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PubMed1997

Tributyltin oxide affects energy production in the yeast Rhodotorula ferulica, a utilizer of phenolic compounds.

Rhodotorula ferulica, a yeast able to utilize phenolic compounds, was chosen for evaluating the effects of tributyltin oxide (TBTO) on this utilization. TBTO reduced respiratory capacity when vanillic or benzoic acid was the energy source. The ATP level of the cells was severely affected by 2 microM TBTO. The mitochondrial ATPase was strongly inhibited by 0.5 microM TBTO, whereas the activity of the plasma membrane ATPase was not affected by concentrations of TBTO up to 30 microM. Our data support the hypothesis that the target for TBTO action is the mitochondrial ATPase, resulting in a severe disturbance of the yeast utilization of aromatic compounds.

Adenosine Triphosphatases↗
PubMed2006

Rapid methylation on carbon frameworks useful for the synthesis of 11CH3-incorporated PET tracers: Pd(0)-mediated rapid coupling of methyl iodide with an alkenyltributylstannane leading to a 1-methylalkene.

The Pd(0)-mediated rapid coupling of methyl iodide with an excess of alkenyltributylstannane was examined with the aim of incorporating a short-lived 11C-labeled methyl group into a biologically significant organic compound with a 1-methylalkene unit for the synthesis of a PET tracer. Four sets of reaction conditions (A-D) were used, all performed in DMF at 60 degrees C for 5 min. Condition B, using CH3I/stannane/Pd2(dba)3/P(o-tolyl)3/CuCl/K2CO3 (1:40:0.5:4-6:2:5), works well in almost all cases. Condition D, using CH3I/stannane/Pd2(dba)3/P(o-tolyl)3/CuX (X = Br, Cl, or I)/CsF (1:40:0.5-5:2-20:2-20:5-50), shows the best results with regard to general applicability to tin substrates, affording the corresponding methylated product in >90% yield based on consumption of methyl iodide. P(t-Bu)2Me was less effective than P(o-tolyl)3, particularly for alpha,beta-unsaturated carbonyl substrates. No regio- or stereoisomerization occurred under these reaction conditions. The efficiency of the protocol was demonstrated by synthesis of an 11C-methylated compound.

Alkenes↗
PubMed2000

Synthesis of new synthons for organofluorine compounds from halothane containing sulfur functional groups.

To develop new synthons for the syntheses of organofluorine compounds, the treatment of Halothane, 2-bromo-2-chloro-1,1,1-trifluoroethane, (1) with 4-methylbenzenethiol (2) in the presence of sodium hydride gave 1-chloro-2,2,2-trifluoroethyl 4-methylphenyl sulfide (3), which was oxidized with m-chloroperbenzoic acid (m-CPBA) to the corresponding sulfoxide (4) and sulfone (5). Reaction of 3 and 5 with allyltributyltin in the presence of 2,2'-azobis(isobutyronitrile) (AIBN) gave 1-(trifluoromethyl)-3-butenyl compounds (9, 11). Sulfoxide 4 was decomposed in this condition. The treatment of 3 with allyltrimethylsilane in the presence of Lewis acids gave 1-(trifluoromethyl)-3-butenyl compounds (9) in good yield. This result suggests that 4-methylphenylthio substituent stabilizes the alpha-carbocation effectively, though the trifluoromethyl group destabilizes it strongly. Aromatic compounds similarly reacted with 3 in the presence of titanium(IV) chloride to give 2-aryl-1,1,1-trifluoro-2-(4-methylphenylthio)ethanes. Thus, sulfur compounds derived from Halothane were found to be useful new synthons for organofluorine compounds.

Halothane↗
PubMed1998

The use of the mitochondrial transmembrane electric potential as an effective biosensor in ecotoxicological research.

