Detection of polycyclic aromatic hydrocarbon metabolites by high-pressure liquid chromatography after purification on immunoaffinity columns in urine from occupationally exposed workers

Bentsen-Farmen, R. K.; Botnen, Ingrid V.; Notø, Hilde; Jacob, Jürgen; Øvrebø, Steinar

doi:10.1007/s004200050355

Cited by 50 publications

(21 citation statements)

References 26 publications

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“…in occupationally exposed persons, which is well comparable to the concentrations measured in our study (Angerer at al. 1997a;Bentsen-Farmen et al 1999;Grimmer et al 1993;Guendel et al 2000;Kuusimaki et al 2004;Popp et al 1997;Serdar et al 2003;Vaananen et al 2003).…”

Section: Discussionmentioning

confidence: 93%

“…More recently hydroxylated metabolites of phenanthrene (Phe) have been used successfully for biomonitoring of PAH exposure in workers and in the general population (Angerer et al 1997a;Becker et al 2003;Bentsen-Farmen et al 1999;Grimmer et al 1993;Guendel et al 1996Guendel et al , 2000Heudorf and Angerer 2001a, b;Kuusimaki et al 2004;Popp et al 1997;Seidel et al 2002;Serdar et al 2003; for review see also DFG 2004). With respect to analytical complexity the determination of especially phenolic Phe metabolits is well comparable to the determination of 1-hydroxypyrene.…”

Section: Introductionmentioning

confidence: 98%

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Biological monitoring of occupational exposure to polycyclic aromatic hydrocarbons (PAH) by determination of monohydroxylated metabolites of phenanthrene and pyrene in urine

Roßbach

Preuss

Letzel

et al. 2007

Int Arch Occup Environ Health

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Considering the results of the correlation analysis hydroxyphenanthrenes in urine should reflect an uptake of lowly condensed volatile PAH rather than an incorporation of highly condensed PAH like BaP which should be reflected better by 1-hydroxypyrene. Therefore, the determination of hydroxyphenanthrenes in addition to the well-established marker 1-hydroxypyrene could offer some further information about the exposure situation at a particular work place.

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Section: Discussionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 98%

Biological monitoring of occupational exposure to polycyclic aromatic hydrocarbons (PAH) by determination of monohydroxylated metabolites of phenanthrene and pyrene in urine

Roßbach

Preuss

Letzel

et al. 2007

Int Arch Occup Environ Health

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“…Although several methods described in the literature used acetonitrile/water as mobile phase in HPLC for the separation of polycyclic aromatic hydrocarbons, including BaP [42][43][44], most BaP HPLC methods [6,29,31,32,38,[45][46][47] used methanol/water as the mobile phase with a gradient program. We tried methanol/water first, however, even after optimization, we did not achieve ideal separation of the three BaP diones with UPLC, and some bile samples showed a peak of unknown endogenous compound that overlaid with the internal standard.…”

Section: Chromatographymentioning

confidence: 99%

“…In 1984, Krahn et al developed a method of biliary PAH quantitation by measuring fluorescence at 380/430 nm excitation/emission to detect "BaP-like" metabolites [28]. This method has been widely accepted as a sensitive and predictable method to detect and monitor PAH contamination [29][30][31][32]. However BaP diones, do not exhibit fluorescence, and the method does not quantitate individual metabolites prohibiting the application of fluorescence detection for a detailed study of BaP metabolism.…”

Section: Introductionmentioning

confidence: 99%

“…High performance liquid chromatography (HPLC) has been widely used for the analysis of drug or environmental contaminant metabolites, including BaP metabolites [25][26][27][28][29][30][31][32], for the last several decades. In the 1970's, HPLC was used for separating BaP metabolites [25][26][27] combined with UV or scintillation counter detection.…”

Section: Introductionmentioning

confidence: 99%

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Simultaneous determination of benzo[a]pyrene and eight of its metabolites in Fundulus heteroclitus bile using ultra-performance liquid chromatography with mass spectrometry

Zhu

Thornton

et al. 2008

Journal of Chromatography B

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A sensitive and fast method was developed to quantitate the carcinogenic polycyclic aromatic hydrocarbon benzo(a)pyrene (BaP) and eight of its oxidized metabolites by ultra-performance liquid chromatography (UPLC) coupling with mass spectrometry (MS). The UPLC method, using an acetonitrile:water gradient as a mobile phase, provided baseline separation of the BaP metabolites including three BaP diones. Linearity of detection was in the range of 0.2 to 5.0 ng/μL, and limits of detection (LODs) were lower than 0.01 ng/μL for BaP and all of the metabolites except BaP tetrol. In order to test this method in environmentally relevant samples, we exposed the small fish Fundulus heteroclitus to BaP and quantitated biliary BaP metabolites. Extraction recovery of all compounds varied from 65.4 ± 21.3% to 92.4 ± 3.0%. In exposed fish bile, the BaP diones, BaP-7,8-dihydrodiol, and 3-hydroxy BaP metabolites predominated, existing mainly as glucuronic acid conjugates. This UPLC-MS method will be useful for further defining the roles of cytochrome P450s with both in vivo and in vitro models in the understanding of the mechanisms of metabolic activation and detoxification of BaP.

