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PubMed2004

Diorganotin(IV) derivatives of substituted benzohydroxamic acids with high antitumor activity.

A series of diorganotin(IV) and dichlorotin(IV) derivatives of 4-X-benzohydroxamic acids, [HL(1) (X = Cl) or HL(2) (X = OCH(3))] formulated as [R(2)SnL(2)] (R = Me, Et, nBu, Ph or Cl; L = L(1) or L(2)), along with their corresponding mixed-ligand complexes [R(2)Sn(L(1))(L(2))] have been prepared and characterized by FT-IR, (1)H, (13)C, and (119)Sn NMR spectroscopy, mass spectrometry, elemental analysis, and melting points. In addition, single-crystal X-ray diffraction analyses were carried out for [Me(2)SnL(2)] (L = L(1) or L(2)), which show coordination structures intermediate between distorted octahedra and bicapped tetrahedra. The hydroxamate ligands are asymmetrically coordinated by the oxygen atoms, the carbonyl oxygen atom is further away from the metal center than the other oxygen atom. The complexes are stable monomeric species; most of them are soluble not only in chlorohydrocarbon solvents, but also in alcohols and hydroalcoholic solutions. In polar solvents, the mixed-ligand complexes gradually decompose into the corresponding single-ligand complex couples. The complexes exhibit in vitro antitumor activities (against a series of human tumor cell lines) which, in some cases, are identical to, or even higher than, that of cisplatin. For the dialkyltin complexes, the activity increases with the length of the carbon chain of the alkyl ligand and is higher in the case of the chloro-substituted benzohydroxamato ligand. The [nBu(2)Sn(L(1))(2)] complex displays a high in vivo activity against H22 liver and BGC-823 gastric tumors, and has a relatively low toxicity.

Antineoplastic Agents↗
PubMed2005

Self-assembly of dialkyltin moieties and mercaptobenzoic acid into macrocyclic complexes with hydrophobic "pseudo-cage" or double-cavity structures: supramolecular infrastructures involving intermolecular C-H...S weak hydrogen bonds and pi-pi interactions.

Four novel organotin complexes of two types--[R2Sn(o-SC6H4CO2)]6 (R = Me, 1 x H2O; nBu, 2) and {[R2Sn(m-CO2C6H4S)R2Sn(m-SC6H4CO2)SnR2]O}2 (R = Me, 3; nBu, 4)--have been prepared by treatment of o- or m-mercaptobenzoic acid and the corresponding R2SnCl2 (R = Me, nBu) with sodium ethoxide in ethanol (95%). All the complexes were characterized by elemental analysis, FT-IR and NMR (1H, (3C, 119Sn) spectroscopy, TGA, and X-ray crystallography diffraction analysis. The molecular structure analyses reveal that both 1 and 2 are hexanuclear macrocycles with hydrophobic "pseudo-cage" structures, while 3 and 4 are hexanuclear macrocycles with double-cavity structures. Furthermore, the supramolecular structure analyses show that looser and more intriguing supramolecular infrastructures were also found in complexes 1-4, which exist either as one-dimensional chains of rings or as two-dimensional networks assembled from the organometallic subunits through intermolecular C-H...S weak hydrogen bonds (WHBs) and pi-pi interactions.

Crystallography, X-Ray↗
PubMed1994

Interactions among endoplasmic reticulum, microtubules, and retrograde movements of the cell surface.

Relationships among the endoplasmic reticulum (ER), microtubules, and bead movements on the cell surface were investigated in the thin peripheral region of A6 cells, a frog kidney cell line. ER tubules were often aligned with microtubules, as shown by double-labeling with DiOC6(3) and anti-tubulin in fixed cells. In living cells stained with DiOC6(3) and observed in time lapse, there were frequent extensions, but few retractions, of ER tubules. In addition, there was a steady retrograde (towards the cell center) movement of all of the ER at approximately 0.3 microns/min. Since microtubules are often aligned with the ER, microtubules must also be moving retrogradely. By simultaneous imaging, it was found that the ER moves retrogradely at the same rate as aminated latex beads on the cell surface. This indicates that the mechanisms for ER and bead movement are closely related. Cytochalasin B stopped bead and ER movement in most of the cells, providing evidence that actin is involved in both retrograde movements. The ER retracted towards the cell center in nocodazole while both ER and microtubules retracted in taxol. Time lapse observations showed that for both drugs, the retraction of the ER is the result of retrograde movement in the absence of new ER extensions. Presumably, ER extensions do not occur in nocodazole because of the absence of microtubules, and do not occur in taxol because taxol-stabilized microtubules move retrogradely and there is no polymerization of new microtubule tracks for ER elongation.

