Bay or baylike regions of polycyclic aromatic hydrocarbons were potent inhibitors of gap junctional intercellular communication

Environmental Health Perspectives

Volumn 106, Issue 1, 1998, Pages 17-22

  Weis, Liliane M ^a   Rummel, Alisa M ^b   Masten, Susan J ^a   Trosko, James E ^b,c   Upham, Brad L ^c  

^a Michigan State University   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Anthracenes; Fluoranthene; Fluorene; Gap junctional intercellular communication; Methylanthracenes; Methylfluorene; Methylnaphthalene; Naphthalene; Phenanthrene; Polycyclic aromatic hydrocarbons

Indexed keywords

1 METHYLNAPHTHALENE; 2 METHYLNAPHTHALENE; ANTHRACENE; ANTHRACENE DERIVATIVE; FLUORANTHENE; FLUORENE; NAPHTHALENE; PHENANTHRENE; POLYCYCLIC AROMATIC HYDROCARBON;

CELL COMMUNICATION; CYTOTOXICITY; GAP JUNCTION; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0031935856     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.9810617     Document Type: Review

References (63)

1. IARC. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Vol 32: Polynuclear Aromatic Compounds, Part 1: Chemical, Environmental and Experimental Data. Lyon: International Agency for Research on Cancer, 1983.
2. Pott P. Cancer scroti. The Chirurgical Works of Percivall Pott. First American edition from the last London edition. Philadelphia, PA:James Webster, 1819;291-295.
3. Lloyd JW. Long-term mortality study of steelworkers. V. Respiratory cancer in coke plant workers. J Occup Med 13:53-68 (1971).
4. Redmond CK, Strobino BR, Cypress RH. Cancer experience among coke by-product workers. Ann NY Acad Sci 271:102-115 (1976).
5. IARC. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Vol. 34: Polynuclear Aromatic Compounds: Industrial Exposures in Aluminum Production, Coal Gasification, Coke Production and Iron and Steel Founding. Lyon:International Agency for Research on Cancer, 1984.
6. Jerina DM, Yagi H, Lehr RE, Thakker DR, Schaefer-Ridder M, Karle JM, Levin W, Wood AW, Chang RL, Conney AH. The bay-region theory of carcinogenesis by polycyclic aromatic hydrocarbons. In: Polycyclic Hydrocarbons and Cancer, Vol 1, Environment, Chemistry, and Metabolism (Gelboin H, Ts'o POP, eds). New York:Academic Press, 1978;173-188.
7. Hoffman D, Lavoie EJ, Hecht SS. Polynuclear aromatic hydrocarbons: effects of chemical structure on tumorigenicity. In: Polynuclear Aromatic Hydrocarbons: Physical and Biological Chemistry (Cooke M, Dennis AJ, Fisher GL, eds). Columbus, OH:Battelle Press, 1982;1-19.
8. Silverman BD, Lowe JP. Diol-epoxide reactivity of methylated polycyclic aromatic hydrocarbons (PAH): ranking the reactivity of the positional monomethyl isomers. In: Polynuclear Aromatic Hydrocarbons: Physical and Biological Chemistry (Cooke M, Dennis AJ, Fisher GL, eds). Columbus, OH:Battelle Press, 1982;743-753.
9. Cooper GM. Classification and development of neoplasms. In: Elements of Human Cancer. Boston, MA:Jones and Bartlett Publishers, 1992;15-30.
10. Harris CC. Chemical and physical carcinogenesis: advances and perspectives for the 1990s. Cancer Res Suppl 51(18 suppl);5023s-5044s (1991).
11. Boutwell RK. Some biological aspects of skin carcinogenesis. Prog Exp Tumor Res 4:207-290 (1964).
12. Holliday R, DNA methylation and epigenetic defects in carcinogenesis. Mutat Res 181:215-217 (1987).
13. Boyd JA, Barrett JC. Genetic and cellular basis of multistep carcinogenesis. Pharmacol Ther 46:469-486 (1990).
