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PubMedDate not supplied

Suppression of uterine decidualization correlated with reduction in serum progesterone levels as a cause of preimplantation embryonic loss induced by diphenyltin in rats.

In our previous study, diphenyltin dichloride (DPTCl) at 16.5 mg/kg and higher on days 0-3 of pregnancy was found to induce preimplantation embryonic loss in rats. In the present study, the effects of DPTCl on uterine decidualization in pseudopregnant rats, effects of ovarian hormones on uterine decidualization in ovariectomized rats, and effects of progesterone on the DPTCl-induced preimplantation embryonic loss in pregnant rats were determined. Female rats were given DPTCl by gastric intubation at 4.1, 8.3, 16.5, or 24.8 mg/kg on days 0-3 of pseudopregnancy and the decidual cell response was induced on day 4 of pseudopregnancy. The uterine weight on day 9 of pseudopregnancy served as an index of uterine decidualization. A significant decrease in uterine weight, which indicates suppression of uterine decidualization, was detected at 16.5 and 24.8 mg/kg. Ovarian weight and number of corpora lutea in the DPTCl-treated groups were comparable to the controls. A significant decrease in the serum progesterone levels was found at 16.5 and 24.8 mg/kg in pseudopregnant rats. The hormonal regimen consisting of progesterone and estrone-supported decidual development in ovariectomized rats given DPTCl. Pregnancy rate and number of implantations were significantly lower in the intact mated groups given DPTCl at 16.5 and 24.8 mg/kg on days 0-3 of pregnancy than in the control group and significantly higher in the groups given DPTCl plus progesterone than in the groups given DPTCl alone. These results show that reduction in serum progesterone levels is correlated with suppression of uterine decidualization and progesterone protects against preimplantation embryonic loss induced by DPTCl.

Administration, Oral↗
PubMedDate not supplied

Suppression of decidual cell response induced by dibutyltin dichloride in pseudopregnant rats: as a cause of early embryonic loss.

In our previous study, dibutyltin dichloride (DBTCl) caused preimplantation embryonic loss and postimplantation embryonic loss in rats following administration at 7.6 mg/kg and above on Days 0-3 and at 3.8 mg/kg and above on Days 4-7 of pregnancy, respectively. This study was designed to assess the effects of DBTCl on uterine function as a cause of early embryonic loss using pseudopregnant rats. DBTCl was given orally to pseudopregnant rats at 3.8, 7.6 or 15.2 mg/kg on pseudopregnant day (PPD) 0-3 or on PPD 4-7. The decidual cell response was induced by bilateral uterine scratch on PPD 4. The uterine weight on PPD 9 served as an index of uterine decidualization. Uterine weight and serum progesterone levels on PPD 9 were significantly decreased after administration of DBTCl at 7.6 mg/kg and above on PPD 0-3 and PPD 4-7. DBTCl had no effect on the serum estradiol levels and number of corpora lutea. Administration of progesterone reversed the suppression of uterine decidualization in rats given DBTCl on PPD 0-3. It can be concluded that DBTCl suppresses the uterine decidual cell response and decreases progesterone levels, and these effects are responsible for early embryonic loss due to DBTCl exposure.

Animals↗
PubMedDate not supplied

Effects of triphenyltin chloride on implantation and pregnancy in rats.

The objective of this study was to characterize the adverse effects of triphenyltin chloride (TPTCl) during early pregnancy. Following successful mating, female rats were given TPTCl by gastric intubation at 3.1, 4.7, or 6.3 mg/kg on days 0 to 3 of pregnancy or at 6.3, 12.5, or 25.0 mg/kg on days 4 to 6 of pregnancy and were sacrificed on day 20 of pregnancy. In successfully mated females, TPTCl totally prevented implantation in a dose-dependent manner. The pregnancy rate was significantly decreased after administration of TPTCl on days 0 to 3 at 4.7 and 6.3 mg/kg and on days 4 to 6 at 12.5 and 25.0 mg/kg. In females having implantations, the numbers of implantations and live fetuses and the incidences of pre- and postimplantation loss and fetal malformations in the TPTCl-treated groups were comparable to the controls. It could be concluded that TPTCl during early pregnancy causes failure in implantation and TPTCl has greater antiimplantation effects when administered during earlier than later stages of blastogenesis.

Animals↗
PubMed2003

Dithioerythritol (DTE) prevents inhibitory effects of triphenyltin (TPT) on the key enzymes of the human sex steroid hormone metabolism.

