholine liposome membranes exposed to the pro-oxidative action of diphenyltin dichloride (DPhT) and triphenyltin chloride (TPhT) induced by UV radiation (lambda = 253.7 nm). The concentrations of kaempferol and its equimolar mixtures with DPhT and TPhT were determined so that they induce 50% inhibition in oxidation of liposomes irradiated with UV. They are 11.6, 10.0, and 4.5 microM/L, which constitute the following sequence of antioxidative activity: kaempferol/triphenyltin > kaempferol/diphenyltin > kaempferol. This relationship is confirmed by the results on the antiradical ability of kaempferol and its mixtures with DPhT and TPhT toward the free radical 2,2-diphenyl-1-picrylhydrazyl. Similar sequences obtained in both studies suggest a possible mechanism of the antiradical action of the mixtures as free radical scavengers. Kaempferol's ability, then documented, to form complexes with phenyltins indicates (a) a possible way to liquidate the peroxidation caused by the free radical forms of phenyltins and (b) the stabilizing role of chelating in the antioxidative action of the kaempferol/phenyltins. The differentiation in the action of the compounds studied may, among others, result from different localizations in the liposome membrane, which is indicated by the results of the fluorometric studies.

Antioxidants↗
PubMed2003

Total synthesis of the marine sponge metabolites (+)-rottnestol, (+)-raspailol A and (+)-raspailol B.

The asymmetric syntheses of (+)-rottnestol (1) and the related marine sponge metabolites (+)-raspailols A (5) and B (6) are described. The key step in each of these sequences was a Stille coupling to form the C9-C10 sp2-sp2 bond and connect the polyene sidechains to the appropriate optically active tetrahydropyran core. For rottnestol (1), both C12 epimers were synthesised by a coupling between stannane 7 and (R)- or (S)-8 followed by acid hydrolysis which allowed for the assignment of the absolute configuration at the remote C12 stereocentre as R upon comparison of chiroptical data of the synthetic material with that reported for the natural product. In accord with this, (12R)-raspailol A (5) was synthesised from stannane 7 and sidechain 9 and this compound also compared well with the data for natural material including sign and absolute value of the specific rotation. Finally, the same C12 epimer of raspailol B (6) was secured via a union between stannane 10 and iodide 9 and this also possessed a similar rotation to that described for the natural product. Thus, all three compounds appear to possess the (12R) configuration, while that of the core tetrahydropyran ring is the same as proposed originally.

Alkenes↗
PubMed2005

Some new butylthiobenzoatotin(IV) compounds: spectral studies and analysis of ligand's bonding.

Five new monorganotin(IV) compounds with thiobenzoate ligand, [BuSn(SOCPh)2]2O (1), [BuSn(O)(SOCPh)]2 (2), BuSn(Cl)(SOCPh)2 (3), BuSn(Cl)2(SOCPh) (4) and [BuSn(OH)(Cl)(SOCPh)]2 (5) were synthesized and characterized by elemental analyses, IR, 1H and 13C NMR spectroscopy. 119Sn NMR spectroscopy was used to determine the coordination geometry around Sn(IV) in the cases of 2 and 4. 1, 2 and 5 are dimeric while 3 and 4 are monomeric. In all these molecules the thiobenzoate ion is coordinated only through its sulfur atom. Molecular structures of the compounds have been optimized by MM2 calculations. Semi-empirical quantum mechanical calculations (PM3 method) were performed to explain the monodentate-bonding pattern of thiobenzoate ligand.

Anions↗
PubMed2005

Evaluation of employee exposure to organic tin compounds used as stabilizers at PVC processing facilities.

Organic tin compounds are primary substances used as heat stabilizers by the polyvinyl chloride (PVC) industry. The use of these compounds in the PVC industry is generally well controlled, usually by automated processes. This study was conducted to provide an overview of worker exposure to organic tin compounds at PVC processing facilities and to verify that these exposures are below the threshold limit value (TLV((R))) set by the American Conference of Governmental Industrial Hygienists for organic tin. The basis of the TLV indicates the principal concern is to minimize adverse effects on immune function and the central nervous system from airborne exposure to organic tin. The TLV has a skin designation based on the potential for percutaneous absorption; the TLVs for inhalation exposures are based on the presumption that there is no concurrent exposure via the skin and oral ingestion routes. Personal exposure monitoring was conducted following the National Institute for Occupational Safety and Health (NIOSH) 5504 sampling method and a modified version of the NIOSH analytical method. The results were reported as"total tin."The data indicated no average exposure levels for individual tasks exceeded the organic tin TLV, and 96%of results the samples were less than 20%of the TLV. Only 1 sample of 102 exceeded the TLV, and the individual was wearing appropriate respiratory protection. Subsequent investigation indicated the highest exposures occurred while the operators were conducting tasks that included manual handling of the organic tin compounds. These data suggest manual operations may have a greater potential for organic tin exposure.

Environmental Monitoring↗