Effect of phenyltin compounds on lipid bilayer organization

Langner, Marek; Gabrielska, Janina; Kleszczyńska, Halina; Pruchnik, Hanna

doi:10.1002/(sici)1099-0739(199802)12:2<99::aid-aoc674>3.0.co;2-k

Cited by 23 publications

(2 citation statements)

References 37 publications

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“…Consequently, both compounds are located in different membrane re gions and affect the lipid bilayer differently. The surface charge introduced onto the membrane sur face by triphenyltin was bigger but disturbance within the hydrophobic core was more eminent when diphenyltin was present (Langner et al, 1998).…”

Section: Resultsmentioning

confidence: 99%

Different Effects of Di- and Triphenyltin Compounds on Lipid Bilayer Dithionite Permeabilization

Gabrielska

Kral

Langner

et al. 2000

Zeitschrift Für Naturforschung C

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Phenyltins, Lipid Bilayer, Membrane PermeabilityPhenyltins are chemicals widely used in industry, hence their occurrence in the human environment is frequent and widespread. Such compounds include hydrophobic phenyl rings bonded to positively charged tin. Tliis molecular structure makes them capable of adsorbing onto and penetrating through biological membranes, hence they are potentially hazardous. Two such compounds, diphenyltin and triphenyltin, show different steric constraints when interacting with the lipid bilayer. It has been demonstrated that these compounds are posi tioned at different locations within model lipid bilayers, causing dissimilarity in their ability to affect membrane properties. In this paper we present a study regarding the ability of these two phenyltins to facilitate the transport of S20 4-2 ions across the lipid bilayer, evaluated by a fluorescence quenching assay. In concentration range of up-to 60 [.i m those compounds do not affect lipid bilayer topology, when evaluated by vesicle size distribution. Both phenyltins facilitate the transfer of S20 4-2 across the model lipid bilayer, but the dependence of dithio nite transport on phenyltin concentration is different for both. In principle, above 20 triphenyltin is more efficient in transfering ions across the lipid bilayer than diphenyltin.

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Section: Resultsmentioning

confidence: 99%

Different Effects of Di- and Triphenyltin Compounds on Lipid Bilayer Dithionite Permeabilization

Gabrielska

Kral

Langner

et al. 2000

Zeitschrift Für Naturforschung C

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“…The ESI-MS (Table 3) and MS/MS data suggested that the additional peak at m/z 764.1 in a mass spectrum of their mixture was derived from TPT and FePCH, demonstrating the existence of the TPT-FePCH complex. A change of signal splitting in 1 H NMR spectrum can be used as a measure of the degree of complex formation (15). In 1 H NMR spectrum (Fig.…”

Section: Discussionmentioning

confidence: 99%

Mechanism of Augmentation of Organotin Decomposition by Ferripyochelin: Formation of Hydroxyl Radical and Organotin-Pyochelin-Iron Ternary Complex

