Disease relevance of tributyltin

• This study assesses targeting of lung metastases in mice with the radioiodinated thymidine analog 5-[(123)I/(125)I]iodo-2'-deoxyuridine ((123)I-IUdR/(125)I-IUdR), formulated with varying amounts of tributyltin precursor and injected intravenously [1].
• Only 11.0% (range 7.7-17.6) of the BAL lymphocytes from sarcoidosis patients were annexin V positive after exposure to the apoptotic stimulus tributyltin compared with 55.0% (range 42.0-62.0) of BAL lymphocytes from healthy controls (p<0.001) [2].
• Red blood cells (RBC) exposed to micromolar concentrations of tributyltin compounds (TBTX) undergo morphological changes and hemolysis [3].
• Isolation of Escherichia coli mutants which are resistant to an inhibitor of H+-ATPase, tributyltin and also to uncouplers of oxidative phosphorylation [4].
• Results indicate that FAD and TBT inhibit aromatase activity in o,p -DDT-treated fish but do not prevent feminization, indicating that increased brain aromatase activity is not critical to EDC-induced male-to-female sex inversion [5].

Psychiatry related information on tributyltin

• Reaction of compound, Ic with tetrabutylammonium bromide in DMF affords the 5'-bromo carbonate Id (77%) which is reduced with tributyltin hydride to the 5'-deoxyuridine 2',3'-cyclic carbonate Ie (70%) [6].
• On membrane motor activity and chloride flux in the outer hair cell: lessons learned from the environmental toxin tributyltin [7].

High impact information on tributyltin

• Compounds that dissipate proton gradients across membranes, like monensin, protonophores, and amines, and compounds that inhibit the acidification process, such as N,N'-dicyclohexylcarbodiimide (DCCD) and tributyltin, inhibited the entry of virus, but not virus binding [8].
• Sponge tissue was exposed to heat shock and tributyltin, which caused an upregulation of gene expression of GCBHP2 [9].
• As prodigiosins hardly inhibit the catalytic activity (ATP hydrolysis) unlike well known OH-/Cl- exchangers (for example, tributyltin chloride), they should provide powerful tools for the study of molecular machinery and cellular activities involving transport of protons and/or chloride [10].
• We also demonstrate that DC5-DC10 can also be transported by an electroneutral mechanism mediated by tributyltin, a potent inhibitor of IMAC [11].
• 3. At pH 5.5, ATP no longer stimulated conversion, and tributyltin and 1,3-dicyclohexylcarbodiimide had no effect [12].

Chemical compound and disease context of tributyltin

• Liposome-water distribution ratios of triphenyltin and tributyltin were determined between pH 3 and pH 8 with the equilibrium dialysis method in the micromolar concentration range, which is the concentration range where acute toxicity is observed [13].
• Toxicity of dibutyltin, tributyltin and other organotin compounds to humans and to experimental animals [14].
• A biosensor (LUMISENS I), based on the inducible bioluminescence of the Escherichia coli strain TBT3 (Ec::luxAB TBT3), was developed for the detection of the biocide tributyltin [15].
• Interaction of tributyltin (TBT) with 3,3',4,4',5-pentachlorobiphenyl (PCB-126)-induced ethoxyresorufin O-deethylase (EROD) activity was examined in vitro using H4IIE rat hepatoma cells [16].
• In contrast with TBT and TPT, the toxicity of the two neurotoxic organotins (TMT and TET) produced an early increase in MTT reduction [17].

Biological context of tributyltin

• Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: access to enantiomerically enriched all-carbon quaternary centers [18].
• TBT represents, to our knowledge, the first example of an environmental endocrine disrupter that promotes adipogenesis through RXR and PPARgamma activation [19].
• Following glycosylation, treatment with tributyltin hydride in toluene at reflux brings about reductive radical fragmentation directly to the 6-deoxy sugar in high yield [20].
• To elucidate the mechanism of triorganotin-induced apoptosis, we studied the effect of tributyltin on mitochondrial function [21].
• Tributyltin is a potent inducer of the heat shock response in human diploid fibroblasts [22].

Anatomical context of tributyltin

• Here we show that the persistent and ubiquitous environmental contaminant, tributyltin chloride (TBT), induces the differentiation of adipocytes in vitro and increases adipose mass in vivo [19].
• Moreover, in utero exposure to TBT leads to strikingly elevated lipid accumulation in adipose depots, liver, and testis of neonate mice and results in increased epididymal adipose mass in adults [19].
• TBT promotes adipogenesis in the murine 3T3-L1 cell model and perturbs key regulators of adipogenesis and lipogenic pathways in vivo [19].
• Protein synthesis as measured by (35)S-methionine incorporation in all cell lines was markedly decreased by treatment with both tributyltin (TBT) and triphenyltin (TPT) at concentrations above 3 x 10(-7) M, due to cytotoxicity [23].
• Tributyltin interacts with mitochondria and induces cytochrome c release [21].

Associations of tributyltin with other chemical compounds

• With a 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetal protected thioglycoside, excellent beta-selectivity was obtained in glycosylation reactions, and subsequent treatment with tributyltin hydride and azoisobutyronitrile brought about clean fragmentation to the 6-deoxy-glycero-beta-D-manno-heptopyranosides [24].
• 3. Trimethyltin, tributyltin and the trialkyl-lead analogues at 1 muM, to varying degrees, also cause a decrease in pyruvate uptake by mitochondria only in the KCl medium [25].
• Inability of tributyltin-induced chloride/hydroxyl exchange to stimulate calcium transport in mitochondria isolated from flight muscle of the sheep blowfly Lucilia cuprina [26].
• SPQ fluorescence was calibrated against intracellular [Cl] using high K solutions containing the ionophores nigericin and tributyltin [27].
• Further studies with phenylarsine oxide agarose revealed that tributyltin interacts with the adenine nucleotide translocator, a functional constituent of the mitochondrial permeability transition pore, which is selectively inhibited by dithiothreitol [21].

Gene context of tributyltin

• Submicromolar concentrations of tributyltin (TBT), a commercially used organotin compound, were found to induce the expression of several stress proteins, most notably HSP89 and HSP70, in IMR-90 human diploid fibroblasts in a time- and dose-dependent manner [22].
• The present results showed that tributyltin is a potent activator of ERK, JNK, and p38 MAPK pathways, and Ca(2+) mobilized from intracellular stores plays an important role for the phosphorylation of MAPKs in this human T cell line [28].
• Expression of CD16, CD18 and CD56 in tributyltin-exposed human natural killer cells [29].
• 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 [30].
• 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 [30].

Analytical, diagnostic and therapeutic context of tributyltin

• Steady-state fluorescence and circular dichroism of trout hemoglobins I and IV interacting with tributyltin [31].
• Animals (n = 257) that displayed various stages of tributyltin (TBT) -induced imposex were collected from sites in southwest England, and their imposex status was determined by physical examination [32].
• Reduced sperm counts in guppies (Poecilia reticulata) following exposure to low levels of tributyltin and bisphenol A [33].
• Simultaneous determination of mono-, di- and tributyltin in environmental samples using isotope dilution gas chromatography mass spectrometry [34].
• Determination of tributyltin ions in estuarine waters by high-performance liquid chromatography with fluorimetric detection using morin in a micellar solution [35].

References