Quantification of the Conjugated Forms of Dichlorobisphenol A (3,3'-Cl 2 BPA) in Rat and Human Plasma Using HPLC-MS/MS.
Journal
Therapeutic drug monitoring
ISSN: 1536-3694
Titre abrégé: Ther Drug Monit
Pays: United States
ID NLM: 7909660
Informations de publication
Date de publication:
01 08 2023
01 08 2023
Historique:
received:
18
08
2022
accepted:
28
10
2022
medline:
13
7
2023
pubmed:
18
1
2023
entrez:
17
1
2023
Statut:
ppublish
Résumé
Bisphenol A (BPA) is a ubiquitous contaminant that has endocrine-disrupting effects. Chlorinated derivatives of BPA are formed during chlorination of drinking water and have higher endocrine-disrupting activity. Dichlorobisphenol A (Cl 2 BPA) is the most abundant chlorinated BPA derivative found in several human biological matrices. Recent in vitro experiments have shown that Cl 2 BPA is metabolized in sulpho- and glucuro-conjugated compounds. To date, no assay has been developed to quantify the sulfo- and glucuro-conjugates of 3,3'-Cl 2 BPA (3,3'-Cl 2 BPA-S and 3,3'-Cl 2 BPA-G, respectively). A high-performance liquid chromatography-tandem mass spectrometry assay for the determination of 3,3'-Cl 2 BPA conjugated forms in plasma samples was developed and validated according to the European Medicines Agency guidelines. Quantification was performed in the multiple reaction monitoring mode for all target analytes using a SCIEX 6500 + tandem mass spectrometer with an electrospray source operating in the negative ionization mode. Chromatographic separation was achieved using a C18 column maintained at 40°C and a binary mobile phase delivered in the gradient mode at a flow rate of 0.35 mL/min. Sample was prepared via simple precipitation using acetonitrile. The assay was validated and applied to rat and human plasma samples. Linearity was demonstrated over the range of 0.006-25 ng/mL for 3,3'-Cl 2 BPA-G and 0.391-100 ng/mL for 3,3'-Cl 2 BPA-S. Intraday and interday bias values were in the 95%-109% range, and the imprecision <9%. Internal standard corrected matrix effects were also investigated. This method enabled quantification of the conjugated forms of 3,3'-Cl 2 BPA in plasma samples. This is the first report on the development and validation of an analytical method for the quantification of 3,3'-Cl 2 BPA-G and 3,3'-Cl 2 BPA-S in the plasma matrix. This study is also the first report on the in vivo occurrence of these metabolites.
Sections du résumé
BACKGROUND
Bisphenol A (BPA) is a ubiquitous contaminant that has endocrine-disrupting effects. Chlorinated derivatives of BPA are formed during chlorination of drinking water and have higher endocrine-disrupting activity. Dichlorobisphenol A (Cl 2 BPA) is the most abundant chlorinated BPA derivative found in several human biological matrices. Recent in vitro experiments have shown that Cl 2 BPA is metabolized in sulpho- and glucuro-conjugated compounds. To date, no assay has been developed to quantify the sulfo- and glucuro-conjugates of 3,3'-Cl 2 BPA (3,3'-Cl 2 BPA-S and 3,3'-Cl 2 BPA-G, respectively).
METHODS
A high-performance liquid chromatography-tandem mass spectrometry assay for the determination of 3,3'-Cl 2 BPA conjugated forms in plasma samples was developed and validated according to the European Medicines Agency guidelines. Quantification was performed in the multiple reaction monitoring mode for all target analytes using a SCIEX 6500 + tandem mass spectrometer with an electrospray source operating in the negative ionization mode. Chromatographic separation was achieved using a C18 column maintained at 40°C and a binary mobile phase delivered in the gradient mode at a flow rate of 0.35 mL/min. Sample was prepared via simple precipitation using acetonitrile. The assay was validated and applied to rat and human plasma samples.
RESULTS
Linearity was demonstrated over the range of 0.006-25 ng/mL for 3,3'-Cl 2 BPA-G and 0.391-100 ng/mL for 3,3'-Cl 2 BPA-S. Intraday and interday bias values were in the 95%-109% range, and the imprecision <9%. Internal standard corrected matrix effects were also investigated. This method enabled quantification of the conjugated forms of 3,3'-Cl 2 BPA in plasma samples.
CONCLUSIONS
This is the first report on the development and validation of an analytical method for the quantification of 3,3'-Cl 2 BPA-G and 3,3'-Cl 2 BPA-S in the plasma matrix. This study is also the first report on the in vivo occurrence of these metabolites.
Identifiants
pubmed: 36649713
doi: 10.1097/FTD.0000000000001074
pii: 00007691-202308000-00013
doi:
Substances chimiques
3,3'-dichlorobisphenol A
0
Banques de données
ClinicalTrials.gov
['NCT04788810']
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
554-561Informations de copyright
Copyright © 2023 Wolters Kluwer Health, Inc. All rights reserved.
