14
Views
1
CrossRef citations to date
0
Altmetric
Research Article

Occupational Cancer and Chemical Structure: Past, Present, and Future

Pages 919-939 | Published online: 22 Sep 2008

References

  • Hill J. Cautions Against the Immoderate Use of Snuff. London 1759
  • Pott P. Cancer scroti. Chirurgial Observations. Hawes, Clarke, and Collins, London 1774; 64–68
  • Yamagiwa K., Ichikawa K. Experimental study of the pathogenesis of carcinoma. J. Cancer Res. 1918; 3: 1–29
  • Cook J. W., Hieger I., Kennaway E. L., Mayneord W. V. The production of cancer by pure hydrocarbons, part I. Proc. R. Soc. London, B 1932; 111: 455–484
  • Cook J. W. The production of cancer by pure hydrocarbons, part II. Proc. R. Soc. London, B 1932; 111: 485–496
  • Barry G., Cook J. W., Haselwood G. A. D., Hewitt C. L., Hieger I., Kennaway E. L. The production of cancer by pure hydrocarbons, part III. Proc. R. Soc. London, B 1935; 117: 381–351
  • Bachmann W. E., Cook J. W., Dansi A., DeNorms G. M., Haselwood G. A. D., Hewitt C. L., Robinson A. M. The production of cancer by pure hydrocarbons, part IV. Proc. R. Soc. London, B 1937; 123: 343–368
  • Badger G. M., Cook J. W., Hewitt C. L., Kennaway E. L., Kennaway N. M., Martin R. H., Robinson A. M. The production of cancer by pure hydrocarbons, part V. Proc. R. Soc. London, B 1940; 148: 439–467
  • Badger G. M., Cook J. W., Hewitt C. L., Kennaway E. L., Kennaway N. M., Martin R. H. The production of cancer by pure hydrocarbons, part VI, Proc. R. Soc. London, B 1942; 131: 170–182
  • Wieland H., Dane H. The constitution of the bile acids. II. The place of attachment of the side chain. Z. Physiol. Chem. 1933; 219: 240–244
  • Cook J. W., Haselwood G. A. D. Conversion of a bile acid into a hydrocarbon derived for 1, 2-benzoanthracene. Chem. Ind. 1933; 38: 758–759
  • McCaustland D. J., Fisher D. L., Kolwyck K. C., Duncan W. P., Wiley J. C., Jr., Menon C. S., Engel J. F., Selkirk J. K., Roller P. P. Polycyclic aromatic hydrocarbon derivatives: Synthesis and physiochemical characterization. Carcinogenesis — A Comprehensive Survey, R. I. Freudenthal, P. Jones. Raven Press, New York 1976; vol. 1: 349–411
  • Ts'o P. O. P., Caspary W. J., Cohen B. I., Leavitt J. C., Lesko S. A., Lorentzen R. J., Schechtman L. M. Basic mechanisms in polycyclic hydrocarbon carcinogenesis. Chemical Carcinogenesis, part A, P. O. P. Ts'o, J. A. DiPaolo. Dekker, New York 1974; 113–147
  • Nagata C., Tagashira Y., Kodama M. Metabolic activation of benzo(a)pyrene: Significance of free radical. Chemical Carcinogenesis, part A, P. O. P. Ts'o, J. A. DiPaolo. Dekker, New York 1974; 87–111
  • Dipple A., Lawley P. D., Brookes P. Theory of tumor initiation by chemical carcinogens: Dependence of activity on structure of ultimate carcinogen. Eur. J. Cancer 1968; 4: 493–506
  • Fried J. One-electron oxidation of polycyclic aromatics as a model for the metabolic activation of carcinogenic hydrocarbons. Chemical Carcinogenesis, part A, P. O. P. Ts'o, J. A. DiPaolo. Dekker, New York 1974; 197–215
  • Cavaliere E., Auerbach R. Reactions between activated benzo(a)pyrene and nucleophillic compounds, with possible implications on the mechanism of tumor induction. J. Natl. Cancer Inst. 1974; 53: 393–397
