7-Substituted-2,3-dichlorodibenzo-p-dioxins as competitive ligands for the Ah receptor: Quantitative structure-activity relationships (QSARs) and a comparison of human receptor with Ah receptor from rodents

Rebecca D. Prokipcak, Cheryl L. Golas, David K. Manchester, Allan B. Okey, Steven Safe, Toshio Fujita

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The competitive binding affinities of thirteen 7-substituted-2,3,-dichlorodibenzo-p-dioxins to the human Ah placental cytosolic Ah receptor were determined versus [3H]-2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) as the radioligand. Multiple parameter linear regression analysis of the competitive binding EC50 values for these compounds gave the following equation: pEC50 (M)=6.246+1.632 π - 1.764σ + 1.282 HB. were π is the substituent lipophilicity, σ the meta-directing electronegativity and HB the hydrogen binding capacity. The equation obtained using human placental receptor was different than correlations previously derived for the binding of the same series of compounds to the rat, mouse, guinea pig or hamster cytosolic Ah receptor, providing further evidence for interspecies differences in the properties of the Ah receptor protein.

Original languageEnglish (US)
Pages (from-to)1221-1228
Number of pages8
JournalChemosphere
Volume20
Issue number7-9
DOIs
StatePublished - 1990

ASJC Scopus subject areas

  • Environmental Engineering
  • Environmental Chemistry
  • Chemistry(all)
  • Pollution
  • Public Health, Environmental and Occupational Health
  • Health, Toxicology and Mutagenesis

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