Actins↗
PubMedDate not supplied

Comparative developmental toxicity of butyltin trichloride, dibutyltin dichloride and tributyltin chloride in rats.

Butyltin trichloride (BT), dibutyltin dichloride (DBT) and tributyltin chloride (TBT) were compared for their developmental toxicity including teratogenic potential following administration during the susceptible period for the teratogenesis of DBT. Pregnant rats were given either BT at a dose of 1000, 1500 or 2000 mg kg-1, DBT at a dose of 10 or 15 mg kg-1 or TBT at a dose of 40 or 80 mg kg-1 by gastric intubation on days 7 and 8 of pregnancy. Although maternal toxicity occurred, as evidenced by a significantly increased maternal lethality at 1500 and 2000 mg kg-1 and decreased maternal weight gain at 1000 and 1500 mg kg-1, no significant increase in the incidences of postimplantation loss and malformed fetuses were observed after treatment with BT. Treatment with DBT resulted in a significantly lower maternal weight gain, lower fetal weight and higher postimplantation embryolethality. A significantly and markedly increased incidence of fetuses with malformations, such as exencephaly, cleft jaw, cleft lip, ankyloglossia, club foot, deformity of the vertebral column in the cervical and thoracic regions and of the ribs and ano- or microphthalmia, was observed in both groups treated with DBT. While treatment with TBT at 40 and 80 mg kg-1 caused a significantly decreased maternal weight gain and increased postimplantation embryolethality, no significantly increased incidence of malformed fetuses occurred. It could be concluded that BT, DBT and TBT are different in the susceptibility and spectrum of developmental toxicity.

Abnormalities, Drug-Induced↗
PubMed1981

Development of a silica-free silicone system for medical applications.

Filler-free silicones are believed to be more blood-compatible than those containing fillers. An ultrapure silica-free room temperature vulcanizing silicone system was prepared and characterized using a swelling experiment, an infrared spectrometer, an x-ray spectrometer, a scanning electron microscope and neutron activation analysis. The polymer was found to be suitable for medical applications needing an extremely smooth surface.

Biocompatible Materials↗
PubMed2006

Functional and structural properties of stannin: roles in cellular growth, selective toxicity, and mitochondrial responses to injury.

Stannin (Snn) was discovered using subtractive hybridization methodology designed to find gene products related to selective organotin toxicity and apoptosis. The cDNAs for Snn were first isolated from brain tissues sensitive to trimethyltin, and were subsequently used to localize, characterize, and identify genomic DNA, and other gene products of Snn. Snn is a highly conserved, 88 amino acid protein found primarily in vertebrates. There is a minor divergence in the C-terminal sequence between amphibians and primates, but a nearly complete conservation of the first 60 residues in all vertebrates sequenced to date. Snn is a membrane-bound protein and is localized, in part, to the mitochondria and other vesicular organelles, suggesting that both localization and conservation are significant for the overall function of the protein. The structure of Snn in a micellar environment and its architecture in lipid bilayers have been determined using a combination of solution and solid-state NMR, respectively. Snn structure comprised a single transmembrane domain (residues 10-33), a 28-residue linker region from residues 34-60 that contains a conserved CXC metal binding motif and a putative 14-3-3xi binding region, and a cytoplasmic helix (residues 61-79), which is partially embedded into the membrane. Of primary interest is understanding how this highly-conserved peptide with an interesting structure and cellular localization transmits both normal and potentially toxic signals within the cell. Evidence to date suggests that organotins such as trimethyltin interact with the CXC region of Snn, which is vicinal to the putative 14-3-3 binding site. In vitro transfection analyses and microarray experiments have inferred a possible role of Snn in several key signaling systems, including activation of the p38-ERK cascade, p53-dependent pathways, and 14-3-3xi protein-mediated processes. TNFalpha can induce Snn mRNA expression in endothelial cells in a PKC-epsilon dependent manner. Studies with Snn siRNA suggest that this protein may be involved in growth regulation, since inhibition of Snn expression alone leads to reduced endothelial cells growth and induction of COP-1, a negative regulator of p53 function. A key piece of the puzzle, however, is how and why such a highly-conserved protein, localized to mitochondria, interacts with other regulatory proteins to alter growth and apoptosis. By knowing the structure, location, and possible signaling pathways involved, we propose that Snn constitutes an important sensor of mitochondrial damage, and plays a key role in the mediation of cross-talk between mitochondrial and nuclear compartments in specific cell types.

