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Review Articles

Hypothesis-based weight-of-evidence evaluation and risk assessment for naphthalene carcinogenesis

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Pages 1-42 | Received 02 Feb 2015, Accepted 09 Jun 2015, Published online: 22 Jul 2015

References

  • Abdo KM, Eustis SL, McDonald M, Jokinen MP, Adkins B, Haseman JK. (1992). Naphthalene: A respiratory tract toxicant and carcinogen for mice. Inhal Toxicol, 4, 393–409.
  • Abdo KM, Grumbein S, Chou BJ, Herbert R. (2001). Toxicity and carcinogenicity study in F344 rats following 2 years of whole–body exposure to naphthalene vapors. Inhal Toxicol, 13, 931–50.
  • Adkins B, Van Stee EW, Simmons JE, Eustis SL. (1986). Oncogenic response of strain A/J mice to inhaled chemicals. J Toxicol Environ Health, 17, 311–22.
  • Agency for Toxic Substances and Disease Registry (ATSDR). (2005). Toxicological Profile for Naphthalene 1–Methylnaphthalene and 2–Methylnaphthalene.
  • Al-Daghri NM. (2008). Serum polycyclic aromatic hydrocarbons among children with and without asthma: Correlation to environmental and dietary factors. Int J Occup Med Environ Health, 21, 211–17.
  • 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, 249–57.
  • 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.
  • Bagchi D, Balmoori J, Bagchi M, Ye X, Williams CB, Stohs SJ. (2002). Comparative effects of TCDD endrin naphthalene and chromium (VI) on oxidative stress and tissue damage in the liver and brain tissues of mice. Toxicology, 175, 73–82.
  • 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, 137–43.
  • Bailey LA, Prueitt RL, Rhomberg LR. (2012). Hypothesis-based weight-of-evidence evaluation of methanol as a human carcinogen. Regul Toxicol Pharmacol, 62, 278–91.
  • Baldwin RM, Jewell WT, Fanucci MV, Plopper CG, Buckpitt AR. (2004). Comparison of pulmonary/nasal CYP2F expression levels in rodents and rhesus macaque. J Pharmacol Exp Ther, 309, 127–36.
  • Battelle Columbus Laboratories (Batelle). (1980a). Subchronic Toxicity Study: Naphthalene (C52904), B6C3F1 Mice. Report to National Toxicology Program (NTP) 25p, March 4.
  • Battelle Columbus Laboratories (Batelle). (1980b). Subchronic Toxicity Study: Naphthalene (C52904), Fischer 344 Rats. Report to National Toxicology Program (NTP) Docket No. EPA-HQ-OW-2002-0021-0075. 56p, March 4.
  • Bergamini CM, Gambetti S, Dondi A, Cervellati C. (2004). Oxygen reactive oxygen species and tissue damage. Curr Pharm Des, 10, 1611–26.
  • Bieniek G. (1994). The presence of 1–naphthol in the urine of industrial workers exposed to naphthalene. Occup Environ Med, 51, 357–9.
  • Bieniek G. (1997). Urinary naphthols as an indicator of exposure to naphthalene. Scand J Work Environ Health, 23, 414–20.
  • Boffetta P, Burstyn I, Partanen T, Kromhout H, Svane O, Langard S, et al. (2003b). Cancer mortality among European asphalt workers: An international epidemiological study. I. Results of the analysis based on job titles. Am J Ind Med, 43, 18–27.
  • Boffetta P, Burstyn I, Partanen T, Kromhout H, Svane O, Langård S, et al. (2003a). Cancer mortality among European asphalt workers: An international epidemiological study. II. Exposure to bitumen fume and other agents. Am J Ind Med, 43, 28–39.
  • Bogen KT, Benson JM, Yost GS, Morris JB, Dahl AR, Clewell HJ, et al. (2008). Naphthalene metabolism in relation to target tissue anatomy physiology cytotoxicity and tumorigenic mechanism of action. Regul Toxicol Pharmacol, 51, 27–36.
  • Bogen KT. (2008). An adjustment factor for mode-of-action uncertainty with dual-mode carcinogens: The case of naphthalene-induced nasal tumors in rats. Risk Anal, 28, 1033–51.
  • Boland B, Lin CY, Morin D, Miller L, Plopper C, Buckpitt A. (2004). Site-specific metabolism of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques. J Pharmacol Exp Ther, 310, 546–54.
  • Bosetti C, Garavello W, Gallus S, La Vecchia C. (2006). Effects of smoking cessation on the risk of laryngeal cancer: An overview of published studies. Oral Oncol, 42, 866–72.
  • Boysen G, Pachkowski BF, Nakamura J, Swenberg JA. (2009). The formation and biological significance of N7-guanine adducts. Mutat Res, 678, 76–94.
  • Brusick D, Small MS, Cavalieri EL, Chakravarti D, Ding X, Longfellow DG, et al. (2008). Possible genotoxic modes of action for naphthalene. Regul Toxicol Pharmacol, 51, 43–50.
