Ercole Cavalieri, DSc: The role of depurinating DNA adducts in the initiation of cancer by aromatic hydrocarbons.
Note: Links are provided for non-copyrighted documents only.

Cavalieri E and Rogan E. 2002. Fluoro substitution of carcinogenic aromatic hydrocarbons: Models for understanding mechanisms of metabolic activation and of oxygen transfer catalyzed by cytochrome P450. In: The Handbook of Environmental Chemistry, Vol. 3N: Organofluorines (A.H. Neilson, ed.), Springer-Verlag, Heidelberg, pp. 277-293. [View]

Cavalieri E, Rogan E, Li K, Todorovic R, Ariese F, Jankowiak R, Grubor N and Small G. 2005. Identification and quantification of the depurinating DNA adducts formed in mouse skin treated with dibenzo[a,l]pyrene (DB[a,l)P), or its metabolites and in rat mammary gland treated with DB[a,l]P. Chem. Res. Toxicol., 18:976-983. [View]

Jankowiak R, Rogan E and Cavalieri E. 2004.The role of fluorescence line-narrowing spectroscopy and related luminescence-based techniques in the elucidation of mechanisms of tumor initiation by polycyclic aromatic hydrocarbons and estrogens.J. Phys. Chem. B, 108:10266-10283. [View]

Mulder P, Devanesan P, van Alem K, Lodder G, Rogan E and Cavalieri E.2003. Fluorobenzo[a]pyrenes as probes of the mechanism of cytochrome P450-catalyzed oxygen transfer in aromatic oxygenations. Free Rad. Biol. & Med., 34:734-745. [View]

Todorovic R, Devanesan P, Rogan E and Cavalieri E. 2005. Identification and quantification of stable DNA adducts of dibenzo[a,l]pyrene or its metabolites in vitro, and in mouse skin and rat mammary gland. Chem. Res. Toxicol., 18:984-990. [View]

Eleanor Rogan, PhD: The role of depurinating DNA adducts in the initiation of cancer by estrogens.
Note: Links are provided for non-copyrighted documents only.

Cavalieri E, Rogan E and Chakravarti D. 2004.The role of endogenous catechol quinones in the initiation of cancer and neurodegenerative diseases. In: Methods in Enzymology, Quinones and Quinone Enzymes, Part B (H. Sies & L. Packer, Eds.), Vol. 382, Elsevier, Duesseldorf, Germany, 293-319. [View]

Cavalieri E., Chakravarti D., Guttenplan J., Hart E., Ingle J., Jankowiak R., Muti P., Rogan E., Russo J., Santen R. and Sutter T. 2006. Catechol estrogen quinones as initiators of breast and other human cancers. Implications for biomarkers of susceptibility and cancer prevention. BBA-Reviews on Cancer, 1766:63-78. [View]

Li K, Todorovic R, Devanesan P, Higginbotham S, Köfeler H, Ramanathan R, Gross M, Rogan E and Cavalieri E. 2004.Metabolism and DNA binding studies of 4- hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo. Carcinogenesis, 25:289-297. [View]

Rogan E, Badawi A, Devanesan P, Meza J, Edney J, West W, Higginbotham S and Cavalieri E. 2003. Relative imbalances in estrogen metabolism and conjugation in breast tissue of women with carcinoma: Potential biomarkers of susceptibility to cancer. Carcinogenesis, 24:697-702. [View]

Stack D, Byun J, Gross M, Rogan E and Cavalieri E.1996.Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides. Chem. Res. Toxicol., 9:851-859. [View]

Dhrubajyoti Chakravarti, PhD: The role of error-prone base excision repair in generating mutations from aromatic hydrocarbon- and estrogen-induced DNA damage.
Note: Links are provided for non-copyrighted documents only.