14. Trosko JE, Chang CC, Medcalf A. Mechanisms of tumor promotion: potential role of intercellular communication. Cancer Invest 1:511-526 (1983).
15. Trosko JE, Chang CC, Madhukar BV, Oh SY. Modulators of gap junction function: the scientific basis of epigenetic toxicology. In Vitro Toxicol 3:9-26 (1990).
16. Trosko JE, Chang CC, Madhukar BV. In vitro analysis of modulators of intercellular communication: implications for biologically based risk assessment models for chemical exposure. Toxicol In Vitro 4:635-643 (1990).
17. Trosko JE, Chang CC, Madhukar BV, Klaunig JE. Chemical, oncogene and growth factor inhibition of gap junctional intercellular communication: an integrate hypothesis. Pathobiol 58:265-278 (1990).
18. Trosko JE, Chang CC, Madhukar BV. The role of modulated gap junctional intercellular communication in epigenetic toxicology. Risk Anal 14(3):303-312 (1994).
19. Trosko JE, Madhukar BV, Chang CC. Endogenous and exogenous modulation of gap junctional intercellular communication: toxicological and pharmacological implications. Life Sci 53:1-19 (1993).
20. Yamasaki H, Naus CCG. Role of connexin genes in growth control. Carcinogenesis 17:1199-1213 (1996).
21. Trosko JE, Chang CC. Nongenotoxic mechanisms in carcinogenesis: role of inhibited intercellular communication. In: Banbury Report 31: New Directions in the Qualitative and Quantitative Aspects of Carcinogen Risk Assessment (Hart RW, Hoerger FD, eds). Cold Spring Harbor, NY:Cold Spring Harbor Laboratory Press, 1988;139-170.
22. Trosko JE, Chang CC, Madhukar BV. Modulation of gap junction intercellular communication by tumor promoting chemicals, oncogenes and growth factors during carcinogenesis. In: Modern Cell Biology, Vol. 7: Gap Junctions (Hertzberg EL, Johnson RG, eds). New York:Alan R. Liss, 1988;435-448.
23. Busby WF Jr, Goldman ME, Newberne PM, Wogan GN. Tumorigenicity of fluoranthene in a newborn mouse lung adenoma bioassay. Carcinogenesis 5:1311-1316 (1984).
24. Wang J-S, Busby WF Jr. Induction of lung and liver tumors by fluoranthene in a preweaning CD-1 mouse bioassay. Carcinogenesis 14:1871-1874 (1993).
25. Stocker KJ, Howard WR, Statham J, Proudlock RJ. Assessment of the potential in vivo genotoxicity of fluoranthene. Mutagenesis 11:493-496 (1996).
26. Upham BL, Masten SJ, Lockwood BR, Trosko JE. Nongenotoxic effects of polycyclic aromatic hydrocarbons and their ozonation by-products on the intercellular communication of rat liver epithelial cells. Fundam Appl Toxicol 23:470-475 (1994).
27. Upham BL, Weis LM, Rummel AM, Masten SJ, Trosko JE. The effects of anthracene and methylated anthracenes on gap junctional intercellular communication in rat liver epithelial cells. Fundam Appl Toxicol 34:260-264 (1996).
28. Severson RF, Snook, ME, Higman HC, Chortyk OT, Akin FJ. Isolation, identification, and quantification of the polynuclear aromatic hydrocarbons in tobacco smoke. In: Chemistry, Metabolism and Carcinogenesis (Freudenthal RI, Jones PW, eds). New York:Raven Press, 1976;253-270.
29. Tsao MS, Smith JD, Nelson KG, Grisham JWA. Diploid epithelial cell line from normal adult rat liver with phenotypic properties of oval cells. Exp Cell Res 154:38-52 (1984).
30. El-Fouly MH, Trosko JE, Chang CC. Scrape-loading and dye transfer. A rapid and simple technique to study gap functional intercellular communication. Exp Cell Res 168:422-430 (1987).
