Glucuronide and sulfate conjugates of tetrabromobisphenol A (TBBPA): Chemical synthesis and correlation between their urinary levels and plasma TBBPA content in voluntary human donors

Ho Ka-Lok; Yuen Ka-Ki; Yau Man-Shan; Murphy Margaret B.; Wan Yi; Fong Bonnie M. -W.; Tam Sidney; Giesy John P.; Leung Kelvin S. -Y.; Lam Michael H. -W.

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Glucuronide and sulfate conjugates of tetrabromobisphenol A (TBBPA): Chemical synthesis and correlation between their urinary levels and plasma TBBPA content in voluntary human donors

机译：四溴双酚A（TBBPA）的葡萄糖醛酸化物和硫酸盐结合物：自愿人类供体的化学合成及其在尿中的含量与血浆TBBPA含量之间的相关性

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3,3', 5,5'-Tetrabromobisphenol-A (TBBPA) is an important brominated flame retardant in epoxy, vinyl esters and polycarbonate resins. Previous studies have already shown the occurrence of its Phase II metabolites, TBBPA-glucuronide and sulfate conjugates, in human urine, after oral administration of TBBPA. The main objective of this work is to examine correlations among level of TBBPA in human blood and those of its Phase II metabolites in human urine. Four water-soluble TBBPA conjugates were synthesized, purified and characterized. An analytical protocol using solid-phase extraction and liquid chromatography-electrospray tandem mass spectrometry (SPE-LC-MS/MS) quantification was developed for the simultaneous analysis of these glucuronide and sulfate conjugates in human urine samples. TBBPA and its Phase II metabolites in paired human plasma and urine samples collected randomly from 140 voluntary donors in Hong Kong SAR, China, were determined. One or more TBBPA conjugates were detected in all of the urine samples, with concentration ranging from 0.19 to 127.24 mu g g(-1)-creatinine. TBBPA was also quantified in >85% of the plasma and urine samples. Strong correlations were observed between TBBPA content in plasma and the total amount of TBBPA-related compounds in urine. (C) 2016 Elsevier Ltd. All rights reserved.

机译：3,3'，5,5'-四溴双酚-A（TBBPA）是环氧，乙烯基酯和聚碳酸酯树脂中的重要溴化阻燃剂。先前的研究已经显示，口服TBBPA后，其II期代谢产物，TBBPA-葡萄糖醛酸和硫酸盐结合物在人尿中发生。这项工作的主要目的是检查人血中TBBPA水平与人尿中其II期代谢产物之间的相关性。合成，纯化和表征了四种水溶性TBBPA缀合物。建立了使用固相萃取和液相色谱-电喷雾串联质谱（SPE-LC-MS / MS）定量的分析方案，用于同时分析人尿液样品中的这些葡糖醛酸苷和硫酸盐结合物。确定了从中国香港特别行政区的140名自愿捐赠者中随机采集的成对人血浆和尿液样本中的TBBPA及其II期代谢产物。在所有尿液样本中检测到一种或多种TBBPA缀合物，浓度范围为0.19至127.24μg g（-1）-肌酸酐。还对> 85％的血浆和尿液样本中的TBBPA进行了定量。血浆中TBBPA含量与尿中TBBPA相关化合物的总量之间存在很强的相关性。（C）2016 Elsevier Ltd.保留所有权利。

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来源
《Environment international》 |2017年第1期|46-53|共8页
作者
Ho Ka-Lok; Yuen Ka-Ki; Yau Man-Shan; Murphy Margaret B.; Wan Yi; Fong Bonnie M. -W.; Tam Sidney; Giesy John P.; Leung Kelvin S. -Y.; Lam Michael H. -W.;
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作者单位

City Univ Hong Kong, Dept Biol & Chem, State Key Lab Marine Pollut, Tat Chee Ave, Kowloon, Hong Kong, Peoples R China;

City Univ Hong Kong, Dept Biol & Chem, State Key Lab Marine Pollut, Tat Chee Ave, Kowloon, Hong Kong, Peoples R China;

City Univ Hong Kong, Dept Biol & Chem, State Key Lab Marine Pollut, Tat Chee Ave, Kowloon, Hong Kong, Peoples R China;

City Univ Hong Kong, Dept Biol & Chem, State Key Lab Marine Pollut, Tat Chee Ave, Kowloon, Hong Kong, Peoples R China;

Univ Saskatchewan, Toxicol Ctr, Dept Vet Biomed Sci, Saskatoon, SK S7N 0W0, Canada|Peking Univ, Coll Urban & Environm Sci, Lab Earth Surface Proc, Beijing, Peoples R China;

