title: Modification of PBDEs (BDE-15, BDE-47, BDE-85 and BDE-126) biological toxicity, bio-concentration, persistence and atmospheric long-range transport potential based on the pharmacophore modeling assistant with the full factor experimental design.
abstract: In this study, the properties of AhR binding affinity, bio-concentration factor, half-life and vapor pressure were selected as the typical indicators of biological toxicity, bio-concentration, persistence and atmospheric long-range transport potential for polybrominated diphenyl ethers (PBDEs), respectively. A three-dimensional pharmacophore modeling assistant with a full factor experimental design for each property was used to reveal the significant pharmacophore features and the substituent effects to obtain reasonable modified schemes for the selected target PBDEs. Finally, the performances of the persistent organic pollutant (POP) properties, the synthesis feasibility and the fire resistance of the modified compounds were evaluated. The most influential pharmacophore feature for all POP properties was the hydrophobic group, especially the vinyl and propyl groups. Modified compounds with two additional hydrophobic groups exhibited a better regulatory performance. The average reduction in the proportions of the four POP properties for the modified compounds (except for 3-phenyl-BDE-15) was 70.60%, 52.44%, 47.04% and 70.88%. In addition, the energy and the C-Br bond dissociation enthalpy of the four typical PBDEs were higher than those of the modified compounds (except for 3-phenyl-BDE-15), indicating the synthesis feasibility and the lower energy barrier of the modified compounds to release Br free radicals to provide fire resistance.
authors.affiliation: Resources and Environmental Research Academy, North China Electric Power University, Beijing 102206, China; MOE Key Laboratory of Regional Energy Systems Optimization, North China Electric Power University, Beijing 102206, China. Electronic address: kaveykikiy@163.com.
authors.forename: Long
authors.initials: L
authors.lastname: Jiang
authors.affiliation: Resources and Environmental Research Academy, North China Electric Power University, Beijing 102206, China; MOE Key Laboratory of Regional Energy Systems Optimization, North China Electric Power University, Beijing 102206, China. Electronic address: liyuxx8@hotmail.com.
authors.forename: Yu
authors.initials: Y
authors.lastname: Li
mesh_terms: D000393:Air Pollutants / Q000737:chemistry / Q000633:toxicity; D005411:Flame Retardants / Q000633:toxicity; D006207:Half-Life; D055768:Halogenated Diphenyl Ethers / Q000737:chemistry / Q000633:toxicity; D057927:Hydrophobic and Hydrophilic Interactions; D008962:Models, Theoretical; D021281:Quantitative Structure-Activity Relationship; D018336:Receptors, Aryl Hydrocarbon / Q000378:metabolism
chemical_list: D000393:Air Pollutants; D005411:Flame Retardants; D055768:Halogenated Diphenyl Ethers; D018336:Receptors, Aryl Hydrocarbon
keywords: Full factor experimental design; Persistent organic pollutant properties; Pharmacophore models; Polybrominated diphenyl ethers; Substituent characteristics