Organotins are known to induce imposex (pseudohermaphroditism) in marine neogastropods and are suggested to act as specific endocrine disruptors, inhibiting the enzyme-mediated conversion of steroid hormones. Therefore, we investigated the in vitro effects of triphenyltin (TPT) on human 5alpha-reductase type 2 (5alpha-Re 2), cytochrome P450 aromatase (P450arom), 17beta-hydroxysteroid dehydrogenase type 3 (17beta-HSD 3), 3beta-HSD type 2 and 17beta-HSD type 1 activity. First, the present study demonstrates that significant amounts of TPT occurred in the blood of eight human volunteers (0.17-0.67 microg organotin cation/l, i.e. 0.49-1.92 nmolcation/l). Second, TPT showed variable inhibitory effects on all the enzymes investigated. The mean IC(50) values were 0.95 microM for 5alpha-Re 2 (mean of n=4 experiments), 1.5 microM for P450arom (n=5), 4.0 microM for 3beta-HSD 2 (n=1), 4.2 microM for 17beta-HSD 3 (n=3) and 10.5 microM for 17beta-HSD 1 (n=3). To exclude the possibility that the impacts of TPT are mediated by oxidizing essential thiol residues of the enzymes, the putative compensatory effects of the reducing agent dithioerythritol (DTE) were investigated. Co-incubation with DTE (n=3) resulted in dose-response prevention of the inhibitory effects of 100 microM deleterious TPT concentrations on 17beta-HSD 3 (EC(50) value of 12.9 mM; mean of n=3 experiments), 3beta-HSD 2 (0.90 mM; n=3), P450 arom (0.91 mM; n=3) and 17beta-HSD 1 (0.21 mM; n=3) activity. With these enzymes, the use of 10mM DTE resulted in an at least 80% antagonistic effect, whereas, the effect of TPT on 5alpha-Re 2 was not compensated. In conclusion, the present study shows that TPT acts as an unspecific, but significant inhibitor of human sex steroid hormone metabolism and suggests that the inhibitory effects are mediated by the interaction of TPT with critical cysteine residues of the enzymes.

17-Hydroxysteroid Dehydrogenases↗
PubMed2002

Convergent synthesis of an inner core GPI of sperm CD52.

An inner core of the GPI anchor of sperm CD52 antigens was synthesized by a highly convergent process using specially modified inositol, glucosamine and phospholipid as key building blocks. This paper also presents a new and efficient procedure to prepare 1,2,6-differentiated derivatives of inositol for GPI syntheses.

Antigens, CD↗
PubMed1998

"Propylene spaced" allyl tin reagents: a new class of fluorous tin reagents for allylations under radical and metal-catalyzed conditions.

A new generation of propylene-spaced fluorous allyltin reagents [(Rf(CH2)3)3SnCH2CH = CH2] is described. These succeed in radical allylations where their lower homologs (ethylene-spaced) fail, and they provide improved performance in transition metal catalyzed allylations. The reagents and byproducts are readily separated by simple fluorous-organic liquid-liquid or solid-liquid extractions.

Aldehydes↗
PubMed1998

Chloramine-T in high-specific-activity radioiodination of antibodies using N-succinimidyl-3-(trimethylstannyl)benzoate as an intermediate.

Monoclonal antibodies C215 and MOv18 have been radiohalogenated, using a single-batch method employing N-succinimidyl-3-(trimethylstannyl)benzoate, m-MeATE. Labelling to the stannyl ester was optimized using chloramine-T as oxidizing agent. The results show that the stannyl ester is effectively labelled with short reaction times giving reproducible yields from 85% to 95%. Subsequent antibody conjugation, 10 to 80 microg MAb, resulted in biologically active, labelled antibodies with overall radiochemical yields of 50% to 80%, with corresponding specific activities of 490-50 kBq(125I)/microg.

Antibodies↗
PubMed1999

Genotoxic effects of triphenyltin acetate and triphenyltin hydroxide on mammalian cells in vitro and in vivo.

Two organotin pesticides, triphenyltin acetate (TPTA) and triphenyltin hydroxide (TPTH), were evaluated for their ability to induce micronuclei (MN) and sister chromatid exchange (SCE) in vitro using cultured Chinese hamster ovary (CHO) cells and in vivo BALB/c mouse erythrocytes. Both pesticides induced a dose-dependent increase but only TPTH induced a significant increase in MN at the highest dose (150 ng/ml) tested in CHO cells. With adding S9 microsomal fractions, both pesticides induced a meaningful MN induction at 150 ng/ml and a dose-dependent significant increase in SCE. In vivo MN induction in erythrocytes was conducted by treating BALB/c mice orally or intraperitoneally with these pesticides either in a single or triple treatments. Oral gavage (p.o.) of TPTA resulted in a dose-related significant increase of MN induction in peripheral blood and of TPTH induced a significant increase in micronucleated reticulocyte (MNRETs) only in a single treatment. Intraperitoneal administration of TPTA or TPTH, however, resulted in meaningless random increases in MN though these increases might be attributable to toxic effects. The MNRETs levels in the treatment with both pesticides were independent to the sampling time. This study demonstrated that TPTA and TPTH was potential chromosome mutagens.