Chakravarti D, Mailander P, Li K, Higginbotham S, Zhang H, Gross M, Cavalieri E and Rogan E. 2001. Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and form mutations in the H-ras gene. Oncogene, 20:7945-7953. [View]

Chakravarti D, Badawi A, Venugopal D, Meza J, Crandall L, Rogan E and Cavalieri E. 2005.Improved measurement of dibenzo[a,l]pyrene-induced abasic sites by the aldehyde-reactive probe assay. Mutat. Res., 588:158-165. [View]

Khan G, Bhattacharya G, Mailander P, Meza J, Hansen L and Chakravarti D. 2005. Harvey-ras gene expressions and epidermal cell proliferation in dibenzo[a,l]pyrene-treated early preneoplastic SENCAR mouse skin. J. Invest. Dermatol., 125:567-574. [View]

Mailander P, Meza J, Higginbotham S and Chakravarti D.2006. Induction of A.T to G.C mutations by erroneous repair of depurinated DNA following estrogen treatment of the mammary gland of ACI rats. J. Steroid Biochem. Mol. Biol., epub ahead of print. [View]

Module A: Naphthalene Animal Bioassays
Note: Links are provided for non-copyrighted documents only.

Abdo, K; Grumbein, S; Chou, BJ; and Herbert R. 2001 Toxicity and carcinogenicity study in F344 rats following 2 years of whole-body exposure to naphthalene vapors. Inhalation Toxicology 13:931-950. [View]

Adkins B Jr; Van Stee E; Simmons J, Eustis S. 1986. Oncogenic response of strain A/J mice to inhaled chemicals. J Toxicol Environ Health 17:311-322. [View]

Long P, Herbert R, Peckham J, Grumbein S, Shackelford C, Abdo K. 2003. Morphology of nasal lesions in F344/N rats following chronic inhalation exposure to naphthalene vapors. Toxicol Pathol. 31(6):655-64. [View]

NTP. 2000. Toxicology and carcinogenesis studies of naphthalene (CAS no. 91-20-3) in F344/N rats (inhalation studies). Natl Toxicol Program Tech Rep Ser. 2000 Dec;(500):1-173. [View]

West, J, G Pakehham, D Morin, C Fleschner, A Buckpitt, and C Plopper. 2001.Inhaled naphthalene causes dose dependent Clara cell cytotoxicity in mice but not in rats . Toxicol Appl Pharmacol 173 (2):114-9. [View]

Secondary references...

Module B: Exposure, Epidemiology and Human Cancer Incidence
Note: Links are provided for non-copyrighted documents only.

Ajao, O; Adenuga, M; Ladipo, J. 1988. Colorectal carcinoma in patients under the age of 30 years: a review of 11 cases. J R Coll Surg Edinburgh 33:277-279. [View]

Campo L, Addario L, Buratti M, Scibetta L, Longhi O, Valla C, Cirla P, Martinotti I, Foa V, Fustinoni S. 2005. Biological monitoring of exposure to polycyclic aromatic hydrocarbons by determination of unmetabolized compounds in urine. Toxicol Lett. 2005 Oct 20; [Epub ahead of print] [View]

Chuang J, Mack G, Kuhlman M, and Wilson N. 1991. Polycyclic aromatic hydrocarbons and their derivatives in indoor and outdoor air in an eight-home study. PB-92-166701/XAB, Battelle, Columbus, OH (United States). [View]

Chuang J, Callahan P, Menton R, Gordon S, Lewis R, and Wilson N. 1995. Monitoring Methods for Polycyclic Aromatic Hydrocarbons and Their Distribution in House Dust and Track-in Soil. Environmental Science & Technology, 29 (2):494-500. [View]

Chuang JC, Callahan PJ, Lyu CW, and Wilson NK. 1999. Polycyclic aromatic hydrocarbon exposures of children in low-income families. Journal of exposure analysis and environmental epidemiology 9 (2):85-98. [View]

Khalili N, Scheff P, and Holsen T. 1995. PAH source fingerprints for coke ovens, diesel and gasoline engines, highway tunnels, and wood combustion emissions. Atmospheric Environment 29 (4):533-542. [View]

