Influence of Lipophilicity on the Toxicity of Bisphenol A and Phthalates to Aquatic Organisms

Mathieu-Denoncourt, Justine; Wallace, Sarah J.; Solla, Shane R. de; Langlois, Valérie S.

doi:10.1007/s00128-016-1812-9

Cited by 77 publications

(21 citation statements)

References 58 publications

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“…This should be a consequence of differences in their genetic background or even within the experimental conditions. Nevertheless, both estimates are within the same order of magnitude typically observed for invertebrates and vertebrates (Mathieu-Denoncourt et al 2016), indicating this ciliate species should be regarded as a good biosensor for the environmental impacts of BPA.…”

Section: Discussionsupporting

confidence: 69%

Toxicological impacts and likely protein targets of bisphenol A in Paramecium caudatum

Senra

2021

Preprint

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Bisphenol A (BPA) is a chemical agent widely used in plastic production and a well-known ubiquitous endocrine disruptor, frequently associated with a series of reproductive, developmental, and transgenerational impacts over wildlife, livestocks, and humans. Although widely studied, toxicological data on the effects of BPA are mostly restricted to mammalian models, remaining largely underexplored for other groups of organisms such as protists, which represents a considerable proportion of eukaryotic diversity. Here, we used acute end-point toxicological assay to evaluate the impacts of BPA over the survival of the cosmopolitan Paramecium caudatum; and a proteome-wide inverted virtual-screening (IVS) to predict the most likely P. caudatum proteins and pathways affected by BPA. This xenobiotic exerts a time-dependent effect over P. caudatum survival, which may be a consequence of impairments to multiple core cellular functions. We discuss the potential use of this ciliate as a biosensor for environmental BPA and as a new model organism to study the general impacts of this plasticizer agent over Eukaryotes. Finally, our data stress the relevance of bioinformatic methods to leverage the current knowledge on the molecular impacts of environmental contaminants over a diversity of biological systems.

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Section: Discussionsupporting

confidence: 69%

Toxicological impacts and likely protein targets of bisphenol A in Paramecium caudatum

Senra

2021

Preprint

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“…The lipophilicity is determinant for the toxicity and bioaccumulation of compounds [41]. Thus, a low lipophilicity points out an inferior affinity of substances for the lipid bilayer of cells [42].…”

Section: Primary Antibiotics Transformation Removal Of the Antimicromentioning

confidence: 99%

Sonochemical degradation of antibiotics from representative classes-Considerations on structural effects, initial transformation products, antimicrobial activity and matrix

Serna-Galvis

Montoya-Rodríguez

Isaza-Pineda

et al. 2019

Ultrasonics Sonochemistry

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In this work, the sonochemical treatment (at 354 kHz and 88 W L) of six relevant antibiotics belonging to fluoroquinolones (ciprofloxacin and norfloxacin), penicillins (oxacillin and cloxacillin) and cephalosporins (cephalexin and cephadroxyl) classes was evaluated. Firstly, the ability of the process to eliminate them was tested, showing that sonodegradation of these antibiotics is strongly chemical structure-dependent. Thus, correlations among initial degradation rate of pollutants (Rd), solubility in water (Sw), water-octanol partition coefficient (Log P) and topological polar surface area (TPSA) were tested. Rd exhibited a good correlation with Log P (i.e., the hydrophobicity degree of antibiotics). The considered penicillins had the fastest elimination and from the constitutional analysis using Lemke method was clear that the functional groups arrangement on these antibiotics made them highly hydrophobics. The penicillins were degraded closer at cavitation bubble than the fluoroquinolones or cephalosporins. The investigation of degradation products showed that sonogenerated hydroxyl radical primary attacked the β-lactam ring of cloxacillin and cephalexin, whereas on norfloxacin induced a decarboxylation. On the other hand, the evolution of antimicrobial activity was also followed. It was evidenced the process capacity to remove antimicrobial activity from treated solutions, which was associated to the transformations of functional groups on antibiotics with important role for interaction with bacteria. Additionally, degradation of antibiotics having the highest (the most hydrophobic, i.e., cloxacillin) and lowest (the most hydrophilic, i.e., cephadroxyl) Rd, was performed in synthetic matrices (hospital wastewater and seawater). Ultrasound degraded both antibiotics; for cloxacillin in such waters higher eliminations than in distilled water were observed (probably due to a salting-out effect exerted by matrix components). Meanwhile, for cephadroxyl a moderate inhibition of degradation in hospital wastewater and seawater respect to distilled water was found, this was related to competition by hydroxyl radical of the other substances in the matrices. These results show the quite selectivity of high frequency ultrasound to eliminate antibiotics form different classes even in complex matrices.

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“…Although some controversial evidence indicates that BPA is not toxic to human health [ 25 , 32 ], several recent studies highlight its harmful effects. Because of its lipophilic nature (logP of 3.4), BPA has the ability to accumulate in different human and animal tissues, compromising their physiological functions and exerting deleterious effects on health [ 21 , 33 , 34 ]. Indeed, studies performed in humans, rodents, and cellular cultures suggest that this compound may be obesogenic through different mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Potential Mechanisms of Bisphenol A (BPA) Contributing to Human Disease

Cimmino

Fiory

Perruolo

et al. 2020

IJMS

274

118

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Bisphenol A (BPA) is an organic synthetic compound serving as a monomer to produce polycarbonate plastic, widely used in the packaging for food and drinks, medical devices, thermal paper, and dental materials. BPA can contaminate food, beverage, air, and soil. It accumulates in several human tissues and organs and is potentially harmful to human health through different molecular mechanisms. Due to its hormone-like properties, BPA may bind to estrogen receptors, thereby affecting both body weight and tumorigenesis. BPA may also affect metabolism and cancer progression, by interacting with GPR30, and may impair male reproductive function, by binding to androgen receptors. Several transcription factors, including PPARγ, C/EBP, Nrf2, HOX, and HAND2, are involved in BPA action on fat and liver homeostasis, the cardiovascular system, and cancer. Finally, epigenetic changes, such as DNA methylation, histones modification, and changes in microRNAs expression contribute to BPA pathological effects. This review aims to provide an extensive and comprehensive analysis of the most recent evidence about the potential mechanisms by which BPA affects human health.

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Influence of Lipophilicity on the Toxicity of Bisphenol A and Phthalates to Aquatic Organisms

Cited by 77 publications

References 58 publications

Toxicological impacts and likely protein targets of bisphenol A in Paramecium caudatum

Toxicological impacts and likely protein targets of bisphenol A in Paramecium caudatum

Sonochemical degradation of antibiotics from representative classes-Considerations on structural effects, initial transformation products, antimicrobial activity and matrix

Potential Mechanisms of Bisphenol A (BPA) Contributing to Human Disease

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