Queen Mary Hosp, Div Clin Biochem, Hong Kong, Hong Kong, Peoples R China|Hong Kong Baptist Univ, Dept Chem, Hong Kong, Hong Kong, Peoples R China;

Queen Mary Hosp, Div Clin Biochem, Hong Kong, Hong Kong, Peoples R China;

City Univ Hong Kong, Dept Biol & Chem, State Key Lab Marine Pollut, Tat Chee Ave, Kowloon, Hong Kong, Peoples R China|Univ Saskatchewan, Toxicol Ctr, Dept Vet Biomed Sci, Saskatoon, SK S7N 0W0, Canada|Michigan State Univ, Dept Zool, E Lansing, MI 48824 USA|Michigan State Univ, Ctr Integrat Toxicol, E Lansing, MI 48824 USA;

Hong Kong Baptist Univ, Dept Chem, Hong Kong, Hong Kong, Peoples R China;

City Univ Hong Kong, Dept Biol & Chem, State Key Lab Marine Pollut, Tat Chee Ave, Kowloon, Hong Kong, Peoples R China;

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收录信息美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《化学文摘》(CA);
原文格式 PDF
正文语种 eng
中图分类
关键词
Tetrabromobisphenol-A; Glucuronide and sulfate conjugates; Body fluids; Human plasma; Human urine;

机译：四溴双酚-A;葡萄糖醛酸和硫酸盐结合物;体液;人体血浆;人体尿液;

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专利

1. Glucuronide and Sulfate Conjugates of Bisphenol A: Chemical Synthesis and Correlation Between Their Urinary Levels and Plasma Bisphenol A Content in Voluntary Human Donors [J] . Ho Ka-Lok, Yuen Ka-Ki, Yau Man-Shan, Archives of Environmental Contamination and Toxicology . 2017,第3期

机译：葡糖和双酚A的硫酸酯和硫酸缀合物A：其泌尿水平与血浆双酚之间的化学合成和相关性志愿人体供体中的含量
2. Dose- and time-dependent changes in tissue levels of tetrabromobisphenol A (TBBPA) and its sulfate and glucuronide conjugates following repeated administration to female Wistar Han Rats [J] . S.J. Borghoff, D. Wikoff, S. Harvey, Toxicology Reports . 2016,第5期

机译：对雌性Wistar汉鼠重复给药后，四溴双酚A（TBBPA）及其硫酸盐和葡萄糖醛酸化物结合物的组织水平随时间和时间变化
3. Identification of Emerging Brominated Chemicals as the Transformation Products of Tetrabromobisphenol A (TBBPA) Derivatives in Soil [J] . Aifeng Liu, Jianbo Shi, Guangbo Qu, Environmental Science & Technology . 2017,第10期

机译：确定新兴的溴化化学品作为土壤中四溴双酚A（TBBPA）衍生物的转化产物
4. Direct Speciation of Estrogen Glucuronide and Sulfate Conjugates in Human Urine by Capillary Electrophoresis-Time of Flight-Mass Spectrometry [C] . Naomi Janson, Dawn Stickle, Julie Marr, American Society for Mass Spectrometry Conference on Mass Spectrometry and Allied Topics . 2011

机译：通过飞行 - 质谱法通过毛细管电泳时间直接对人尿中硫酸糖醛酸和硫酸盐缀合物的直接形态
5. Effects of flame retardants, hexabromocyclododecane (HBCD) and tetrabromobisphenol a (TBBPA), on secretion of tumor necrosis factor alpha (TNFα) from human immune cells [D] . Yasmin, Sharia 2016

机译：阻燃剂六溴环十二烷（HBCD）和四溴双酚a（TBBPA）对人免疫细胞分泌肿瘤坏死因子α（TNFα）的影响
6. Dose- and time-dependent changes in tissue levels of tetrabromobisphenol A (TBBPA) and its sulfate and glucuronide conjugates following repeated administration to female Wistar Han Rats [O] . S.J. Borghoff, D. Wikoff, S. Harvey, 2016

机译：对雌性Wistar汉鼠重复给药后四溴双酚A（TBBPA）及其硫酸盐和葡萄糖醛酸化物结合物的组织水平随时间和时间变化
7. Dose- and time-dependent changes in tissue levels of tetrabromobisphenol A (TBBPA) and its sulfate and glucuronide conjugates following repeated administration to female Wistar Han Rats [O] . S.J. Borghoff, D. Wikoff, S. Harvey, 2016

机译：雌性Wistar Han大鼠重复给药后四溴双酚a（TBBpa）及其硫酸盐和葡萄糖醛酸结合物组织水平的剂量和时间依赖性变化

Glucuronide and sulfate conjugates of tetrabromobisphenol A (TBBPA): Chemical synthesis and correlation between their urinary levels and plasma TBBPA content in voluntary human donors

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