31. Borenfreund E, Puerner J. Toxicology determined in vitro by morphological alterations and neutral red absorption. Toxicol Lett 24:119-124 (1985).
32. Vuchetich PJ, Bagchi D, Bagchi M, Hassoun EA, Tang L, Stohs SJ. Naphthalene-induced oxidative stress in rats and the protective effects of vitamin E succinate. Free Radical Biol Med 21:577-590 (1996).
33. Upham BL, Kang K-S, Cho H-Y, Trosko JE. Hydrogen peroxide inhibits gap junctional intercellular communication in glutathione sufficient but not glutathione deficient cells. Carcinogenesis 18:37-42 (1997).
34. Hu J, Engman L, Cotgreave IA. Redox-active chalcogen-containing glutathione peroxidase mimetics and antioxidants inhibit tumor promoter-induced down regulation of gap junctional intercellular communication between WB-F344 rat liver epithelial cells. Carcinogenesis 16:1815-1824 (1995).
35. Hu J, Speisky H, Cotgreave IA. The inhibitory effects of boldine, glaucine, and probucol on TPA-induced down regulation of gap junction function. Relationships to intracellular peroxides, protein kinase C translocation and connexin43 phosphorylation. Biochem Pharmacol 50:1635-1643 (1995).
36. Rusch HP, Kline BE, Baumann CA. The nonadditive effect of ultraviolet light and other carcinogenic procedures. Cancer Res 2:183-188 (1942).
37. Roe FJ. Effect of phenanthrene on tumor-initiation by 3,4-benzpyrene. Cancer 16:503-506 (1963).
38. van Duuren BL, Goldscmidt BM. Cocarcinogenic and tumor-promoting agents in tobacco Carcinogenesis. J Natl Cancer Inst 56:1237-1242 (1976).
39. Steiner PE, Falk HL. Summation and inhibition effects of weak and strong carcinogenic hydrocarbons:1:2-benzanthracene, chrysene, 1:2:5:6-dibenzanthracene, and 20-methylchoanthrene. Cancer Res 11:56-63 (1951).
40. Falk HL, Kotin P, Thompson S. Inhibition of Carcinogenesis. Arch Environ Health 9:169-179 (1964).
41. Hoffmann D, Rathkamp G, Nesnow S, Wynder EL. Fluoranthenes: quantitative determination in cigarette smoke, formation by pyrolysis, and tumor-initiating activity. J Natl Cancer Inst 49:1165-1175 (1972).
42. Norpoth K, Kemena A, Jacob J, Schümann C. The influence of 18 environmentally relevant polycyclic aromatic hydrocarbons and Clophen A50, as liver monooxygenase inducers, on the mutagenic activity of benz(a)anthracene in the Ames test. Carcinogenesis 5(6):747-752 (1984).
43. Myers SR, Blake JW, Flesher JW. Bioalkylation and biooxidation of anthracene, in vitro and in vivo. Biochem Biophys Res Commun 151(3):1441-1445 (1988).
44. Hecht SS, Loy M, Hoffmann D. On the structure and carcinogenicity of the methylchrysenes. In: Carcinogenesis - Vol 1 Polynuclear Aromatic Hydrocarbons: Chemistry, Metabolism and Carcinogenesis (Freudenthal RI, Jones PW, eds). New York:Raven Press, 1976;325-340.
45. Slaga T-J, Bowden GT, Scribner JD, Boutwell RK. Dose - response studies on the ability of 7,12-dimethylbenz(a)anthracene and benz(a)anthracene to initiate skin tumors. J Natl Cancer Inst 53: 1337-1340 (1974).
46. Slaga TJ, Iyer RP, Lyga W, Secrist A, Daub GH, Harvey RG. Comparison of the skin tumor-initiating activities of dihydrodiols, dioleperoxides, and methylated derivatives of various polycyclic aromatic hydrocarbons. In: Polynuclear Aromatic Hydrocarbons: Chemistry and Biological Effects (Bjerseth A, Dennis AJ, eds). Columbus, OH:Battelle Press, 1980:753-769.
47. LaVoie EJ, Coleman DT, Rice JE, Geddie NG, Hoffman D. Tumor-initiating activity, mutagenicity, and metabolism of methylated anthracenes. Carcinogenesis 6(10):1483-1488 (1985).
