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PubMed1996

A Ca(2+)-mobilising carbohydrate-based polyphosphate: synthesis of 2-hydroxyethyl alpha-D-glucopyranoside 2',3,4-trisphosphate.

Two routes to a glucose-based mimic of the second messenger 1D-myo-inositol 1,4,5-trisphosphate related to adenophostin A are described. Fischer glycosidation of D-glucose with allyl alcohol in the presence of a strong cation-exchange resin gave a 7:3 alpha: beta-anomeric mixture of allyl glucopyranosides (5ab) from which the pure alpha anomer 5a was isolated by crystallisation. Treatment of 5ab with 1.05 equiv of dibutyltin oxide followed by 2.1 equiv of benzoyl chloride gave allyl 2,6-di-O-benzoyl-alpha-D-glucopyranoside, which was converted in 3 steps into allyl 2,6-di-O-benzyl-3,4-O-isopropylidene-alpha-D-glucopyranoside (4). Alternatively, treatment of 5a with 2.5 equiv of dibutyltin oxide followed by benzyl bromide gave allyl 2,6-di-O-benzyl-alpha-D-glucopyranoside (9) which was also converted into 4. Compound 4 was elaborated to the phosphorylation precursor 2-hydroxyethyl 2,6-di-O-benzyl-alpha-D-glucopyranoside (12) in a convenient one-pot reaction, and 12 was phosphorylated and deblocked to afford 2-hydroxyethyl alpha-D-glucopyranoside 2',3,4-trisphosphate. The 2,6-di-O-benzyl derivative 9 was converted in high yield into 2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-D-glucopyranose, a useful intermediate for the synthesis of adenophostin A and related compounds.

Adenosine↗
PubMed1991

Accumulation of tri-n-butyltin chloride and triphenyltin chloride by oral and via gill intake of goldfish (Carassius auratus).

1. The bioconcentration factors (BCF) of both chemicals via gill intake of goldfish reached plateaux after 21 days of exposure. The average BCF values of Bu3SnCl and Ph3SnCl (N = 2) were 1976 and 1384, respectively, after 21-28 days of exposure. 2. The BCF values by oral intake of goldfish reached plateaux after 28 days for Bu3SnCl but did not for Ph3SnCl. The BCF values of Bu3SnCl and Ph3SnCl were 0.04 and 0.10, respectively, after 35 days. 3. The order of the BCF values via gill intake was reversed compared with that by oral intake. Further, the contamination of freshwater fish by these compounds was discussed using the results of these experiments.

Administration, Oral↗
PubMed2005

Butyltins in the sediments of Kochi and Mumbai harbours, west coast of India.

Surface sediment samples were collected from various locations in the Mumbai and Kochi harbours, west coast of India, to assess the presence of butyltin compounds. Tributyltin (TBT) and dibutyltin (DBT) varied from 16 to 16,816 ng/g dry wt. and from undetected to 469 ng/g dry wt., respectively, of the sediment in Kochi harbour. In Mumbai harbour, the values of TBT and DBT ranged between 4.5 and 1193 ng/g dry wt. and from undetected to 131 ng/g dry wt. of the sediments, respectively. The concentrations of both TBT and DBT showed strong seasonal variation probably due to the effect of tides and currents. Nevertheless, the levels of butyltin compounds were generally higher at sites influenced by shipping activities such as navigation, dry dock and ship-building activities. The presence of DBT indicates the abiotic or microbiological degradation of TBT. Compared to TBT, DBT was relatively less abundant, suggesting either fresh inputs of TBT and/or less degradation of TBT. The concentrations of TBT showed significant positive relationships with organic carbon and lipid, implying that both lipophilic and ionic interactions were probably involved in controlling the abundance of TBT at these sediments. The observed levels of butyltin compounds are much higher than those required to induce toxic effects on marine organisms, suggesting that these sediments were contaminated with butyltin compounds.

Carbon↗
PubMed2006

Assessment of butyltin and phenyltin pollution in the sea mullet, Mugil cephalus, along the Moroccan and Spanish coasts (Mediterranean Sea).