Déclaration de conflit d'intérêts
The authors declare no conflict of interest.
Références
ANSES, Evaluation des risques du bisphenol A (BPA) pour la santé humaine. In: Bergman Å. United Nations Environment Programme, World Health Organization. State of the Science of Endocrine Disrupting Chemicals—2012 an Assessment of the State of the Science of Endocrine Disruptors. Geneva: WHO: UNEP; 2013.
Fukazawa H, Hoshino K, Shiozawa T, et al. Identification and quantification of chlorinated bisphenol A in wastewater from wastepaper recycling plants. Chemosphere. 2001;44:973–979.
Gallart-Ayala H, Moyano E, Galceran MT. On-line solid phase extraction fast liquid chromatography-tandem mass spectrometry for the analysis of bisphenol A and its chlorinated derivatives in water samples. J Chromatogr A. 2010;1217:3511–3518.
Takemura H, Ma J, Sayama K, et al. In vitro and in vivo estrogenic activity of chlorinated derivatives of bisphenol A. Toxicology. 2005;207:215–221.
Hu JY, Aizawa T, Ookubo S. Products of aqueous chlorination of bisphenol A and their estrogenic activity. Environ Sci Technol. 2002;36:1980–1987.
Andra SS, Makris KC. Association between urinary levels of bisphenol A and its monochlorinated derivative and obesity. J Environ Sci Health A. 2015;50:1169–1179.
Andra SS, Kalyvas H, Andrianou XD, et al. Preliminary evidence of the association between monochlorinated bisphenol A exposure and type II diabetes mellitus: a pilot study. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2015;50:243–259.
Hu C, Schottker B, Venisse N, et al. Bisphenol A, Chlorinated derivatives of bisphenol A and occurrence of myocardial infarction in patients with type 2 diabetes: nested case-control studies in two European cohorts. Environ Sci Technol. 2019;53:9876–9883.
Kalyvas H, Andra S, Charisiadis P, et al. Influence of household cleaning practices on the magnitude and variability of urinary monochlorinated bisphenol A. Sci Total Environ. 2014;490:254–261.
Zhou Y, Chen M, Zhao F, et al. Ubiquitous occurrence of chlorinated byproducts of bisphenol A and nonylphenol in bleached food contacting papers and their implications for human exposure. Environ Sci Technol. 2015;49:7218–7226.
Kitamura S, Jinno N, Ohta S, et al. Thyroid hormonal activity of the flame retardants tetrabromobisphenol A and tetrachlorobisphenol A. Biochem Biophysical Res Commun. 2002;293:554–559.
Nieuwenhuijsen M, Paustenbach D, Duarte-Davidson R. New developments in exposure assessment: the impact on the practice of health risk assessment and epidemiological studies. Environ Int. 2006;32:996–1009.
Liao C, Kannan K. Determination of free and conjugated forms of bisphenol A in human urine and serum by liquid chromatography-tandem mass spectrometry. Environ Sci Technol. 2012;46:5003–5009.
Fernandez MF, Arrebola J, Taoufiki J, et al. Bisphenol-A and chlorinated derivatives in adipose tissue of women. Reprod Toxicol. 2007;24:259–264.
Cariot A, Dupuis A, Albouy-Llaty M, et al. Reliable quantification of bisphenol A and its chlorinated derivatives in human breast milk using UPLC-MS/MS method. Talanta. 2012;100:175–182.
Migeot V, Dupuis A, Cariot A, et al. Bisphenol A and its chlorinated derivatives in human colostrum. Environ Sci Technol. 2013;47:13791–13797.
Li A, Zhuang T, Shi W, et al. Serum concentration of bisphenol analogues in pregnant women in China. Sci Total Environ. 2020;707:136100.
Del Olmo M, Zafra A, Suarez B, et al. Use of solid-phase microextraction followed by on-column silylation for determining chlorinated bisphenol A in human plasma by gas chromatography-mass spectrometry. J Chromatogr B. 2005;817:167–172.
Cambien G, Venisse N, Migeot V, et al. Simultaneous determination of bisphenol A and its chlorinated derivatives in human plasma: development, validation and application of a UHPLC-MS/MS method. Chemosphere. 2020;242:125236.
Vela-Soria F, Jimenez-Diaz I, Rodriguez-Gomez R, et al. A multiclass method for endocrine disrupting chemical residue analysis in human placental tissue samples by UHPLC–MS/MS. Anal Methods. 2011;3:2073.
Jimenez-Diaz I, Zafra-Gomez A, Ballesteros O, et al. Determination of bisphenol A and its chlorinated derivatives in placental tissue samples by liquid chromatography-tandem mass spectrometry. J Chromatogr B. 2010;878:3363–3369.
Andra SS, Charisiadis P, Arora M, et al. Biomonitoring of human exposures to chlorinated derivatives and structural analogs of bisphenol A. Environ Int. 2015;85:352–379.