Kokel, D, Y Li, and D Xing. 2006. The nongenotoxic carcinogens naphthalene and para-dichlorobenzene suppress apoptosis in Caenorhabditis elegans. Nature Chemical Biology 2 (6) 338:345. [View]

Kostiainen R. 1995. Volatile organic compounds in the indoor air of normal and sick houses. Atmospheric Environment 29 (6):693-702. [View]

Lofgren L, Persson K, Stromvall A, and Petersson G. 1991. Exposure of commuters to volatile aromatic hydrocarbons from petrol exhaust. The Science of the total environment 108 (3):225-33.[View]

McDonald J, Zielinska B, Fujita E, Sagebiel J, Chow J, and Watson J. 2000. Fine Particle and Gaseous Emission Rates from Residential Wood Combustion. Environ. Sci. Technol. 34 (11):2080-2091.[View]

Preuss R, Koch H, Wilhelm M, Pischetsrieder M, and Angerer J. 2004. Pilot study on the naphthalene exposure of German adults and children by means of urinary 1- and 2-naphthol levels. International journal of hygiene and environmental health 207 (5):441-5. [View]

Preuss R, H Drexler, M Böttcher, M Wilhelm, T Brüning, and J Angerer. 2005. Current external and internal exposure to naphthalene of workers occupationally exposed to polycyclic aromatic hydrocarbons in different industries. International Archives of Occupational and Environmental Health 78 (5):355-362. [View]

Rappaport S, Waidyanatha S, Serdar B. 2004. Naphthalene and its biomarkers as measures of occupational exposure to polycyclic aromatic hydrocarbons. J Environ Monit. May;6(5):413-6. [View]

Schauer J, Kleeman M, Cass G, and Simoneit B. 1999. Measurement of Emissions from Air Pollution Sources. 2. C₁ through C₃₀ Organic Compounds from Medium Duty Diesel Trucks. Environ. Sci. Technol. 33 (10):1578-1587. [View]

Schauer J, Kleeman M, Cass G, and Simoneit B. 2001. Measurement of emissions from air pollution sources. 3. C1-C29 organic compounds from fireplace combustion of wood. Environmental science & technology 35 (9):1716-28. [View]

Shah S, Ogunyoku T, Miller J, and Cocker D, 3rd. 2005. On-road emission rates of PAH and n-alkane compounds from heavy-duty diesel vehicles. Environmental science & technology 39 (14):5276-84. [View]

Wolf, O. 1976. Cancer diseases in chemical workers in a former naphthalene cleaning plant. Dtsch Gesundheitswes 31:996-999. (Ger.) (Cited in U.S. EPA, 1987; NTP, 1992) [View PDF]

Wolf, O. 1978. Arbeitshygiene und arbeitsschutz. Z Ges Hyg 24:737-739.[View PDF]

Zhu L, Shen X, and Liu Y. 2003. Determination of polycyclic aromatic hydrocarbons in indoor and outdoor air with chromatographic methods. Journal of environmental science and health 38 (5):779-92. [View]

Secondary references...

Module C: Anatomy, Physiology, and Metabolic Activation and Deactivation
Note: Links are provided for non-copyrighted documents only.

Baldwin, R, M Shultz, and A Buckpitt. 2005. Bioactivation of the pulmonary toxicants naphthalene and 1-nitronaphthalene by rat CYP2F4 . J Pharmacol Exp Ther 312 (2):857-865. [View]

Boland, B., C Lin, D Morin, L Miller, C Plopper, and A Buckpitt. 2004. Site-specific metabolism of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques . J Pharmacol Exp Ther 310 (2):546-54. [View]

Buckpitt, A, M Buonarati, L Avey, A Chang, D Morin, and C Plopper. 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 (1):364-372. [View]

