Polychlorinated biphenyls as hormonally active structural analogues

Journal Article · Tue Mar 01 00:00:00 EST 1994 · Environmental Health Perspectives; (United States)

DOI:https://doi.org/10.1289/ehp.94102290· OSTI ID:6755625

McKinney, J D ^[1]; Waller, C L ^[2]

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1. Environmental Protection Agency, Research Triangle Park, NC (United States)
2. Washington Univ., St. Louis, MO (United States)

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 physiocochemical properties determine the molecular reactivities of PCBs and are responsible for their recognition as biological acceptors and receptors, as well as for triggering molecular mechanisms that lead to tissue response. [open quotes]Coplanarity[close quotes] of PCB phenyl rings and [open quotes]laterality[close quotes] 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. Steriodlike activity requires conformational restriction and possibility 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. 53 refs., 6 figs.

• OSTI ID: 6755625
• Journal Information: Environmental Health Perspectives; (United States), Vol. 102:3; ISSN 0091-6765
• Country of Publication: United States
• Language: English

Related Subjects

63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
POLYCHLORINATED BIPHENYLS
BIOCHEMICAL REACTION KINETICS
MOLECULAR STRUCTURE
RECEPTORS
STRUCTURE-ACTIVITY RELATIONSHIPS
BIOLOGICAL PATHWAYS
THYROID HORMONES
TOXICITY
AROMATICS
CHLORINATED AROMATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HORMONES
KINETICS
MEMBRANE PROTEINS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
PEPTIDE HORMONES
PROTEINS
REACTION KINETICS
560300* - Chemicals Metabolism & Toxicology