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

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

doi:10.1016/j.envint.2016.09.018

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

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

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

43 Citations (Scopus)

Abstract

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 μg 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.

Original language	English
Pages (from-to)	46-53
Number of pages	8
Journal	Environment International
Volume	98
DOIs	https://doi.org/10.1016/j.envint.2016.09.018
Publication status	Published - 1 Jan 2017

Scopus Subject Areas

Environmental Science(all)

User-Defined Keywords

Body fluids
Glucuronide and sulfate conjugates
Human plasma
Human urine
Tetrabromobisphenol-A

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10.1016/j.envint.2016.09.018

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Ho, K. L., Yuen, K. K., Yau, M. S., Murphy, M. B., Wan, Y., Fong, B. M. W., Tam, S., Giesy, J. P., LEUNG, K. S. Y., & Lam, M. H. W. (2017). Glucuronide and sulfate conjugates of tetrabromobisphenol A (TBBPA): Chemical synthesis and correlation between their urinary levels and plasma TBBPA content in voluntary human donors. Environment International, 98, 46-53. https://doi.org/10.1016/j.envint.2016.09.018

@article{99d9ad60f40f4b61b9b38555c872dc92,

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

abstract = "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 μg 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.",

keywords = "Body fluids, Glucuronide and sulfate conjugates, Human plasma, Human urine, Tetrabromobisphenol-A",

author = "Ho, {Ka Lok} and Yuen, {Ka Ki} and Yau, {Man Shan} and Murphy, {Margaret B.} and Yi Wan and Fong, {Bonnie M.W.} and Sidney Tam and Giesy, {John P.} and LEUNG, {Kelvin S Y} and Lam, {Michael H.W.}",

note = "Funding Information: This work is support by the State Key Laboratory for Marine Pollution, City University of Hong Kong , and a GRF grant CityU 160513 from the Research Grants Council of the Hong Kong Special Administrative Region, China. Prof. Giesy was supported by the program of 2012 “Great Concentration Foreign Experts” (#GDW20123200120) funded by the State Administration of Foreign Experts Affairs, the P.R. China to Nanjing University and the Einstein Professor Program of the Chinese Academy of Sciences. He was also supported by the Canada Research Chair program, a Visiting Distinguished Professorship in the Department of Biology and Chemistry and State Key Laboratory in Marine Pollution, City University of Hong Kong. ",

year = "2017",

month = jan,

day = "1",

doi = "10.1016/j.envint.2016.09.018",

language = "English",

volume = "98",

pages = "46--53",

journal = "Environment International",

issn = "0160-4120",

publisher = "Elsevier Ltd.",

}

Ho, KL, Yuen, KK, Yau, MS, Murphy, MB, Wan, Y, Fong, BMW, Tam, S, Giesy, JP, LEUNG, KSY & Lam, MHW 2017, 'Glucuronide and sulfate conjugates of tetrabromobisphenol A (TBBPA): Chemical synthesis and correlation between their urinary levels and plasma TBBPA content in voluntary human donors', Environment International, vol. 98, pp. 46-53. https://doi.org/10.1016/j.envint.2016.09.018

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 et al.
In: Environment International, Vol. 98, 01.01.2017, p. 46-53.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Glucuronide and sulfate conjugates of tetrabromobisphenol A (TBBPA)

T2 - Chemical synthesis and correlation between their urinary levels and plasma TBBPA content in voluntary human donors

AU - Ho, Ka Lok

AU - Yuen, Ka Ki

AU - Yau, Man Shan

AU - Murphy, Margaret B.

AU - Wan, Yi

AU - Fong, Bonnie M.W.

AU - Tam, Sidney

AU - Giesy, John P.

AU - LEUNG, Kelvin S Y

AU - Lam, Michael H.W.

N1 - Funding Information: This work is support by the State Key Laboratory for Marine Pollution, City University of Hong Kong , and a GRF grant CityU 160513 from the Research Grants Council of the Hong Kong Special Administrative Region, China. Prof. Giesy was supported by the program of 2012 “Great Concentration Foreign Experts” (#GDW20123200120) funded by the State Administration of Foreign Experts Affairs, the P.R. China to Nanjing University and the Einstein Professor Program of the Chinese Academy of Sciences. He was also supported by the Canada Research Chair program, a Visiting Distinguished Professorship in the Department of Biology and Chemistry and State Key Laboratory in Marine Pollution, City University of Hong Kong.

PY - 2017/1/1

Y1 - 2017/1/1

N2 - 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 μg 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.

AB - 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 μg 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.

KW - Body fluids

KW - Glucuronide and sulfate conjugates

KW - Human plasma

KW - Human urine

KW - Tetrabromobisphenol-A

UR - http://www.scopus.com/inward/record.url?scp=84997683098&partnerID=8YFLogxK

U2 - 10.1016/j.envint.2016.09.018

DO - 10.1016/j.envint.2016.09.018

M3 - Journal article

C2 - 27717582

AN - SCOPUS:84997683098

SN - 0160-4120

VL - 98

SP - 46

EP - 53

JO - Environment International

JF - Environment International

ER -

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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