Comparison of liquid chromatography-mass spectrometry interfaces for the analysis of polar metabolites of benz[ a ]pyrene

Koeber, Robert; Bayona, Josep M.

doi:10.1007/s002160050571

Cited by 22 publications

(20 citation statements)

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“…This approach has already been applied successfully in a recent study 13 for the identification of several partially oxidized benzo[a]pyrene derivatives at trace levels. Based on the low detection limits for partially oxidized B[a]P derivatives reached in previous LC/APCI-MS measurements ($10 pg), 17,18 and on the high signal-to-noise ratios obtained with the sample amounts used in this study, subnanogram detection limits can also be expected for most of the compounds investigated here, except for the phenyl and naphthyl hydroxides. Thus future measurements will be focused on the identification and quantification of the investigated compounds and similar substances at trace levels in real samples (e.g.…”

Section: Discussionmentioning

confidence: 62%

“…15,16 APCI-MS techniques for the determination of B[a]P derivatives at trace levels. 17,18 Thereby APCI was found to provide higher sensitivity than the thermospray method, and for several oxy-PAHs detection limits in the order of 10 pg were achieved. 17,18 However, only parent ions could be detected, and thus it was expected that either LC/MS/MS, or ion-trap instruments capable of LC/MS n data acquisition, would be required to obtain structural information about the analytes.…”

mentioning

confidence: 99%

“…17,18 Thereby APCI was found to provide higher sensitivity than the thermospray method, and for several oxy-PAHs detection limits in the order of 10 pg were achieved. 17,18 However, only parent ions could be detected, and thus it was expected that either LC/MS/MS, or ion-trap instruments capable of LC/MS n data acquisition, would be required to obtain structural information about the analytes. 19 Nevertheless, recent investigations have shown that a single quadrupole LC/APCI-MS system can also be used to obtain such information for the identification of B[a]P derivatives.…”

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confidence: 99%

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In-source fragmentation of partially oxidized mono- and polycyclic aromatic hydrocarbons in atmospheric pressure chemical ionization mass spectrometry coupled to liquid chromatography

Letzel

Pöschl

Rosenberg

et al. 1999

Rapid Commun. Mass Spectrom.

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Partially oxidized derivatives of polycyclic aromatic hydrocarbons (PAHs) are known to be important environmental pollutants. For the identification of these substances in complex mixtures, e.g. atmospheric aerosol samples, liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization (LC/APCI-MS) has been found to be a suitable analytical technique. In this study 31 derivatives of mono- and polycyclic aromatic hydrocarbons with up to five condensed aromatic rings carrying different functional groups (carboxyl, dicarboxylic anhydride, lactone, hydroxyl, and carbonyl) were characterized by LC/APCI-MS. Each substance was measured in positive and negative ion detection mode at four different fragmentor voltages (90 to 190 V). For the first time, the results show that characteristic and well-interpretable fragmentation patterns can be obtained for these classes of compounds by in-source collision-induced dissociation in a single quadrupole LC/APCI-MS system. For each class of compounds typical spectral features and optimum measurement conditions are reported, and fragmentation pathways are proposed. The study demonstrates the applicability of LC/APCI-MS for the determination of most of the investigated compounds at trace levels, and it provides a database for the identification of unknown partially oxidized aromatic hydrocarbons. Copyright 1999 John Wiley & Sons, Ltd.

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Section: Discussionmentioning

confidence: 62%

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confidence: 99%

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confidence: 99%

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In-source fragmentation of partially oxidized mono- and polycyclic aromatic hydrocarbons in atmospheric pressure chemical ionization mass spectrometry coupled to liquid chromatography

Letzel

Pöschl

Rosenberg

et al. 1999

Rapid Commun. Mass Spectrom.