Buckpitt, A, AM Chang, A Weir, L Van Winkle, X Duan, R Philpot, and C Plopper. 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 (1):74-81. [View]

Buckpitt, A, B Boland, M Isbell, D Morin, M Shultz, R Baldwin, K Chan, A Karlsson, C Lin, A Taff, J West, M Fanucchi, L Van Winkle, and C Plopper. 2002. Naphthalene-induced respiratory tract toxicity: metabolic mechanisms of toxicity . Drug Metab Rev 34 (4):791-820. [View]

Buckpitt, A , and R Franklin. 1989. Relationship of naphthalene and 2-methylnaphthalene metabolism to pulmonary bronchiolar epithelial cell necrosis. Pharmacol Ther 41 (1):393-410. [View]

Buckpitt, A, and L Bahnson. 1986. Naphthalene metabolism by human lung microsomal enzymes. Toxicology 41 (3):333-341. [View]

Chichester, C, A Buckpitt, A Chang, and C Plopper. 1994. Metabolism and cytotoxicity of naphthalene and its metabolites in isolated murine Clara cells. Mol Pharmacol 45 (4):664-72. [View]

Ghanem, A, Shuler M. 2000. Characterization of a perfusion reactor utilizing mammalian cells on microcarrier beads . Biotechnol Prog. 16(3):471-9. [View]

Lakritz, J, A Chang, A Weir, S Nishio, D Hyde, R Philpot, A Buckpitt, and C Plopper. 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. JPharmacol Exp Ther 278 (3):1408-1418. [View]

Lin,C, B Boland, Y Lee, M Salemi, D Morin, L Miller, C Plopper, and A Buckpitt.2006.Identification of proteins adducted by reactive metabolites of naphthalene and 1-nitronaphthalene in dissected airways of rhesus macaques. Proteomics. Feb.;6.(3):972.-82. 6:972-982. [View]

McCoull,K, D Rindgen, I Blair, and T Penning. 1999. Synthesis and characterization of polycyclic aromatic hydrocarbon o-quinone depurinating N7-guanine adducts. Chem Res.Toxicol. 12:237-246.

Phimister, A, H Nagasawa, A Buckpitt, and C Plopper. 2005. Prevention of naphthalene-induced pulmonary toxicity by glutathione prodrugs: Roles for glutathione depletion in adduct formation and cell injury. Journal of Biochemical and Molecular Toxicology 19 (1):42-51. [View]

Phimister, A, G Lee, D Morin, A Buckpitt, and C Plopper. 2004. Glutathione depletion is a major determinant of inhaled naphthalene respiratory toxicity and naphthalene metabolism in mice. Toxicol. Sci. 82 (1):268-278. : [View]

Phimister, A, K Williams, L Van Winkle, and C Plopper. 2005.Consequences of abrupt glutathione depletion in murine Clara cells: Ultrastructural and biochemical investigations into the role of glutathione loss in naphthalene cytotoxicity. J Pharmacol Exp Ther 314 (2):506-13. [View]

Plopper, C, L Van Winkle, M Fanucchi, S Malburg, S Nishio, A Chang, and A Buckpitt. 2001. Early events in naphthalene-induced acute Clara cell toxicity. II. Comparison of glutathione depletion and histopathology by airway location. Am J Respir Cell Mol Biol 24 (3):272-81. [View]

Shultz, M, P Choudary, and A Buckpitt. 1999. Role of murine cytochrome P-450 2F2 in metabolic activation of naphthalene and metabolism of other xenobiotics. J Pharmacol Exp Ther 290 (1):281-288. [View]

Shultz, M, D Morin, A Chang, and A Buckpitt. 2001. Metabolic capabilities of CYP2F2 with various pulmonary toxicants and its relative abundance in mouse lung subcompartments. J Pharmacol Exp Ther 296 (2):510-519. [View]

Stelck, R, G Baker, K Sutherland, and L Van Winkle. 2005. Estrous cycle alters naphthalene metabolism in female mouse airways. Drug Metab Dispos:dmd.105.005124. [View]

