Tri-n-butyltin: A membrane toxicant

Gray, Brian H.; Porvaznik, Partin; Flemming, Carlyle D.; Lee, Lanfong H.

doi:10.1016/0300-483x(87)90159-4

Cited by 41 publications

(21 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Therefore, they can easily penetrate into cells, causing toxic damages up to cell death because of ATP loss and phospholipid oxidation (Gray et al, 1987). It is difficult to compare the classes of organotin derivatives, even if the chemical nature of the alkyl, aryl, or cyclohexyl group has a strong influence on the physical and biological properties.…”

Section: Discussionmentioning

confidence: 99%

Toxicity of Organotin Compounds on Embryos of a Marine Invertebrate (Styela plicata;Tunicata)

Cima

Ballarin

Bressa

et al. 1996

Ecotoxicology and Environmental Safety

View full text Add to dashboard Cite

Section: Discussionmentioning

confidence: 99%

Toxicity of Organotin Compounds on Embryos of a Marine Invertebrate (Styela plicata;Tunicata)

Cima

Ballarin

Bressa

et al. 1996

Ecotoxicology and Environmental Safety

View full text Add to dashboard Cite

“…Secondly, both organotins, but especially DBT, were also shown to shut down the Ca 2+ pump (Gray et al 1987, Cima et al 1998. Bouchard et al (1999) hypothesized that DBT appears to be a better competitor for calcium sites than TBT because the ionic form of DBT is a double-charged cation like Ca 2+ and is a much smaller moiety than TBT, which brings only 1 positive charge.…”

Section: Discussionmentioning

confidence: 99%

Hemocyte functions and bacterial clearance affected in vivo by TBT and DBT in the blue mussel Mytilus edulis

St-Jean¹,

Pelletier²,

Courtenay³

2002

Mar. Ecol. Prog. Ser.

View full text Add to dashboard Cite

“…Solubility depends on both the number and length of organic groups bound to the tin atom. 2 Therefore, trialkyltin compounds (R 3 SnX) have the highest lipophilicity values: TBT has an octanol±water partition coefficient (log P ow ) between 3.19 and 3.84 for distilled water and 3.54 for sea water, 3,4 whereas dibutyltin (DBT) has a solubility in water of 1.5 M. 5 Owing to its high lipophilicity, TBT can easily cross biological membranes and interact with several intracellular targets, 6 thus irreversibly accumulating in both invertebrates and vertebrates. In particular, in mammals and fish, it preferably compartmentalizes in liver, kidney, brain and lymphoid organs.…”

Section: Introductionmentioning

confidence: 99%

Butyltins and calmodulin: which interaction?

Cima

Dominici

Mammi

et al. 2002

Applied Organom Chemis

View full text Add to dashboard Cite

Tributyltin (TBT), widely used as an antifouling biocide, is the most abundant pesticide in coastal environments. One of its main toxic effects is immunosuppression in both vertebrates and invertebrates. At sublethal doses of TBT, phagocytes lose their ability to move towards and ingest foreign particles. For short-term cultures of haemocytes (60 min at 25 °C) of a marine invertebrate, the colonial ascidian Botryllus schlosseri, exposed to 10−5M TBT, we previously reported dose- and time-dependent impairment of yeast phagocytosis and changes in cell morphology related to cytoskeleton disorganization. These effects are Ca2+-dependent, since inactivation of Ca2+-adenosine triphosphatase and a sustained increase in cytosolic Ca2+ occurred. As TBT can antagonize the effect of chlorpromazine, a specific calmodulin (CaM) inhibitor, and the co-presence of exogenous CaM and TBT in the incubation medium resulted in the absence of effects, we hypothesized an interaction between TBT and CaM. TBT may remove endogenous CaM from cell proteins, thus inactivating them and causing alteration of Ca2+ homeostasis. With the aim of confirming the hypothesis of a direct TBT–CaM interaction, we first studied the effects of co-incubation of TBT with other exogenous proteins on restoring the ability of phagocyte morphology. Although bovine serum albumin was never able to restore cell morphology, the effect of human spectrin was similar to that described for CaM, suggesting a common non-specific mechanism of action based on the interaction of TBT with exposed hydrophobic pouches. We also analysed the conformational changes of pure CaM (10−5M) in the presence of various concentrations (10−4 to 10−3M) of TBT and its degradation products, dibutyltin (DBT) and monobutyltin (MBT), by circular dichroism. Results indicate the dose- and time-dependent interaction of TBT with CaM. This interaction is a non-covalent interaction, probably hydrophobic in nature, between the aliphatic chains of TBT and the hydrophobic regions of Ca2+-activated CaM. DBT and MBT turned out to be less active in inducing CaM conformational changes, without any significant differences between the two compounds

show abstract

Tri-n-butyltin: A membrane toxicant

Cited by 41 publications

References 28 publications

Toxicity of Organotin Compounds on Embryos of a Marine Invertebrate (Styela plicata;Tunicata)

Toxicity of Organotin Compounds on Embryos of a Marine Invertebrate (Styela plicata;Tunicata)

Hemocyte functions and bacterial clearance affected in vivo by TBT and DBT in the blue mussel Mytilus edulis

Butyltins and calmodulin: which interaction?

Contact Info

Product

Resources

About