  • Brusick D. (2008). Critical assessment of the genetic toxicity of naphthalene. Regul Toxicol Pharmacol, 51, 37–42.
  • Buckpitt A, Boland B, Isbell M, Morin D, Shultz M, Baldwin R, et al. (2002). Naphthalene-induced respiratory tract toxicity: Metabolic mechanisms of toxicity. Drug Metab Rev, 34, 791–820.
  • Buckpitt A, Buonarati M, Avey LB, Chang AM, Morin D, Plopper CG. (1992). Relationship of cytochrome P450 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, 364–72.
  • Buckpitt A, Morin D, Murphy S, Edwards P, Van Winkle L. (2013). Kinetics of naphthalene metabolism in target and non-target tissues of rodents and in nasal and airway microsomes from the Rhesus monkey. Toxicol Appl Pharmacol, 270, 97–105.
  • Buckpitt AR, Bahnson LS. (1986). Naphthalene metabolism by human lung microsomal enzymes. Toxicology, 41, 333–41.
  • 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.
  • Campbell JL, Andersen ME, Clewell HJ. (2014). A hybrid CFD–PBPK model for naphthalene in rat and human with IVIVE for nasal tissue metabolism and cross–species dosimetry. Inhal Toxicol, 26, 333–44.
  • Cauffiez C, Lo–Guidice JM, Quaranta S, Allorge D, Chevalier D, Cenne S, et al. (2004). Genetic polymorphism of the human cytochrome CYP2A13 in a French population: Implication in lung cancer susceptibility. Biochem Biophys Res Commun, 317, 662–9.
  • Chang JH, Kochansky CJ, Shou M. (2006). The role of P-glycoprotein in the bioactivation of raloxifene. Drug Metab Dispos, 34, 2073–8.
  • Cho M, Chichester C, Morin D, Plopper C, Buckpitt A. (1994). Covalent interactions of reactive naphthalene metabolites with proteins. J Pharmacol Exp Ther, 269, 881–9.
  • Cho TM, Rose RL, Hodgson E. (2006). In vitro metabolism of naphthalene by human liver microsomal cytochrome P450 enzymes. Drug Metab Dispos, 34, 176–83.
  • Cichocki JA, Smith GJ, Mendoza R, Buckpitt AR, Van Winkle LS, Morris JB. (2014). Sex differences in the acute nasal antioxidant/antielectrophilic response of the rat to inhaled naphthalene. Toxicol Sci, 139, 234–44.
  • Clewell HJ, Efremenko A, Campbell JL, Dodd DE, Thomas RS. (2014). Transcriptional responses in the rat nasal epithelium following subchronic inhalation of naphthalene vapor. Toxicol Appl Pharmacol, 280, 78–85.
  • Consonni D, Pesatori AC, Tironi A, Bernucci I, Zocchetti C, Bertazzi PA. (1999). Mortality study in an Italian oil refinery: Extension of the follow–up. Am J Ind Med, 35, 287–94.
  • Cruzan G, Bus J, Banton M, Gingell R, Carlson G. (2009). Mouse specific lung tumors from CYP2F2-mediated cytotoxic metabolism: An endpoint/toxic response where data from multiple chemicals converge to support a mode of action. Regul Toxicol Pharmacol, 55, 205–18.
  • Cruzan G, Bus J, Hotchkiss J, Harkema J, Banton M, Sarang S. (2012). CYP2F2-generated metabolites not styrene oxide are a key event mediating the mode of action of styrene-induced mouse lung tumors. Regul Toxicol Pharmacol, 62, 214–20.
  • Cruzan G, Bus J, Hotchkiss J, Sura R, Moore C, Yost G, et al. (2013). Studies of styrene oxide and 4-hydroxystyrene toxicity in CYP2F2 knockout and CYP2F1 humanized mice support lack of human relevance for mouse lung tumors. Regul Toxicol Pharmacol, 66, 24–9.
  • DeStefano-Shields C, Morin D, Buckpitt A. (2010). Formation of covalently bound protein adducts from the cytotoxicant naphthalene in nasal epithelium: Species comparisons. Environ Health Perspect, 118, 647–52.
  • Ding X, Kaminsky LS. (2003). Human extrahepatic cytochromes P450: Function in xenobiotic metabolism and tissue–selective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol, 43, 149–73.
  • Ding X, Li L, Hartog MA, Wang Y, Van Winkle LS. (2014). Role of human CYP2A13 and CYP2F1 in naphthalene bioactivation and toxicity in the lung and nasal mucosa of a CYP2A13/2F1–humanized mouse. Toxicologist, 138, 137.
  • D’Mello TA, Yamane GK. (2007). Occupational Jet Fuel Exposure and Invasive Cancer Occurrence in the United States Air Force 1989–2003. Air Force Institute for Operational Health: Brooks City–Base TX. (IOH–RS–BR–TR–2007–0001).