In this work, the mitochondrial transmembrane electric potential (delta psi) of isolated mitochondria was used to evaluate the toxicity of some chemicals (endosulfan, 3,4-dichloroaniline, parathion, tributyltin and cadmium) and wastewater. Mitochondria were isolated from rat liver, and the delta psi measured in a suitable assay medium, using a sensitive tetraphenylphosphonium (TPP+) electrode. The test substance was pre-incubated in a rotenone-containing medium during 3 min with 1.0 mg of mitochondrial protein. Mitochondria were energised with succinate and after the establishment of a constant maximal potential ADP was added to induce the phosphorylative cycle. Chosen endpoints were the membrane potential from mitochondria oxidising succinate and the depolarisation induced by ADP. After the appropriate transformations the EC50 (effective concentration) was calculated for each toxicant. Even very low concentrations of a toxicant were able to affect the delta psi, thus showing its suitability as a biosensor in ecotoxicology and results were reproducible between tests. The utilisation of delta psi in screening tests of pure substances and wastewater seems to be very effective and can be carried out routinely.

Aniline Compounds↗
PubMed1996

Cytotoxic action of tri-n-butyltin on dissociated rat cerebellar neurones: a flow-cytometric study.

The effects of tri-n-butyltin on cell viability and intracellular Ca2+ concentration ([CA2+]i) were examined by a flow cytometer in rat cerebellar neurones to reveal the contribution of tri-n-butyltin-induced increased in the [Ca2+]i to its cytotoxicity. Tri-n-Butyltin decreased the cell viability in association with increased [Ca2+]i at concentrations of 0.3 microM or more. Decrease or increase of the extracellular Ca2+ concentration ([Ca2+]o) respectively decreased or increased the cell viability. However, cell viability in the presence of ionomycin which increased [Ca2+]i more significantly than tri-n-butyltin was higher than that in the presence of tri-n-butyltin. Tri-n-butyltin also decreased cell viability under nominally [Ca2+]o-free conditions although the [Ca2+]i increase by tri-n-butyltin was still lower than the control [Ca2+]i under normal [Ca2+]o (2 mM). Therefore, it is unlikely that neuronal death induced by tri-n-butyltin is entirely dependent on the tri-n-butyltin-induced increase in [Ca2+]i.

Aniline Compounds↗
PubMed1985

Inhibitors for distinction of three types of human glutathione transferase.

A set of inhibitors that are useful for distinction of three types of human cytosolic glutathione transferase is presented. The near-neutral transferase is inhibited most effectively by Cibacron blue (I50 = 0.05 microM), the acidic transferase by Cibacron blue (I50 = 0.5 microM), and the basic transferase by tributyltin acetate (I50 = 0.1 microM). The use of any of these two compounds makes possible differentiation between all three types of human transferase.

Cytosol↗
PubMed2006

[Study on the contamination status of butyltins in Taihu Lake].

Butyltins in surface water, sediments and biota samples from Taihu Lake were determined. The results show that butyltins content in most of the surface water samples is under the limit of the detection; five out of ten sediment samples are measured detectable butyltins. Monobutyltin (MBT) was the main species with the concentrations ranging from below the detection limits to 0.95 ng/g; while all biota samples were detected relatively higher butyltin concentrations with a range of 27.05 - 181.23 ng/g due to the obvious bioaccumulation. Tributyltin (TBT) was the main composition that occupied almost 70% of the total butyltins. The antifouling paints applied on the aquatic cultural box and boats was the possible main source of butyltin compounds in Taihu Lake.

China↗
PubMed2000

Prevention of marine biofouling using natural compounds from marine organisms.

All surfaces that are submerged in the sea rapidly become covered by a biofilm. This process, called biofouling, has substantial economic consequences. Paints containing tri-butyl-tin (TBT) and copper compounds are used to protect marine structures by reducing biofouling. However, these compounds have damaging effects on the marine environment, as they are not biodegradable. It has been noted that many seaweeds and invertebrates found in the sea are not covered by a mature biofilm. This is due to the release of compounds into the surrounding seawater that deter the settlement of fouling organisms. In addition, seaweeds and invertebrates have bacteria on their surfaces that produce compounds to deter settling organisms. The production of compounds by bacteria and their living hosts work in concert to protect the hosts' surfaces. All of these compounds can be collected so they may be natural alternatives to TBT and copper compounds. However, the benefits associated with the use of bacteria as sources of these compounds means that bacteria are the organisms of choice for obtaining natural products for antifouling coatings.

