Abstract
For many years naphthalene had been considered as a non-carcinogenic polycyclic aromatic hydrocarbon (PAH). Airborne naphthalene concentrations have always been observed to be below the limit values of various national committees, such as the threshold limit value (TLV) of the American Conference of Governmental Industrial Hygienists (ACGIH) and the MAK of the Deutsche Forschungsgemeinschaft (DFG) (10 ppm). Since 2000, when the US National Toxicology Program revealed clear evidence of the carcinogenic activity of naphthalene in rats, international agencies [the International Agency for Research on Cancer (IARC), the US Environmental Protection Agency (US EPA), DFG] have reclassified naphthalene as a potential human carcinogen, and the European Union (EU) is currently preparing a new risk assessment report. It is presently unknown how to protect humans from health risks resulting from occupational and environmental naphthalene exposure. Knowledge about the external and internal exposure of humans serves as the key determinant in a comprehensive risk assessment. We review here ambient monitoring studies concerning the external naphthalene exposure that results from ubiquitous environmental sources (indoor and outdoor air, water, soil, food) and from a variety of critical workplaces (coking plants, creosote impregnation, distillation of coal tar and naphthalene, manufacture of refractories, graphite electrodes, aluminium and mothballs). Based on results of ambient monitoring studies published so far, a new hygiene-based exposure limit of 1.5 mg naphthalene per cubic metre of air (0.3 ppm) is proposed. Furthermore, results from biological monitoring studies are summarised in this article. The internal burden was almost exclusively determined by means of the urinary metabolites 1-naphthol and 2-naphthol, but it is currently not possible for one to evaluate a biological tolerance level (BAT) or a biological exposure index (BEI). Based on the toxicokinetics and metabolism of naphthalene, the central question on its carcinogenicity is briefly sketched. Naphthoquinones play an important role in this context. Their adducts with macromolecules may be the parameters of choice for the estimation of effects to human health.
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References
Aamot E, Steinnes E, Schmid R (1996) Polycyclic aromatic hydrocarbons in Norwegian forest soils: impact of long range atmospheric transport. Environ Pollut 92:275–280
Agency for Toxic Substances and Disease Registry (ATSDR) (1995) Toxicological profile for naphthalene (update). Department of Health and Human Services, CRC Press, Boca Raton, Fla, USA
Akiyama T, Koga M (1983) Priority pollutants in the Kitakyushu water supply. Jpn J Hyg 37:833–835
Aldis H, Osborn J, Wolf F (1983) Investigation of soil and water contamination at Western Processing, King County, Washington. National Conference on Management of Uncontrolled Hazardous Waste Sites 43–53. Hazardous Materials Control Research Institute, Silver Spring
Alfheim I, Jebens A, Johansen S (1985) Sampling ambient air for mutagenicity testing by high volume filtration on glass fibre filters and on XAD-2. Environ Int 11:111–118
Al-Yakoob S, Saeed T, Al-Hashash H (1993) Polycyclic aromatic hydrocarbons in edible tissue of fish from the Gulf after 1991 oil spill. Mar Pollut Bull 27:297–301
American Conference of Governmental Industrial Hygienists (ACGIH) (1999) TLVs and BEIs. Threshold limit values for chemical substances and physical agents. Biological Exposure Indices. Cincinnati, Ohio, USA
Andersson K, Levin JO, Nilsson CA (1983) Sampling and analysis of particulate and gaseous polycyclic aromatic hydrocarbons from coal tar sources in the working environment. Chemosphere 12:197–207
Andreoli R, Manini P, Bergamaschi E, Mutti A, Franchini I, Niessen WM (1999) Determination of naphthalene metabolites in human urine by liquid chromatography–mass spectrometry with electrospray ionization. J Chromatogr A 847:9–17
Angerer J (2001) Das Biological Monitoring in der Arbeits- und Umweltmedizin-dezeitiger Stand und künftige Entwicklungen. In: Angerer, et al. (eds) Biological monitoring. VCH Verlagsgesellschaft, Weinheim, pp 5–15
Angerer J, Gündel J (1996) Biomonitoring and occupational medicine. Possibilities and limitations. Ann Ist Super Sanita 32:199–206
Angerer J, Schaller KH (1998) Biological materials, analyses of hazardous substances. In: Meyers RA (ed) Encyclopedia of environmental analysis and remediation (EEAR). Wiley, New York, pp 702–731
Angerer J, Mannschreck C, Gündel J (1997) Biological monitoring and biochemical effect monitoring of exposure to polycyclic aromatic hydrocarbons. Int Arch Occup Environ Health 70:365–377
Arey J, Zielinska B, Atkinson R, Winer AM (1987) Polycyclic aromatic hydrocarbon and nitroarene concentrations in ambient air during a wintertime high-NO2 episode in the Los Angeles basin. Atmos Environ 6:1437–1444
Ashok BT, Saxena S, Singh KP, Musarrat (1995) Biodegradation of polycyclic aromatic hydrocarbons in soil around Mathura oil refinery, India. World J Microbiol Biotechnol 11:691–692
Bagchi D, Bagchi M, Balmoori J, Vuchetich PJ, Stohs SJ (1998a) Induction of oxidative stress and DNA damage by chronic administration of naphthalene to rats. Res Commun Mol Pathol Pharmacol 101:249–257
Bagchi M, Bagchi D, Balmoori J, Ye X, Stohs SJ (1998b) Naphthalene-induced oxidative stress and DNA damage in cultured macrophage J774A.1 cells. Free Radic Biol Med 25:137–143
Bagchi D, Balmoori J, Bagchi M, Ye X, Williams CB, Stohs SJ (2000) Role of p53 tumor suppressor gene in the toxicity of TCDD, endrin, naphthalene, and chromium (VI) in liver and brain tissues of mice. Free Radic Biol Med 28:895–903
Bakke J, Struble C, Gustafsson JA (1985) Catabolism of premercapturic acid pathway metabolites of naphthalene to naphthols and methylthio-containing metabolites in rats. Proc Natl Acad Sci U S A 82:668–671
Ball J (1987) Soil and groundwater contamination at wood preserving plants. Proceedings of 41st Purdue University Industrial Waste Conference
Barker JF, Barbash JE, Labonte M (1988) Groundwater contamination at a landfill sited on fractured carbonate and shale. J Contam Hydrol 3:1–25
Barreveld (1992) Organische micro verontreinigingen in Rijn en Maas. RIZA, Netherlands, Nota 92.009.