  • Dodd DE, Gross EA, Miller RA, Wong BA. (2010). Nasal olfactory epithelial lesions in F344 and SD rats following 1– and 5–day inhalation exposure to naphthalene vapor. Int J Toxicol, 29, 175–84.
  • Dodd DE, Wong BA, Gross EA, Miller RA. (2012). Nasal epithelial lesions in F344 rats following a 90-day inhalation exposure to naphthalene. Inhal Toxicol, 24, 70–9.
  • European Union European Commission Joint Research Centre European Chemicals Bureau (EUR). (2003). European Union Risk Assessment Report: Naphthalene (CAS NO. 91–20–3) (EINECS No. 202–049–5). Office for Official Publications of the European Communities. Luxembourg. (EUR 20763 EN, 1 st Priority List Volume 33).
  • Eustis SL. (1989). The sequential development of cancer: A morphological perspective. Toxicol Lett, 49, 267–81.
  • Fayerweather WE. (2007). Meta-analysis of lung cancer in asphalt roofing and paving workers with external adjustment for confounding by coal tar. J Occup Environ Hyg, 4, 175–200.
  • Flowers-Geary L, Bleczinki W, Harvey RG, Penning TM. (1996). Cytotoxicity and mutagenicity of polycyclic aromatic hydrocarbon ortho–quinones produced by dihydrodiol dehydrogenase. Chem Biol Interact, 99, 55–72.
  • Fukami T, Katoh M, Yamazaki H, Yokoi T, Nakajima M. (2008). Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: Naphthalene styrene and toluene. Chem Res Toxicol, 21, 720–5.
  • Genter MB, Marlowe J, Kerzee JK, Dragin N, Puga A, Dalton TP, Nebert DW. (2006). Naphthalene toxicity in mice and aryl hydrocarbon receptor-mediated CYPs. Biochem Biophys Res Commun, 348, 120–3.
  • Green T, Lee R, Toghill A, Meadowcraft S, Lund V, Foster J. (2001). The toxicity of styrene to the nasal epithelium of mice and rats: Studies on the mode of action and relevance to humans. Chem Biol Interact, 137, 185–202.
  • Griego FY, Bogen KT, Price PS, Weed DL. (2008). Exposure epidemiology and human cancer incidence of naphthalene. Regul Toxicol Pharmacol, 51, 22–6.
  • Harkema J. (2001). Attachment F: Pathology review of NTP chronic study of naphthalene in rats for the American Chemistry Council. Report to American Chemistry Council (ACC) Naphthalene Panel. Submitted to National Toxicology Program (NTP). In Comments of the Naphthalene Panel of the American Chemistry Council on Draft Report on Carcinogens Background Document for Naphthalene. August 26, 2002.
  • Hu J, Sheng L, Li L, Zhou X, Xie F, D’Agostino J, et al. (2014). Essential role of the cytochrome P450 enzyme CYP2A5 in olfactory mucosal toxicity of naphthalene. Drug Metab Dispos, 42, 23–7.
  • International Agency for Research on Cancer (IARC). (2002). Some traditional herbal medicines some mycotoxins naphthalene and styrene: Section on naphthalene. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans (Volume 82). Lyon: International Agency for Research on Cancer (IARC). Geneva: World Health Organization (WHO).
  • Jedrychowski W, Galas A, Pac A, Flak E, Camman D, Rauh V, Perera F. (2005). Prenatal ambient air exposure to polycyclic aromatic hydrocarbons and the occurrence of respiratory symptoms over the first year of life. Eur J Epidemiol, 20, 775–82.
  • Jin Y, Penning TM. (2007). Aldo–keto reductases and bioactivation/detoxication. Annu Rev Pharmacol Toxicology, 47, 263–92.
  • Kapuci M, Ulker Z, Gurkan S, Alpsoy L. (2012). Determination of cytotoxic and genotoxic effects of naphthalene 1–naphthol and 2–naphthol on human lymphocyte culture. Toxicol Ind Health, 30, 82–9.
  • Karagiannis TC, Li X, Tang MM, Orlowski C, El-Osta A, Tang ML, Royce SG. (2012). Molecular model of naphthalene-induced DNA damage in the murine lung. Hum Exp Toxicol, 31, 42–50.
  • Karlgren M, Miura S, Ingelman–Sundberg M. (2005). Novel extrahepatic cytochrome P450s. Toxicol Appl Pharmacol, 207, 57–61.
  • Kedderis GL, Shepard KG, Recio L. (2014). Cytotoxicity of naphthalene toward cells from target and non-target organs in vitro. Chem Biol Interact, 209, 85–95.
  • Kim HY, Finneman JI, Harris CM, Harris TM. (2000). Studies of the mechanisms of adduction of 2′-deoxyadenosine with styrene oxide and polycyclic aromatic hydrocarbon dihydrodiol epoxides. Chem Res Toxicol, 13, 625–37.
