Fast simultaneous determination of urinary 1-hydroxypyrene and 3-hydroxybenzo[a]pyrene by liquid chromatography–tandem mass spectrometry

Fan, Ruifang; Dong, Yiyang; Zhang, Wenbing; Wang, Yu; Yu, Zhiqiang; Sheng, Guoying; Fu, Jiamo

doi:10.1016/j.jchromb.2006.03.044

Cited by 52 publications

(38 citation statements)

References 33 publications

(36 reference statements)

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“…The largest single problem has been one of sensitivity, since levels of 3-OH-B [a] P are 10 3 to 10 5 less than that seen for 1-hydroxypyrene (63). Attempts to solve this problem have utilized LC-APCI/MS methodology with some success (62). The remaining issue is that 3-OH-B[a]P does not reflect levels of B [a]P metabolites that would have carcinogenic properties.…”

Section: Discussionmentioning

confidence: 99%

Metabolism of Benzo[a]pyrene in Human Bronchoalveolar H358 Cells Using Liquid Chromatography–Mass Spectrometry

Jiang

Gelhaus

Mangal

et al. 2007

Chem. Res. Toxicol.

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Benzo [a]pyrene (B[a]P), a representative polycyclic aromatic hydrocarbon (PAH), is metabolically activated by three enzymatic pathways; by peroxidases (e.g. cytochrome P450-peroxidase) to yield radical cations; by P4501A1/1B1 monoxygenation plus epoxide hydrolase to yield diol-epoxides; and by P4501A1/1B1 monoxygenation, epoxide hydrolase plus aldo-keto reductases (AKRs) to yield o-quinones. In humans, a major exposure site for environmental and tobacco smoke PAH is the lung, however, the profile of B[a]P metabolites formed at this site has not been well characterized. In this study, human bronchoalveolar H358 cells were exposed to B[a]P, and metabolites generated by peroxidase (B[a]P-1,6-and B[a]P-3,6-diones), from cytochrome P4501A1/1B1 monooxygenation (3-hydroxyl-B[a]P, B[a]P-7,8-and 9,10-trans-dihydrodiols, and B[a]P -r-7,t-8,t-9,c-10-tetrahydrotetrol (B[a]P -tetrol-1)), and from AKRs (B[a]P-7,8-dione) were detected and quantified by RP-HPLC-with in line photo-diode array and radiometric detection, and identified by LC-MS. Progress curves showed a lag-phase in the formation of 3-hydroxy-B[a]P, B[a]P-7,8-transdihydrodiol, B[a]P-tetraol-1 and B[a]P-7,8-dione over 24 h. Northern blot analysis showed that B [a]P induced P4501B1 and AKR1C isoforms in H358 cells in a time-dependent manner providing an explanation for the lag-phase. Pretreatment of H358 cells with 10 nM 2,3,7,8-tetrachlorodibenzop-dioxin, (TCDD) eliminated this lag-phase, but did not alter the levels of the individual metabolites observed, suggesting that both B[a]P and TCDD induction ultimately yield the same B[a]P-metabolic profile. The one exception was B[a]P-3,6-dione which was formed without a lag-phase in the absence and presence of TCDD, suggesting that the peroxidase responsible for its formation was neither P4501A1 nor 1B1. Candidate peroxidases that remain include PGH synthases and uninduced P450 isoforms. This study shows that the P4501A1/1B1 and AKR pathways are inducible in human lung cells and that the peroxidase pathway was not. It also provides evidence that each of the pathways of PAH-activation yield their distinctive metabolites in H358 human lung cells and that each pathway may contribute to the carcinogenic process.

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Section: Discussionmentioning

confidence: 99%

Metabolism of Benzo[a]pyrene in Human Bronchoalveolar H358 Cells Using Liquid Chromatography–Mass Spectrometry

Jiang

Gelhaus

Mangal

et al. 2007

Chem. Res. Toxicol.

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“…The instrumental detection limit of 1-OHP-G was 0.13 fmol/injection (signal-to-noise ratio >3). This method was found to be more sensitive than previous LC-MS/MS methods for the determination of 1-OHP [16,19]. In most cases, the fragmentations, loss of CO (28 Da) from the [M-H] -ion [16,18] and loss of a water molecule from [M+H] + [19] of 1-OHP were monitored as the product ion.…”

Section: Optimization Of Mobile Phasementioning

confidence: 99%

“…This method was found to be more sensitive than previous LC-MS/MS methods for the determination of 1-OHP [16,19]. In most cases, the fragmentations, loss of CO (28 Da) from the [M-H] -ion [16,18] and loss of a water molecule from [M+H] + [19] of 1-OHP were monitored as the product ion. The product ions used in the previous studies may have been difficult to fragment in the collision cell because of the highly conjugated and rigid chemical structure of 1-OHP [17].…”