Bedient PB, Rodgers AC, Bouvette TC, Tomson MB, Wang TH (1984) Groundwater quality at a creosote waste site. Ground Water 22:318–329
Bender, EM, Huggett RJ (1989) Polynuclear aromatic hydrocarbon residues in shellfish: species variations and apparent intraspecific differences. In: Kaiser HE (ed) Comparative aspects of tumor development. Kluwer Academic Publishers, Dordrecht, The Netherlands, pp 27:226
Benfenati E, DiToro N, Fanelli R, Lualdi G, Tridico R, Stella G, Buscaini P, Stimilli L (1992) Characterisation of organic and inorganic pollutants in the Adige river (Italy). Chemosphere 25:1665–1674
Benoit FM, LeBel GL, Williams DT (1979) Polycyclic aromatic hydrocarbon levels in eastern Ontario drinking waters (1978). Bull Environ Contam Toxicol 23:774–778
Berglind L (1982) Determination of polycyclic aromatic hydrocarbons in industrial discharges and other aqueous effluents (Nordic PAH Project). Central Institute for Industrial Research, report no. 16, Oslo, pp 21
BGBl (1993) Bekanntmachungen des Bundesgesundheitsamtes. Bewertung der Luftqualität in Innenräumen. Bundesgesundheitsblatt Nr. 3, 117–118
Bieniek G (1994) The presence of 1-naphthol in the urine of industrial workers exposed to naphthalene. Occup Environ Med 51:357–359
Bieniek G (1996) Simultaneous determination of phenol, cresol, xylenol isomers and naphthols in urine by capillary gas chromatography. J Chromatogr B Biomed Appl 682:167–172
Bieniek G (1997) Urinary naphthols as an indicator of exposure to naphthalene. Scand J Work Environ Health 23:414–420
Bieniek G (1998) Aromatic and polycyclic hydrocarbons in air and their urinary metabolites in coke plant workers. Am J Ind Med 34:445–454
Bieniek G, Wilczok T (1986) Separation and determination of phenol, alpha-naphthol m- and p-, o-cresols and 2,5-xylenol, and catechol in the urine after mixed exposure to phenol, naphthalene, cresols, and xylenols. Br J Ind Med 43:570–571
Bjorseth A, Bjorseth O, Fjeldstad PE (1978a) Polycyclic aromatic hydrocarbons in the work atmosphere. I. Determination in an aluminum reduction plant. Scand J Work Environ Health 4:212–223
Bjorseth A, Bjorseth O, Fjeldstad PE (1978b) Polycyclic aromatic hydrocarbons in the work atmosphere. II. Determination in a coke plant. Scand J Work Environ Health 4:224–236
Bjorseth A, Bjorseth O, Fjeldstad PE (1981) Polycyclic aromatic hydrocarbons in the work atmosphere. Determination of area-specific concentrations and job-specific exposure in a vertical pin Soderberg aluminium plant. Scand J Work Environ Health 7:223–232
Bock KW, von Clausbruch US, Winne D (1979) Absorption and metabolism of naphthalene and benzo(a)pyrene in the rat jejunum in situ. Med Biol 57:262–264
Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ (2000) Role of quinones in toxicology. Chem Res Toxicol 13:135–160
Bouchard M, Pinsonneault L, Tremblay C, Weber JP (2001) Biological monitoring of environmental exposure to polycyclic aromatic hydrocarbons in subjects living in the vicinity of a creosote impregnation plant. Int Arch Occup Environ Health 74:505–513
Bouchertall F (1986) Volatile hydrocarbons in the atmosphere of the Kiel Bight (Western Baltic). Mari Chem 19:153–160
Boyland E, Sims P (1958) Metabolism of polycyclic compounds: 12. An acid-labile precursor of 1-naphthylmercapturic acid and naphthol: an N-acetyl-S-(1:2-dihydroxynaphthyl)-l-cysteine. Biochem J 68:440–447
BUA (1989) Beratergremium für umweltrelevante Altstoffe der Gesellschaft Deutscher Chemiker (GDCh). GDCh Advisory committee on existing chemicals of environmental relevance. BUA report 39, VCH, Weinheim
Buchet JP, Ferreira M, Burrion JB, Leroy T, Kirsch-Volders M, Van Hummelen P, Jaques J, Cupers L, Delavignette JP, Lauwerys R (1995) Tumor markers in serum, polyamines and modified nucleosides in urine, and cytogenetic aberrations in lymphocytes of workers exposed to polycyclic aromatic hydrocarbons. Am J Ind Med 27:523–543
Buckpitt AR, Warren DL (1983) Evidence for hepatic formation, export and covalent binding of reactive naphthalene metabolites in extrahepatic tissues in vivo. J Pharmacol Exp Ther 225:8–16
Buckpitt AR, Richieri P (1984) Comparative biochemistry and metabolism, part 2. Naphthalene lung toxicity. Wright-Patterson Air Force Base (Oh), Air Force Systems Command, Aerospace Medical Division, Air Force Aerospace Medical Research Laboratory. AFAMRL-TR-84-058
Buckpitt AR, Bahnson LS (1986) Naphthalene metabolism by human lung microsomal enzymes. Toxicology 41:333–341
Buckpitt AR, Castagnoli N, Nelson SD, Jones AD, Bahnson LS (1987) Stereoselectivity of naphthalene epoxidation by mouse, rat, and hamster pulmonary, hepatic and renal microsomal enzymes. Drug Metab Dispos 15: 491–498
Buckpitt A, Buonarati M, Avey LB, Chang AM, Morin D, Plopper CG (1992) Relationship of cytochrome P-450 activity to clara cell cytotoxicity. II. Comparison of stereoselectivity of naphthalene epoxidation in lung and nasal mucosa of mouse, hamster, rat and rhesus monkey. J Pharmacol Exp Ther 261:364–372
Buckpitt A, Chang AM, Weir A, Van Winkle L, Duan X, Philpot R, Plopper C (1995) Relationship of cytochrome P450 activity to clara cell cytotoxicity. IV. Metabolism of naphthalene and naphthalene oxide in microdissected airways from mice, rats and hamsters. Mol Pharmacol 47:74–81
Buckpitt A, Boland B, Isbell M, Morin D, Shultz M, Baldwin R, Chan K, Karlsson A, Lin C, Taff A, West J, Fanucchi M, Van Winkle L, Plopper C (2002) Naphthalene-induced respiratory tract toxicity: metabolic mechanisms of toxicity. Drug Metab Rev 34:791–820
Buonarti M, Jones AD, Buckpitt A (1990) In vivo metabolism of isomeric naphthalene oxide glutathione conjugates. Drug Metab Dispos 18:183–189
Burczynski ME, Lin HK, Penning TM (1999) Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res 59:607–614
Catallo W, Gambrell RP (1987) The effects of high levels of polycyclic aromatic hydrocarbons on sediment physicochemical properties and benthic organisms in a polluted stream. Chemosphere 16:1053–1063
Catoggio JA, Succar SD, Roca AE (1989) Polynuclear aromatic hydrocarbon content of particulate matter suspended in the atmosphere of La Plata, Argentina. Sci Total Environ 79:43–58
Chakravarti D, Pelling JC, Cavalieri EL, Rogan EG (1995) Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras mutations in mouse skin papillomas: the role of apurinic sites. Proc Natl Acad Sci U S A 92:10422–10426
Chang A, Plopper C, Weir A, Sassme H, Buckpitt A (1991) Correlation of species selective pulmonary toxicity to naphthalene (NA) with immuni-histochemical localization of cytochrome P450MN and the stereoselective epoxidation of NA in airways explant incubations. Toxicologist 11:59
Chen CS, Rao PSC, Lee LS (1996) Evaluation of extraction and detection methods for determining polynuclear aromatic hydrocarbons from coal tar contaminated soils. Chemosphere 32:1123–1132
Chen KC, Dorough HW (1979) Glutathione and mercapturic acid conjugations in the metabolism of naphthalene and 1-naphthyl-N-methylcarbamate (Carbaryl). Drug Chem Toxicol 2:331–354
Cho M, Jedrychowski R, Hammock B, Buckpitt A (1994a) Reactive naphthalene metabolite binding to hemoglobin and albumin. Fundam Appl Toxicol 22:26–33