  • Kim JH, Kim JK, Son BK, Oh JE, Lim DH, Lee KH, et al. (2005). Effects of air pollutants on childhood asthma. Yonsei Med J, 46, 239–44.
  • Kim SJ, Jajoo HK, Kim HY, Zhou L, Horton P, Harris CM, Harris TM. (1995). An efficient route to N6 deoxyadenosine adducts of diol epoxides of carcinogenic polycyclic aromatic hydrocarbons. Bioorg Med Chem, 3, 811–22.
  • Kitteringham NR, Davis C, Howard N, Pirmohamed M, Park BK. (1996). Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: Studies with cis-stilbene oxide carbamazepine 10 11-epoxide and naphthalene. J-Pharmacol Exp Ther, 278, 1018–27.
  • Klotz K, Schindler BK, Angerer J. (2011). 1,2-Dihydroxynaphthalene as biomarker for a naphthalene exposure in humans. Int J Hyg Environ Health, 214, 110–14.
  • Krieg EF Jr, Mathias PI, Toennis CA, Clark JC, Marlow KL, B'hymer C, et al. (2012). Detection of DNA damage in workers exposed to JP-8 jet fuel. Mutat Res, 747, 218–27.
  • Lanza DL, Code E, Crespi CL, Gonzalez FJ, Yost GS. (1999). Specific dehydrogenation of 3-methylindole and epoxidation of naphthalene by recombinant human CYP2F1 expressed in lymphoblastoid cells. Drug Metab-Dispos, 27, 798–803.
  • Leclerc J, Tournel G, Courcot-Ngoubo Ngangue E, Pottier N, Lafitte JJ, Jaillard S, et al. (2010). Profiling gene expression of whole cytochrome P450 superfamily in human bronchial and peripheral lung tissues: Differential expression in non-small cell lung cancers. Biochimie, 92, 292–306.
  • Lee MG, Phimister A, Morin D, Buckpitt A, Plopper C. (2005). In situ naphthalene bioactivation and nasal airflow cause region-specific injury patterns in the nasal mucosa of rats exposed to naphthalene by inhalation. J-Pharmacol Exp Ther, 314, 103–10.
  • Lewis DF, Ito Y, Lake BG. (2009). Molecular modelling of CYP2F substrates: Comparison of naphthalene metabolism by human rat and mouse CYP2F subfamily enzymes. Drug Metab Drug Interact, 24, 229–57.
  • Lewis RJ, Schnatter AR, Drummond I, Murray N, Thompson FS, Katz AM, et al. (2003). Mortality and cancer morbidity in a cohort of Canadian petroleum workers. Occup Environ Med, 60, 918–28.
  • Lewis RJ. (2012). Naphthalene animal carcinogenicity and human relevancy: Overview of industries with naphthalene-containing streams. Regul Toxicol Pharmacol, 62, 131–7.
  • Li L, Wei Y, Van Winkle L, Zhang QY, Zhou X, Hu J, et al. (2011). Generation and characterization of a Cyp2f2-Null mouse and studies on the role of CYP2F2 in naphthalene-induced toxicity in the lung and nasal olfactory mucosa. J Pharmacol Exp Ther, 339, 62–71.
  • Lin CY, Boland BC, Lee YJ, Salemi MR, Morin D, Miller LA, et al. (2006). Identification of proteins adducted by reactive metabolites of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques. Proteomics, 6, 972–82.
  • Lin CY, Isbell MA, Morin D, Boland BC, Salemi MR, Jewell WT, et al. (2005). Characterization of a structurally intact in situ lung model and comparison of naphthalene protein adducts generated in this model vs lung microsomes. Chem Res Toxicol, 18, 802–13.
  • Lin PH, Chen DR, Wang TW, Lin CH, Chuang MC. (2009). Investigation of the cumulative tissue doses of naphthoquinones in human serum using protein adducts as biomarker of exposure. Chem Biol Interact, 181, 107–14.
  • Long PH, Herbert RA, Peckham JC, Grumbein SL, Shackelford CC, Abdo K. (2003). Morphology of nasal lesions in F344/N rats following chronic inhalation exposure to naphthalene vapors. Toxicol Pathol, 31, 655–64.
  • Marczynski B, Raulf-Heimsoth M, Spickenheuer A, Pesch B, Kendzia B, Mensing T, et al. (2011). DNA adducts and strand breaks in workers exposed to vapours and aerosols of bitumen: Associations between exposure and effect. Arch Toxicol, 85, S53–S64.
  • McCarty KM, Ryan L, Houseman EA, Williams PL, Miller DP, Quamruzzaman Q, et al. (2007). A case-control study of GST polymorphisms and arsenic related skin lesions. Environ Health, 6, 5.
  • Meng F, Wang Y, Myers MB, Wong BA, Gross EA, Clewell HJ III, et al. (2011). P53 codon 271 CGT to CAT mutant fraction does not increase in nasal respiratory and olfactory epithelia of rats exposed to inhaled naphthalene. Mutat Res, 721, 199–205.