Heindel JJ, Skalla LA, Joubert BR, et al. Review of developmental origins of health and disease publications in environmental epidemiology. Reprod Toxicol. 2017;68:34–48.
Schonfelder G, Wittfoht W, Hopp H, et al. Parent bisphenol A accumulation in the human maternal-fetal-placental unit. Environ Health Perspect. 2002;110:703–707.
Somm E, Schwitzgebel VM, Toulotte A, et al. Perinatal exposure to bisphenol A alters early adipogenesis in the rat. Environ Health Perspect. 2009;117:1549–1555.
Bosquiazzo VL, Varayoud J, Munoz-de-Toro M, et al. Effects of neonatal exposure to bisphenol A on steroid regulation of vascular endothelial growth factor expression and endothelial cell proliferation in the adult rat uterus. Biol Reprod. 2010;82:86–95.
Bromer JG, Zhou Y, Taylor MB, et al. Bisphenol-A exposure in utero leads to epigenetic alterations in the developmental programming of uterine estrogen response. FASEB J. 2010;24:2273–2280.
Chen M, Fan Z, Zhao F, et al. Occurrence and maternal transfer of chlorinated bisphenol A and nonylphenol in pregnant women and their matching embryos. Environ Sci Technol. 2016;50:970–977.
Grignon C, Dupuis A, Albouy-Llaty M, et al. Validation of a probe for assessing deconjugation of glucuronide and sulfate phase II metabolites assayed through LC-MS/MS in biological matrices. J Chromatogr B Analyt Technol Biomed Life Sci. 2017;1061–1062:72–78.
Calafat AM, Koch HM; Endorsees. BPA and risk assessment. Lancet Diabetes Endocrinol. 2020;8:269–270.
European Medicines Agency. Guideline on Bioanalytical Method of Validation. Sciences Medicines Health; 2012:23. Available at: https://www.ema.europa.eu/en/documents/scientific-guideline/guideline-bioanalytical-method-validation_en.pdf .
Grignon C, Venisse N, Rouillon S, et al. Ultrasensitive determination of bisphenol A and its chlorinated derivatives in urine using a high-throughput UPLC-MS/MS method. Anal Bioanal Chem. 2016;408:2255–2263.
Dupuis A, Rabouan S, Migeot V, et al. BPA and risk assessment. Lancet Diabetes Endocrinol. 2020;8:270–271.
Calafat AM, Koch HM, Swan SH, et al. Misuse of blood serum to assess exposure to bisphenol A and phthalates. Breast Cancer Res. 2013;15:403.
Plattard N, Venisse N, Carato P, et al. Hepatic metabolism of chlorinated derivatives of Bisphenol A (ClxBPA) and interspecies differences between rats and humans. Arch Toxicol. 2022;96:783–792.
Gerona R, Vom Saal FS, Hunt PA. BPA: have flawed analytical techniques compromised risk assessments? Lancet Diabetes Endocrinol. 2020;8:11–13.
Glauser M, Metrailler M, Gerber-Lemaire S, et al. Enzyme and acid deconjugation of plasma sulfated metanephrines. Clinica Chim Acta. 2014;430:125–128.
Sonker AK, Bhateria M, Karsauliya K, et al. Investigating the glucuronidation and sulfation pathways contribution and disposition kinetics of bisphenol S and its metabolites using LC-MS/MS-based nonenzymatic hydrolysis method. Chemosphere. 2021;273:129624.
Ye X, Bishop AM, Reidy JA, et al. Temporal stability of the conjugated species of bisphenol A, parabens, and other environmental phenols in human urine. J Expo Sci Environ Epidemiol. 2007;17:567–572.
Ginsberg G, Rice DC. Does rapid metabolism ensure negligible risk from bisphenol A? Environ Health Perspect. 2009;117:1639–1643.
Takahashi O, Oishi S. Disposition of orally administered 2, 2-Bis(4-hydroxyphenyl)propane (bisphenol A) in pregnant rats and the placental transfer to fetuses. Environ Health Perspect. 2000;108:931–935.
Riu A, le Maire A, Grimaldi M, et al. Characterization of novel ligands of ERα, Erβ, and PPARγ: the case of halogenated bisphenol A and their conjugated metabolites. Toxicol Sci. 2011;122:372–382.
Volkel W, Bittner N, Dekant W. Quantitation of bisphenol A and bisphenol A glucuronide in biological samples by high performance liquid chromatography-tandem mass spectrometry. Drug Metab Dispos. 2005;33:1748–1757.
Vandenberg LN, Gerona RR, Kannan K, et al. A round robin approach to the analysis of bisphenol A (BPA) in human blood samples. Environ Health. 2014;13:25.
Andra SS, Austin C, Yang J, et al. Recent advances in simultaneous analysis of bisphenol A and its conjugates in human matrices: exposure biomarker perspectives. Sci Total Environ. 2016;572:770–781.