Cho M, Chichester C, Morin D, Plopper C, Buckpitt A (1994b) Covalent interactions of reactive naphthalene metabolites with proteins. J Pharmacol Exp Ther 269:881–889
Chuang JC, Mack GA, Kuhlman MR, Wilson NK (1991) Polycyclic aromatic hydrocarbons and their derivatives in indoor and outdoor air in an eight-home study. Atmos Environ 25B:369–380
Chuang JC, Callahan PJ, Lyu CW, Wilson NK (1999) Polycyclic aromatic hydrocarbon exposures of children in low-income families. J Exp Anal Environ Epidemiol 2:85–98
Clark C, Henderson T, Royer R, Brooks A, McClellan R, Marshall W, Naman T (1982) Mutagenicity of diesel exhaust particulate extracts: influence of fuel composition in two diesel engines. Fundam Appl Toxicol 2:38–43
Cole RH, Frederick RE, Healy RP, Rolan RG (1984) Preliminary findings of the priority pollutant monitoring project of the nationwide urban runoff program. Journal WPCF 56:898–908
Collins MJ, Williams PL, MacIntosh DL (2001) Ambient air quality at the site of a former manufactured gas plant. Environ Monit Assess 68:137–152
CONCAWE (1987) A survey of exposures to gasoline vapour. Report no. 4/87, CONCAWE, The Hague
Coons S, Byrne M, Goyer M (1982) An exposure and risk assessment for benzo(a)pyrene and other polycyclic aromatic hydrocarbons: Vol II. Naphthalene. Final draft report. US Environmental Protection Agency, Office of Water Regulations and Standards, Washington, DC
Czuczwa J, Leuenberger C, Giger W (1988) Seasonal and temporal changes of organic compounds in rain and snow. Atmos Environ 22:907–916
DeBortoli M, Knöppel H, Pecchio E, Peil A, Rogora L, Schauenberg H, Schlitt H, Vissers H (1984) Integrating "real life" measurements of organic pollution in indoor and outdoor air of homes in Northern Italy. Proceedings of the 3rd International Conference on Indoor Air Quality and Climate, vol 4, issue PB85-104214, pp 21–26
DeLeon IR, Byrne CJ, Peuler EA, Antoine SR, Schaeffer J, Murphy RC (1986) Trace organic and heavy metal pollutants in the Mississippi river. Chemosphere 15:795–805
Denissenko MF, Pao A, Tang M, Pfeifer GP (1996) Preferential formation of benzo(a)pyrene adducts at lung cancer mutational hotspots in P53. Science 274:430–432
Department of the Environment, Transport and the Regions (DETR) (2000) Risk reduction strategy and analysis of advantages and drawbacks for naphthalene, stage 4, report. Contract no. CDEP 1/41/17
Deutsche Forschungsgemeinschaft (DFG), Commission for the investigation of health hazards of chemical compounds in the work area (2001) MAK and BAT values 2001. Report no. 37. Wiley-VCH, Weinheim
Doherty MA, Cohen GM, Smith MT (1984) Mechanism of toxic injury to isolated hepatocytes by 1-naphthol. Biochem Pharmacol 33:543–549
Doherty MA, Makowski R, Gibson GG, Cohen GM (1985) Cytochrome P-450 dependent metabolic activation of 1-naphthol to naphthoquinones and covalent binding species. Biochem Pharmacol 34:2261–2267
Ehrhardt MG, Burns KA (1990) Petroleum-derived dissolved organic compounds concentrated from inshore waters in Bermuda. J Exp Mar Biol Ecol 138:35–47
Eisele GR (1985) Naphthalene distribution in tissues of laying pullets, swine, and dairy cattle. Bull Environ Contam Toxicol 34:549–556
Elovaara E, Heikkilä P, Pyy L, Mutanen P, Riihimäki V (1995) Significance of dermal and respiratory uptake in creosote workers: exposure to polycyclic aromatic hydrocarbons and urinary excretion of 1-hydroxypyrene. Occup Environ Med 52:196–203
Elovaara E, Väänänen V, Mikkola J (2003) Simultaneous analysis of naphthols, phenanthrols, and 1-hydroxypyrene in urine as biomarkers of polycyclic aromatic hydrocarbon exposure: intraindividual variance in the urinary metabolite excretion profiles caused by intervention with beta-naphthoflavone induction in the rat. Arch Toxicol, in press
Flowers-Geary L, Harvey RG, Penning TM (1993) Cytotoxicity of polycyclic aromatic hydrocarbon o-quinones in rat and human hepatoma cells. Chem Res Toxicol 6:252–260
Foster P, Laffond M, Baussand P, Jacob V, Denis I (1991) VOC measurements in the Grenoble area and study of the benzaldehyde behaviour in a simulation chamber. Pollut Atmos 175–191
Gelboin HV (1980) Benzo(a)pyrene metabolism, activation and carcinogenesis: role and regulation of mixed-function oxidases and related enzymes. Physiol Rev 60:1107–1166
Glatt HR, Vogel K, Bentley P, Oesch F (1979) Reduction of benzo(a)pyrene mutagenicity by dihydrodiol dehydrogenase. Nature 277:319–320
Goerlitz DF (1992) A review of studies of contaminated groundwater conducted by the US geological survey organics project, Menlo Park (CA), 1961–1990, In: Lesage S, Jackson RE (eds) Groundwater contamination and analysis at hazardous waste sites. Marcel Dekker, New York
Gold KW, Naugle DF, Berry MA (1993) Indoor concentrations of environmental carcinogens. IARC Sci Publ 109:41–71
Gomez-Belinchon JI, Grimalt JO, Albaigès J (1991) Volatile organic compounds in two polluted rivers in Barcelona (Catalonia, Spain). Water Res 25:577–589
Gonzalez-Vila FJ, Lopez JL, Martin F (1988) Determination of polycyclic aromatic compounds in composted municipal refuse and compost-amended soils by a simple cleanup procedure. Biomed Environ Mass Spectrom 16:423–425
Greene JF, Zheng J, Grant DF, Hammock BD (2000) Cytotoxicity of 1,2-epoxynaphthalene is correlated with protein binding and in situ glutathione depletion in cytochrome P4501A1 expressing Sf-21 cells. Toxicol Sci 53:352–360
Grob K, Grob G (1974) Organic substances in potable waters and in its precursor. Part 2. Applications in the area of Zürich. J Chromatogr 90:303–313
Gschwend PM, Zafiriou OC, Mantoura RFC, Schwarzenbach RP, Gagosian RB (1982) Volatile organic compounds at a coastal site. 1. Seasonal variations. Environ Sci Technol 16:31
Gündel J, Schaller KH, Angerer J (2000), Occupational exposure to polycyclic aromatic hydrocarbons in a fireproof stone producing plant: biological monitoring of 1-hydroxypyrene, 1-, 2-, 3-, and 4-hydroxyphenanthrene, 3-hydroxybenz(a)-anthracene and 3-hydroxybenzo(a)pyrene. Int Arch Occup Environ Health 73:270–274
Hansen AM, Poulsen OM, Christensen JM, Hansen SH (1992a) Determination of α-naphthol in human urine by high performance liquid chromatography. J Liquid Chromatogr 15:479–499
Hansen AM, Olsen IL, Poulsen OM (1992b) Polycyclic aromatic hydrocarbons in air samples of meat smokehouses. Sci Total Environ 126:17–26
Hansen AM, Poulsen OM, Menne T (1993) Longitudinal study of excretion of metabolites of polycyclic aromatic hydrocarbons in urine from two psoriatic patients. Acta Derm Venereol 73:188–190
Hansen AM, Omland O, Poulsen OM, Sherson D, Sigsgaard T, Christensen JM, Overgaard E (1994a) Correlation between work process-related exposure to polycyclic aromatic hydrocarbons and urinary levels of alpha-naphthol, beta-naphthylamine and 1-hydroxypyrene in iron foundry workers. Int Arch Occup Environ Health 65:385–394
Hansen AM, Poulsen OM, Sigsgaard T, Christensen JM (1994b) The validity of determination of alpha-naphthol in urine as a marker for exposure to polycyclic aromatic hydrocarbons. Anal Chim Acta 291:341–347
Hansen AM, Christensen JM, Sherson D (1995) Estimation of reference values for urinary 1-hydroxypyrene and alpha-naphthol in Danish workers. Sci Total Environ 163:211–219