Sun

Zhong

2006

Appl Environ Microbiol

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Pyochelin (PCH), a kind of siderophore secreted by Pseudomonas aeruginosa, was recently found to have triphenyltin (TPT)-decomposing capacity. In this work, significant augmentation of TPT decomposition by ferripyochelin (FePCH), the chelating compound of PCH with iron, was demonstrated in Tris-HCl buffer (pH 8.0). The generation of hydroxyl radical (HO·) in the presence of FePCH was observed. Inhibition of HO· generation by adding catalase and HO· scavengers (methanol and dimethyl sulfoxide) decreased TPT decomposition, while an increase in HO· formation in the presence of H 2 O 2 enhanced its decomposition. Our findings indicated that HO· generated in the reaction system was responsible for the enhanced TPT decomposition by FePCH versus PCH. The existence of the TPT-pyochelin-iron ternary complex was demonstrated by electron spray ionization-mass spectrometry, tandem mass spectrometry, and 1 H nuclear magnetic resonance. On the basis of the above results, HO· produced in the presence of FePCH was deduced to be in close proximity to TPT and has more opportunity to attack the Sn-C bond, which resulted in the enhanced organotin decomposition. The information obtained may have considerable environmental significance.Triorganotin compounds, in particular triphenyltin (TPT), have been introduced into the aquatic environment in large quantities due to their extensive use as pesticides in agriculture and as antifouling agents in boat paints (11). As a highly toxic compound, TPT has caused harmful effects on a variety of nontarget organisms, such as mollusks and fish (2, 12), even at aqueous concentrations of a few nanograms per liter (2). Although organotins are banned in most developed countries, they are still being introduced into water and sediment around the world, causing an obvious health risk that has raised public interest in the removal of organotin in and from the environment (14). Microorganisms play a crucial role in organotin removal from the natural environment because of their surprising ability under evolution to degrade xenobiotics (26).Several strains have been isolated from the sediment or soil, and TPT degradation by these strains was investigated under pure culture conditions (13, 24). Although microbe-mediated dealkylation of organotin has been reported, information about details of the mechanism of microbial TPT degradation/ decomposition is still limited (13,14). Walts and Walsh (25) demonstrated that only a few kinds of organotins were substrates for bacterial organomercurial lyase. Most organotin compounds, such as tributyltin and triethyltin, were not substrates for lyase, and some even caused irreversible inhibition of enzymes. Inoue and coworkers (13, 14) have identified a kind of siderophore, pyoverdine (PVD), which was produced by Pseudomonas chlororaphis and was capable of decomposing triphenyltin and tributyltin. We recently showed that pyochelin (PCH), a siderophore secreted by Pseudomonas aeruginosa, could decompose triphenyltin, and its decomposition mechanism was proposed as che...

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Adsorption of phenyltin compounds onto phosphatidylcholine / cholesterol bilayers

Langner

Gabrielska

Przestalski

2000

Appl. Organometal. Chem.

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Phenyltin compounds are known to be biologically active and, whan widely spread, are potentially hazardous. As their chemical structure suggests, they interact with the lipid fraction of the cell membrane. Their effect on the model phosphatidylcholine/cholesterol bilayer has been studied using fluorescence and 1H NMR techniques. The change in the fluorescein‐PE fluorescence intensity indicates the amount of charge added by phenyltin compounds to the membrane surface. Although the presence of cholesterol alone does not alter membrane interface properties measured with fluorescein‐PE, 1H NMR measurements show that lipid mobility is altered throughout the hydrophobic core of the membrane. Cholesterol in the phosphatidylcholine bilayer does not alter tetraphenyltin interaction with the membrane, though the effect of diphenyltin dichloride, penetrating deeply into the hydrophobic core of the membrane, is reduced when the amount of cholesterol in the membrane is increased, suggesting decreased compound adsorption. Triphenyltin chloride has a qualitatively different effect on the lipid bilayer, when observed using this fluorescence technique. The adsorption of triphenyltin onto the phosphatidylcholine/cholesterol membrane induces a lateral phase separation of membrane components. Since triphenyltin chloride is known to be adsorbed onto the interface of the lipid bilayer, this separation mechanism must originate in this region and does not seem to be electrostatic in origin. 1H NMR measurements have confirmed the observation that these two active phenyltin compounds interact with the phosphatidylcholine/cholesterol membrane differently, disrupting different regions of the bilayer to a different degree. Copyright © 2000 John Wiley & Sons, Ltd.

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Effect of phenyltin compounds on lipid bilayer organization

Cited by 23 publications

References 37 publications

Different Effects of Di- and Triphenyltin Compounds on Lipid Bilayer Dithionite Permeabilization

Different Effects of Di- and Triphenyltin Compounds on Lipid Bilayer Dithionite Permeabilization

Mechanism of Augmentation of Organotin Decomposition by Ferripyochelin: Formation of Hydroxyl Radical and Organotin-Pyochelin-Iron Ternary Complex

Adsorption of phenyltin compounds onto phosphatidylcholine / cholesterol bilayers

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