48. LaVoie EJ, Tulley-Freiler L, Bedenko V, Hoffmann D. Mutagenicity, tumor-initiating activity, and metabolism of methylphenanthrenes. Cancer Res 41:3441-3447 (1981).
49. Kurihara T, Motohashi N, Pang G-L, Higano M, Kiguchi K, Molnar J. Correlations between topological resonance energy of methyl-substituted benz(c)acridines, benzo(a)phenothiazines and chrysenes, and their carcinogenic or anti-tumor activities. Anticancer Res 16:2757-2766 (1996).
50. Flesher JW, Myers SR, Stansbury KH. The site of substitution of the methyl group in the bioalkylation of benzo(a)pyrene. Carcinogenesis 11:493-496 (1990).
51. Flesher JW, Myers SR. Rules of molecular geometry for predicting carcinogenic activity of unsubstituted polynuclear aromatic hydrocarbons. Teratog Carcinog Mutagen 11:41-54 (1991).
52. Flesher JW, Myers SR. Bioakylation of benz(a)anthracene as a biochemical probe for carcinogenic activity: lack of bioakylation in a series of six noncarcinogenic polynuclear aromatic hydrocarbons. Drug Metab Dispos 18:163-167 (1991).
53. Myers SR, Flesher JW. Bioakylation of benz(a)anthracene, 7-methylbenz(a)anthracene and 12-methylbenz(a)anthracene in rat lung cytosol preparations. Biochem Pharmacol 41:1683-1690 (1991).
54. Yang SK, Chou MW, Fu PP. Microsomal oxidations of methyl-substituted and unsubstituted aromatic hydrocarbons of monomethylbenz(a)anthracene. In: Polynuclear Aromatic Hydrocarbons: Chemical Analysis and Biological Fate (Cooke M, Dennis AJ, eds). Columbus, OH:Battelle Press, 1980;253-264.
55. Watabe T, Ishizuka T, Isobe M, Ozawa NA. 7-Hydroxymethyl sulfate ester as an active metabolite of 7,12-dimethylbenz(a)anthracene. Science 215:403-405 (1982).
56. Surh YJ, Liem A, Miller EC, Miller JA. Metabolic activation of the carcinogen 6-hydroxymethylbenzo(a)pyrene: formation of an electrophilic sulfuric acid ester and benzylic DNA adducts in rat liver in vivo and in reactions in vitro. Carcinogenesis 10:1519-1528 (1989).
57. Surh YJ, Liem A, Miller EC, Miller JA. 7-Sulfooxymethyl-12-methylbenz(a)anthracene is an electrophilic mutagen, but does not appear to play a role in carcinogenesis by 7,12-dimethylbenz(a)anthracene or 7-hydroxymethyl-12-methylbenz(a)anthracene. Carcinogenesis 12:333-348 (1991).
58. Surh YJ, Liem A, Miller EC, Miller JA. The strong hepatocarcinogenicity of the electrophilic and mutagenic metabolite 6-sulfoxymethylbenzo(a)pyrene and its formation of benzylic DNA adducts in the liver of infant male B6C3F-1 mice. Biochem Biophys Res Comm 172:85-91 (1990).
59. Trosko JE. Challenge to the simple paradigm that 'carcinogens' are 'mutagens' and to the in vitro and in vivo assays used to test the paradigm. Mutat Res 373:245-249 (1997).
60. Cheung YL, Gray TJB, Ioannides C. Mutagenicity of chrysene, its methyl and benzo derivatives, and their interactions with cytochromes P-450 and the Ahreceptor: relevance to their carcinogenic potency. Toxicology 81(1):69-86 (1993).
61. 2+ and cell proliferation in primary human mammary epithelial cells. Carcinogenesis 18:1177-1182 (1997).
62. Zhang Y, Ramos KS. The induction of proliferate vascular smooth muscle cell phenotypes by benzo(a)pyrene does not involve mutational activation of ras genes. Mutat Res 373:285-292 (1997).
63. Mackay D, Shu WY, Ma KC, eds. Polynuclear aromatic hydrocarbons, polychlorinated dioxins, dibenzofurans. In: Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals. VII, Chelsea, MI:Lewis Publishers, 1992;597.