Biofilms↗
PubMedDate not supplied

[Suppression of Penicillium purpurogenum growth by organotin compounds].

We studied the effect of organotin compounds and their mixtures with N-cetylpyridinium chloride on the accumulation of biomass by Penicillium purpurogenum. Ditributylstannylic ester of fumaric acid at a concentration of 0.005 micrograms/ml was shown to inhibit the accumulation of biomass. If an organotin compound was used in combination with N-cetylpyridinium chloride, the fungicide effect was greater at a lower dose of the organotin compound in the mixture. Organotin compounds and their mixtures with N-cetylpyridinium chloride suppress protein biosynthesis in the fungal mycelium, increasing protein content in the cultural broth. The mechanism of action of organotin compounds on the growth of P. purpurogenum is discussed.

Cetylpyridinium↗
PubMed2002

Horizontal and vertical distribution of butyltin compounds in sediments from shipyards in Korea.

Butyltin compounds were quantitatively determined in surface sediment and sediment core samples near shipyards in the south coast of Korea, which is one of the major ship building industries in the world. Tributyltin (TBT) concentrations reached up to 46100 ng Sn/g on a dry-weight basis at the front of the shipyard. Horizontal distribution of butyltin compounds was closely related to dry-docking activities. Butyltin concentrations were relatively low where remote from the sources. The vertical distribution of TBT in sediment cores showed active use of TBT in Korean peninsula for the past decades. The increase of TBT concentrations in sediment core according to estimated sediment age demonstrated a positive correlation with the increase of gross tonnage of ships built in the shipyard for 20 years. High TBT residue levels in sediment core samples raise concerns over persistence of the compound in the marine environment.

Environmental Monitoring↗
PubMed1990

Suppression of murine natural killer cell activity by tributyltin: in vivo and in vitro assessment.

The effects of tributyltin chloride (TBTCl) and inorganic tin (IT) on murine natural killer (NK) cell activity were tested in vivo and in vitro. In vivo studies demonstrated that mice fed with TBT (10 and 100 ppm) daily for 1 week exhibited suppression in NK activity 38-46% at effector:target (E:T) ratio = 50:1 compared to control mice. On the other hand, animals treated with inorganic tin showed no change in activity of NK cells. In vitro studies showed leukocytes, preincubated with TBTCl (0.01-0.1 ppm) at room temperature for 1 h and then washed three times, demonstrated significant suppression in NK activity (41 and 85%) at concentrations 0.01 and 0.05 ppm, respectively. Increasing the dose to 0.1 ppm, resulted in complete inhibition of the activity of NK cells. In contrast, IT had no effect on NK activity in vitro at the same concentrations of TBTCl. The effect of TBTCl appears to be due to interference with the binding capacity of effector cells, a necessary prerequisite for target cell lysis. In conclusion, TBTCl proved to be a very potent inhibitor of NK activity; this inhibition may predispose animals to malignancy, which is a characteristic feature reported recently for some TBT compounds.

Animals↗
PubMedDate not supplied

The evaluation of data-derived safety factors for bis(tri-n-butyltin)oxide.