  • Merletti F, Boffetta P, Ferro G, Pisani P, Terracini B. (1991). Occupation and cancer of the oral cavity or oropharynx in Turin Italy. Scand J Work Environ Health, 17, 248–54.
  • Miller RL, Garfinkel R, Horton M, Camann D, Perera FP, Whyatt RM, Kinney PL. (2004). Polycyclic aromatic hydrocarbons environmental tobacco smoke and respiratory symptoms in an inner-city birth cohort. Chest, 126, 1071–8.
  • Moore NP, McFadden LG, Landenberger BD, Thomas J. (2013). Gender differences in the incidence of background and chemically induced primary pulmonary neoplasms in B6C3F1 mice: A retrospective analysis of the National Toxicology Program (NTP) carcinogenicity bioassays. Exp Toxicol Pathol, 65, 1109–15.
  • Morley N, Rapp A, Dittmar H, Salter L, Gould D, Greulich KO, Curnow A. (2006). UVA-induced apoptosis studied by the new apo/necro-Comet-assay which distinguishes viable apoptotic and necrotic cells. Mutagenesis, 21, 105–14.
  • Morris JB, Buckpitt AR. (2009). Upper respiratory tract uptake of naphthalene. Toxicol Sci, 111, 383–91.
  • Morris JB. (2013). Nasal dosimetry of inspired naphthalene vapor in the male and female B6C3F1 mouse. Toxicology, 309, 66–72.
  • Munday R, Smith BL, Munday CM. (2007). Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone. J Appl Toxicol, 27, 262–9.
  • Nagata K, Martin BM, Gillette JR, Sasame HA. (1990). Isozymes of cytochrome P-450 that metabolize naphthalene in liver and lung of untreated mice. Drug Metab Dispos, 18, 557–64.
  • Nan HM, Kim H, Lim HS, Choi JK, Kawamoto T, Kang JW, et al. (2001). Effects of occupation lifestyle and genetic polymorphisms of CYP1A1 CYP2E1 GSTM1 and GSTT1 on urinary 1-hydroxypyrene and 2-naphthol concentrations. Carcinogenesis, 22, 787–93.
  • National Cancer Institute (NCI). (2014). “SEER Fast Stats: Compare statisics by data type, 1975-–2011.” Surveillance, Epidemiology, and End Results (SEER) Program. Accessed at http://seer.cancer.gov/faststats/selections.php.
  • National Institute for Occupational Safety and Health (NIOSH). (2000). Hazard Review: Health Effects of Occupational Exposures to Asphalt. (United States Dept. of Health and Human Services NIOSH Publication No. 2001–110).
  • National Toxicology Program (NTP). (2011). Naphthalene (CAS No. 91–20–3). In Report on Carcinogens (12th Edition). US Dept. of Health and Human Services Public Health Service: National Toxicology Program.
  • National Toxicology Program (NTP). (1992).Toxicology and Carcinogenesis Studies of Naphthalene (CAS No. 91–20–3) in B6C3F1 Mice (Inhalation Studies). US Public Health Service: National Institutes of Health. (NTP–TR–410, NIH Publication No. 92–3141).
  • National Toxicology Program (NTP). (December 2000). NTP Technical Report on the Toxicology and Carcinogenesis Studies of Naphthalene (CAS No. 91–20–3) in F344/N Rats (Inhalation Studies). US Public Health Service: National Institutes of Health. (NTP–TR–500, NIH Publication No. 01–4434).
  • National Toxicology Program (NTP). 2012. Long–term bioassay study search options for C52904C. [Online] Available from: http://tools.niehs.nih.gov/ntp_tox/index.cfm?fuseaction = longtermbioassaydata.datasearch&&study_no = C52904C&&study_length = 2%20Years. [Accessed August 2012].
  • Neafsey P, Ginsberg G, Hattis D, Johns DO, Guyton KZ, Sonawane B. (2009). Genetic polymorphism in CYP2E1: Population distribution of CYP2E1 activity. J Toxicol Environ Health B Crit Rev, 12, 362–88.
  • Nishimura M, Naito S. (2006). Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II metabolizing enzymes. Drug Metab Pharmacokinet, 21, 357–74.
  • North DW, Abdo KM, Benson JM, Dahl AR, Morris JB, Renne R, Witschi H. (2008). A review of whole animal bioassays of the carcinogenic potential of naphthalene. Regul Toxicol Pharmacol, 51, 6–14.
  • O’Connor T, Ireland LS, Harrison DJ, Hayes JD. (1999). Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members. Biochem J, 343, 487–504.
  • Oliver JR, Kushwah R, Wu J, Cutz E, Yeger H, Waddell TK, Hu J. (2009). Gender differences in pulmonary regenerative response to naphthalene-induced bronchiolar epithelial cell injury. Cell Prolif, 42, 672–87.
