BINDING OF SOME DIOXINS AND DIBENZOFURANS TO THE AH RECEPTOR - A QSARMODEL-BASED ON COMPARATIVE MOLECULAR-FIELD ANALYSIS (COMFA)

Citation
A. Poso et al., BINDING OF SOME DIOXINS AND DIBENZOFURANS TO THE AH RECEPTOR - A QSARMODEL-BASED ON COMPARATIVE MOLECULAR-FIELD ANALYSIS (COMFA), Journal of molecular structure. Theochem, 101(3), 1993, pp. 259-264
Citations number
16
Categorie Soggetti
Chemistry Physical
ISSN journal
01661280
Volume
101
Issue
3
Year of publication
1993
Pages
259 - 264
Database
ISI
SICI code
0166-1280(1993)101:3<259:BOSDAD>2.0.ZU;2-E
Abstract
Based on comparative molecular field analysis (CoMFA), a quantitative structure-activity relationship, model for the cytosolic aryl hydrocar bon (Ah) receptor binding affinity of 50 chlorinated dibenzo-para-diox in and dibenzofuran analogues is presented. The electronic structures of these compounds were calculated using the semiempirical AM 1 method . Their extreme stabilities were rationalized using the frontier molec ular orbital theory. The results indicate that their binding affinity was mainly influenced by steric and electrostatic interactions, wherea s charge-transfer and hydrogen bonding mechanisms are probably of mino r importance.