Harrison RM, Smith DJT, Luhana L (1996) Source apportionment of atmospheric PAHs collected from an urban location in Birmingham, U.K. Environ Sci Technol 30:825–832
Hawthorne SB, Sievers RE (1984) Emission of organic air pollutants from shale oil wastewaters. Environ Sci Technol 18:483–490
Hawthorne SB, Poppendieck DG, Grabanski CB, Loehr RC (2002) Comparing PAH availability from manufactured gas plant soils and sediments with chemical and biological tests. 1. PAH release during water desorption and supercritical carbon dioxide extraction. Environ Sci Technol 36:4795–4803
Heikkilä P, Luotamo M, Pyy L, Riihimaki V (1995) Urinary 1-naphthol and 1-pyrenol as indicators of exposure to coal tar products. Int Arch Occup Environ Health 67:211–217
Heikkilä PR, Hameila M, Pyy L, Raunu P (1987) Exposure to creosote in the impregnation and handling of impregnated wood. Scand J Work Environ Health 13:431–437
Heikkilä PR, Luotamo M, Riihimaki V (1997) Urinary 1-naphthol excretion in the assessment of exposure to creosote in an impregnation facility. Scand J Work Environ Health 23:199–205
Hemminki K, Koskinen M, Rajaniemi H, Zhao C (2000) DNA adducts, mutations, and cancer 2000. Regul Toxicol Pharmacol 32:264–275
Heudorf U, Angerer J (2001) Urinary monohydroxylated phenanthrenes and hydroxypyrene—the effects of smoking habits and changes induced by smoking on monooxygenase-mediated metabolism. Int Arch Occup Environ Health 74:177–183
Hill RH, Head SL, Baker S, Gregg M, Shealy DB, Bailey SL, Williams CC, Sampson EJ, Needham LL (1995a) Pesticide residues in urine of adults living in the United States: reference range concentrations. Environ Res 71:99–108
Hill RH Jr, Shealy DB, Head SL, Williams CC, Bailey SL, Gregg M, Baker SE, Needham LL (1995b) Determination of pesticide metabolites in human urine using an isotope dilution technique and tandem mass spectrometry. J Anal Toxicol 19:323–329
Hoff RM, Chan KW (1987) Measurement of polycyclic aromatic hydrocarbons in the air along the Niagara River. Environ Sci Technol 21:556–561
Hoffmann D, Hoffmann I, El-Bayoumy K (2001) The less harmful cigarette: a controversial issue. A tribute to Ernst L. Wynder. Chem Res Toxicol 14:767–790
Horning MG, Stillwell WG, Griffin GW, Tsang WS (1980) Epoxide intermediates in the metabolism of naphthalene by the rat. Drug Metab Dispos 8:404–414
Howard PH (1989) Handbook of environmental fate and exposure data for organic chemicals, vol 1, Lewis, pp 408–421
Hung IF, Fang HF, Lee TS (1992) Aliphatic and aromatic hydrocarbons in indoor air. Bull Environ Contam Toxicol 48:579–584
Hutchins SR, Ward CH (1984) A predictive laboratory study of trace organic contamination of groundwater: preliminary results. J Hydrol 67:223–235
Huynh CP, Vu Duc T, Debonneville C, Boiteux P (1984) Pollution de L'air interieur par les hydrocarbures polynucleaires de la fumee e tabac. Sozial Preventivmed 29:201–202
International Agency for Research on Cancer (IARC) (1973) Monographs on the evaluation of carcinogenic risk of the chemical to man. Certain polycyclic aromatic hydrocarbons and heterocyclic compounds, Vol 3, IARC, Lyons
International Agency for Research on Cancer (IARC) (1983) Monographs on the evaluation of carcinogenic risk of the chemical to humans. Polynuclear aromatic compounds, part 1. Chemical, environment and experimental data, vol 32, IARC, Lyons
International Agency for Research on Cancer (IARC) (2002) Monographs on the evaluation of carcinogenic risks to humans: some traditional herbal medicines, some mycotoxins, naphthalene and styrene, vol 82, IARC, Lyons
IPCS (1998) Environmental health criteria 202. Selected non-heterocyclic polycyclic aromatic hydrocarbons. WHO, Geneva
Jansen EHJM, Schenk E, den Engelsman G, van de Werken G (1995) Use of biomarkers in exposure assessment of polycyclic aromatic hydrocarbons. Clin Chem 41:1905–1906
Jerina DM, Daly JW, Witkop B, Zaltzman-Nirenberg P, Udenfriend S (1970) 1,2-Naphthalene oxide as an intermediate in the microsomal hydroxylation of naphthalene. Biochemistry 9:147–156
Jez JM, Penning TM (2001) The aldo-keto reductase (AKR) superfamily: an update. Chem Biol Interact 130:499–525
Jez JM, Flynn TG, Penning TM (1997) A new nomenclature for the aldo-keto reductase superfamily. Biochem Pharmacol 54:639–647
Johnston JJ, Wong JP, Feldman SE, Ilnicki LP (1994) Purge and trap/gas chromatography/mass spectrometry method for determining smoke contamination of foods and packaging materials. J Agric Chem 42:1954–1958
Jones KC, Stratford JA, Waterhouse KS, Johnston AE (1987) Polynuclear aromatic hydrocarbons in UK soils: long-term temporal trends and current levels. Trace Subst Environ Health 2:140–148
Jones KC, Stratford JA, Waterhouse KS, Vogt NB (1989a) Organic contaminants in Welsh soils: polynuclear aromatic hydrocarbons. Environ Sci Technol 23:540–550
Jones KC, Stratford JA, Tidridge P, Waterhouse KS, Johnston AE (1989b) Polynuclear aromatic hydrocarbons in an agricultural soil: long-term changes in profile distribution. Environ Pollut 56:337–351
Juchau MR, Boutelet-Bochan H, Huang Y (1998) Cytochrome P450-dependent biotransformation of xenobiotics in human and rodent embryonic tissue. Drug Metab Rev 30:541–568
Kanekal S, Plopper C, Morin D, Buckpitt A (1990) Metabolic activation and bronchiolar Clara cell necrosis from naphthalene in the isolated perfused mouse lung. J Pharmacol Exp Ther 252:428–437
Kanekal S, Plopper C, Morin D, Buckpitt A (1991) Metabolism and cytotoxicity of naphthalene oxide in the isolated perfused mouse lung. J Pharmacol Exp Ther 256:391–401
Kaplan I, Lu ST, Lee RP, Warrick G (1996) Polycyclic hydrocarbon biomarkers confirm selective incorporation of petroleum in soil and kangaroo rat liver samples near an oil well blowout site in the Western San Joaquin Valley, California. Environ Toxicol Chem 15:696–707
Kayal SI, Connell DW (1989) Occurrence and distribution of polycyclic aromatic hydrocarbons in surface sediments and water from the Brisbane River estuary, Australia. Estuarine Coastal Shelf Sci 29:473–487
Keimig SD, Morgan DP (1986) Urinary 1-naphthol as a biological indicator of naphthalene exposure. Appl Ind Hyg 1:61–65
Kerndorff H, Schleyer R, Milde G, Plumb RH (1992) Geochemistry of groundwater pollutants at German waste disposal sites. In: Lesage S, Jackson RE (eds) Groundwater contamination and analysis at hazardous waste sites. Marcel Dekker, New York
Khalili NR, Scheff PA, Holsen TM (1995) PAH source fingerprints for coke ovens, diesel and gasoline engines, highway tunnels, and wood combustion emissions. Atmos Environ 29:533–542
Kilanowicz A, Czerski B, Sapota A (1999) The disposition and metabolism of naphthalene in rats. Int J Med Environ Health 12:209–219
Kim H, Kim YD, Lee H, Kawamoto T, Yang M, Katoh T (1999) Assay of 2-naphthol in human urine by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl 734:211–217
Kim H, Cho SH, Kang JW, Kim YD, Nan HM, Lee CH, Lee H, Kawamoto T (2001) Urinary 1-hydroxypyrene and 2-naphthol concentrations in male Koreans. Int Arch Occup Environ Health 74:59–62