Levels of three butyltin (BTs) compounds, monobutyltin (MBT), dibutyltin (DBT) and tributyltin (TBT), and three phenyltin (PTs) compounds, monophenyltin (MPhT), diphenyltin (DPhT), and triphenyltin (TPhT), were determined in the sea mullet, Mugil cephalus, collected along the northern Mediterranean coast of Morocco, and the south Mediterranean coast of Spain. Also, sediment samples from the Guadalquivir River (Spain) near to its mouth in the Mediterranean Sea were analysed. TBT and TPhT were the predominant compounds in the analyzed samples, and TBT concentrations were higher in liver than in muscle. In general, the total content of BTs in these samples was higher than PT levels. In the Moroccan coast, the highest value of BTs (18.00 mg/Kg wet weight) was found in the west harbour of the Tangier site, while the lowest concentration (0.01 mg/Kg wet weight) was detected in the Oued Laoue site. Concerning PTs compounds, the highest value (4.00 mg/Kg wet weight) was found in the harbour of the M'diq Site and the lowest value (0.01 mg/Kg wet weight) was detected in the Oued Laoue site. On the other hand, organotin (OT) residues were not detected in the water samples of the Spanish coast although TBT was identified in four of the nine sediment samples from the Guadalquivir River at concentrations between 15.45 and 245.07 mg/Kg wet weight.

Animals↗
PubMed2006

Sulfotransferase activities towards xenobiotics and estradiol in two marine fish species (Mullus barbatus and Lepidorhombus boscii): characterization and inhibition by endocrine disrupters.

We have characterized hepatic phenol sulfotransferase (SULT) activities in two benthic fish species, Mullus barbatus and Lepidorhombus boscii, using p-nitrophenol, dopamine, 17beta-estradiol, 4-nonylphenol, and 1-naphthol as substrates. High affinity sulfation of 17beta-estradiol was observed in both species (Km=28-75 nM), suggesting the presence of a specific estrogen sulfotransferase that catalyzes the formation of estradiol-3 sulfate. Among the tested compounds, 1-naphthol was the most effective substrate for sulfation, with Vmax/Km ratios several hundred-fold higher than the other substrates examined. Both species sulfated the tested compounds, but only M. barbatus was able to sulfate dopamine. We also tested the inhibitory effects of common marine pollutants with estrogenic (4-nonylphenol) and androgenic (tributyltin, triphenyltin) properties on p-nitrophenol and 17beta-estradiol SULT activities. 4-Nonylphenol and triphenyltin inhibited sulfation of both substrates at micromolar concentrations in both species. However, tributyltin was only effective against SULTs from L. boscii, again at micromolar concentrations. The data indicate that M. barbatus and L. boscii are able to sulfate a range of xenobiotics and endogenous compounds, and inhibition of these activities by environmental pollutants may contribute to the known toxic effects of these compounds.

Animals↗
PubMed2004

Search for the contamination source of butyltin compounds in wine: agglomerated cork stoppers.

A possible butyltin contamination source in wine was studied in this paper. Agglomerated cork stoppers, which were produced in Portugal, Spain, and Italy, used in wine bottles were examined. The domestic cork products, cork granules, and mucus used for cork products were also analyzed. The levels of mono- and dibutyltin compounds in corks were found in the range from <0.0024 to 3.3 and from <0.0029 to 6.7 microg of Sn/g, respectively. A low level of tributyltin contamination was also found in 2 of 31 tested samples. The presence of butyltin compounds in agglomerated cork stoppers was confirmed by GC-MS. Experimental results indicated that all overseas agglomerated cork stoppers studied contained mono- and/or dibutyltins. Butyltins were not detected in cork granules, mucus, most of the natural cork stoppers, and domestic agglomerated cork products. The concentrations of mono- and dibutyltins increased with the time in a 30-day experiment, showing that butyltin compounds can leach from agglomerated cork to the wine. When the butyltin concentrations in wine samples were compared with their levels in the corresponding agglomerated cork stoppers, a correlation was found. The potential harm of such food contamination was evaluated by the toxic research of butyltin compounds using Daphnia sp. as the experimental model.