  • Flesher J. W., Syndor K. L. Possible role of β-hydroxylmethylbenzo(a)pyrene as a proximate carcinogen of benzo(a)pyrene and β-methylbenzo(a)pyrene. Int. J. Cancer 1973; 11: 433–437
  • Sloane N. H., Davis T. K. Hydroxymethylation of the benzene ring: Microsomal hydroxymethylation of benzo(a)pyrene to 6-hydroxymethylbenzo(a)pyrene. Arch. Biochem. Biophys. 1974; 163: 46–52
  • Newman M. S., Olson D. R. A new hypothesis concerning the reactive species in carcinogenesis by 7,12-dimethyl-benz(a)anthracene: The 5-hydroxy, 7,12-di-methyl-benz(a)anthracen-5-(6H)-one equilibrium. J. Am. Chem. Soc. 1974; 96: 6207–6208
  • Jerina D. M., Daly J. W. Arene oxides: A new aspect of drug metabolism. Science 1974; 185: 537–582
  • Baird W. M., Diamond L. The nature of benzo(a)-pyrene: DNA adducts formed in hamster embryo cells depends on the length of time of exposure to benzo(a) -pyrene. Biochem. Biophys. Res. Commun. 1977; 77: 162–167
  • Yang S. K., Gelboin H. V., Trump B. F., Astrup H., Harris C. C. Metabolic activation of benzo(a)pyrene and binding to DNA in cultured human bronchus. Cancer Res. 1977; 37: 1210–1215
  • Becker A. R., Janusz J. M., Rogers D. Z., Bruice T. C. Structural features which determine the carcinogenesis, mutagenesis, and rates of acid- and water-mediated solvolysis of a nucleophilic attack upon diol epoxides, bay-region and non-bay-region tetrahydro epoxides, and K-region and non-K-region arene oxides. J. Am. Chem. Soc. 1978; 100: 3244–3246
  • Preussmann R. Chemical carcinogens in the human environment: Problems and quantitative aspects. Oncology 1976; 33: 51–57
  • Rehn L. Blasengeschwulste bei Fuchsin-Arbeitern. Arch. Klin. Chirugie 1895; 50: 588–600
  • Lurie A. P. Benzidine and related diaminobiphenyls. Kirk-Othmer Encyclopedia of Chemical Technology, 2nd ed., R. E. Kirk, D. F. Othmer. Inter-science, New York 1964; vol. 3: 408–420
  • Miller J. A., Miller E. C. The metabolic activation of carcinogenic aromatic amines and amides. Prog. Exp. Tumor Res. 1969; 11: 273–301
  • Miller J. A., Miller E. C. Guest editorial: Chemical carcinogenesis: Mechanisms and approaches to its control. J. Natl. Cancer Inst. 1971; 47: V–XIV
  • Gehrmann G. H. Papilloma and carcinoma of the bladder in dye workers. J. Am. Med. Assoc. 1936; 107: 1436–1439
  • Yamamoto C., Tadokoro M., Hayashi T., Nakaoka H. Acute hemorrhagic cystitis which is found in employees of benzidine manufacturing factories. Japan Sci. Rev. Med. Sci. 1959; 7: 546
  • Haley T. J. Benzidine revisited: A review of the literature and problems associated with the use of benzidine and its congeners. Clin. Toxicol. 1975; 8: 13–42
  • Haley T. J. Metabolism and pharmacokinetics of benzidine and its congeners in man and animals. Drug Metab. Rev. 1982; 13: 473–483
  • Walker R. The metabolism of azo compounds: A review of the literature. Food Cosmet. Toxicol. 1970; 8: 659–676
  • Yoshida O., Miyakawa M. Etiology of bladder cancer: Metabolic aspects. Analytical and Experimental Epidemiology of Cancer, W. Nakahara, T. Hirayama, K. Nishioka, H. Sugano. University Park Press, Baltimore, MD 1973; 31–39
  • Korosteleva T. A., Skachkova A. P., Shvaidetsky I. I. Appearance of carcinogen-proteinic antigens in the blood serum of workers dealing with aniline dyestuffs. Gig. Tr. Prof. Zabol. 1974; 5: 21–24