Kim KB, Lee BM (1997) Oxidative stress to DNA, protein, and antioxidant enzymes (superoxide dismutase and catalase) in rats treated with benzo(a)pyrene. Cancer Lett 113:205–212
Kipopoulou AM, Manoli E, Samara C (1999) Bioconcentration of polycyclic aromatic hydrocarbons in vegetables grown in an industrial area. Environ Pollut 106:369–380
Kliest J, Fast T, Boley JSM, van de Wiel H, Bloemen H (1989) The relationship between soil contaminated with volatile organic compounds and indoor air pollution. Environ Int 15:419–425
Krahn MM, Brown DW, Collier TK, Friedman AJ, Jenkins RG, Malins DC (1980) Rapid analysis of naphthalene and its metabolites in biological systems: determination by high-performance liquid chromatography/ fluorescence detection and by plasma desorption/chemical ionization mass spectrometry. J Biochem Biophys Methods 2:233–246
Kubiak R, Belwoski J, Szczeklik J, Smolik E, Mielzynksa D, Baj M, Szczesna A (1999) Biomarkers of carcinogenesis in humans exposed to polycyclic aromatic hydrocarbons. Mutat Res 445:175–180
Kuusimaki L, Peltonen Y, Kyyro E, Mutanen P, Peltonen K, Savela K (2002) Exposure of garbage truck drivers and maintenance personnel at a waste handling centre to polycyclic aromatic hydrocarbons derived from diesel exhaust. J Environ Monit 4:722–727
Kveseth K, Sortland B, Bokn T (1982) Polycyclic aromatic hydrocarbons in sewage, mussels and tap water. Chemosphere 11:623–639
La Regina J, Bozzeli JW, Harkov R, Gianti S (1986) Volatile organic compounds at hazardous waste sites and a sanitary landfill in New Jersey: an up-to-date review of the present situation. Environ Prog 5:18–28
Lakritz J, Chang A, Weir A, Nishio S, Heyde D, Philpot R, Buckpitt A, Plopper C (1996) Cellular and metabolic basis of clara cell tolerance to multiple doses of cytochrome P450-activated cytotoxicants. I: Bronchiolar epithelial reorganization and expression of cytochrome P450 monooxygenases in mice exposed to multiple doses of naphthalene. J Pharmacol Exp Ther 278:1408–1418
Larssen S (1984) Automotive emission factors: an indirect exposure measurement method applied to polycyclic aromatic hydrocarbon and lead emissions. Proceedings of the 77th Annual Meeting of the Air Pollution Control Association, paper 84-72.4
Lau OW, Wong SK, Leung KS (1995) Naphthalene contamination of sterilized milk drinks contained in low-density polyethylene bottles. Part 2. Effect of naphthalene vapour in air. Analyst 120:1125–1128
LeBel GL, Williams DT, Benoit FM (1987) Use of large volume resin cartridges for the determination of organic contaminants in drinking water derived from the Great Lakes. In: Organic pollutants in water, American Chemical Society, pp 309–325
Lee CY, Lee JY, Kang JW, Kim H (2001) Effects of genetic polymorphisms of CYP1A1, CYP2E1, GSTM1, and GSTT1 on the urinary levels of 1-hydroxypyrene and 2-naphthol in aircraft maintenance workers. Toxicol Lett 123:115–124
Lesage J, Perrault G, Durand P (1987) Evaluation of worker exposure to polycyclic aromatic hydrocarbons. Am Ind Hyg Assoc J 48:753–759
Li CS, Ro YS (2000) Indoor characteristics of polycyclic aromatic hydrocarbons in the urban atmosphere of Taipei. Atmos Environ 34:611–620
Ligocki MP, Leuenberger C, Pankow JF (1985) Trace organic compounds in rain. II—gas scavenging of neutral organic compounds. Atmos Environ 19:1609–1617
Lin TC, Chang FH, Hsieh JH, Chao HR, Chao MR (2002) Characteristics of polycyclic aromatic hydrocarbons and total suspended particulate in indoor and outdoor atmosphere of a Taiwanese temple. J Hazard Mater 95:1–12
Lindhardt B, Christensen TH, Andersen L (1996) Volatilisation of aromatic hydrocarbons from soil, part I. Fluxes from coal tar contaminated surface soils. Water Air Soil Pollut 89:129–146
Liu Y, Zhu L, Shen X (2001) Polycyclic aromatic hydrocarbons (PAHs) in indoor and outdoor air of Hangzhou, China. Environ Sci Technol 35:840–844
Lofgren L, Persson K, Stromevall AM, Petersson G (1991) Exposure of commuters to volatile aromatic hydrocarbons from petrol exhaust. Sci Total Environ 108:225–233
Mackell JV, Rieders F, Brieger H (1951) Acute hemolytic anemia due to ingestion of naphthalene moth balls. I. Clinical aspects. Pediatrics 7:722–727
MAK (1995) Gesundheitsschädliche Arbeitsstoffe. Toxikologisch-arbeitsmedizinische Begründungen von MAK-Werten. Naphthalin. 21. Lieferung, VCH, Weinheim
MAK (2001) Gesundheitsschädliche Arbeitsstoffe. Toxikologisch-arbeitsmedizinische Begründungen von MAK-Werten. Naphthalin. 33. Lieferung, VCH, Weinheim
Manoli E, Samara C, Konstantinou I, Albanis T (2000) Polycyclic aromatic hydrocarbons in the bulk precipitation and surface waters of Northern Greece. Chemosphere 41:1845–1855
Marchand M, Caprais JC, Pignet P (1988) Hydrocarbons and halogenated hydrocarbons in coastal waters of the Western Mediterranean (France). Mar Environ Res 25:131–159
Massey KA, van Engelen DL, Warner IM (1995) Determination of Carbaryl as its primary metabolite, 1-naphthol, by reversed-phase high-performance liquid chromatography with fluorometric detection. Talanta 42:1457–1463
Mastron TA, Dietrich AM, Gallagher DL, Grizzard TJ (1994) Distribution of polyaromatic hydrocarbons in the water column and sediments of a drinking water reservoir with respect to boating activity. Water Res 28:2353–2366
Mattox CF, Humenick MJ (1980) Organic groundwater contaminants from UGC. In Situ 4:129–151
McCoull KD, Rindgen D, Blair IA, Penning TM (1999) Synthesis and characterization of polycyclic aromatic hydrocarbon o-quinone depurinating N7-guanine adducts. Chem Res Toxicol 12:237–246
McCreary JJ, Jackson JG, Zoltek J Jr (1983) Toxic chemicals in an abandoned phenolic waste site. Chemosphere 12:1619–1632
McDougal JN, Pollard DL, Weisman W, Garrett CM, Miller TE (2000) Assessment of skin absorption and penetration of JP-8 jet fuel and its components. Toxicol Sci 55:247–255
McFall JA, Antoine SR, DeLeon IR (1985) Organics in the water column of Lake Pontchartrain. Chemosphere 14:1253–1265
Meyer CR (1983) Liver dysfunction in residents exposed to leachate from a toxic waste dump. Environ Health Perspect 48:9–13
Michael LC, Pellizzari ED, Norwood DL (1991) Application of the master analytical scheme to the determination of volatile organics in wastewater influents and effluents. Environ Sci Technol 25:150–155
Miles AK, Roster N (1999) Enhancement of polycyclic aromatic hydrocarbons in estuarine invertebrates by surface runoff at a decommissioned military fuel depot. Mar Environ Res 47:49–60
Murty VS, Penning TM (1992) Polycyclic aromatic hydrocarbon (PAH) ortho-quinone conjugate chemistry: kinetics of thiol addition to PAH ortho-quinones and structures of thioether adducts of naphthalene-1,2-dione. Chem Biol Interact 84:169–188
Nan HM, Kim H, Lim HS, Choi JK, Kawamoto T, Kang JW, Lee CH, Kim YD, Kwon EH (2001) Effects of occupation, lifestyle and genetic polymorphisms of CYP1A1, CYP2E1, GSTM1 and GSTT1 on urinary 1-hydroxypyrene and 2-naphthol concentrations. Carcinogenesis 22:787–793
National Institute for Occupational Safety and Health (NIOSH) (1997) Pocket guide to chemical hazards. US Department of Health and Human Services, Public Health Service, Centers for Disease Control and Prevention (CDC), Cincinnati, Ohio, USA