  • Olsson A, Kromhout H, Agostini M, Hansen J, Lassen CF, Johansen C, et al. (2010). A case-control study of lung cancer nested in a cohort of European asphalt workers. Environ Health Perspect, 118, 1418–24.
  • Orjuela M, Liu X, Miller RL, Warburton D, Tang DL, Jobanputra V, et al. (2012). Urinary naphthol metabolites and chromosomal aberrations in 5 yr old children. Cancer Epidemiol Biomarkers Prev, 21, 1191–202.
  • 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, 24799–808.
  • Penning TM, Drury JE. (2007). Human aldo-keto reductases: Function gene regulation and single nucleotide polymorphisms. Arch Biochem Biophys, 464, 241–50.
  • Pfuhler S, Fellows M, van Benthem J, Corvi R, Curren R, Dearfield K, et al. (2011). In vitro genotoxicity test approaches with better predictivity: Summary of an IWGT workshop. Mutat Res, 723, 101–7.
  • Pham NT, Jewell WT, Morin D, Buckpitt AR. (2012a). Analysis of naphthalene adduct binding sites in model proteins by tandem mass spectrometry. Chem Biol Interact, 199, 120–8.
  • Pham NT, Jewell WT, Morin D, Jones AD, Buckpitt AR. (2012b). Characterization of model Peptide adducts with reactive metabolites of naphthalene by mass spectrometry. PLoS ONE, 7, e42053.
  • Phimister AJ, Lee MG, Morin D, Buckpitt AR, Plopper CG. (2004). Glutathione depletion is a major determinant of inhaled naphthalene respiratory toxicity and naphthalene metabolism in mice. Toxicol Sci, 82, 268–78.
  • Piccirillo VJ, Bird MG, Lewis RJ, Bover WJ. (2012). Preliminary evaluation of the human relevance of respiratory tumors observed in rodents exposed to naphthalene. Regul Toxicol Pharmacol, 62, 433–40.
  • Plopper CG, Macklin J, Nishio SJ, Hyde DM, Buckpitt AR. (1992a). Relationship of cytochrome P-450 activity to Clara cell cytotoxicity. III. Morphometric comparison of changes in the epithelial populations of terminal bronchioles and lobar bronchi in mice hamsters and rats after parenteral administration of naphthalene. Lab Invest, 67, 553–65.
  • Plopper CG, Suverkropp C, Morin D, Nishio S, Buckpitt A. (1992b). Relationship of cytochrome P-450 activity to Clara cell cytotoxicity. I. Histopathologic comparison of the respiratory tract of mice rats and hamsters after parenteral administration of naphthalene. J Pharmacol Exp Ther, 261, 353–63.
  • Prueitt RL, Goodman JE, Bailey LA, Rhomberg LR. (2011). Hypothesis-based weight-of-evidence evaluation of the neurodevelopmental effects of chlorpyrifos. Crit Rev Toxicol, 41, 822–903.
  • Raunio H, Hakkola J, Hukkanen J, Lassila A, Paivarinta L, Pelkonen O, et al. (1999). Expression of xenobiotic-metabolizing CYPs in human pulmonary tissue. Exp Toxicol Pathol, 51, 412–17.
  • Recio L, Shepard KG, Hernandez LG, Kedderis GL. (2012). Dose-response assessment of naphthalene-induced genotoxicity and glutathione detoxication in human TK6 lymphoblasts. Toxicol Sci, 126, 405–12.
  • Rhomberg L. (2014). Hypothesis-based weight-of-evidence: An approach to assessing causation and its application to regulatory toxicology. Risk Anal, doi:10.1111/risa.12206.
  • Rhomberg LR, Bailey LA, Goodman JE, Hamade A, Mayfield D. (2011). Is exposure to formaldehyde in air causally associated with leukemia? – A hypothesis-based weight-of-evidence analysis. Crit Rev Toxicol, 41, 555–621.
  • Rhomberg LR, Bailey LA, Goodman JE. (2010). Hypothesis-based weight of evidence: A tool for evaluating and communicating uncertainties and inconsistencies in the large body of evidence in proposing a carcinogenic mode of action – Naphthalene as an example. Crit Rev Toxicol, 40, 671–96.
  • Ribble D, Goldstein NB, Norris DA, Shellman YG. (2005). A simple technique for quantifying apoptosis in 96-well plates. BMC Biotechnol, 5, 12.
  • Richieri PR, Buckpitt AR. (1987). Efflux of naphthalene oxide and reactive naphthalene metabolites from isolated hepatocytes. J Pharmacol Exp Ther, 242, 485–92.
  • Roberts ES, Alworth WL, Hollenberg PF. (1998). Mechanism-based inactivation of cytochromes P450 2E1 and 2B1 by 5-phenyl-1-pentyne. Arch Biochem Biophys, 354, 295–302.