  • Genin V. Formation of blastomagenic diphenyl amine derivatives as a result of direct azo dye metabolism. Vopr. Onkol. 1977; 23: 5–52
  • Boeniger M. The carcinogenicity and metabolism of azo dyes, especially those derived from benzidine, unpublished NIOSH Report. DHEW Public Health Service, Center for Disease Control. 1978
  • Lynn R. K., Donielson D. W., Ilias A. M., Kennish J. M., Wong K., Matthews H. B. Metabolism of bisazobi-phenyl dyes derived from benzidine, 3, 3′-dimethylbenzidine or 3,3′-dimethoxybenzidine to carcinogenic aromatic amines in the dog and rat. Toxicol. Appl. Pharmacol. 1980; 58: 248–258
  • Leuschner F. Carcinogenicity studies on different di-arylide yellow pigments in mice and rats. Toxicol Lett. 1978; 2: 253–260
  • Modino A., Achari R., Dubinin M., Marchisio M. A., Silvestri S., Zanolo G. Absence of dichlorobenzidine in the urine of rats, rabbits and monkeys treated with C. I. Pigment Yellow 13. Med. Lavoro 1978; 69: 693–697
  • Gerarde H. W., Gerarde D. F. Industrial experience with 3,3′-dichlorobenzidine: An epidemiological study of a chemical manufacturing plant. J. Occup. Med. 1974; 16: 322–344
  • Gadian T. Carcinogens in industry, with special reference to dichlorobenzidine. Chem. Ind. 1975; 19: 821–830
  • MacIntyre I. Experience of tumors in a British plant handling 3,3′-dichlorobenzidine. J. Occup. Med. 1975; 17: 23–26
  • Arrhenius E. Comparative metabolism of aromatic amines. Chemical Carcinogenesis Essays, R. Montesano, L. Tomatis. International Agency for Research on Cancer, LyonFrance 1974; 25–37
  • Hathway D. E. Biotransformations. Foreign Compound Metabolism in Mammals. The Chemical Society, London 1970; vol. 1: 455
  • Parke D. V. The Biochemistry of Foreign Compounds. Pergamon Press, New York 1968; 269
  • Englebertz P., Babel E. Nachweis von Benzidin und seinen umwandlungs Produkten im Harn und in Organteilen. Zentr. Arbeitsmed. Arbeitsschutz 1953; 3: 161–168
  • Sciarinin L. J., Meigs J. W. The Biotransformation of benzidine. II. Studies in mouse and man. Arch. Environ. Health 1961; 2: 423–428
  • Vigliani E. C., Barsotti M. Environmental tumors of the bladder in some Italian dye-stuff factories. Acta Unio Int. Contra Cancrum 1962; 18: 699–675
  • Adler O. Die Wirkung und das Schicksal des Benzidins im Tierkorper. Arch. Exp. Pathol. Pharmakol. 1908; 58: 167
  • Troll W., Belman S., Rinde E. N-Hydroxy acetyl amino compounds, urinary metabolites of aromatic amines in man. Proc. Am. Assoc. Cancer Res. 1963; 4: 68
  • Dieteren H. M. L. The biotransformation of o-tolidine. Arch. Environ. Health 1966; 12: 30–32
  • Sciarinin L. J., Meigs J. W. Biotransformation of the benzidines. III. Studies on diorthotolidine, di-anisidine, and dichlorobenzidine. Arch. Environ. Health 1961; 2: 584–588
  • Morrison R. T., Boyd R. N. Organic Chemistry, 3rd ed. Allyn and Bacon, Boston, MA 1974; 1258
  • IARC. IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Some Aromatic Amines, Hydrazine and Related Substances, N-Nitroso Compounds and Miscellaneous Alkylating Agents. International Agency for Research on Cancer, LyonFrance 1974; vol. 4: 286
  • Geuther A. Ueber die Enwirklung von Saltpetrigs auren Kali auf salzsauers Diathylamin. Lieb. Ann. 1863; 128: 515–516