National Toxicology Program (NTP) (1992) Toxicology and carcinogenesis studies of naphthalene (CAS no. 91-20-3) in B6C3F1 mice (inhalation studies). Technical report series no. 410. NIH Publication no. 92-3141. US Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park, NC, USA
National Toxicology Program (NTP) (2000) Toxicology and carcinogenesis studies of naphthalene (CAS no. 91-20-3) in F344/N rats (inhalation studies). Technical report series no. 91-20-3. NIH Publication no. 01-4434. US Department of Health and Human Services, Public Health Service, National Institutes of Health, Research Triangle Park NC, USA
Navarro HA, Price CJ, Marr MC, Myers CB, Heindel JJ, Schwetz BA (1991) Final report on the developmental toxicity of naphthalene (CAS no. 91-20-3) in Sprague–Dawley CD rats on gestational days 6 through 15. NTIS report
Naylor LM, Loehr RC (1982) Priority pollutants in municipal sewage sludge. Biocycle 18–22
Nhamburo PT, Kimura S, McBride OW, Kozak CA, Gelboin HV, Gonzalez FJ (1990) The human CYP2F gene subfamily: identification of a cDNA encoding a new cytochrome P450, cDNA-directed expression, and chromosome mapping. Biochemistry 29:5491–5499
Nisbet ICT, LaGoy PK (1992) Toxic equivalency factors (TEFs) for polycyclic aromatic hydrocarbons (PAHs). Regul Toxicol Pharmacol 16:290–300
Nordholm L, Espensen IM, Jensen HS, Holst E (1986) Polycyclic aromatic hydrocarbons in smokehouses. Scand J Work Environ Health 12:614–618
O'Brien KAF, Smith LL, Cohen GM (1985) Differences in naphthalene-induced toxicity in the mouse and rat. Chem Biol Interact 55:109–122
Occupational Safety and Health Administration (OSHA) (1998) Occupational safety and health standards, toxic and hazardous substances. Code of Federal Regulations 29 CFR 1910.1000
Omland O, Sherson D, Hansen AM, Sigsgaard T, Autrup H, Overgaard E (1994) Exposure of iron foundry workers to polycyclic aromatic hydrocarbons: benzo(a)pyrene-albumin adducts and 1-hydroxypyrene as biomarkers for exposure. Occup Environ Med 51:513–518
Onodera S (1991) Characterisation and determination of organic compounds in the mutagenic XAD-2 extracts of drinking water. J Chromatogr 557:413–427
Ou Z, Chang S, Gao Z, Sun T, Qi E, Ma X, Li P, Zhang L, Yang G, Han S, Song Y, Zhang H, Ren L, Qu X (1992) Paddy rice slow-rate land treatment systems, II. Hydraulic balances and results of 4 years' operation. Water Res 26:1487–1494
Owa JA, Izedonmwen OE, Ogundaini AO, Ogungbamila FO (1993) Quantitative analysis of 1-naphthol in urine of neonates exposed to mothballs: the value in infants with unexplained anaemia. Afr J Med Med Sci 22:71–76
Pakenham G, Lango J, Buonarati M, Morin D, Buckpitt A (2002) Urinary naphthalene mercapturates as biomarkers of exposure and stereoselectivity of naphthalene epoxidation. Drug Metab Dispos 30:247–253
Palackal NT, Burczynski ME, Harvey RG, Penning TM (2001a) The ubiquitous aldehyde reductase (AKR1A1) oxidizes proximate carcinogen trans-dihydrodiols to o-quinones: potential role in polycyclic aromatic hydrocarbon activation. Biochemistry 40:10901–10910
Palackal NT, Burczynski ME, Harvey RG, Penning TM (2001b) Metabolic activation of polycyclic aromatic hydrocarbon trans-dihydrodiols by ubiquitously expressed aldehyde reductase (AKR1A1). Chem Biol Interact 130–132:815–824
Palackal NT, Lee SH, Harvey RG, Blair IA, Penning TM (2002) Activation of polycyclic aromatic hydrocarbon trans-dihydrodiol proximate carcinogens by human aldo-keto reductase (AKR1C) enzymes and their functional overexpression in human lung carcinoma (A549) cells. J Biol Chem 277:24799–24808
Pankow JF, Isabelle LM, Asher WE, Kristensen TJ, Peterson ME (1983) Organic compounds in Los Angeles and Portland rain: identities, concentrations and operative scavenging mechanisms. In: Pruppacher (ed) Precipitation, scavenging, dry deposition and resuspension. Elsevier Science, pp 403–415
Pankow JF, Isabelle LM, Asher WE (1984) Trace organic compounds in rain. 1. Sampler design and analysis by adsorption/thermal desorption (ATD). Environ Sci Technol 18:310–318
Parker RJ, Wolfe RDA (1990) Groundwater contamination assessment of gasworks sites. Water 20–23
Patton GW, Cooper AT, Blanton ML (1997) Measurement and estimated health risks of semivolatile organic compounds (PCBs, PAHs, pesticides, and phthalates) in ambient air at the Hanford Site. Report no. PNNL-11650, DOE/EH USDOE Assistant Secretary for Environment, Safety, and Health, Washington, DC
Pellizzari ED, Castillo NP, Willis S, Smith D, Bursey JT (1979) Identification of organic components in aqueous effluents from energy-related processes. Measurement of organic pollutants in water and wastewater, ASTM STP, 686, In: van Hall CE (ed) American Society for Testing and Materials, pp 256–274
Penning TM (1993) Dihydrodiol dehydrogenase and its role in polycyclic aromatic hydrocarbon metabolism. Chem Biol Interact 89:1–34
Penning TM, Burczynski ME, Hung CF, McCoull KD, Palackal NT, Tsuruda LS (1999) Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox active o-quinones. Chem Res Toxicol 12:1–18
Pereira WE, Domagalski JL, Hostettler FD, Brown LR, Rapp JB (1996) Occurrence and accumulation of pesticides and organic contaminants in river sediment, water and clam tissues from the San Joaquin river and tributaries, California. Environ Toxicol Chem 15:172–180
Plopper CG, Suverkropp C, Morin D, Nishio S, Buckpitt A (1992) Relationship of cytochrome P-450 activity to clara cell cytotoxicity. I. Histopathological comparison of the respiratory tract of mice, rats and hamsters after parenteral administration of naphthalene. J Pharmacol Ther 261:353–363
Posthumus R, Canton H (1995) Naphthalene in the aquatic environment, CSTE/DG XI, Doc. CSTE 91/95/11
Preuss R, Gonzalez-Reche LM, Philippeit G, Rossbach B, Angerer J (2002) Naphthalinbelastung in der deutschen Allgemeinbevölkerung—Bestimmung von 1- und 2-naphthol im Urin von Rauchern und Nichtrauchern. Joint conference of the Gesellschaft für Hygiene, Umweltmedizin und öffentliche Gesundheit (GHU) and the International Society of Environmental Medicine (ISEM), Greifswald, Germany
Preuss R, Rossbach B, Mueller J, Angerer J (2003) Eine Deutschlandweite Studie zur inneren und äusseren Exposition gegenüber Polyzyklischen Aromatischen Kohlenwasserstoffen (PAK) am Arbeitsplatz. Gefahrstoffe Reinhalt Luft:1–2:7–14
Propper R (1988) Polycyclic aromatic hydrocarbons (PAH). A candidate toxic air contaminant. Air Resources Board. National Technical Information Service. TR SS-88-01,Springfield, Va
Puisieux A, Lim S, Groopman J, Ozturk M (1991) Selective targeting of p53 gene mutational hotspots in human cancers by etiologically defined carcinogens. Cancer Res 51:6185–6189
Raymond A, Guiochon G (1974) Gas chromatographic analysis of C8-C18 hydrocarbons in Paris air. Environ Sci Technol 8:143–148
Reinhard M, Goodman NL, Barker JF (1994) Occurrence and distribution of organic chemicals in 2 landfill leachate plumes. Environ Sci Technol 18:953–961
Renk RR, Crader SE, Lindblom SR, Covell JR (1990) Hoe Creek Groundwater Restoration 1989 Report, DOE/MC/11076–2948. NTIS Order No. DE91002026