Section: Optimization Of Mobile Phasementioning

confidence: 99%

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Direct measurement of the glucuronide conjugate of 1-hydroxypyrene in human urine by using liquid chromatography with tandem mass spectrometry

Kakimoto

Toriba

Ohno

et al. 2008

Journal of Chromatography B

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To evaluate human exposure to polycyclic aromatic hydrocarbons (PAHs), we developed a rapid, simple and sensitive method for determining 1-hydroxypyrene-glucuronide (1-OHP-G) in human urine. To improve precision, a deuterated glucuronide was used as an internal standard. The method requires only 1 mL of urine. The urine was treated with a mixed-mode anion-exchange and reversed-phase solid-phase extraction cartridge (Oasis MAX). The analytes were analyzed with a C 18 reversed-phase column with a gradient elution, followed by tandem mass spectrometry with electrospray ionization in negative ion mode. The detection limit of 1-OHP-G (corresponding to a signal-to-noise ratio of 3) was 0.13 fmol/injection. Urinary concentrations of 1-OHP-G determined by this method were strongly correlated (r 2 =0.961) with concentrations of 1-hydroxypyrene by conventional HPLC with fluorescence detection.

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“…Compounds with phenolic groups have been determined by a variety of methods including gas chromatography/mass spectrometry (GC/MS) after solid phase extraction (SPE) and derivatization by trimethylsilation [5][6][7] and high-performance liquid chromatography (HPLC) with fluorescence detection [8]. Recently, liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS) and tandem mass spectrometry (LC-ESI-MS/MS) in the negative ion mode have been employed to analyze these compounds [9][10][11][12]. However, many phenols are not strong acids and therefore show low ionization efficiency in ESI-MS, leading to higher detection limits compared with the limits that are obtained for many highly ionizable compounds.…”

Section: Introductionmentioning

confidence: 99%

1,2-Dimethylimidazole-4-sulfonyl chloride, a novel derivatization reagent for the analysis of phenolic compounds by liquid chromatography electrospray tandem mass spectrometry: Application to 1-hydroxypyrene in human urine

Spink

2007

Journal of Chromatography B

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A novel derivatization method employing 1,2-dimethylimidazole-4-sulfonyl chloride (DMISC) to improve the mass spectrometric response for phenolic compounds in liquid chromatography electrospray ionization mass spectrometry (LC-ESI-MS) and tandem mass spectrometry (LC-ESI-MS/MS) is described. Several environmentally relevant compounds, including chloro-, aryl-and alkylphenols, steroidal estrogens, and hydroxy-polycyclic aromatic hydrocarbons (OHPAHs), were selected to evaluate this technique. A facile derivatization procedure employing DMISC results in dimethylimidazolesulfonyl (DMIS) derivatives that are stable in aqueous solution. These DMIS derivatives produced intense [M+H] + ions in positive-ion LC-ESI-MS. The product ion spectra of the [M+H] + ions of simple phenols were dominated by ions representing the DMIS and dimethylimidazole moieties, whereas product ion spectra of the DMIS derivatives of OHPAHs with three or more fused aromatic rings showed prominent ArO + ions, the relative intensity of which increased with the number of rings. The DMIS derivatives of the selected phenolic compounds showed excellent chromatographic properties. To substantiate the utility of derivatization with DMISC, an analytical method employing enzyme hydrolysis, solid phase extraction, derivatization with DMISC, and analysis by LC-ESI-MS/MS with multiple reaction monitoring for determination in human urine of 1-hydroxypyrene, a widely used biomarker for the assessment of human exposure to PAHs, was developed and validated.

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Fast simultaneous determination of urinary 1-hydroxypyrene and 3-hydroxybenzo[a]pyrene by liquid chromatography–tandem mass spectrometry

Cited by 52 publications

References 33 publications

Metabolism of Benzo[a]pyrene in Human Bronchoalveolar H358 Cells Using Liquid Chromatography–Mass Spectrometry

Metabolism of Benzo[a]pyrene in Human Bronchoalveolar H358 Cells Using Liquid Chromatography–Mass Spectrometry

Direct measurement of the glucuronide conjugate of 1-hydroxypyrene in human urine by using liquid chromatography with tandem mass spectrometry

1,2-Dimethylimidazole-4-sulfonyl chloride, a novel derivatization reagent for the analysis of phenolic compounds by liquid chromatography electrospray tandem mass spectrometry: Application to 1-hydroxypyrene in human urine

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