  • Druckrey H., Preussmann R., Ivankovic S. N-Nitroso compounds in organotropic and transplacental carcinogenesis. Ann. N.Y. Acad. Sci. 1969; 163: 676–695
  • IARC. Science Monographs 3, 9, 14, and 19. International Agency for Research on Cancer, LyonFrance 1972, 1974, 1976, 1978
  • Fine D. H. N-Nitroso compounds in the environment. Advances in Environmental Science and. Technology, J. N. Pitts, R. L. Metcalf, D. Grosjean. Wiley-Interscience, New York 1980; vol. 9
  • Buglass A. J., Challis R. B., Osborne M. R. Transnitrosation and decomposition of nitrosamines. N-Nitroso Compounds in the Environment, P. Bogovski, E. A. Walker. International Agency for Research on Cancer, LyonFrance 1974; 94–100, IARC Monograph no. 9
  • Singer S. S., Lijinsky W., Singer G. M. Transnitro-sations: An important aspect of the chemistry of aliphatic nitroamines. Environmental Aspects of N-Nitroso Compounds, E. A. Walker, M. Castegnaro, L. Griciute, R. E. Lyle. International Agency for Research on Cancer, LyonFrance 1978; 175–181, IARC Monograph no. 19
  • Fan T. Y., Vita R., Fine D. H. C-Nitroso compounds: A new class of nitrosating agents. Toxicol. Lett. 1978; 2: 5–10
  • Magee P. N., Montesana R., Preusmann R. N-Nitroso-compounds and related carcinogens. Chemical Carcinogens, C. E. Seale. American Chemical Society, Washington, DC 1976, ACS Monograph 173, chap. 2
  • Mirvish S. S. Formation of N-nitroso compounds: Chemistry, kinetics, in vivo occurrence. Toxicol. Appl. Pharmacol. 1975; 31: 325–351
  • Mirvish S. S. N-Nitroso compounds: Their chemical and in vivo formation and possible importance as environmental carcinogens. J. Toxicol. Environ. Health 1977; 2: 1267–1277
  • Fine D. H., Ross R., Rounbehler D. P., Silvergleid A., Song L. Formation in vivo of volatile N-nitrosamines in man after ingestion of cooked bacon and spinach. Nature 1977; 265: 753–755
  • Crosby N. T. Nitrosamines in foodstuffs. Residue Rev. 1976; 64: 77–135
  • Crosby N. T., Sawyer R. N-Nitrosamines: A review of chemical and biological properties and their estimation in foodstuffs. Adv. Food Res. 1976; 22: 1–71
  • IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, vol. 17, Some N-Nitroso Compounds. International Agency for Research on Cancer, LyonFrance 1978
  • Fishbein L. Teratogenic, mutagenic and carcinogenic effects of insecticides. Insecticide Biochemistry and Physiology, C. F. Wolkinson. Plenum Press, New York 1976; 555–603
  • McGee P. N. Possibilities of hazard from nitrosamines in industry. Ann. Occup. Hyg. 1972; 15: 19–22
  • Fajen J. M., Carson G. A., Rounbehler D. P., Fan T. Y., Vita R., Wolf M., Edwards G. S., Fine D. H., Goff U., Reinhold F., Biemann K. N-Nitrosamines in the rubber and tire industry. Science 1979; 205: 1262–1264
  • Rounbehler D. F., Krull J. S., Goff U. E., Mills K. M., Morrison J., Edwards G. S., Fine D. H., Fajen J. M., Carson G. A., Reinhold V. Occupational exposure to dimethylnitrosamine in a leather tannery, Food Cosmet. Toxicol. 1979; 17: 487–491
  • Bretschneider K., Matz J. Occurrence and analysis of nitrosamines in air. Environmental N-Nitroso Compounds Analysis and Formation, E. A. Walker, P. Bogovski, L. Griciute. International Agency for Research on Cancer, LyonFrance 1976; 395–399, IARC Monograph no. 14