Riley RT, Mix MC, Schaffer RL, Bunting DL (1981) Uptake and accumulation of naphthalene by the oyster Ostrea edulis, in a flow-through system. Mar Biol 61:267–276
RIVM (1993) Milieurapportage III. Jaaroverzicht luchtkwaliteit 1992. The Netherlands
Roberts (ed) (1999) Metabolic pathways of agrochemicals, part 2. Insecticides and fungicides. Royal Society of Chemistry, London, pp 15–33
Rozman K, Summer KH, Rozman T, Greim H (1982) Elimination of thioethers following administration of naphthalene and diethylmaleate to the rhesus monkey. Drug Chem Toxicol 5:265–275
Saeed T, Al-Yakoob S, Al-Hashash H (1995) Preliminary exposure assessment for Kuwaiti consumers to polycyclic aromatic hydrocarbons in seafood. Environ Int 21:255–263
Sagher D, Strauss B (1983) Insertion of nucleotides opposite apurinic/apyrimidinic sites in deoxyribonucleic acid during in vitro synthesis: uniqueness of adenine nucleotides. Biochemistry 22:4518–4526
Sampson EJ, Needham LL, Pirkle JL, Hannon WH, Miller DT, Patterson DG, et al. (1994) Technical and scientific developments in exposure marker methodology. Clin Chem 40:1376–1384
Sasaki JC, Arey J, Eastrmond DA, Parks KK, Grosovsky AJ (1997) Genotoxicity induced in human lymphoblasts by atmospheric reaction products of naphthalene and phenanthrene. Mutat Res 393:23–35
Sato S, Sugiyama K, Lee YS, Kador PF (1999) Prevention of naphthalene-1,2-dihydrodiol-induced lens protein modifications by structurally diverse aldose reductase inhibitors. Exp Eye Res 68:601–608
Schmeltz I, Tosk J, Hoffmann D (1976) Formation and determination of naphthalenes in cigarette smoke. Anal Chem 48:645–650
Schmeltz I, Tosk J, Hilfrich J, et al. (1978) Bioassays of naphthalene and alkylnaphthalenes for co-carcinogenic activity. Relation to tobacco carcinogenesis. In: Jones PW, Freudenthal RI (eds) Carcinogenesis, vol. 3. Polynuclear aromatic hydrocarbons. Raven, New York, NY, pp 47–60
Schoket B, Poirier MC, Mayer G, Török G, Kolozsi-Ringelham A, Bognar G, Bigbee WL, Vincze I (1999) Biomonitoring of human genotoxicity induced by complex occupational exposures. Mutat Res 445:193–203
Serdar B, Waidyanatha S, Zheng Y, Rappaport SM (2003) Simultaneous determination of urinary 1- and 2-naphthols, 3- and 9-phenanthrols, and 1-pyrenol in coke oven workers. Biomarkers 8:93–109
Shafik MT, Sullivan HC, Enos HF (1971) A method for the determination of 1-naphthol in urine. Bull Environ Contam Toxicol 53:274–279
Shah JJ, Heyerdahl EK (1988) National ambient volatile organic compounds (VOCs) data base update. US Environmental Protection Agency, Atmospheric Sciences Research Laboratory, Office of Research and Development. EPA/600/3–88/010a. Research Triangle Park, NC, USA
Shealy DB, Barr JR, Ashley DL, Patterson DG Jr, Camann DE, Bond AE (1997) Correlation of environmental Carbaryl measurements with serum and urinary 1-naphthol measurements in a farmer applicator and his family. Environ Health Perspect 105:510–513
Shultz MA, Choudary PV, Buckpitt AR (1999) Role of murine cytochrome P450 2F2 in metabolic activation of naphthalene and metabolism of other xenobiotics. J Pharmacol Exp Ther 290:281–288
Siegel E, Wason S (1986) Mothball toxicity. Pediatr Clin North Am 33:369–374
Smith CJ, Walcott CJ, Huang W, Maggio V, Grainger J, Patterson DG (2002) Determination of selected monohydroxy metabolites of 2-, 3- and 4-ring polycyclic aromatic hydrocarbons in urine by solid-phase microextraction and isotope dilution gas chromatography–mass spectrometry. J Chromatogr B 778:157–164
Snyder JM, King JW, Nam KS (1996) Determination of volatile and semivolatile contaminants in meat by supercritical fluid extraction/gas chromatography/mass spectrometry. J Sci Agric 72:25–30
Staples CA, Werner AF, Hoogheem TJ (1985) Assessment of priority pollutant concentrations in the United States using STORET database. Environ Toxicol Chem 4:131–142
Steurmer DH, Ng DJ, Morris CJ (1982) Organic contaminants in groundwater near an underground coal gasification site in Northeastern Wyoming. Environ Sci Technol 16:582–587
Stillwell WG, Bouwsma OJ, Thenot JP, Horning MG, Griffin GW, Ishikawa K, Takaku M (1978) Methylthio metabolites of naphthalene excreted by the rat. Res Commun Chem Pathol Pharmacol 20:509–530
Stillwell WG, Horning MG, Griffin GW, Tsang WS (1982) Identification of new sulfur-containing metabolites of naphthalene in mouse urine. Drug Metab Dispos 10:624–631
Stohs SJ, Ohia S, Bagchi D (2002) Naphthalene toxicity and antioxidant nutrients. Toxicology 180:97–105
Strunk P, Ortlepp K, Heinz H, Rossbach B, Angerer J (2002) Ambient and biological monitoring of coke plant workers—determination of exposure to polycyclic aromatic hydrocarbons. Int Arch Occup Environ Health 75:354–358
Sugiyama K, Wang TC, Simpson JT, Rodriguez L, Kador PF, Sato S (1999) Aldose reductase catalyzes the oxidation of naphthalene-1, 2-dihydrodiol for the formation of ortho-naphthoquinone. Drug Metab Dispos 27:60–67
Summer KH, Rozman K, Coulston F, Greim H (1979) Urinary excretion of mercapturic acids in chimpanzees and rats. Toxicol Appl Pharmacol 50:207–212
Sweetman AJ, Rogers HR, Harms H, Mosbaek H (1992) Organic contaminants in sewage sludge and their effects on soil and crops. WRC final report to the Department of the Environment. DoE 2745 (P)
Szeliga J, Dipple A (1998) DNA adduct formation by polycyclic aromatic hydrocarbon dihydrodiol epoxides. Chem Res Toxicol 11:1–11
Tan GH, Goh SH, Vijayaletchumy K, Loong CP, Ang KL (1990) Monitoring of water-borne organic chemical pollution in the Klang River Basin. Bull Sing N I Chem 18:67–77
Tester DJ, Harker RJ (1981) Groundwater pollution investigations in the Great Ouse Basin. Water Pollut Control 614–631
Thomson BM, Lake RJ, Lilli RE (1996) The contribution of margarine to cancer risk from polycyclic aromatic hydrocarbons in the New Zealand diet. Polycyclic Aromat Compound 11:177–184
Thompson MJ, Ballinger LN, Cross SE, Roberts MS (1996) High-performance liquid chromatographic determination of phenol, 4-nitrophenol, beta-naphthol and a number of their glucuronide and sulphate conjugates in organ perfusate. J Chromatogr B Biomed Appl 677:117–122
Thrane KE (1987) Ambient air concentrations of polycyclic aromatic hydrocarbons, fluoride, suspended particles and particulates in areas near aluminium production plants. Atmos Environ 21:617–628
Thrane KE (1988) Application of air pollution models: a comparison of different techniques for estimating ambient air pollution levels and source contributions. Atmos Environ 22:587–594
Tingle MD, Pirmohamed M, Templeton E, Wilson AS, Madden S, Kitteringham NR, Park BK (1993) An investigation of the formation of cytotoxic, genotoxic, protein-reactive and stable metabolites from naphthalene by human liver microsomes. Biochem Pharmacol 46:1529–1538
Tomson M, Curran C, King J, Wang H, Dauchy J, Gordy V, Ward BH (1984) Characterisation of soil disposal system leachates. Report EPA 600/2-84-101, order no. PB84-196229
TRGS 900 (2003) Technische Regel für Gefahrstoffe—Grenzwerte in der Luft am Arbeitsplatz–Luftgrenzwerte: BArbBl. 10/2000 in der Fassung von 03/2003
Troester MA, Lindstrom AB, Waidyanatha S, Kupper LL, Rappaport SM (2002) Stability of hemoglobin and albumin adducts of naphthalene oxide, 1,2-naphthoquinone, and 1,4-naphthoquinone. Toxicol Sci 68:314–321
