The DOI matches its Crossref record; 27 of the 27 references it cites were found in a registry or an index.
Polychlorinated biphenyls as hormonally active structural analogues.
Open accessAbstract
Among the environmental chemicals that may be able to disrupt the endocrine systems of animals and humans, the polychlorinated biphenyls (PCBs) are a chemical class of considerable concern. One possible mechanism by which PCBs may interfere with endocrine function is their ability to mimic natural hormones. These actions reflect a close relationship between the physicochemical properties encoded in the PCB molecular structure and the responses they evoke in biological systems. These physicochemical properties determine the molecular reactivities of PCBs and are responsible for their recognition at biological acceptors and receptors, as well as for triggering molecular mechanisms that lead to tissue response. "Coplanarity" of PCB phenyl rings and "laterality" of chlorine atoms are important structural features determining specific binding behavior with proteins and certain toxic responses in biological systems. We compare qualitative structure-activity relationships for PCBs with the limited information on the related non-coplanar chlorinated diphenyl ethers, providing further insights into the nature of the molecular recognition processes and support for the structural relationship of PCBs to thyroid hormones. Steroidlike activity requires conformational restriction and possibly hydroxylation. We offer some simple molecular recognition models to account for the importance of these different structural features in the structure-activity relationships that permit one to express PCB reactivities in terms of dioxin, thyroxine, and estradiol equivalents. The available data support the involvement of PCBs as mimics of thyroid and other steroidal hormones. The potential for reproductive and developmental toxicity associated with human exposure to PCBs is of particular concern.(ABSTRACT TRUNCATED AT 250 WORDS)
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Cites
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Self-citationEstrogenic and antiestrogenic actions of PCBs in the female rat: In vitro and in vivo studies
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Neurotoxicity of polychlorinated biphenyls: Structure-activity relationship of individual congeners
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Endocrine-Disrupting Chemicals: An Endocrine Society Scientific Statement
Diamanti-Kandarakis, E., Bourguignon, J.-P., Giudice, L. C., Hauser, R., Prins, G. S., Soto, A. M., Zoeller, R. T., & Gore, A. C. (2009) · Endocrine Reviews · doi:10.1210/er.2009-0002 · Cited by 4,585
Toxic equivalency factors (TEFs) for PCBs, PCDDs, PCDFs for humans and wildlife.
Van den Berg, M., Birnbaum, L., Bosveld, A. T., Brunström, B., Cook, P., Feeley, M., Giesy, J. P., Hanberg, A., Hasegawa, R., Kennedy, S. W., et al. (1998) · Environmental Health Perspectives · doi:10.1289/ehp.98106775 · Cited by 3,301
Herman-Giddens, M. E., Slora, E. J., Wasserman, R. C., Bourdony, C. J., Bhapkar, M. V., Koch, G. G., & Hasemeier, C. M. (1997) · PEDIATRICS · doi:10.1542/peds.99.4.505 · Cited by 1,709
Polybrominated diphenyl ethers: occurrence, dietary exposure, and toxicology.
Darnerud, P. O., Eriksen, G. S., Jóhannesson, T., Larsen, P. B., & Viluksela, M. (2001) · Environmental Health Perspectives · doi:10.1289/ehp.01109s149 · Cited by 1,046
Thyroid Hormone Action Is Disrupted by Bisphenol A as an Antagonist
Moriyama, K., Tagami, T., Akamizu, T., Usui, T., Saijo, M., Kanamoto, N., Hataya, Y., Shimatsu, A., Kuzuya, H., & Nakao, K. (2002) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jc.2002-020209 · Cited by 812
Metadata
- Authors
- McKinney, J. D., & Waller, C. L.
- Venue
- Environmental Health Perspectives
- Publisher
- American Chemical Society (ACS)
- Published
- 1994-03
- Volume
- 102
- Issue
- 3
- Pages
- 290-297
- ISSN
- 0091-6765 (ISSN-L)
- 1552-9924
- OpenAlex
- W2012211548
- Cited by
- 306
- References
- 27
- FWCI
- 11.27
- Type
- journal article
- Language
- en
- Open access
- gold
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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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