  • Fine D. H., Morrison J., Rounbehler D. P., Silvergleid A., Song L. N-Nitrosamines in the air environment. Toxic-Substances in the Air Environment, J. G. Spengler. Air Pollution Control Association, Pittsburgh, PA 1977; 168–181
  • Fine D. H., Rounbehler D. P., Sawicki E., Krost K., DeMarrais G. A. N-Nitroso compounds in the ambient community air of Baltimore, Maryland. Anal. Lett. 1976; 9: 595–604
  • Fine D. H., Rounbehler D. P., Pellizzari E. D., Bunch J. E., Berkley R. W., McCrae J., Bursey J. T., Sawicki E., Krost K., DeMarrais G. A. N-Nitrosodimethylamine in air. Bull. Environ. Contam. Toxicol. 1976; 15: 739–747
  • Brunnemann K. D., Hoffmann D. Chemical studies on tobacco smoke. LIX. Analysis of volatile nitrosamines in tobacco smoke and polluted indoor environments. Environmental Aspects of N-Nitroso Compounds, E. A. Walker, M. Castegnaro, L. Griciute, R. E. Lyle. International Agency for Research on Cancer, LyonFrance 1978; 343–356, IARC Monograph no. 19
  • Hoffmann D., Rathkamp G., Lin Y. Y. Chemical studies on tobacco smoke. XXVI. On the isolation and identification of volatile and nonvolatile N-nitrosamines and hydrazines in cigarette smoke. N-Nitroso Compounds in the Environment, P. Bogovski, E. A. Walker. International Agency for Research on Cancer, LyonFrance 1974; 159–165, IARC Monograph no. 9
  • Hoffmann D., Hecht S. S., Ornaf R. M., Wynder E. L., Tso T. C. Chemical studies on tobacco smoke. XLII. Nitrosonornicotine: Presence in tobacco, formation and carcinogenicity. Environmental N-Nitroso Compounds Analysis and Formation, E. A. Walker, P. Bogovski, L. Griciute. International Agency for Research on Cancer, LyonFrance 1976; 307–320, IARC Monograph no. 14
  • Eisenbrand G., Spiegelhalder B., Janzowski C., Kann J., Preussmann R. Volatile and nonvolatile N-nitroso compounds in foods and environmental media. Environmental Aspects of N-Nitroso Compounds, E. A. Walker, M. Casteg-naro, L. Griciute, R. E. Lyle. International Agency for Research on Cancer, LyonFrance 1978; 311–324, IARC Monograph no. 19
  • Krull I. S., Goff U., Silvergleid A., Fine D. H. N-Nitroso contaminants in prescription and nonprescription drugs. Arzneim. Forsch. 1978; 28: 870–874
  • Fan T. Y., Goff U., Song L., Fine D. H., Arsenault G. P., Biemann K. N-Nitrosodiethanolamine in cosmetics, lotions and shampoos. Food Cosmet. Toxicol. 1977; 15: 423–430
  • Fan T. Y., Morrison J., Rounbehler D. P., Ross R., Fine D. H., Miles W., Sen N. P. N-Nitrosodiethanolamine in synthetic cutting fluids: A part-per-thousand impurity. Science 1977; 196: 70–71
  • Rappe C., 2nd, Zingmark P. A. Formation of nitroso-amines in cutting fluids. Environmental Aspects of N-Nitroso Compounds, E. A. Walker, M. Castegnaro, L. Griciute, R. E. Lyle. International Agency for Research on Cancer, LyonFrance 1978; 213–218, IARC Monograph no. 19
  • Stephany R. W., Freudenthal J., Schuller P. L. N-Nitroso-5-methyl-1, 3-oxazolidine identified as an impurity in a commercial cutting fluid. Rec. J.R. Neth. Chem. Soc. 1978; 97: 177–178
  • McGee P. N., Barnes J. M. In vivo reactions of nitroso compounds. Adv. Cancer Res. 1967; 10: 163–246
  • Parodi S., Zunino A., Ottaggio L., DeFerrari M., Santi L. Quantitative correlation between carcinogenicity and sister chromatid exchange induction in vivo for a group of 11 N-nitroso derivatives. J. Toxicol. Environ. Health 1983; 11: 337–346
