Benzotriazole UV-stabilizers and benzotriazole: Antiandrogenic activity in vitro and activation of aryl hydrocarbon receptor pathway in zebrafish eleuthero-embryos

Fent, Karl; Chew, Geraldine; Li, Jun; Góméz, Elena

doi:10.1016/j.scitotenv.2014.02.109

Cited by 106 publications

(72 citation statements)

References 68 publications

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“…For each chemical, 3 doses were investigated (1, 10, 100 mg/L). The test concentrations of chemicals were selected based upon data presented in Fent et al (2014). Embryos were maintained in an incubator at 26 ± 1 C and exposed to the same light to dark schedule as above.…”

Section: Experimental Designmentioning

confidence: 99%

“…In terms of their toxicity, UV-P and UV-326 are involved in the activation of the AHR-pathway in zebrafish embryos (Fent et al, 2014). Additionally, mRNA level of thyroid hormone receptor a in zebrafish embryos was observed to be significantly decreased following exposure to 690 mg/L UV-P (Fent et al, 2014), whereas, none of the tested BUVSs showed ligand activity against the human thyroid hormone receptors (Nagayoshi et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

“…Due to their high production volume and wide application, BUVSs have been frequently detected in various environmental matrices such as municipal waste water, sewage sludge, sediment, soil, and indoor dust (Lai et al, 2014;Ramos et al, 2016;Wang et al, 2013a). Most BUVSs are detected in aquatic environments at mean concentrations ranging from 2.3 to 544.9 ng/L (Carpinteiro et al, 2010(Carpinteiro et al, , 2012García-Guerra et al, 2016;Kameda et al, 2011;Liu et al, 2011;Montesdeoca-Esponda et al, 2012;Song et al, 2014). Among these BUVSs, UV-326, UV-327, and UV-328 appear to be the most frequently detected compounds in environmental samples (Cantwell et al, 2015;Kameda et al, 2011;Langford et al, 2015;Liu et al, 2011;Nakata et al, 2009;Ruan et al, 2012;Song et al, 2014;Wick et al, 2016;Zhang et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

“…Recent studies in mammals and fish have reported on their endocrine disrupting effects (Fent et al, 2014;Kawamura et al, 2003;Morohoshi et al, 2005;Nagayoshi et al, 2015;Zhuang et al, 2017). UV-P, UV-9, UV-326, and UV-090 show significant ligand activity against human aryl hydrocarbon receptor (AhR) (Nagayoshi et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, mRNA level of thyroid hormone receptor a in zebrafish embryos was observed to be significantly decreased following exposure to 690 mg/L UV-P (Fent et al, 2014), whereas, none of the tested BUVSs showed ligand activity against the human thyroid hormone receptors (Nagayoshi et al, 2015). Thyroid hormones (THs) play fundamental roles in regulating development, differentiation, and metabolism of all vertebrates (Power et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

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Benzotriazole ultraviolet stabilizers alter the expression of the thyroid hormone pathway in zebrafish (Danio rerio) embryos

Liang

Martyniuk

et al. 2017

Chemosphere

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h i g h l i g h t sBUVSs decreased heart rate of zebrafish in all treatments by 6.9%e21.4%. BUVSs affected transcriptional levels of HPT axis-related genes. Disruption of thyroid-related transcripts was dependent on the structure of BUVSs. Gene networks and pathways were predicted using IMP. a r t i c l e i n f o a b s t r a c tBenzotriazole ultraviolet stabilizers (BUVSs) are widely used in industrial products as well as personalhygiene products to protect the material or skin from harmful UV-radiation. Due to their persistence and bioaccumulation, BUVSs have been ubiquitously detected in aquatic environments. Although the toxicological effects of BUVSs in aquatic organisms have been previously examined, the effects of BUVSs on the thyroid system have not been adequately addressed. In this study, we assessed putative thyroid disrupting effects of BUVSs (UV-234, UV-326, UV-329 and UV-P) in zebrafish embryos at 1, 10 and 100 mg/L for 96 h. The heart rate was assessed in zebrafish and was observed to be decreased by 6.9% e21.4% in exposure of tested BUVSs. We also observed that the transcript levels of HPT axis-related genes were affected by the 4 BUVSs tested in different ways. Specifically, mRNA levels of thyroid hormone receptors (thraa and thrb) in zebrafish embryos were differentially expressed and the direction of change in these transcripts was isoform and BUVSs dependent. Pathway analysis of the targeted genes measured indicated that cellular processes putatively affected by BUVSs included response to organic substance, regulation of transcription from RNA polymerase II promoter, intracellular receptor signaling pathway, and hypothyroidism. Upon expansion of the network, novel genes involved in this predicted gene network may provide insight into the mechanisms of thyroid disrupting mechanisms of BUVSs. Taken together, our results indicate that BUVSs can potentially impact the thyroid system, and that this is dependent upon the type or structure of BUVSs.