Animals↗
PubMed1988

Acute pancreatitis after cutaneous exposure to an organophosphate insecticide.

Pancreatitis secondary to organophosphate insecticide toxicity is extremely rare. The few previously reported cases have resulted from oral ingestion of these agents. We present the first reported case of acute pancreatitis occurring after cutaneous exposure to an organophosphate insecticide. Symptoms of pancreatitis persisted for 6 months, followed by total resolution. The proposed mechanisms of pancreatic injury caused by organophosphate compounds are discussed.

Acute Disease↗
PubMed1998

Dimethyltin(IV) carboxylate compounds; synthesis, characterization and in vitro cytotoxic activity.

Six dimethyltin(IV) carboxylate compounds of the general formula Me2SnX2, where X = 1/2 O2(CO)2 (oxalate), 1/2 O2(CO)2CH2 (malonate), 1/2 O2(CO)2CH = CH (maleate), 1/2 O2(CO)2C-CH2CH2CH2 (cyclobutyl dicarboxylate), O(CO)C6H11 (cyclohexane carboxylate) and O(CO)CMe3 (pivolate) have been prepared and characterized physicochemically and spectroscopically. The cytotoxic activities of these carboxylates have been studied against HeLa, Hep-2, RD, L20B and P388 cell lines using the MTT-colorimetric assay. These activities were compared with the cytotoxic activities of the three reference standards, cisplatin, carboplatin and oxaliplatin. The compounds were X = 1/2 malonate, 1/2 maleate, cyclohexane carboxylate and pivolate exhibited a range of significant activities against the cell lines used, whereas no cytotoxic activities were exhibited by the rest of the six compounds. The significance of these results is given and discussed.

Antineoplastic Agents↗
PubMed2005

New diorganotin(IV) derivatives of 7-hydroxycoumarin (umbelliferone) and their adducts with 1,10-phenanthroline.

New diorganotin(IV) derivatives of the general formula R2Sn(Umb)2 (where R = n-Bu, n-Oct and Ph; Umb = umbelliferone anion) have been synthesized either by the reaction of R2SnO with umbelliferone under azeotropic removal of water or by the reaction of R2SnCl2 with sodium salt of umbelliferone. Further, the adducts of the general formula R2Sn(Umb)2.phen (where R = n-Bu and n-Oct; phen = 1,10-phenanthroline) have also been synthesized by the interaction of R2Sn(Umb)2 with 1,10-phenanthroline. The bonding and coordination behavior in these derivatives are discussed on the basis of IR and 119Sn Mössbauer spectroscopic studies in solid state. Their coordination behavior in solution is discussed by the multinuclear (1H, 13C and 119Sn) NMR spectral studies. The Mössbauer and IR studies indicate that umbelliferone acts as a monoanionic bidentate ligand in R2Sn(Umb)2 coordinating through O(7) and O(1). A distorted octahedral geometry around tin has been proposed for R2Sn(Umb)2 as well as for R2Sn(Umb)2.phen in solid state. The newly synthesized derivatives have been tested for their anti-inflammatory and cardiovascular activities. The average LD50 value >1000 mg kg(-1) of these compounds indicates their safety margin.

Animals↗
PubMed2002

Survey on the presence of butyltin compounds in chinese alcoholic beverages, determined by using headspace solid-phase microextraction coupled with gas chromatography-flame photometric detection.

The use of butyltin compounds in some food packaging leads to the contamination of liquid food and may result in subsequent adverse effects on people's health through the food chain. A survey of butyltin compounds in Chinese alcoholic beverages purchased from retail markets was carried out by using solid-phase microextraction (SPME) followed by gas chromatography coupled with flame photometric detection. Forty-four samples including wine, liquor, and champagne were studied. The levels of monobutyltin and dibutyltin ranged from <0.016 to 5.687 and from <0.0022 to 33.257 microg of Sn/L, respectively. Low levels of tributyltin were detected. The presence of dibutyltin in wine samples was further confirmed by GC-MS. The result indicated that dry wines generally contained more dibutyltin than sweet wines. The concentrations of butyltin compounds in liquor samples were lower than those in wine samples.

Alcoholic Beverages↗