In this report the evaluation of a safety factor is assessed, according to the decision tree suggested by Renwick (1991a,b), to determine a Tolerable Daily Intake (TDI) value for the environmental contaminant bis(tri-n-butyltin)oxide (TBTO). Based on available literature the nature of the most sensitive parameter of TBTO-toxicity was perceived to be on lymphoid organs and lymphoid function. Subsequently, safety factors were derived in relation to published data on inter-species and inter-individual differences in both kinetics and dynamics of TBTO. Lack of information on human data concerning the nature of toxicity as well as kinetics and dynamics of TBTO finally resulted in a safety factor of 100. A TDI of 5 or 0.25 mg/kg bw per day was assessed based on reductions of lymphoid organ weights (thymus) or lymphoid function (resistance to T. spiralis), respectively. In addition, based on available data in rodents on kinetics and dynamics of TBTO, it is suggested that a combined TDI value for both tri- and dibutyltin compounds might have to be considered.

Animals↗
PubMed1986

The effect of trimethyltin on three glutamergic and gabaergic transmitter parameters in vitro: high affinity uptake, release and receptor binding.

The effects of trimethyltin (TMT) on high-affinity uptake, release and sodium-independent binding of glutamic acid and gamma-aminobutyric acid (GABA) were studied in vitro in homogenates of hippocampal tissue. TMT (50 micron) increased the release of glutamic acid from synaptosomes in the resting state (5 mM K+), whereas the release of GABA was only slightly affected. High affinity uptake of glutamate was inhibited by TMT in the same concentration range as release. The uptake of GABA was only affected by TMT-concentrations from 500 micron to 5 mM. The sodium independent binding of both glutamate and GABA, usually assumed to be binding to receptor sites, were inhibited with 50 microM or more TMT in the incubation medium. The results indicate that TMT can interfere with several different events of the neurotransmission process in the central nervous system at concentrations which can be obtained in the brain of rats after a sublethal dose of the compound.

Animals↗
PubMed1985

[Resistance to organic tin compounds mediated by plasmids of bacteria of Pseudomonas genus].

Resistance to organic tin compounds of P. aeruginosa and E. coli carrying antibiotic resistance plasmids and to P. putida containing biodegradation plasmids was studied. It was shown that 5 resistance plasmids and the biodegradation CAM plasmid of Pseudomonas increased 3-4 times the strain resistance to triethylstannylsuccinylimide and triethylstannylmaleinimide. All these plasmids belong to the P-2 incompatibility group and also determine the bacterial resistance to potassium tellurite. Isolation and investigation of the mutant plasmids loosing simultaneously the capacity for determination of resistance to potassium tellurite and organic tin compounds suggest that resistance to these compounds in the investigated plasmids is determined by the same genetic system.

Drug Resistance, Microbial↗
PubMed1987

Organotin-induced hemolysis, shape transformation and intramembranous aggregates in human erythrocytes.

Organotin compounds examined in this study exhibited a relative order of potency for induction of in vitro hemolysis in human erythrocytes as follows: tri-n-butyltin greater than tri-n-propyltin greater than tetra-n-butyltin greater than triphenyltin chloride greater than tri-n-ethyltin bromide greater than dibutyltin dichloride greater than stannous chloride greater than tri-n-methyltin chloride = butyltin chloride dihydroxide. All of the organotin compounds induced erythrocyte shape transformation from the normal discocyte to an echinocyte and, in addition, triphenyltin chloride, tetra-n-butyltin and tri-n-ethyltin bromide also elicited stomatocyte formation at higher concentrations. Select organotin compounds also formed tin-containing aggregates within the plasma membrane. The relative order of effectiveness for organotin induction of intramembranous aggregates was tri-n-butyltin greater than tri-n-propyltin greater than tetra-n-butyltin greater than tri-n-ethyltin bromide, which was based upon the lowest concentration at which they were observed. These results support the previously suggested theory that organotins are membrane effectors because of their comparatively high hydrophobic, lipid partitioning properties. The relatively lipophilic compound, triphenyltin chloride, appeared to be anomalous because it did not readily promote hemolysis or induce the formation of intramembranous aggregates in human erythrocytes. A log-linear statistical model demonstrated an association of hemolysis with both tri-n-butyltin aggregate formation and shape transformation. Select organotin compounds should be useful probes in membrane studies because of their numerous effects.

Erythrocyte Aggregation↗