Structure-activity relationship for noncoplanar polychlorinated biphenyl congeners toward the ryanodine receptor-Ca2+ channel complex type 1 (RyR1)

Chem Res Toxicol. 2006 Jan;19(1):92-101. doi: 10.1021/tx050196m.

Abstract

Ryanodine receptor isoforms are expressed in both excitable and nonexcitable tissues where they form microsomal Ca2+ release channels broadly involved in shaping cellular signaling. In this report, we provide a detailed structure-activity relationship (SAR) for polychlorinated biphenyl (PCB) congeners and metabolites necessary for enhancing ryanodine receptor type 1 (RyR1) activity using [3H]ryanodine ([3H]Ry) binding analysis. The 2,3,6-Cl PCB configuration is most important for optimal recognition by the RyR1 complex and/or critical for sensitizing its activation. Para substitution(s) diminishes the activity with para-chloro having a higher potency than the corresponding para-hydroxy derivative. The addition of a more bulky para-methyl-sulfonyl group eliminates the activity toward RyR1, supporting the importance of the para positions in binding RyR1. The requirement for an intact major T cell immunophilin FKBP12-RyR1 complex was observed with each of 12 active PCB congeners indicating a common mechanism requiring an immunophilin-regulated Ca2+ release channel. An excellent correlation between the relative potencies for doubling [3H]Ry binding and the corresponding initial rates of PCB-induced Ca2+ efflux indicates that [3H]Ry binding analysis provides a measure of dysregulation of microsomal Ca2+ transport. The SAR for activating RyR1 is consistent with those previously reported in several in vivo and in vitro studies, suggesting that a common mechanism may contribute to the toxicity of noncoplanar PCBs. A practical application of the receptor-based screen developed here with RyR1 is that it provides a quantitative SAR that may be useful in predicting biological activity and risk of mixtures containing noncoplanar PCB congeners that have low or a lack of aryl hydrocarbon receptor activity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Calcium / metabolism
  • Complex Mixtures / analysis
  • Environmental Pollutants / analysis
  • Environmental Pollutants / toxicity*
  • Immunosuppressive Agents / pharmacology
  • In Vitro Techniques
  • Polychlorinated Biphenyls / analysis
  • Polychlorinated Biphenyls / toxicity*
  • Quantitative Structure-Activity Relationship*
  • Rabbits
  • Risk Assessment
  • Ryanodine / metabolism
  • Ryanodine Receptor Calcium Release Channel / drug effects*
  • Ryanodine Receptor Calcium Release Channel / metabolism
  • Sarcoplasmic Reticulum / metabolism
  • Sirolimus / pharmacology
  • Tacrolimus Binding Protein 1A / antagonists & inhibitors
  • Tacrolimus Binding Protein 1A / metabolism

Substances

  • Complex Mixtures
  • Environmental Pollutants
  • Immunosuppressive Agents
  • Ryanodine Receptor Calcium Release Channel
  • Ryanodine
  • Polychlorinated Biphenyls
  • Tacrolimus Binding Protein 1A
  • Calcium
  • Sirolimus