Thornton-Manning, J, and A Dahl. 1997. Metabolic capacity of nasal tissue interspecies comparisons of xenobiotic-metabolizing enzymes. Mutat Res 380 (1):43-59. [View]

Van Winkle, L, Gunderson A, Shimizu J, Baker G, and Brown C 2002. Gender differences in naphthalene metabolism and naphthalene-induced acute lung injury. Am J Physiol Lung Cell Mol Physiol 282:L1122-L1134. [View]

Van Winkle, L, A Buckpitt, S Nishio, J Isaac, and C Plopper. 1995. Cellular response in naphthalene-induced Clara cell injury and bronchiolar epithelial repair in mice. Am J Physiol Lung Cell Mol Physiol 269 (6):L800-818. [View]

Van Winkle, L, C Brown, J Shimizu, A Gunderson, M Evans, and C Plopper. 2004. Impaired recovery from naphthalene-induced bronchiolar epithelial injury in mice exposed to aged and diluted sidestream cigarette smoke. Toxicology Letters 154 (1):1-9. [View]

Van Winkle L, Johnson Z, Nishio S, Brown C, and Plopper C. 1999. Early events in naphthalene-induced acute Clara cell toxicity. Comparison of membrane permeability and ultrastructure. Am J Respir Cell Mol Biol 21:44-53. [View]

Warren, D, D Brown, and A Buckpitt. 1982. Evidence for cytochrome P-450 mediated metabolism in the bronchiolar damage by naphthalene. Chemico-Biological Interactions 40 (3):287-303. [View]

Waidyanatha, S, M Troester, A Lindstrom, and S Rappaport.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. [View]

Watt, K and A Buckpitt. 2000. Species differences in the regio- and stereoselectivity of 1-nitronaphthalene metabolism . [View]

West, J, L Van Winkle, D Morin, C Fleschner, H Forman, and C Plopper. 2003. Repeated inhalation exposures to the bioactivated cytotoxicant naphthalene (NA) produce airway-specific Clara cell tolerance in mice. Toxicol Sci 75 (1):161-8. [View]

Secondary references...

Module D: Genotoxic Modes of Action
Note: Links are provided for non-copyrighted documents only.

Dawling, S, Hachey, D, Roodi, N, Parl, F. 2004. In Vitro Model of Mammary Estrogen Metabolism: Structural and Kinetic Differences between Catechol Estrogens 2- and 4-Hydroxyestradiol. Chem. Res. Toxicol. 17 (9): 1258-1264. [View]

Diodovich, C, I Malerba, G Bowe, F Acquati, M Bianchi, R. Taramelli, D. Parent-Massin and L. Gribaldo. 2003. Naphthalene Exposure: Effects on Gene Expression and Proliferation in Human Cord Blood Cells. J. Biochem Molecular Toxicology 17 (5): 286-294. [View]

Office of Research and Development. 2004. Chapter 4.4.4. Genotoxicity Studies. In Toxicological Review Of Naphthalene, In Support of Summary Information on the Integrated Risk Information System (IRIS), [External Review Draft]. Washington D.C.: U.S. Environmental Protection Agency; pp. 33-47.

Schreiner, C. 2003. Genetic Toxicity of Naphthalene: A Review. Journal of Toxicology and Environmental Health (Part B). 6: 161-183. [View]

Secondary references...

General:
Note: Links are provided for non-copyrighted documents only.

ad hoc Naphthalene Coalition. 2004. ORD-2004-0007-0007 (NC comments), Preliminary Comments of the Naphthalene Coalition on EDOCKET #ORD-2004-0007. Toxicological Review of Naphthalene [and IRIS Summary] (External Review Draft) NCEA -S-1707 (dated June 2004) and Charge to External Reviewers for the IRIS Reassessment of the Inhalation Carcinogenicity of Naphthalene.

ad hoc Naphthalene Coalition. 2004. ORD-2004-0007-0009 (ACC comments attachment), Preliminary Comments of the Naphthalene Coalition on EDOCKET #ORD-2004-0007. Toxicological Review of Naphthalene [and IRIS Summary] (External Review Draft) NCEA -S-1707 (dated June 2004) and Charge to External Reviewers for the IRIS Reassessment of the Inhalation Carcinogenicity of Naphthalene.