  • Roco A, Quinones L, Agundez JA, Garcia-Martin E, Squicciarini V, Miranda C, et al. (2012). Frequencies of 23 functionally significant variant alleles related with metabolism of antineoplastic drugs in the Chilean population: Comparison with Caucasian and Asian populations. Front Genet, 3, 229.
  • Rushton L. (1993). A 39-year follow-up of the U.K. oil refinery and distribution center studies: Results for kidney cancer and leukemia. Environ Health Perspect, 101, 77–84.
  • Saarikoski ST, Rivera SP, Hankinson O, Husgafvel-Pursiainen K. (2005). CYP2S1: A short review. Toxicol Appl Pharmacol, 207, 62–9.
  • Saeed M, Higginbotham S, Gaikwad N, Chakravarti D, Rogan E, Cavalieri E. (2009). Depurinating naphthalene-DNA adducts in mouse skin related to cancer initiation. Free Radic Biol Med, 47, 1075–81.
  • Saeed M, Higginbotham S, Rogan E, Cavalieri E. (2007). Formation of depurinating N3adenine and N7guanine adducts after reaction of 12-naphthoquinone or enzyme-activated 12-dihydroxynaphthalene with DNA. Implications for the mechanism of tumor initiation by naphthalene. Chem Biol Interact, 165, 175–88.
  • Salam MT, Lin PC, Avol EL, Gauderman WJ, Gilliland FD. (2007). Microsomal epoxide hydrolase glutathione S-transferase P1 traffic and childhood asthma. Thorax, 62, 1050–7.
  • Schmahl D. (1955). Testing of naphthalene and anthracene for carcinogenic effect in rats. Z Krebsforsch, 60, 697–710.
  • Schreiner CA. (2003). Genetic toxicity of naphthalene: A review. J Toxicol Environ Health B Crit Rev, 6, 161–83.
  • Seidegard J, Ekstrom G. (1997). The role of human glutathione transferases and epoxide hydrolases in the metabolism of xenobiotics. Environ Health Perspect, 105, 791–9.
  • Shultz CA, Quinn AM, Park JH, Harvey RG, Bolton JL, Maser E, Penning TM. (2011). Specificity of human aldo-keto reductases NAD(P)H:quinone oxidoreductase and carbonyl reductases to redox-cycle polycyclic aromatic hydrocarbon diones and 4-hydroxyequilenin-o-quinone. Chem Res Toxicol, 24, 2153–66.
  • Simmonds AC, Ghanayem BI, Sharma A, Reilly CA, Millen B, Yost GS, Forkert PG. (2004). Bioactivation of 11-dichloroethylene by CYP2E1 and CYP2F2 in murine lung. J Pharmacol Exp Ther, 310, 855–64.
  • Su T, Bao Z, Zhang QY, Smith TJ, Hong JY, Ding X. (2000). Human cytochrome P450 CYP2A13: Predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res, 60, 5074–9.
  • Sudakin DL, Stone DL, Power L. (2011). Naphthalene mothballs: Emerging and recurring issues and their relevance to environmental health. Curr Top Toxicol, 7, 13–19.
  • Sutherland KM, Edwards PC, Combs TJ, Van Winkle LS. (2012). Sex differences in the development of airway epithelial tolerance to naphthalene. Am J Physiol Lung Cell Mol Physiol, 302, L68–L91.
  • Talamini R, Bosetti C, La Vecchia C, Dal Maso L, Levi F, Bidoli E, et al. (2002). Combined effect of tobacco and alcohol on laryngeal cancer risk: A case-control study. Cancer Causes Control, 13, 957–64.
  • Thornton-Manning JR, Dahl AR. (1997). Metabolic capacity of nasal tissue interspecies comparisons of xenobiotic-metabolizing enzymes. Mutat Res, 380, 43–59.
  • Tournel G, Cauffiez C, Billaut-Laden I, Allorge D, Chevalier D, Bonnifet F, et al. (2007). Molecular analysis of the CYP2F1 gene: Identification of a frequent non-functional allelic variant. Mutat Res, 617, 79–89.
  • United States Environmental Protection Agency (US EPA). (2004). Toxicological Review of Naphthalene (CAS No. 91–20–3) (External review draft). (NCEA–S–1707).
  • United States Environmental Protection Agency (US EPA). (2012a). Benchmark Dose Technical Guidance. Risk Assessment Forum. (EPA/100/R–12/001).
  • United States Environmental Protection Agency (US EPA). (2012b). Benchmark Dose Software (BMDS) (Version 2.3.1). National Center for Environmental Assessment (NCEA). [Online] Available from: http://www.epa.gov/ncea/bmds/.
  • United States Environmental Protection Agency (US EPA). (2014). Mouse Lung Tumor Workshop. [Online]Available from: http://www.epa.gov/iris/irisworkshops/mltw/.
  • United States Environmental Protection Agency (US EPA). (1998). “Toxicological Review of Naphthalene (CAS No. 91-–20-3).” 116p.