  • McGee P. N. In vivo reactions of nitroso compounds. Ann. N.Y. Acad. Sci. 1969; 163: 717–729
  • U.S. International Trade Commission. Synthetic Organic Chemicals, U.S. Production and Sales, USITC publ. 833. U.S. Government Printing Office, Washington, DC 1977; 131
  • Lijinski W., Reuber M. D., Blackwell B. N. Liver tumors induced in rats by oral administration of the antihistamine methapyrilene hydrochloride. Science 1980; 209: 817
  • Rao G. S., Kirshna G., Gillette J. R. Drug nitrite interactions: In vivo formation of N-nitroso derivative in the rat. Pharmacologist 1973; 15: 191
  • Rao G. S., Kirshna G., Gillette J. R. Metabolism, tissue distribution and covalent binding of tripelennamine and its N-nitroso derivative in the rat. J. Pharmacol. Exp. Ther. 1975; 195: 433–440
  • Rao G. S., Kirshna G., Gillette J. R. Enzymatic formation of chemically reactive metabolites of N-nitroso-desmethyltripelennamine by a mechanism other than N-dealkylation. Biochem. Pharmacol. 1975; 24: 1707–1711
  • Lijinski W. Reaction of drugs with nitrous acid as a source of carcinogenic nitrosamines. Cancer Res. 1974; 34: 255–258
  • Gold B., Miruish S. S. N-Nitroso derivatives of hydrochlorothiazide, niridazole and tolbutamide. Toxicol. Appl. Pharmacol. 1977; 40: 131–136
  • Pliss G. B. On some regular relationships between carcinogenicity of aminodiphenyl derivatives and the structure of substance. Acta Unio Int. Contra Cancerum 1963; 19: 499–501
  • Mundy R. L., Bowman M. C., Farmer J. H., Haley T. J. Quantitative structure activity study of a series of substituted O, O-dimethyl O-(p-nitrophenyl) phos-phorothioates and O-analogs. Arch. Toxicol. 1978; 41: 111–123
  • The Use of Alternatives in Drug Research, A. N. Rowman, C. J. Stratmann. The Macmillan Press, London 1980; 190
  • Di Carlo F. J. Carcinogenesis bioassay data: Correlation by species and sex. Drug Metab. Rev. 1984; 15(3)409–413
  • Holden H. T., Lichter W., Sigel M. M. Quantitative methods for measuring cell growth and death. Tissue Culture: Methods and Application, P. Kruse, Jr., M. K. Patterson, Jr. Academic Press, New York 1973; 408–411
  • Nardone R. M. The effect of ionizing radiation on strain L monolayers. I. Cytological aberrations and cell multiplication. Life Sci. 1963; 2: 113–119
  • Chayen I., Bittersky L. Cell injury. Cell Biology in Medicine, E. E. Bittnar. Wiley, New York 1973; 595–678
  • Walton J., Buckley I. K. Cell models in the study of the mechanisms of toxicity. Agents Actions 1975; 5: 68–88
  • Dillingham E. O., Mast R. W., Bass G. E., Autian J. Toxicity of methyl- and halogen-substituted alcohols in tissue culture relative to structure-activity models and acute toxicity in mice. J. Pharm. Sci. 1973; 63: 22–30
  • Flaxman B. A. Replication and differentiation in vitro of epidermal cells from normal human skin and from benign (psoriasis) and malignant (basal cell cancer) hyperplasia. In Vitro 1972; 8: 237–250
  • Paine A. J., Ord M. J., Neal G. E., Skilleter D. N. Cell models in the study of toxic mechanisms. The Use of Alternatives in Drug Research, A. N. Rowan, C. J. Stratmann. The Macmillian Press, London 1980; 71–84

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.