Anonymous. 2005. ORD-2005-0008-0004 (new literature), List of Literature Published Since the Release of the External Review Draft Toxicological Review of Naphthalene.

Baird S. 2004. ORD-2004-0007-0012 (Baird comments), Comments on the "Toxicological Review and Integrated Risk Information System (IRIS) Summary for Naphthalene Human Health Reassessment. Inhalation Carcinogenicity.

Green LC and Crouch EAC. 2004. ORD-2004-0007-0010 (Green & Crouch comments), Comments for the External Peer Review Panel regarding the Draft Toxicological Review of Naphthalene. In Support of Summary Information on the Integrated Risk Information System (IRIS).

LeHuray AP, Ph.D. 2004. ORD-2004-0007-0008 (ACC comments), Subject: Preliminary Comments from the ad hoc Naphthalene Coalition for Consideration of the Naphthalene External Peer Review Panel (To: EPA [Docket # ORD-2004-0007]).

National Asphalt Pavement Association and Acott M. 2004. ORD-2004-0007-0011 (NAPA comments), Re: Docket # Ord-2004-0007 (To Peter W. Preuss, Ph.D.).

Office of Research and Development. 2004. ORD-2004-0007-0002 (charge), Charge to External Reviewers for the IRIS Reassessment of the Inhalation Carcinogenicity of Naphthalene.

Office of Research and Development. 2004. ORD-2004-0007-0003 (Proposed IRIS summary), This IRIS Summary is an external review draft of the reassessment of the inhalation carcinogenicty of Naphthalene. Changes from the curent IRIS Summary (1998) are indcated in highlighting. U.S. Environmental Protection Agency.

Office of Research and Development. 2004. ORD-2004-0007-0005 (Tox Review), Toxicological Review Of Naphthalene, In Support of Summary Information on the Integrated Risk Information System (IRIS), [External Review Draft]. NCEA-S-1707: U.S. Environmental Protection Agency.

Office of Research and Development. 2004. ORD-2004-0007-0006 (EIMS Summary), EPA is hereby providing for public information a draft Toxicological Review, draft IRIS Summary, and charge to external peer reviewers for EPA's health assessment of naphthalene. U.S. Environmental Protection Agency.

Office of Research and Development. 2004. Chapter 4.4.4. Genotoxicity Studies T. In Toxicological Review Of Naphthalene, In Support of Summary Information on the Integrated Risk Information System (IRIS), [External Review Draft]: U.S. Environmental Protection Agency; pp. 33-47.[View PDF]

Office of Research and Development. 2005. ORD-2005-0008-0001, Peer Consultation Workshop on Research Needs Related to the IRIS Draft Toxicological Review of Naphthalene. Federal Register 70:11240. [View].

Office of Research and Development (US EPA). 2005. ORD-2005-0008-0002 peer consultation charge, Charge for the Peer Consultation Workshop on Research Needs Related to the IRIS Draft Toxicological Review of Naphthalene.

US EPA. 2005. NAPHTHALENEPEERCONSULTCHARGE, Charge for the Peer Consultation Workshop on Research Needs Related to the IRIS Draft Toxicological Review of Naphthalene.

US EPA. 2005. NAPHTHALENE-PEER-CONSULT, Peer Consultation Workshop on Research Needs Related to the IRIS Draft Toxicological Review of Naphthalene, Final Report.

Secondary references...

Stakeholder Contributions:
Note: Links are provided for non-copyrighted documents only.

Secondary references...