Bioorganotin chemistry: Reactions of tributyltin derivatives with a cytochrome P-450 dependent monooxygenase enzyme system

Fish, Richard H.; Kimmel, Ella C.; Casida, John E.

doi:10.1016/s0022-328x(00)80816-5

Cited by 79 publications

(32 citation statements)

References 30 publications

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“…Briefly, TBTC can be primarily transformed to di-n-butyl(1-hydroxybutyl)tin dichloride or di-n-butyl(2-hydroxybutyl)tin dichloride by 1-or 2-hydroxylation. However, these hydroxylated compounds at the 1-or 2-position of a butyl moiety are too unstable to be isolated and degraded to DBTC immediately after formation or during extraction (Fish et al, 1976). On the other hand, the products formed via oxidation at the 3-or 4-position of TBTC (T3OH, T4OH, and T3CO) are stable and can be isolated.…”

Section: Resultsmentioning

confidence: 99%

Accumulation, Metabolism, and Depuration of Organotin Compounds in the Marine Mussels Mytilus graynus and Mytilus edulis under Natural Conditions

Suzuki

Yamamoto

Kaniwa

et al. 1998

J. Agric. Food Chem.

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The accumulation, transformation, and depuration of tri-n-butyltin (TBT) were studied over periods of approximately 60-70 days using marine mussels, Mytilus graynus and Mytilus edulis, under natural conditions. M. graynus collected at a lightly polluted site were transplanted to a highly polluted site and M. edulis collected at a highly polluted site were transplanted to a lightly polluted site. TBT taken up in M. graynus showed a bioconcentration factor of 10 500 in the accumulation phase. Di-n-butyl(3-oxobutyl)tin, which is a main metabolite of TBT in M. edulis, showed a longer half-life (8.13 days) than that of the parent compound (4.82 days) in the depuration phase. On the other hand, another metabolite, di-n-butyl(3-hydroxybutyl)tin, showed a shorter half-life (3.98 days) than that of the parent compound. The different half-lives among TBT and its metabolites are responsible for the different metabolic patterns in blue mussels at each sampling time.

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Section: Resultsmentioning

confidence: 99%

Accumulation, Metabolism, and Depuration of Organotin Compounds in the Marine Mussels Mytilus graynus and Mytilus edulis under Natural Conditions

Suzuki

Yamamoto

Kaniwa

et al. 1998

J. Agric. Food Chem.

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“…Metabolism of TBT ingested with food was also observed in starfish (Mercier et al 1994): the daily ingestion of a live mussel contaminated with around 5 pg TBT g-' wet mass led to sequential debutylation within 2 wks. Metabolism of TBT by marine animals is usually correlated with the presence of the cytochrome P-450 dependent mixed-function oxidase (MFO) system (Fish et al 1976, Lee 1991. Although its presence and high activity have been demonstrated in crustaceans (Lee 1991) and echinoderms (Den Besten et al 1990), its occurrence is still speculative in freshwater cnidarians (Khan et al 1972).…”

Section: Discussionmentioning

confidence: 99%

Toxicological response of the symbiotic sea anemone Aiptasia pallida to butyltin contamination

Mercier¹,

Pelletier²,

Jf³

1996

Mar. Ecol. Prog. Ser.

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This study investigates the fate of tributyltin (TBT), a widespread biocide mainly used in antifouling paints, and of its derivative dibutyltin (DBT) in sea anemones Aiptasia pallida exposed via water or food. Experiments were conducted on both symbiotic and aposymbiotic (lacking zooxanthellae) individuals under a 12 h light: 12 h dark photoperiod or in total darkness. TBT and DBT concentrations in the animal and vegetal compartments were measured over 24 h, 30 h, 5 d. 7 d and 28 d periods. Uptake and accumulation from seawater, mainly as DBT due to natural degradation of TBT, was found to be dependent on the presence and illumination of zooxanthellae. DBT concentratlons in symbiotic anemones exposed to light were roughly twlce those found in individuals maintained ~n total darkness, and about 10 times greater than in aposymbiotic anemones. A peak accumulation in animal and vegetal tissues occurred after 24 to 4 8 h in all symbiotic anemones. A 28 d exposure of symbiotic anemones to a nominal 50 ng TBT 1-' resulted in butyltin concentrations under 1 ng mg-' dry mass. Accumulation most probably occurs through butyltln uptake by zooxanthellae, while their expulsion from the host acts as a depuration process. The presence of zooxanthellae also seems determinant in the regulation and degradation of butyltin ingested with food. Daily ingestion of TBT-contaminated mussel tissue led to sequential debutylation into DBT and monobutyltin (MBT) in symbiotic A . pallida but not in aposymbiotic ones. Over 7 d. aposymbiotic anemones showed close to 100% retention of ingested TBT, while all butyltin species remained undetected in symbiotic anemones. After 28 d, the retention efficiency was -68% in symbiotic anemones in which -59% of the butyltin was in the form of DBT

