Effects of Ugilec-141®, a PCB substitute based on tetrachlorobenzyltoluenes, on hepatic mono-oxygenase induction in estuarine fish

Addison, R.F.; Hansen, Peter-Diedrich; Pluta, H.-J.; Willis, D.E.

doi:10.1016/0141-1136(91)90024-3

Cited by 19 publications

(11 citation statements)

References 12 publications

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“…However, the in vivo effects of TBT on CN‐ECOD activity have not been previously investigated. Furthermore, CN‐ECOD activity in fish has only be measured in a very limited number of laboratory [33] and field [34,35] studies. From those studies, however, it emerged as a more sensitive indicator of induction than EROD.…”

Section: Discussionmentioning

confidence: 99%

Mutual in vivo interactions between benzo[a]pyrene and tributyltin in brook trout (Salvelinus fontinalis)

Padrós

Pelletier

Reader

et al. 2000

Enviro Toxic and Chemistry

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Tributyltin (TBT), an organometal used as an antifouling biocide, has been reported to inhibit cytochrome P450 (P450) 1A isozyme. Benzo[a]pyrene (BaP), a widespread carcinogenic polycyclic aromatic hydrocarbon, is both metabolized and bioac‐tivated to carcinogenic BaP diol‐epoxide (BPDE) metabolites primarily by hepatic P450 1A. Hence, TBT may inhibit the metabolism and bioactivation of BaP This study was therefore designed to examine the potential in vivo interactions between BaP and TBT in a model fish. Male brook trout (Salvelinus fontinalis) were given a single intraperitoneal injection of either BaP (10 mg/kg), TBT (10 mg/kg), or both in combination. After 48 h, blood, bile, and liver samples were collected and analyzed for a suite of biomarkers associated with P450 activity, BaP metabolism and bioactivation, and TBT metabolism. The results showed that TBT significantly (p < 0.05; two‐way analysis of variance) inhibited (a) the induction of hepatic P450 1A‐mediated ethoxyresorufin O‐deethylase (EROD) and P450‐mediated 3‐cyano‐7‐ethoxycoumarin‐O‐deethylase (CN‐ECOD) activities by BaP, (b) the formation of biliary BaP metabolites, and (c) the formation of (+)‐anti‐BPDE‐plasma albumin adducts as measured by high‐performance liquid chromatography/fluorescence. Notably, TBT alone did not inhibit EROD activity but induced CN‐ECOD activity (p < 0.05). Gas chromatography/mass spectrometry analysis indicated that the combined BaP + TBT dose resulted in higher levels of dibutyltin metabolites in the bile (p < 0.05). The present study supports the hypothesis that a single, high dose of TBT can antagonize the metabolism and bioactivation of BaP at least by inhibiting the induction of P4501A. On the other hand, BaP unexpectedly potentiated the metabolism of TBT, suggesting that hepatic isoforms other than P4501A may be responsible for TBT metabolism. Finally, this study supports the utility of a biomarker approach to screen potential xenobiotic interactions in aquatic organisms and to obtain mechanistic insights.

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Section: Discussionmentioning

confidence: 99%

Mutual in vivo interactions between benzo[a]pyrene and tributyltin in brook trout (Salvelinus fontinalis)

Padrós

Pelletier

Reader

et al. 2000

Enviro Toxic and Chemistry

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“…7-Ethoxycoumarin-o-deethylase (ECOD) activity has been reported from molluscs (Dauberschmidt, Dietrich, & Schlatter, 1997;Livingstone, Kirchin, & Wiseman, 1989). ECOD activity measured here as cyano-ECOD (CN-ECOD) is a cytochrome P450 (CYP) associated xenobiotic biotransformation enzyme (Addison et al, 1991(Addison et al, , 1994White, 1988). This particular enzyme activity is believed to be due to a CYP1A isoform in mammals (De Matteis et al, 2002).…”

Section: Discussionmentioning

confidence: 96%

“…Fluorescent molecular probes used in this study included 3,3 0 -dihexyloxacarbocyanine iodide (DiOC 6 (3)) for ER (Moore, 1992), 3-cyano-7-ethoxycoumarin for ECOD (Addison et al, 1991(Addison et al, , 1994De Matteis et al, 2002;White, 1988) and Texas Red conjugated albumin for endocytosis (Moore, 1992). With the exception of the conjugated albumin, the probes were prepared as stock solutions in DMSO and used at a dilution of 10 À4 in culture medium, as described above.…”

Section: Biomarker Testsmentioning

confidence: 99%

“…Four biomarkers were used to determine toxic impact and evidence of recovery: these were lysosomal neutral red retention as an integrative measure of general health status; endocytosis as an indicator of membrane processing; proliferation of endoplasmic reticulum (ER) as a generalized response to xenobiotics; and 3-cyano-7-ethoxycoumarin-odeethylase (CN-ECOD) as a more specific response to PAH (Addison, Hansen, Pluta, & Willis, 1991;Addison, Willis, & Zinck, 1994;De Matteis, Dawson, Pons, & Pipino, 2002;Moore, 1992;Moore, Köhler, Lowe, & Simpson, 1994;White, 1988).…”

Section: Biomarker Testsmentioning

confidence: 99%

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Pathological reactions and recovery of hepatopancreatic digestive cells from the marine snail Littorina littorea following exposure to a polycyclic aromatic hydrocarbon

Lowe

Moore

Readman

2006

Marine Environmental Research

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“…The objective of the present work was to get, besides the few toxicological studies [14][15][16], some more information on the possibility of TCBTs to exhibit a dioxin-type toxicity. As no data are available on the molecular and intermolecular descriptors, such as stacking distance, polarizability, electronegativity and hydrogen-bonding capacity for substituents, the limited, but, however very useful and informative, structural properties, namely a planar aromatic ring and a rectangular shape, were used in the present study as starting points.…”

Section: Introductionmentioning

confidence: 99%

On the Possible Coplanar Conformation and Dioxin‐type Toxicity of Tetrachlorobenzyltoluenes

Haelst

Tromp

Govers

et al. 1997

Quant. Struct.‐Act. Relat.

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Semi-empirical molecular modelling calculations of ring rotational energy barriers were carried out for 96 tetrachlorobenzyltoluenes (TCBTs) to provide insight in the possible coplanarity of these compounds, which is required for dioxin-type toxicity. Comparative calculations were performed for the structurally related polychlorinated biphenyls (PCBs) and polychlorinated diphenylethers (PCDEs). On account of this comparison PCBs, PCDEs and TCBTs were divided into groups of different energy barriers. PCDEs and TCBTs were classified into the same relatively high energyebarrier groups. Using the criterion of fitting within a 3 * 10A geometry and using structure activity relationships, our results indicate that two out of the 91 coplanar TCBTs can interact with the dioxin (Ah) receptor. energy of unconstrained molecule; AErOt, difference in energy between the energy minimizations of the unconstrained molecule and the molecule under the constraint of coplanarity; 4, angle of rotation.

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Effects of Ugilec-141®, a PCB substitute based on tetrachlorobenzyltoluenes, on hepatic mono-oxygenase induction in estuarine fish

Cited by 19 publications

References 12 publications

Mutual in vivo interactions between benzo[a]pyrene and tributyltin in brook trout (Salvelinus fontinalis)

Mutual in vivo interactions between benzo[a]pyrene and tributyltin in brook trout (Salvelinus fontinalis)

Pathological reactions and recovery of hepatopancreatic digestive cells from the marine snail Littorina littorea following exposure to a polycyclic aromatic hydrocarbon

On the Possible Coplanar Conformation and Dioxin‐type Toxicity of Tetrachlorobenzyltoluenes

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