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“…26 In another report, A LOD of 20 fmol was reported for B[ a ]P-7,8-diol based on a LC-APCI method. 25 Our method is superior to these earlier reports.…”

Section: Discussionmentioning

confidence: 48%

“…25 Direct infusions of metabolite standards (B[ a ]P-tetrol-1, B[ a ]P-7,8-diol, B[ a ]P-9,10-diol, B[ a ]P-1,6-dione, B[ a ]P-3,6-dione, B[ a ]P-7,8-dione, B[ a ]P-3-OH) were performed to optimize ionization parameters for their identification. Full scan spectra of all the hydroxylated (mono-, di- or tetra-OH) standards under positive APCI conditions were dominated by dehydrated precursors, which likely resulted from a gas-phase dehydration process involving loss of H 2 O.…”

Section: Resultsmentioning

confidence: 99%

Quantitation of Benzo[a]pyrene Metabolic Profiles in Human Bronchoalveolar (H358) Cells by Stable Isotope Dilution Liquid Chromatography–Atmospheric Pressure Chemical Ionization Mass Spectrometry

Ding

Harvey

Blair

et al. 2011

Chem. Res. Toxicol.

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Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants and are carcinogenic in multiple organs and species. Benzo[a]pyrene (B[a]P) is a representative PAH and has been studied extensively for its carcinogenicity and toxicity. B[a]P itself is chemically inert and requires metabolic activation to exhibit its toxicity and carcinogenicity. Three major metabolic pathways have been well documented. The signature metabolites generated from the radical cation (peroxidase or monooxygenase mediated) pathway are B[a]P-1,6-dione and B[a]P-3,6-dione, the signature metabolite generated from the diol-epoxide (P450 mediated) pathway is B[a]P-r-7,t-8,t-9,c-10-tetrahydrotetrol (B[a]P-tetrol-1) and the signature metabolite generated from the o-quinone (aldo-keto reductase mediated) pathway is B[a]P-7,8-dione. The contributions of these different metabolic pathways to cancer initiation and the exploitation of this information for cancer prevention are still under debate. With the availability of a library of [13C4]-labeled B[a]P metabolite internal standards, we developed a sensitive stable isotope dilution atmospheric pressure chemical ionization tandem mass spectrometry method to address this issue by quantitating B[a]P metabolites from each metabolic pathway in human lung cells. This analytical method represents a 500 fold increased sensitivity compared with a method using HPLC-radiometric detection. The limit of quantitation (LOQ) was determined to be 6 fmol on column for 3-hydroxybenzo[a]pyrene (3-OH-B[a]P), the generally accepted biomarker for B[a]P exposure. This high level of sensitivity and robustness of the method was demonstrated in a study of B[a]P metabolic profiles in human bronchoalveolar H358 cells induced or uninduced with the AhR ligand, 2,3,7,8-tetrachlorodibenzodioxin (TCDD). All the signature metabolites were detected and successfully quantitated. Our results suggest that all three metabolic pathways contribute equally in the overall metabolism of B[a]P in H358 cells with or without TCDD induction. The sensitivity of the method should permit the identification of cell-type differences in B[a]P activation and detoxication and could also be used for biomonitoring human exposure to PAH.

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Atmospheric Pressure Ionization Mass Spectrometry

Tarr

Zhu

Cole

2000

Encyclopedia of Analytical Chemistry

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The atmospheric pressure ionization (API) techniques serve to transform neutral analytes into ionic species that may then be analyzed by mass spectrometry (MS). Ionization takes place under ambient pressure (∼1 atm), and formed ions are subsequently directed into the low‐pressure regions of the mass spectrometer for mass analysis. The API techniques have offered notable successes in enabling ionization of nonvolatile compounds contained in solution that are not amenable to “classical” mass spectrometric ionization techniques such as electron ionization and conventional chemical ionization. Under favorable API conditions, neutral analytes may be converted to ionic forms in extremely high efficiencies approaching 100%. Fundamental aspects and applications of the two most widely used API techniques, atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI), are discussed at length in this article.

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Comparison of liquid chromatography-mass spectrometry interfaces for the analysis of polar metabolites of benz[ a ]pyrene

Cited by 22 publications

References 1 publication

In-source fragmentation of partially oxidized mono- and polycyclic aromatic hydrocarbons in atmospheric pressure chemical ionization mass spectrometry coupled to liquid chromatography

In-source fragmentation of partially oxidized mono- and polycyclic aromatic hydrocarbons in atmospheric pressure chemical ionization mass spectrometry coupled to liquid chromatography

Quantitation of Benzo[a]pyrene Metabolic Profiles in Human Bronchoalveolar (H358) Cells by Stable Isotope Dilution Liquid Chromatography–Atmospheric Pressure Chemical Ionization Mass Spectrometry

Atmospheric Pressure Ionization Mass Spectrometry

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