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Section: Experimental Designmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Benzotriazole ultraviolet stabilizers alter the expression of the thyroid hormone pathway in zebrafish (Danio rerio) embryos

Liang

Martyniuk

et al. 2017

Chemosphere

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Traditional and innovative protective coatings for outdoor bronze: Application and performance comparison

Salvadori

Cagnini

Galeotti

et al. 2017

J of Applied Polymer Sci

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A comparative evaluation of traditional and innovative coatings for outdoor bronze surfaces was carried out, including blending or pre-treatment with non-toxic corrosion inhibitors on bare and patinated bronze surfaces to simulate both as cast and aged surfaces. Coatings recently applied in bronze conservation practice, commercially available coatings and an innovative endcapped poly(lactic acid) with a benzotriazole (BTA) moiety have been tested, as well as a triple-layer system (wax/acrylic polymer/ wax). BTA, single-layer Soter wax, and double layer Incral44/Soter wax were used as a reference. The products were evaluated in terms of aesthetic features, molecular structure, and corrosion protection by means of colorimetric, spectroscopic, and electrochemical tests. All inhibitors showed similar or significantly better results compared to BTA. In particular, sodium oleate and tolyltriazole could be considered as promising lower-toxicity alternatives to BTA, while the triple-layer coating applied without pre-filming inhibitors proved to give a very high protection against corrosion.

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Electrochemical Oxidation of the Phenolic Benzotriazoles UV‐234 and UV‐327 in Organic Solvents

Chan

Webster

2018

ChemElectroChem

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The electrochemical behavior of selected phenolic benzotriazoles (BZTs), namely 2‐(2H‐benzotriazol‐2‐yl)‐4,6‐bis(1‐methyl‐1‐phenylethyl)phenol and 2,4‐di‐tert‐butyl‐6‐(5‐chlorobenzotriazol‐2‐yl)phenol (commercial names UV234 and UV327, respectively) were examined with cyclic voltammetry (CV) and controlled potential electrolysis (CPE) in acetonitrile and dichloromethane solutions. CV indicated that both phenolic BZTs undergo a chemically irreversible oxidation process at approximately Ep°x=+1.0 V vs. Fc/Fc+ (where Ep°x is the anodic peak potential and Fc=ferrocene) to form compounds that cannot be electrochemically converted back to the starting material on the voltammetric timescale. In basic conditions, cyclic voltammetry experiments indicated that the corresponding phenolates (prepared by reacting the phenols with equiv. mols of n‐Bu4NOH) were oxidized at Ep°x∼−0.2 V vs. Fc/Fc+ via a one‐electron diffusion controlled process with anodic (ip°x) to cathodic (ipred) peak current ratios (ip°x/ipred)≫1, suggesting that the produced phenoxyl radicals decomposed rapidly via a chemical step. However, electron paramagnetic resonance (EPR) experiments performed on the bulk electrolyzed solutions of the phenolates after one‐electron bulk oxidation indicated long lifetimes of the UV234. and UV327. phenoxyl radicals. Therefore, the long timescale CPE and spectroscopic (UV‐vis and EPR) studies provided good evidence of a reversible dimerization mechanism between the phenoxyl radicals, which explained the apparent discrepancy with the short timescale CV experiments.

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Benzotriazole UV-stabilizers and benzotriazole: Antiandrogenic activity in vitro and activation of aryl hydrocarbon receptor pathway in zebrafish eleuthero-embryos

Cited by 106 publications

References 68 publications

Benzotriazole ultraviolet stabilizers alter the expression of the thyroid hormone pathway in zebrafish (Danio rerio) embryos

Benzotriazole ultraviolet stabilizers alter the expression of the thyroid hormone pathway in zebrafish (Danio rerio) embryos

Traditional and innovative protective coatings for outdoor bronze: Application and performance comparison

Electrochemical Oxidation of the Phenolic Benzotriazoles UV‐234 and UV‐327 in Organic Solvents

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