Tsuruda LS, Lame MW, Jones AD (1995) Formation of epoxide and quinone protein adducts in B6C3F1 mice treated with naphthalene, sulfate conjugate of 1,4-dihydroxynaphthalene and 1,4-naphthoquinone. Arch Toxicol 69:362–367
Turkall RM, Skowronski GA, Kadry MA, Abdel-Rahman MS (1994) A comparative study of the kinetics and bioavailability of pure and soil-absorbed naphthalene in dermally exposed male rats. Arch Environ Contam Toxicol 26:504–509
Turney GL, Goerlitz DF (1990) Organic contamination of ground water at Gas Works Park, Seattle, Washington. Ground Water Monit Rev 10:187–198
UBA (1998) Umweltbundesamt: Umwelt-Survey, Berlin 1998. http://www.umweltbundesamt.de/survey/us98/pak.htm
US Environmental Protection Agency (US EPA) (1983) VOCs in the atmosphere: an assessment of available data (final report, September 1980-December 1982). Odzinsky et al. USEPA report no. EPA/DF-83/005A
US Environmental Protection Agency (US EPA) (1998) Toxicological review of naphthalene (CAS no. 91-20-3) in support of summary information on the integrated risk information system (IRIS). National Center for Environmental Assessment, Cincinnati, Ohio, USA
US Environmental Protection Agency (US EPA) (1999) Integrated risk information system (IRIS) on naphthalene. National Center for Environmental Assessment, Office of Research and Development, Washington, DC
US Environmental Protection Agency (US EPA) (2002) Health effects support document for naphthalene, external review draft. EPA 822-R-02-031. Washington, DC
US Environmental Protection Agency (US EPA) (2003) http://www.epa.gov/ttn/atw/hlthef/naphthal.html#ref7
UK Environment Agency (UKRAR) (1999) Risk assessment for naphthalene, prepared by Building Research Establishment, draft report of February 1999 for the Environment Agency and Department of the Environment, Transport and the Regions
van Bladeren PJ, Vyas KP, Sayer JM, Ryan DE, Thomas PE, Levin W, Jerina DM (1984) Stereoselectivity of cytochrome P-450c in the formation of naphthalene and anthracene 1,2-oxides. J Biol Chem 259:8966–8973
Van Delft JH, Steenwinkel MJ, van Asten JG, de Vogel N, Bruijntjes-Rozier TC, Schouten T, Cramers P, Maas L, van Herwijnen MH, van Schooten FJ, Hopmans PM (2001) Biological monitoring the exposure to polycyclic aromatic hydrocarbons of coke oven workers in relation to smoking and genetic polymorphisms for GSTM1 and GSTT1. Ann Occup Hyg 45:395–408
Van Steenderen RA, Theron SJ, Hassett AJ (1987) The occurrence of organic micropollutants in the Vaal River between Grootdrai Dam and Parys. Water S A 13:209–214
van Winkle LS, Buckpitt AR, Plopper CG (1996) Maintenance of differentiated murine Clara cells in microdissected airway cultures. Am J Respir Cell Mol Biol 14:586–598
Viau C, Hakizimana G, Bouchard M (2000) Indoor exposure to polycyclic aromatic hydrocarbons and carbon monoxide in traditional houses in Burundi. Int Arch Occup Environ Health 73:331–338
Vogt NB, Brakstad F, Thrane K, Nordenson S, Krane J, Aamot E, Kolset K, Esbensen K, Steinnes E (1987) Polycyclic aromatic hydrocarbons in soil and air: statistical analysis and classification by the SIMCA method. Environ Sci Technol 21:35–44
Vuchetich PJ, Bagchi D, Bagchi M, Hassoun EA, Tang L, Stohs SJ (1996) Naphthalene-induced oxidative stress in rats and the protective effects of vitamin E succinate. Free Radic Biol Med 21:577–590
Vyskocil A, Fiala Z, Fialova D, Krajak V, Viau C (1997) Environmental exposure to polycyclic aromatic hydrocarbons in Czech Republic. Hum Exp Toxicol 16:589–595
Waidyanatha S, Troester MA, Lindstrom AB, Rappaport SM (2002) Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats. Chem Biol Interact 141:189–210
Webber MD, Lesage S (1989) Organic contaminants in Canadian municipal sludges. Waste Manage Res 7:63–82
Wells PG, Wilson B, Lubek BM (1989) In vivo murine studies on the biochemical mechanism of naphthalene cataractogenesis. Toxicol Appl Pharmacol 99:466–473
White RD (1999) Refining and blending of aviation turbine fuels. Drug Chem Toxicol 22:143–153
Whitmore RW, Immerman FW, Camman DE, Bond AE, Lewis RG, Schaum JL (1994) Non-occupational exposure to pesticides for residents of two US cities. Arch Environ Contam Toxicol 26:47–59
Wild SR, Waterhouse KS, McGrath SP, Jones KC (1990) Organic contaminants in an agricultural soil with a known history of sewage sludge amendments: polynuclear aromatic hydrocarbons. Environ Sci Technol 24:1706–1711
Williams DT, Nestmann ER, LeBel GL, Benoit FM, Otson R, Lee EGH (1982) Determination of mutagenic potential and organic contaminants of Great Lakes drinking water. Chemosphere 11:263–276
Wilson AS, Tingle MD, Kelly MD, Park BK (1995) Evaluation of the generation of genotoxic and cytotoxic metabolites of benzo(a)pyrene, aflatoxin B1, naphthalene and tamoxifen using human liver microsomes and human lymphocytes. Hum Exp Toxicol 14:507–515
Wilson AS, Davis CD, Wiliams DP, Buckpitt AR, Pirmohamed M, Park BK (1996) Characterisation of the toxic metabolite(s) of naphthalene. Toxicology 114:233–242
Wu MT, Mao IF, Ho CK, Wypij D, Lu PL, Smith TJ, Chen ML, Christiani DC (1998) Urinary 1-hydroxypyrene concentrations in coke oven workers. Occup Environ Med 55:461–467
Yang M, Koga M, Katoh T, Kawamoto T (1999) A study for the proper application of urinary naphthols, new biomarkers for airborne polycyclic aromatic hydrocarbons. Arch Environ Contam Toxicol 36:99–108
Yrjäniheikki E, Pyy L, Hakala E, Lapinlampli T, Lisko A, Vähäkangas K (1995) Exposure to polycyclic aromatic hydrocarbons in a new coking plant. Am Ind Hyg Assoc J 56:782–787
Yu D, Berlin JA, Penning TM, Field J (2002) Reactive oxygen species generated by PAH o-quinones cause change-in-function mutations in p53. Chem Res Toxicol 15:832–842
Yu X, Wang X, Bartha R, Rosen JD (1990) Supercritical fluid extraction of coal tar contaminated soil. Environ Sci Technol 24:1732–1738
Zheng J, Hammock BD (1996) Development of polyclonal antibodies for detection of protein modification by 1,2-naphthoquinone. Chem Res Toxicol 9:904–909
Zheng J, Cho M, Jones AD, Hammock BD (1997) Evidence of quinone metabolites of naphthalene covalently bound to sulfur nucleophiles of proteins of murine clara cells after exposure to naphthalene. Chem Res Toxicol 10:1008–1014
Zoetman BCJ (1981) Sources, types and quantities of contaminants in ground waters. First International Conference on Groundwater Quality Research, Houston, Texas
Zuelzer WW, Apt L (1949) Acute hemolytic anemia due to naphthalene poisoning: a clinical and experimental study. J Am Med Assoc 141:185–190
Acknowledgement
We kindly thank the Hauptverband der gewerblichen Berufsgenossenschaften (HVBG), Sankt Augustin, Germany for financial and scientific support of the German PAH study and all the participants mentioned in Preuss et al. (2003).
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Preuss, R., Angerer, J. & Drexler, H. Naphthalene—an environmental and occupational toxicant. Int Arch Occup Environ Health 76, 556–576 (2003). https://doi.org/10.1007/s00420-003-0458-1
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DOI: https://doi.org/10.1007/s00420-003-0458-1