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Hormone Activity of Hydroxylated Polybrominated Diphenyl Ethers on Human Thyroid Receptor-β: In Vitro and In Silico Investigations
Open accessAbstract
BACKGROUND: Hydroxylated polybrominated diphenyl ethers (HO-PBDEs) may disrupt thyroid hormone status because of their structural similarity to thyroid hormone. However, the molecular mechanisms of interactions with thyroid hormone receptors (TRs) are not fully understood. OBJECTIVES: We investigated the interactions between HO-PBDEs and TRbeta to identify critical structural features and physicochemical properties of HO-PBDEs related to their hormone activity, and to develop quantitative structure-activity relationship (QSAR) models for the thyroid hormone activity of HO-PBDEs. METHODS: We used the recombinant two-hybrid yeast assay to determine the hormone activities to TRbeta and molecular docking to model the ligand-receptor interaction in the binding site. Based on the mechanism of action, molecular structural descriptors were computed, selected, and employed to characterize the interactions, and finally a QSAR model was constructed. The applicability domain (AD) of the model was assessed by Williams plot. RESULTS: The 18 HO-PBDEs tested exhibited significantly higher thyroid hormone activities than did PBDEs (p < 0.05). Hydrogen bonding was the characteristic interaction between HO-PBDE molecules and TRbeta, and aromaticity had a negative effect on the thyroid hormone activity of HO-PBDEs. The developed QSAR model had good robustness, predictive ability, and mechanism interpretability. CONCLUSIONS: Hydrogen bonding and electrostatic interactions between HO-PBDEs and TRbeta are important factors governing thyroid hormone activities.
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Cites
PLS-regression: a basic tool of chemometrics
Wold, S., Sjöström, M., & Eriksson, L. (2001) · Chemometrics and Intelligent Laboratory Systems · doi:10.1016/s0169-7439(01)00155-1 · Cited by 10,084
Handbook of Molecular Descriptors
Todeschini, R., & Consonni, V. (2000) · Methods and Principles in Medicinal Chemistry · doi:10.1002/9783527613106 · Cited by 4,107 · cited 1×
“IA was calculated by DRAGON software (Todeschini and Consonni 2000).”
Golbraikh, A., & Tropsha, A. (2002) · Journal of Molecular Graphics and Modelling · doi:10.1016/s1093-3263(01)00123-1 · Cited by 3,735 · cited 2×
“3, indicating no over fitting in the model (Golbraikh and Tropsha 2002).”
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EDC-2: the endocrine society's second scientific statement on endocrine-disrupting chemicals
Gore, A. C., Chappell, V. A., Fenton, S. E., Flaws, J. A., Nadal, A., Prins, G. S., Toppari, J., & Zoeller, R. T. (2015) · Endocrine Reviews · doi:10.1210/er.2015-1010 · Cited by 2,407
Thyroid effects of endocrine disrupting chemicals
Boas, M., Feldt-Rasmussen, U., & Main, K. M. (2012) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2011.09.005 · Cited by 620
Metadata
- Authors
- Li, F., Xie, Q., Li, X., Li, N., Chi, P., Chen, J., Wang, Z., & Hao, C.
- Venue
- Environmental Health Perspectives
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-05
- Volume
- 118
- Issue
- 5
- Pages
- 602-606
- ISSN
- 0091-6765 (ISSN-L)
- 1552-9924
- OpenAlex
- W2078495475
- Cited by
- 228
- References
- 3
- FWCI
- 8.05
- Type
- journal article
- Language
- en
- Open access
- gold
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- Li, F., Xie, Q., Li, X., Li, N., Chi, P., Chen, J., Wang, Z., & Hao, C. (2010). Hormone Activity of Hydroxylated Polybrominated Diphenyl Ethers on Human Thyroid Receptor-β: In Vitro and In Silico Investigations. Environmental Health Perspectives. https://doi.org/10.1289/ehp.0901457
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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