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

doi:10.1016/0045-6535(90)90249-S

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 journal › Article › peer-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_m° + 1.282 HB. were π is the substituent lipophilicity, σ_m° 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 language	English (US)
Pages (from-to)	1221-1228
Number of pages	8
Journal	Chemosphere
Volume	20
Issue number	7-9
DOIs	https://doi.org/10.1016/0045-6535(90)90249-S
State	Published - 1990

ASJC Scopus subject areas

Environmental Engineering
Environmental Chemistry
General Chemistry
Pollution
Public Health, Environmental and Occupational Health
Health, Toxicology and Mutagenesis

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Prokipcak, R. D., Golas, C. L., Manchester, D. K., Okey, A. B., Safe, S., & Fujita, T. (1990). 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. Chemosphere, 20(7-9), 1221-1228. https://doi.org/10.1016/0045-6535(90)90249-S

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. / Prokipcak, Rebecca D.; Golas, Cheryl L.; Manchester, David K. et al.
In: Chemosphere, Vol. 20, No. 7-9, 1990, p. 1221-1228.

Research output: Contribution to journal › Article › peer-review

Prokipcak, RD, Golas, CL, Manchester, DK, Okey, AB, Safe, S & Fujita, T 1990, '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', Chemosphere, vol. 20, no. 7-9, pp. 1221-1228. https://doi.org/10.1016/0045-6535(90)90249-S

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title = "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",

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 - 1.764σm° + 1.282 HB. were π is the substituent lipophilicity, σm° 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.",

author = "Prokipcak, \{Rebecca D.\} and Golas, \{Cheryl L.\} and Manchester, \{David K.\} and Okey, \{Allan B.\} and Steven Safe and Toshio Fujita",

note = "Funding Information: The financial assistance of the National Cancer Institute of Canada to A.B.O. and the National Institutes of Health (ES03554) to S.S. is gratefully acknowledged. S. Safe is a Burroughs Wellcome Toxicology Scholar (1989-1994).",

year = "1990",

doi = "10.1016/0045-6535(90)90249-S",

language = "English (US)",

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pages = "1221--1228",

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T1 - 7-Substituted-2,3-dichlorodibenzo-p-dioxins as competitive ligands for the Ah receptor

T2 - Quantitative structure-activity relationships (QSARs) and a comparison of human receptor with Ah receptor from rodents

AU - Prokipcak, Rebecca D.

AU - Golas, Cheryl L.

AU - Manchester, David K.

AU - Okey, Allan B.

AU - Safe, Steven

AU - Fujita, Toshio

N1 - Funding Information: The financial assistance of the National Cancer Institute of Canada to A.B.O. and the National Institutes of Health (ES03554) to S.S. is gratefully acknowledged. S. Safe is a Burroughs Wellcome Toxicology Scholar (1989-1994).

PY - 1990

Y1 - 1990

N2 - 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 - 1.764σm° + 1.282 HB. were π is the substituent lipophilicity, σm° 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.

AB - 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 - 1.764σm° + 1.282 HB. were π is the substituent lipophilicity, σm° 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.

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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

Abstract

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