Animals↗
PubMed2004

Structural analysis of 2,6-[bis(alkyloxy)methyl]-phenyltin derivatives using electrospray ionization mass spectrometry.

Electrospray ionization (ESI) mass spectrometry was applied to the structural analysis of 23 2,6-[bis(alkyloxy)methyl]phenyltin(IV) derivatives. The mass spectra were measured in both polarity modes and multistage tandem mass spectrometric (MS(n)) measurements were performed on the ion trap analyser for positively charged tin-containing ions. The sum of complementary ions observed in the positive-ion mode (i.e. [M-R(3)](+) ion) and in the negative-ion mode (i.e. [R(3)](-) ion) permits molecular mass determination in spite of the fact that the molecular adducts were often missing even in the first-order mass spectra. The subsequent fragmentation of [M-R(3)](+) ions studied by MS(n) and the correlation of observed fragment ions with the expected structures of synthesized organotin(IV) compounds allowed us to understand the fragmentation behaviour and the mechanism of the ion formation for studied compounds. The typical neutral losses are alkenes, alcohols and aldehydes. The fragmentation pattern of one selected compound was supported by MS(n) measurements of an isotopically labelled analogue to confirm unusual ion-molecule reactions of some fragment ions with water in the ion trap.

Journal Article↗
PubMed1980

Antimicrobial activity of N-substituted N-(triphenylstannyl)cyanamides and triethylammonium (organocyanoamino)chlorotriphenylstannates.

N-Substituted N-(triphenylstannyl)cyanamides were studied and found to be better antifungal agents than the previously tested N-substituted N'-cyano-S-(triphenylstannyl)isothioureas and N-substituted N'-cyano-O-(triphenylstannyl)isoureas. They were similar in activity to the previously tested ethyl N-aryl-S-(triphenylstannyl)-isothiocarbamates. The antifungal activity of triethylammonium (organocyanoamino)chlorotriphenylstannates, which are the triethylammonium chloride complexes of N-substituted N-(triphenylstannyl)-cyanamides, was similar to or better than that of the N-substituted N-(triphenylstannyl)cyanamides. Triethylammonium (acetylcyanoamino)chlorotriphenylstannate and triethylammonium dichlorotriphenylstannate were highly inhibitory toward Gram-positive bacteria.

Anti-Bacterial Agents↗
PubMed2005

Determination of the acaricide fenbutatin oxide in water samples by automated headspace-SPME-GC/MS.

The analysis of the acaricide fenbutatin oxide (FBTO) having a molecular weight of 1052.66 g mol(-1) in water samples by capillary GC/MS after in-situ derivatization with sodium tetraethylborate (NaBEt4) and headspace-SPME enrichment is described. Automated SPME is performed at 80 degrees C for 30 min. Detection is carried out in the ion monitoring mode with deuterated triphenyltin (TPhTd15) as internal standard. Good linearity (R2 = 0.9993) was obtained in the dynamic range 20 to 1000 ng L(-1) with a limit of detection of 16 ng L(1) (LOD at 3 S/N) and a limit of quantitation of 50 ng L(-1) (LOQ at 10 S/N). Intra-day RSD% for n=6 was 8.9 at the LOQ level.

Animals↗
PubMed1994

Implication that potassium flux and increase in intracellular calcium are necessary for the initiation of sperm motility in salmonid fishes.