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“…The metabolism of the butyltin compounds by cytochrome P450 enzymes has been suggested to play an important role in the induction of biological effects; tributyltin was found to undergo hydroxylation followed by dealkylation to produce dibutyltin, monobutyltin and inorganic compounds in the presence of microsomes and NADPH in vitro (Casida et al 1971;Fish 1984;Fish et al 1976;Kimmel et al 1977). Moreover, several studies have shown that a variety of metabolites are formed in rat (Matsuda et al 1993) and mouse liver (Ueno et al 1997) during the metabolism of TBTC in vivo.…”

Section: Introductionmentioning

confidence: 99%

Comparison of hepatotoxicity and metabolism of butyltin compounds in the liver of mice, rats and guinea pigs

et al. 2003

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The hepatotoxicity of tributyltin chloride (TBTC) and dibutyltin dichloride (DBTC) was compared among mice, rats and guinea pigs in vivo. Further, the metabolism of these butyltin compounds in the liver was also investigated in these species. The oral administration of TBTC and DBTC to mice induced obvious liver injury, as demonstrated by both serodiagnosis and histopathological diagnosis. The concentrations of TBTC and DBTC that induced hepatotoxicity in mice at 24 h after oral administration were 180 and 60 micro mol/kg, respectively. In the case of rats, the liver injury induced by TBTC and DBTC was detected at 24 h by the serodiagnosis, but not by histopathological diagnosis. On the other hand, in guinea pigs, TBTC and DBTC administration did not produce any clear liver injury at 24 h, as evaluated by these two diagnostic methods. Thus, the following ranking was obtained with regard to increasing order of sensitivity to liver injury caused by TBTC and DBTC: mice, rats and guinea pigs. The total butyltin contents in the liver of mice were equivalent at 3 h and 24 h after the administration of TBTC or DBTC; however, the contents in the liver of rats and guinea pigs were relatively lower at 3 h and higher at 24 h than those of mice, although there were no differences between rats and guinea pigs in the total liver butyltin content. Concerning the liver metabolism of these butyltin compounds, the main form of butyltin compounds in these animals treated with TBTC was DBTC within 3 h after oral administration, while the main metabolites at 24 h were different in each species, indicating that the liver metabolism of TBTC might vary by animal type. When the animals were treated with DBTC orally, DBTC was hardly metabolized in the livers of these animals even at 24 h, and the liver levels of DBTC were two times greater in mice and guinea pigs than in rats at 3 h and were lower in mice at 24 h than in rats and guinea pigs. The analysis of cellular distributions of DBTC in the liver at 3 h after the administration showed that the levels of DBTC in the nuclear, microsomal and mitochondrial fractions of mice hepatocytes were relatively higher than in those of rats, which were greater than in those of guinea pigs. These results suggest differences in the sensitivity of mice, rats and guinea pigs to hepatotoxicity caused by butyltin compounds and demonstrate that the difference in the sensitivity of these animals to the hepatotoxicity induced by TBTC and DBTC may be partly due to differences in hepatic metabolism of TBTC and in the distribution of DBTC within cell organelles, respectively.

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Bioorganotin chemistry: Reactions of tributyltin derivatives with a cytochrome P-450 dependent monooxygenase enzyme system

Cited by 79 publications

References 30 publications

Accumulation, Metabolism, and Depuration of Organotin Compounds in the Marine Mussels Mytilus graynus and Mytilus edulis under Natural Conditions

Accumulation, Metabolism, and Depuration of Organotin Compounds in the Marine Mussels Mytilus graynus and Mytilus edulis under Natural Conditions

Toxicological response of the symbiotic sea anemone Aiptasia pallida to butyltin contamination

Comparison of hepatotoxicity and metabolism of butyltin compounds in the liver of mice, rats and guinea pigs

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