Tetrabromobisphenol A (TBBPA) exhibits specific antimicrobial activity against Gram-positive bacteria without detectable resistance

Ji, Fang; Wang, Chang; Wang, Huimin; Liu, Guangliang; Chen, Bolei; Hu, Ligang; Jiang, Guibin; Song, Maoyong; Liang, Yong

doi:10.1039/c7cc00613f

Cited by 12 publications

(13 citation statements)

References 21 publications

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“…In the susceptibility studies, the common pathogens Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumanii, Pseudomonas aeruginosa and Escherichia coli were tested. TBBPA selectively exerted antimicrobial effects against Gram-positive bacteria, consistent with our previous findings (7). TBBPA inhibited the in vitro growth of SA and MRSA at a concentration of 4 or 2 µg/mL, respectively (Table 1).…”

supporting

confidence: 92%

“…TBBPA is used in epoxy resins to retard fire (6). Previous findings from our laboratory showing Gram-positive specific antimicrobial activity of TBBPA (7) led us to further study this activity against common pathogens, focusing on in vitro and in vivo antibacterial activity against SA. The primary objective of this study was to evaluate the use of TBBPA as a treatment for bacterial infection.…”

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confidence: 99%

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Antimicrobial Activity of Tetrabromobisphenol A (TBBPA) against Staphylococcus aureus Skin Infections

Wang

Chen

et al. 2018

Preprint

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Tetrabromobisphenol A (TBBPA) is a brominated flame retardant with selective 16 antimicrobial activity against Gram-positive bacteria. We show that TBBPA exerts bactericidal 17 effects by damaging the cell wall and membrane of Staphylococcus aureus (SA) without inducing 18 antimicrobial resistance. In vivo skin infection assays indicate that a low dose of TBBPA could 19contribute to wound closure and attenuate SA infection and inflammatory infiltration. TBBPA has 20 potential for use as an antimicrobial agent against Gram-positive pathogens.

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confidence: 92%

mentioning

confidence: 99%

Antimicrobial Activity of Tetrabromobisphenol A (TBBPA) against Staphylococcus aureus Skin Infections

Wang

Chen

et al. 2018

Preprint

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“…A recent study showed that halogen substitution neighboring the phenolic hydroxyl groups of bisphenol A analogues significantly enhanced their antimicrobial activity. 7 Despite the importance of the molecular structure of organic pollutants, extracting this information can be a great challenge for substances of unknown or variable composition, complex reaction products, and biological materials (UVCBs). 8 In particular, this challenge has existed for decades for the UVCBs known as chlorinated paraffins (CPs).…”

Section: Introductionmentioning

confidence: 99%

Chlorines Are Not Evenly Substituted in Chlorinated Paraffins: A Predicted NMR Pattern Matching Framework for Isomeric Discrimination in Complex Contaminant Mixtures

Yuan

Lysak

Soong

et al. 2020

Environ. Sci. Technol. Lett.

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Chlorinated paraffins (CPs) can be mixtures of nearly a half-million possible isomers. Despite the extensive use of CPs, their isomer composition and effects on the environment remain poorly understood. Here, we reveal the isomeric distributions of nine CP mixtures with single-chain lengths (C 14/15 ) and varying degrees of chlorination. The molar distribution of C n H 2 n+ 2 –m Cl m in each mixture was determined using high-resolution mass spectrometry (MS). Next, the mixtures were analyzed by applying both one-dimensional 1 H, 13 C and two-dimensional nuclear magnetic resonance (NMR) spectroscopy. Due to substantially overlapping signals in the experimental NMR spectra, direct assignment of individual isomers was not possible. As such, a new NMR spectral matching approach that used massive NMR databases predicted by a neural network algorithm to provide the top 100 most likely structural matches was developed. The top 100 isomers appear to be an adequate representation of the overall mixture. Their modeled physicochemical and toxicity parameters agree with previous experimental results. Chlorines are not evenly distributed in any of the CP mixtures and show a general preference at the third carbon. The approach described here can play a key role in understanding of complex isomeric mixtures such as CPs that cannot be resolved by MS alone.

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“…[3 -15] The levels of TCBPA, TBBPA/S, and their derivatives and transformations are increasing year by year in the environment, which leads to potential environmental and human-health risks. [1,[16][17][18][19][20][21][22][23] For instance, they have been detected in umbilical-cord serum and in breast milk with concentrations up to 649.45 ng/g and 11 ng/g, respectively. [24,25] Evidence suggests that HFRs exhibit potential neurotoxicity, endocrine disruption effects on bio-organisms, and reproductive-development toxicity.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, HFRs have become ubiquitous environmental contaminants and are detected frequently in various matrices, such as air, sewage sludge, sediment, soil, mankind and animal tissues [3–15] . The levels of TCBPA, TBBPA/S, and their derivatives and transformations are increasing year by year in the environment, which leads to potential environmental and human‐health risks [1,16–23] . For instance, they have been detected in umbilical‐cord serum and in breast milk with concentrations up to 649.45 ng/g and 11 ng/g, respectively [24,25] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted‐Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant

Guo

Cao

et al. 2020

Chemistry & Biodiversity

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As an important branch of halogenated bisphenol compounds, the halogenated bisphenol monosubstitutedether compounds have received a lot of attention in environmental health science because of their toxicity and variability. In this study, a synthetic method for bisphenol monosubstituted-ether byproduct libraries was developed. By using the versatile and efficient method, tetrachlorobisphenol A, tetrabromobisphenol A, and tetrabromobisphenol S monosubstituted alkyl-ether compounds were accessed in 39-82 % yield. Subsequently, the cytotoxicity of 27 compounds were screened using three different cell lines (HepG2, mouse primary astrocytes and Chang liver cells). Compound 2,6-dibromo-4-[3,5-dibromo-4-(2-hydroxyethoxy)benzene-1sulfonyl]phenol was more toxic than other compounds in various cells, and the sensitivity of this compound to the normal hepatocytes and cancer cells was inconsistent. The compounds 2,6-dichloro-4-(2-{3,5-dichloro-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-yl)phenol and 2,6-dibromo-4-(2-{3,5-dibromo-4-[(prop-2-en-1-yl)oxy]-phenyl}propan-2-yl)phenol were the most toxic to HepG2 cells, and most of the other compounds inhibited cell proliferation. Moreover, typical compounds were also reproductive and developmental toxic to zebrafish embryos at different concentrations. The synthetic byproduct libraries could be used as pure standard compounds and applied in research on environmental behavior and the transformation of halogenated flame retardants.

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Tetrabromobisphenol A (TBBPA) exhibits specific antimicrobial activity against Gram-positive bacteria without detectable resistance

Abstract: We report here the antimicrobial ability of tetrabromobisphenol A (TBBPA) against Gram-positive bacteria without detectable resistance.

Cited by 12 publications

References 21 publications

Antimicrobial Activity of Tetrabromobisphenol A (TBBPA) against Staphylococcus aureus Skin Infections

Antimicrobial Activity of Tetrabromobisphenol A (TBBPA) against Staphylococcus aureus Skin Infections

Chlorines Are Not Evenly Substituted in Chlorinated Paraffins: A Predicted NMR Pattern Matching Framework for Isomeric Discrimination in Complex Contaminant Mixtures

Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted‐Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant

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