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Metabolic study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to the enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in vitro in human bronchial epithelial cells using chiral capillary electrophoresis
Yang, Youyou1; Yu, Cong1; Zhou, Meng2; Pang, Nannan1; Li, Ning2; Nie, Honggang1; Liao, Jie2; Bai, Yu1; Liu, Huwei1
2011-09-16
Source PublicationJOURNAL OF CHROMATOGRAPHY A
ISSN0021-9673
Volume1218Issue:37Pages:6505-6510
Abstract4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) with one chiral center at the carbinol is a major metabolite of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). As tobacco specific N-nitrosamines (TSNAs), NNK and NNAL are the most pulmonary carcinogens in tobacco products and smoke. In this paper, a chiral CE method modified with highly sulfated beta-cyclodextrin (S-beta-CD) was developed to investigate the stereoselective formation of NNAL from NNK in vitro in normal human bronchial epithelial (NHBE) cells. Combined with solid phase extraction (SPE) of the cell samples. NNK and NNAL enantiomers were baseline separated under the proposed CE conditions, with satisfactory recoveries (72.5-113% for NNK and (+/-)-NNAL) and low limits of detection (LOD, 2.5-3 mu g/mL for NNK and (+/-)-NNAL). The cytotoxicity of NNK in NHBE cells was investigated through the cell counting kit (CCK) assay and proved to be highly dependent on the NNK's concentration. The metabolic results obtained from CE analysis demonstrated that NNK was preferentially metabolized to (+)-NNAL through carbonyl reduction. Meanwhile, the ratio of [(+)-NNAL]/[(-)-NNAL] was independent of NHBE cells incubation time with NNK, but could be changed according to the original incubation concentration of NNK. This chiral CE method could be useful for the study on toxicology and metabolic transformations of related TSNAs. (C) 2011 Elsevier B.V. All rights reserved.
KeywordChiral Ce Cytotoxicity 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol Sulfated Beta-cyclodextrin Stereoselectively Metabolic Transformation Tobacco Specific N-nitrosamines
DOI10.1016/j.chroma.2011.07.009
Indexed BySCI
Language英语
WOS IDWOS:000295113600035
PublisherELSEVIER SCIENCE BV
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/73008
Collection中国科学院化学研究所
Corresponding AuthorLiu, Huwei
Affiliation1.Peking Univ, Coll Chem & Mol Engn, Inst Analyt Chem,Beijing Natl Lab Mol Sci, Key Lab Bioorgan Chem & Mol Engn,Minist Educ, Beijing 100871, Peoples R China
2.Gen Hosp Chinese PLA, Med Expt & Anal Ctr, Beijing 100853, Peoples R China
Recommended Citation
GB/T 7714
Yang, Youyou,Yu, Cong,Zhou, Meng,et al. Metabolic study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to the enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in vitro in human bronchial epithelial cells using chiral capillary electrophoresis[J]. JOURNAL OF CHROMATOGRAPHY A,2011,1218(37):6505-6510.
APA Yang, Youyou.,Yu, Cong.,Zhou, Meng.,Pang, Nannan.,Li, Ning.,...&Liu, Huwei.(2011).Metabolic study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to the enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in vitro in human bronchial epithelial cells using chiral capillary electrophoresis.JOURNAL OF CHROMATOGRAPHY A,1218(37),6505-6510.
MLA Yang, Youyou,et al."Metabolic study of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone to the enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in vitro in human bronchial epithelial cells using chiral capillary electrophoresis".JOURNAL OF CHROMATOGRAPHY A 1218.37(2011):6505-6510.
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