Flux of K+ and changes in intracellular Ca2+ in the sperm of salmonid fishes were measured with spectrophotometry, ion electrode, microscopic fluorometry, and radioisotope accumulation. Release of K+ occurred at the initiation of sperm motility which is induced by decrease in external K+ and the K+ efflux and sperm motility were inhibited by K+ channel blockers. Intracellular Ca2+ increased within a short period in K(+)-free condition, and the accumulation of 45Ca in sperm cells was higher in motile sperm than that in immotile sperm. The efflux of K+ and the increase in intracellular Ca2+ were suppressed when external K+ concentration increased, i.e., sperm remained immotile. These results suggest that efflux of K+ through K+ channel and subsequent increase in intracellular Ca2+ are prerequisite for the initiation of sperm motility.

4-Aminopyridine↗
PubMed2001

Electrospray ionization mass spectrometric study of the hydrolysis-polycondensation process of Sn(OBu(t))(4).

The oligomerization of Sn(OBu(t))(4) in the sol-gel process has been studied by several different analytical approaches. Electrospray ionization (ESI) mass spectrometry was highly effective in describing the first species produced by the hydrolysis-polycondensation reactions. Mössbauer spectroscopy has elucidated the fast behavior of the hydrolytic oligomerization process, while calorimetric data have demonstrated the high enthalpy of the reaction in the presence of different solvents.

Air Pollutants↗
PubMed1998

Triphenyltin as an inhibitor of membrane-bound pyrophosphatase of Rhodospirillum rubrum.

The effect of triphenyltin on the activity of membrane-bound pyrophosphatase of Rhodospirillum rubrum was investigated. Triphenyltin inhibits the hydrolysis of chromatophore membrane-bound pyrophosphatase in a pH-dependent pattern, being maximal at pH 9-10. At basic pH values, the inhibition produced by this organotin on membrane-bound pyrophosphatase is very similar to that produced on the chromatophore H+ATPase (I50 = 14.4 and 10 microM, respectively). Detergent-solubilized membrane-bound pyrophosphatase is also inhibited by triphenyltin, but the cytoplasmic enzyme of R. rubrum is inhibited only slightly. The inhibitory effect of triphenyltin on membrane-bound pyrophosphatase is the same with Mg-PPi or Zn-PPi, and is dependent on the chromatophore membrane concentration. Triphenyltin modified mainly the Vmax of the enzyme, and only slightly its Km. Free Mg2+ does not reverse the inhibition. Reducing agents prevent triphenyltin inhibition of the membrane-bound pyrophosphatase, but their effect is due to an alteration of the inhibitor, and not to a modification of thiol groups of the enzyme. The most likely site for triphenyltin inhibition in chromatophore membrane-bound pyrophosphatase is a component either within or closely associated with the membrane.

Dicyclohexylcarbodiimide↗
PubMed1996

A mixture toxicity study employing combinations of tributyltin chloride, dibutyltin dichloride, and tin chloride using the marine bacterium Vibrio harveyi as the test organism.

Mixture toxicity studies in dual combinations for three metals, tributyltin chloride, dibutyltin dichloride, and tin chloride, and one experiment using all chemicals were performed using the bioluminescent marine bacterium Vibrio harveyi as the test organism in a direct toxicity test procedure. Combination toxicity was evaluated using an additive index equation method and two isopleth procedures, isobole plot and isobologram. Additive index values were determined at both estimated effective median concentration (EC50) and one-third EC50 values for each dual combination and all three chemicals for one-third EC50 values. Isopleths employed chemical combinations at 20% intervals of the EC50 concentrations. Additive index values for various mixtures were either additive or antagonistic (less than additive). Isobolograms for all mixtures were descriptively additive or synergistic (greater than additive). Isobole plots were also descriptively additive or synergistic, although a few measurements were statistically different for synergism. Statistical evaluation between mixtures and single values, using the z test, were in some cases different at the 5% level. Bioluminescent counts were determined to be normally distributed using a statistical test for small sample numbers at the 1% level. Evaluation for outliers, using the Dixon test, was also performed and found one mixture to have an outlier. This single outlier had no influence on the combined toxicity results. The use of low-cost and rapid bioluminescent microbial toxicity tests for mixture studies is discussed.

Drug Interactions↗
PubMed2001

Environmental dissipation of fungicide triphenyltin acetate and its potential as a groundwater contaminant.