Animals↗
PubMed2003

Delayed gametogenesis and progesterone levels in soft-shell clams (Mya arenaria) in relation to in situ contamination to organotins and heavy metals in the St. Lawrence River (Canada).

There is a growing awareness that contaminants in the aquatic environment may alter steroid hormone levels and affect the reproductive success of the invertebrates. To verify if heavy metals and organotins affect sexual maturation in Mya arenaria, individuals were collected from July to November 1998, at different sites along the South coast of the St. Lawrence maritime estuary. Near the Rimouski harbour, clams showed high levels of tributyltin (TBT), DBT in the gonad, along with a lower gonado-somatic index [GSI=gonad wet weight (g)/body wet weight without shell (g)x100], low progesterone levels and a delay in sexual maturation when compared to the reference site. Sites that had intermediate levels of contaminants exhibited intermediate responses of hormones and sexual maturation stages. It is therefore suggested that TBT, DBT are endocrine disruptors in clams. Further studies will however be necessary to investigate in more details how contaminants as TBT can affect the steroid hormones production in the gonads of M. arenaria.

Animals↗
PubMed2002

Evaluation of accelerated solvent extraction for butyltin speciation in PACS-2 CRM using double-spike isotope dilution-GC/ICPMS.

Pressurized liquid extraction using the accelerated solvent extractor (Dionex ASE 200) has been evaluated for the determination of mono-, di- and tributyltin (MBT, DBT, and TBT, respectively) in PACS-2 certified reference material. A double-enriched spike containing 119Sn-enriched MBT and TBT and 118Sn-enriched DBT allowed for the simultaneous determination of the three butyltin species and the factors governing species interconversion. The stability of the spike was evaluated by reverse isotope dilution experiments covering more than one year with satisfactory results. Quantitative recoveries using ASE for TBT and DBT were obtained at temperatures above 110 degrees C. The effect of the extraction time and number of static cycles was evaluated. Results suggest that extraction efficiency was quantitative with extraction times as low as 10 min for all butyltin species at 110 degrees C. Decomposition reactions were only detected at the higher temperatures assayed (140 and 175 degrees C) and that was only for the degradation of DBT to MBT (approximately 4%). The results found for MBT were approximately 25% higher than the certified value for the PACS-2 sediment reference material in agreement with previous results obtained by ultrasonic and microwave assisted extraction.

Environmental Pollutants↗
PubMed1999

Tin speciation in the femtogram range in open ocean seawater by gas chromatography/inductively coupled plasma mass spectrometry using a shield torch at normal plasma conditions.

A sensitive method for the determination of ultratrace organotin species in seawater is described. The merits and demerits of derivatization methods using Grignard reagent or sodium tetraethylborate (NaBEt4) were evaluated in terms of derivatization efficiency, applicability to the programmed temperature vaporization (PTV) method, and procedural blanks. The sensitivity of the gas chromatography/inductively coupled plasma mass spectrometry (GC/ICPMS) was improved by more than 100-fold by operating the shield torch at normal plasma conditions, compared with that obtained without using it. The absolute detection limit as tin reached subfemtogram (fg) levels. Furthermore, the detection limit in terms of relative concentration was improved 100-fold by using the PTV method, which enabled the injection of a large sample volume of as much as 100 microL without loss of analyte. When the organotin species in seawater were extracted into hexane with a preconcentration factor of 1000 after ethylation with NaBEt4 and a 100 microL aliquot of the extract was injected into the GC, the instrumental detection limit in relative concentration reached 0.01 pg/L in original seawater. Sources of contamination of organotin species during the sample preparation were examined, and a purification method of NaBEt4 was developed. Finally, the method was successfully applied to open ocean seawater samples containing organotin species at the level of 1-100 pg/L.

Borates↗
PubMedDate not supplied

Synthesis of 3-(triethylstannyl)propanoic acid: an organotin mass label for DNA.

The synthesis of 3-(triethylstannyl)propanoic acid (TESPA), an organometallic reporter group that enables the mass labeling of oligonucleotides with stable isotopes of tin, is described. Synthesized from commercially available isotopically-enriched SnO2 in a five step process, the NHS ester of TESPA is produced with an overall yield of 40%. This simplification of the standard synthetic scheme, with two less synthetic steps and a coincident 60% yield increase, is accomplished through the use of the reagent N-(acryloxy)succinimide and the free radical initiator AMPN. The conditions for the attachment of the reporter group to priming oligonucleotides and the subsequent HPLC isolation of the labeled primers are also detailed.

Alloys↗