Atropisomeric determination of chiral hydroxylated metabolites of polychlorinated biphenyls using HPLC-MS

Guangshu Zhai; Xianai Wu; Hans-Joachim Lehmler; Jerald Schnoor

doi:10.1186/1752-153X-7-183

Back

Atropisomeric determination of chiral hydroxylated metabolites of polychlorinated biphenyls using HPLC-MS

Journal article

Open access

Peer reviewed

Atropisomeric determination of chiral hydroxylated metabolites of polychlorinated biphenyls using HPLC-MS

Guangshu Zhai, Xianai Wu, Hans-Joachim Lehmler and Jerald Schnoor

Chemistry Central Journal, Vol.7(1), pp.1-9

12/2013

DOI: 10.1186/1752-153X-7-183

PMCID: PMC3879188

PMID: 24360245

Files and links (1)

url

https://doi.org/10.1186/1752-153X-7-183View

Published (Version of record) Open Access

Abstract

Polychlorinated biphenyls (PCBs) are a group of environmental persistent organic pollutants, which can be metabolized into a series of metabolites, including hydroxylated metabolites (OH-PCBs) in biota. Nineteen of 209 PCB congeners can form chiral stable isomers. However, atropisomeric determination of the hydroxylated metabolites of these chiral PCBs has never been reported by LC methods. In this work, a novel HPLC-MS method was developed to detect five chiral OH-PCBs (4OH-PCB91, 5OH-PCB91, 4OH-PCB95, 5OH-PCB95 and 5OH-PCB149) using HPLC-MS without a derivatization step.The influences of column-type, column temperature, flow rate and ratio of the mobile phase on the atropisomeric separation were investigated in detail. In the final method, calibration curves, based on peak areas against concentration, were linear in a range of 1–100 ng mL-1 of five chiral OH-PCBs with correlation coefficients ranging from 0.9996 to 0.9999 for all atropisomers of OH-PCBs. The relative standard deviations measured at the 10.0 ng mL-1 level for atropisomers of five chiral OH-PCBs were in the range of 0.60-7.55% (n = 5). Calculated detection limits (S/N = 3) of five chiral OH-PCBs were between 0.31 and 0.60 ng mL-1 for all OH-PCB atropisomers.This HPLC-MS method was developed to detect chiral OH-PCBs and further successfully applied to measure OH-PCB atropisomer levels and enantiomeric fractions (EFs) in rat liver microsomal samples. The results from LC-MS method were highly consistent with those from GC-ECD method. It is the first time to report these OH-PCB atropisomers detected in microsomes by HPLC-MS. The proposed method might be applied also to detect chiral OH-PCBs in environmental samples and for metabolites of PCBs in vivo.

Rat liver microsome

Chemistry

Chemistry/Food Science, general

Hydroxylated metabolites

HPLC-MS

Chiral polychlorinated biphenyls

Details

Title: Subtitle: Atropisomeric determination of chiral hydroxylated metabolites of polychlorinated biphenyls using HPLC-MS
Creators: Guangshu Zhai - Department of Civil and Environmental Engineering and IIHR Hydroscience and Engineering The University of Iowa Iowa City 52242 IA USA
Xianai Wu - Department of Occupational and Environmental Health The University of Iowa Iowa City 52242 IA USA
Hans-Joachim Lehmler - Department of Occupational and Environmental Health The University of Iowa Iowa City 52242 IA USA
Jerald Schnoor - Department of Occupational and Environmental Health The University of Iowa Iowa City 52242 IA USA
Resource Type: Journal article
Publication Details: Chemistry Central Journal, Vol.7(1), pp.1-9
DOI: 10.1186/1752-153X-7-183
PMID: 24360245
PMCID: PMC3879188
NLM abbreviation: Chem Cent J
ISSN: 1752-153X
eISSN: 1752-153X
Publisher: Springer International Publishing; Cham
Language: English
Date published: 12/2013
Academic Unit: Civil and Environmental Engineering; Occupational and Environmental Health; Iowa Neuroscience Institute
Record Identifier: 9983991942402771

Metrics

22 Record Views

20 Times Cited - Web of Science