  • Van Heyningen R, Pirie A. (1967). The metabolism of naphthalene and its toxic effect on the eye. Biochem J, 102, 842–52.
  • Van Winkle LS, Buckpitt AR, Nishio SJ, Isaac JM, Plopper CG. (1995). Cellular response in naphthalene-induced Clara cell injury and bronchiolar epithelial repair in mice. Am J Physiol, 269, L800–L818.
  • 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, 586–98.
  • Van Winkle LS, Cichocki J, Mendoza R, Edwards P, Morris JB. (2014). Sex differences in glutathione levels and cytotoxicity following naphthalene or acrolein exposure in nasal epithelium. Toxicologist, 138, 322.
  • Van Winkle LS, Gunderson AD, Shimizu JA, Baker GL, Brown CD. (2002). Gender differences in naphthalene metabolism and naphthalene-induced acute lung injury. Am J Physiol Lung Cell Mol Physiol, 282, L1122–L1134.
  • Van Winkle LS, Isaac JM, Plopper CG. (1997). Distribution of epidermal growth factor receptor and ligands during bronchiolar epithelial repair from naphthalene–induced Clara cell injury in the mouse. Am J Pathol, 151, 443–59.
  • Vineis P, Schatzkin A, Potter JD. (2010). Models of carcinogenesis: An overview. Carcinogenesis, 31, 1703–9.
  • Waidyanatha S, Rappaport SM. (2008). Hemoglobin and albumin adducts of naphthalene-12-oxide 12-naphthoquinone and 14-naphthoquinone in Swiss Webster mice. Chem Biol Interact, 172, 105–14.
  • Waidyanatha S, Troester MA, Lindstrom AB, Rappaport SM. (2002). Measurement of hemoglobin and albumin adducts of naphthalene-12-oxide 12-naphthoquinone and 14-naphthoquinone after administration of naphthalene to F344 rats. Chem Biol Interact, 141, 189–210.
  • Wang H, Tan W, Hao B, Miao X, Zhou G, et al. (2003). Substantial reduction in risk of lung adenocarcinoma associated with genetic polymorphism in CYP2A13 the most active cytochrome P450 for the metabolic activation of tobacco-specific carcinogen NNK. Cancer Res, 63, 8057–61.
  • Warren DL, Brown DL Jr., Buckpitt AR. (1982). Evidence for cytochrome P-450 mediated metabolism in the bronchiolar damage by naphthalene. Chem Biol Interact, 40, 287–303.
  • West JA, Buckpitt AR, Plopper CG. (2000). Elevated airway GSH resynthesis confers protection to Clara cells from naphthalene injury in mice made tolerant by repeated exposures. J Pharmacol Exp Ther, 294, 516–23.
  • West JA, Pakehham G, Morin D, Fleschneer CA, Buckpitt AR, Plopper CG. (2001). Inhaled naphthalene causes dose dependent Clara cell cytotoxicity in mice but not in rats. Toxicol Appl Pharmacol, 173, 114–19.
  • Willems BA, Melnick RL, Kohn MC, Portier CJ. (2001). A physiologically based pharmacokinetic model for inhalation and intravenous administration of naphthalene in rats and mice. Toxicol Appl Pharmacol, 176, 81–91.
  • Wilson AS, Davis CD, Williams DP, Buckpitt AR, Pirmohamed M, Park BK. (1996). Characterisation of the toxic metabolite(s) of naphthalene. Toxicology, 114, 233–42.
  • Wong O, Harris F. (2005). Retrospective cohort mortality study and nested case-control study of workers exposed to creosote at 11 wood-treating plants in the United States. J Occup Environ Med, 47, 683–97.
  • Wong O, Raabe GK. (2000). A critical review of cancer epidemiology in the petroleum industry with a meta–analysis of a combined database of more than 350000 workers. Regul Toxicol Pharmacol, 32, 78–98.
  • Wu R, Waidyanatha S, Henderson AP, Serdar B, Zheng Y, Rappaport SM. (2005). Determination of dihydroxynaphthalenes in human urine by gas chromatography–mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci, 826, 206–13.
  • Wu X, Gwyn K, Amos CI, Makan N, Hong WK, Spitz MR. (2001). The association of microsomal epoxide hydrolase polymorphisms and lung cancer risk in African-Americans and Mexican-Americans. Carcinogenesis, 22, 923–8.
  • Xu GT, Zigler JS Jr., Lou MF. (1992a). Establishment of a naphthalene cataract model in vitro. Exp Eye Res, 54, 73–81.
  • Xu GT, Zigler JS Jr., Lou MF. (1992b). The possible mechanism of naphthalene cataract in rat and its prevention by an aldose reductase inhibitor (ALO1576). Exp Eye Res, 54, 63–72.
  • Yamane GK. (2006). Cancer incidence in the U.S. Air Force: 1989–2002. Aviat Space Environ Med, 77, 789–94.
  • 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.
  • 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, 1008–14.