The effects of various factors on fungicide triphenyltin acetate dissipation in selected soil types were studied; temperature is clearly the most important factor of these. Residues of this fungicide in Fangtzupo clay loam and Lanyang loam incubated at 30 degrees C for 32 days (water content 100, 70, or 40% of field capacity) were 25% of the original amounts. In soil samples incubated at 10, 30, or 40 degrees C with 100% field capacity water content, residues were 80, 26, and 5.5% for Fangtzupo soil, respectively, and 83, 26, and 7.0% for Lanyang soil, respectively. No significant difference in dissipation rate was found between sterilized and unsterilized soil, suggesting that microbial degradation is not an important factor in this process. Rapid degradation rates were observed-half-lives of 8.3 to 19.4 days in Fangtzupo clay loam and 8.0 to 16.3 days in Lanyang loam at temperatures ranging from 30 to 40 degrees C (soil water content of 100, 70, and 40% of field capacity). Significant increases in half-life (approximately 150 days) occurred at lower temperatures (10 degrees C) in both soil types. The potential of triphenyltin acetate to contaminate groundwater was tested using the behavior assessment and groundwater pollution-potential models. Results indicate that the leaching rate of the fungicide is very slow (1.0 cm day(-1)) under normal conditions.

Biodegradation, Environmental↗
PubMed1996

NF-kappaB activation by triphenyltin triggers apoptosis in HL-60 cells.

Trisubstituted organotin pesticides are lethal for different cell types. In this study we investigated whether triphenyltin chloride (TPT) causes apoptosis in HL-60 promyelocytic cells and, if so, by what mechanisms. We report that 5 microM TPT increased intracellular Ca2+ in HL-60 cells within seconds; concomitantly actin depolymerization was detected 30 s and 1 min after the treatment. This was followed 15 min later by NF-kappaB activation, and apoptotic bodies and DNA fragmentation were evident after 3 and 6 h, respectively. At these times TPT also induced the release of tumor necrosis factor-alpha (TNF-alpha). Prior treatment of the cells with a polyclonal antibody to human TNF-alpha abolished TPT-induced DNA fragmentation, which suggests that the ultimate effect of TPT may be mediated by TNF-alpha. Prior treatment of the cells with 100 microM pyrrolidine dithiocarbamate, an antioxidant and potent inhibitor of NF-kappaB activation, prevented actin depolymerization, NF-kappaB activation, and DNA fragmentation, although it did not affect TPT-induced Ca2+ mobilization. These findings suggest that TPT increases intracellular Ca2+, alters actin polymerization and the cytoskeleton, and induces NF-kappaB activation, TNF-alpha synthesis, DNA degradation, and apoptosis. Reactive oxygen species seem to be essential to NF-kappaB activation, TNF-alpha synthesis, and the subsequent steps.

Actins↗
PubMed1996

Stress proteins (HSP) and chemical-induced autoimmunity.

Various environmental and iatrogenic chemicals have been implicated in the induction of autoimmune responses and biomarkers for identification of such chemicals are imperative. The present study was initiated to examine whether induction of stress protein (HSP) synthesis is a common effect of immunoactive chemicals. This would be interesting because HSP-induction could result in the presentation of HSP-derived T cell epitopes, and recognition of these epitopes by HSP-reactive T cells could facilitate the initiation of (auto)immune responses. Such a role for HSP would clarify early aspects of chemical induction of immune responses and could provide a valuable biomarker for the identification of potentially immunoactive chemicals. It was found that of eight immunoactive chemicals, only HgCl2, dinitrochlorobenzene, and dibutyltin dichloride induced synthesis of HSC73/HSP72 and HSP90 in murine splenocytes in vitro. The induction by HgCl2 was identical in splenocytes from mice susceptible or not for Hg-induced autoimmunity. Following footpad injection of HgCl2, but not diphenylhydantoin, a marginal induction of HSC73 and possibly HSP72 but not HSP90 was found to precede the chemical-induced lymphoproliferation in draining lymph nodes of BALB/c mice. Finally, using stimulation of the IgG1 response to TNP-ficoll as a model for non-antigen-linked, T cell-dependent B cell stimulation, it was found that stimulation of this response by chemicals is independent of HSP induction. From these results, we conclude that it is unlikely that HSP function as general initiating neoantigens in chemically induced autoimmune responses.

Animals↗