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Polycyclic and Heterocyclic Aromatic Hydrocarbons

Warshawsky¹

2000

Patty's Toxicology

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Aromatic hydrocarbons are the class of chemicals that include multi‐ring aromatic compounds. Smaller aromatic hydrocarbons, one to two rings, are of considerable economic importance as industrial raw materials, solvents, and components of innumerable commercial and consumer products. However, aromatics differ vastly in chemical, physical, and biological characteristics from the aliphatic and alicyclic hydrocarbons. In addition, aromatics are more toxic to humans and other mammals. Of prime importance are the carcinogenicity of styrene and the polycyclic aromatic hydrocarbons. Chemically, aromatic hydrocarbons can be divided into three groups: (a) alkyl‐, aryl‐, and alicyclic‐substituted benzene derivatives, (b) di‐ and polyphenyls, and (c) polycyclic compounds composed of two or more fused benzene ring systems. The basic chemical entity is the benzene nucleus, which occurs alone, substituted, joined, or fused. Aromatics are moderately reactive and undergo photochemical degradation in the atmosphere. Aromatic compounds occur in liquid, vapor, or solid form. The lower molecular weight derivatives possess higher vapor pressures, volatility, absorbability, and solubility in aqueous media than the comparable aliphatic or alicyclic compounds. These properties contribute to their biological activities. They are characterized also by miscibility or conversion to compounds soluble in aqueous body fluids, high lipid solubility, and donor–acceptor and polar interaction. Because of their low surface tension and viscosity, aromatics may be aspirated into the lungs during ingestion, where they can cause chemical pneumonitis. Aromatics are primary skin irritants, and repeated or prolonged skin contact may cause dermatitis, dehydrating, and defatting of the skin. Eye contact with aromatic liquids may cause lacrimation, irritation, severe burns from prolonged contact. Naphthalene causes cataracts in the eyes of experimental animals. Its vapors are respiratory and mucous membrane irritants and may cause severe systemic injury. Direct aerosol deposition or contact from ingestion and subsequent aspiration can cause severe pulmonary edema, pneumonitis, and hemorrhage. Alkylbenzenes that have C 1 to C 4 side chains are readily aspirated and can produce instant death via cardiac arrest and respiratory paralysis. For example, in hexylbenzene exposure, death occured in 18 min, during which extensive pulmonary edema occured, resulting in a considerable increase in lung weight. The higher alkylbenzenes showed few or no effects. The unique effects of benzene on bone marrow and blood‐forming mechanisms are of major importance. In general, the acute toxicity of alkylbenzenes is higher for toluene than for benzene and decreases further with increasing chain length of the substituent, except for highly branched C 8 to C 18 derivatives. The toxicity increases again for vinyl derivatives. Pharmacologically, the alkylbenzenes are CNS depressants, since they exhibit a particular affinity to nerve tissues. Aromatic hydrocarbons cause local irritation and changes in endothelial cell permeability and are absorbed rapidly. Secondary effects have been observed in the liver, kidney, spleen, bladder, thymus, brain, and spinal cord in animals. Aromatic hydrocarbons, even from a single dose, exhibit a special affinity to nerve tissue. Animals dosed with alkylbenzenes exhibit signs of CNS depression, sluggishness, stupor, anesthesia, and coma. This is in sharp contrast with benzene, which is a neuroconvulsant and produces tremors and convulsions. The CNS depressant potency of the alkylbenzenes depends on branching or side‐chain length. It diminishes with increasing numbers of substituents or side‐chain carbon number up to dodecylbenzene, which has practically no CNS depressant activity. Aromatic hydrocarbons accumulate in marine animals to a greater extent and are retained longer than alkanes. In all species tested, the accumulation of aromatic hydrocarbons depended primarily on the octanol/water partition coefficient. Once absorbed, higher molecular weight hydrocarbons are released more slowly. Polycyclic aromatic hydrocarbons are mainly solid materials that are soluble in fats, oils, and organic solvents. The mutagenic or carcinogenic properties of PAHs have been linked to physicochemical properties, such as electronegativity or K‐ and L‐region reactivity, electrophilic potency, dipole moment, intramolecular and subcellular binding, hydrophobicity, and others. However, these characteristics alone are inadequate for specific predictions. Polynuclear aromatics are practically nontoxic for acute ingestion and acute dermal application. Enzyme systems, such as aryl hydrocarbon hydroxylase (AHH), are present in almost all human and animal cell tissues and are inducible by noncarcinogenic and potentially carcinogenic hydrocarbons. The stability of cytochrome P450 epoxidase may depend on immunologic competence, as does the epoxide hydrase. BaP is both teratogenic and mutagenic in rodents. Four‐ and five‐ring PAHs are carcinogenic. They include the benz(a)anthracenes, benzofluoranthracenes, benzo(a)pyrenes, chrysenes, and dibenz(a,h)anthracene. The OSHA and ACGIH ceiling for coal tar pitch volatiles that contain one or more PAHs is 0.2 ppm with a cancer notation. Sampling techniques include collecting air particles using an absorbent glass sampler, desorption with pentane, and quantification using spectral analysis. Collection on acrylonitrile‐PVC filters is also recommended. Analytic quantification is also achieved by using gas chromatography high‐resolution mass spectrometry or chemiluminescence. Methods for cleanup from waste water are also available.

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Detection of polycyclic aromatic hydrocarbon metabolites by high-pressure liquid chromatography after purification on immunoaffinity columns in urine from occupationally exposed workers

Cited by 50 publications

References 26 publications

Biological monitoring of occupational exposure to polycyclic aromatic hydrocarbons (PAH) by determination of monohydroxylated metabolites of phenanthrene and pyrene in urine

Biological monitoring of occupational exposure to polycyclic aromatic hydrocarbons (PAH) by determination of monohydroxylated metabolites of phenanthrene and pyrene in urine

Simultaneous determination of benzo[a]pyrene and eight of its metabolites in Fundulus heteroclitus bile using ultra-performance liquid chromatography with mass spectrometry

Polycyclic and Heterocyclic Aromatic Hydrocarbons

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