Abstract
Aromatic amines were among the first chemical agents recognized to be carcinogenic. This suspicion was first voiced by Rehn in 1895 (1) after he noticed three cases of bladder cancer among workers employed at an amine-derived dye factory in Germany. Prior to the industrialized production of synthetic organic chemicals (thus occasioning long-term exposure of significant amounts to many people), this disease was sufficiently rare to make the situation noteworthy. As large-scale human exposure continued, particularly in the virtual absence of sound hygenic practices, enough cases of malignant disease arose to permit an epidemiological assignment of cause. In this way, 4-aminobiphenyl was identified as a human carcinogen (and its use banned) in 1955 (2), and both benzidine and 2-naphthylamine were similarly classified, following indications derived from animal models, in 1954. (3). The dog was initially selected as a test species of choice for chemically-induced bladder cancer because of its sensitivity to the disease. Dosing studies of the three compounds cited above showed that 4-aminobiphenyl is the most potent, followed by 2-naphthylamine (4), while benzidine clearly shows a lower order of response (5). These studies, and those of the induction of liver tumors in rodents (6), indicate that individual aromatic amines of superficially similar structure differ widely in their carcinogenic potential. In addition, the disparate sites of tumor formation shown by these compounds indicates that they require enzymatic transformation prior to eliciting their effects, as described in more detail in other chapters in this volume.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Rehn L: Blasengeschwulste bei fuchsinarbeitern. Arch Klin Chir (50): 588–600, 1895.
Case RAM, Hosker ME, McDonald DB, Pearson JT: Tumours of the urinary bladder in workmen engaged in the manufacture and use of certain dyestuff intermediates in the British chemical industry. Br J Ind Med (11): 75–104, 1954.
Melick WF, Escue, HM, Naryka JJ, Mezera RA, Wheeler ER: The first reported cases of human bladder tumors due to a new carcinogen-xenylamine. J Urol (74): 760–766, 1955.
Deichmann WB, Radomski J, Glass E, Anderson, WAD, Coplan M, Woods F: Synergism among oral carcinogens. III.Simultaneous feeding of four bladder carcinogens to dogs.Ind Med Surg (34): 640–649, 1965.
Spitz S, Maguigan WH, Dobriner K: The carcinogenic action of benzidine. Cancer (3): 789–804, 1950.
Boyland E, Harris J, Horning, ES: The induction of carcinoma of the bladder in rats with acetamidofluorene. Br J Cancer (8): 647–654, 1954.
Marnett LJ: Polycyclic aromatic hydrocarbon oxidation during prostaglandin biosynthesis. Life Sci (29): 531–546, 1981.
Gale PH, Egan RW: Prostaglandin endoperoxide synthase catalyzed oxidation reactions. In: Pryor WA (ed) Free Radicals in Biology, Vol VI. Academic Press, Orlando, Florida, 1984, pp 1–38.
Marnett LJ, Fling TE: Cooxidation during prostaglandin biosynthesis: A pathway for the metabolic activation of xenobiotics. in: Hodgson F, Rend JR, Philpot RM (eds) Reviews in Biochemical Toxicology, Vol 5. Elsevier, New York, 1983, pp 135–172.
Sivarajah K, Lasker JM, Fling TE: Prostaglandin synthetase-dependent cooxidation of (+1-henzo(a)pyrene-7,8dihydrodiol by human lung and other mâmnalian tissues. Cancer Res (41): 1834–1839, 1981.
Wise RW, Zenser TV, Kadlubar FF, Davis RB: Metabolic activation of carcinogenic aromatic amines by dog bladder and kidney prostaglandin H synthase. Cancer Res (44): 1893–1897, 1984.
Cohen SM, Zenser TV, Murasaki G, Fukushima S, Mattamnal MB, Rapp NS, Davis RB: Aspirin inhibition of N-[4(5-nitro-2-furyl)-2-thiazolyl]formamide-induced lesions of the urinary bladder correlated with inhibition of metabolism by bladder prostaglandin endoperoxide synthetase. Cancer Res (41): 3355–3359, 1981.
Van Der Ouderaa FJ, Buytenhek M, Nugteren DH, Van Dorp DA: Purification and characterisation of prostaglandin endoperoxide synthetase from sheep vesicular glands. Biochim Riophys Acta (487): 315–331, 1977.
Kulmacz RJ, Lands WEM: Prostaglandin H synthase: Stoichiometry of heme cofactor. J Biol Chem 2591: 6358–6363, 1984.
Rollins TE, Smith WL: Subcellular localization of prostaglandin-forming cyclooxygenase in Swiss mouse 3T3 fibroblasts by electron microscopic imnunocytochemistry. J Biol Chem (255): 4872–4875, 1980.
Roth GJ, Stanford N, Majerus PW: Acetylation of prostaglandin synthase by aspirin. Proc Nat Acad Sci USA (72): 3073–3076, 1975.
Walsh C: Enzymatic Reaction Mechanisms. W.H. Freeman and Co., San Francisco, 1979, pp 488–493.
Dophin D: The electronic configurations of catalases and peroxidases in their high oxidation states: A definitive assessment. Israel J Chem (21): 67–71, 1981.
Kalyanaraman B, Mason RP, Tainer B, Fling TE: The free radical formed during the hydroperoxide-mediated deactivation of ram seminal vesicles is hemoprotein-derived. J Biol Chem (257): 4764–4768, 1987.
McCarthy M-B, White RE: Functional differences between peroxidase compound I and the cytochrome P-450 reactive oxygen intermediate. J Biol Chem (258): 9153–9158, 1983.
White RE, Coon MJ: Oxygen activation by cytochrome P-450. Ann Rev Biochem (49): 315–356, 1980.
Rapp NS, Zenser TV, Brown WW, Davis RB: Metabolism of benzidine by a prostaglandin-mediated process in renal inner medullary slices. J Pharmacol F.xp Ther (215): 401–406, 1980.
Egan RW, Gale PH, Baptista FM, Kennicott KL, VandenHeuvel WJA, Walker RW, Eagerness PE, Kuehl Jr. FA: Oxidation reactions by prostaglandin cyclooxygenase-hydroperoxidase. J Biol Chem (256): 7352–7361, 1981.
Zenser TV, Mattammal MB, Davis BB: Demonstration of separate pathways for the metabolism of organic compounds in rabbit kidney. J Pharmacol Exp Ther (208): 418–421, 1979.
Mohandas J, Duggin GG, Horvath JS, Tiller DJ: Metabolic oxidation of acetaminophen (paracetamol) mediated by cytochrome P-450 mixed-function oxidase and prostaglandin endoperoxide synthetase in rabbit kidney. Toxicol App] Pharmacol (61): 252–259, 1981.
Boyd JA, Eling TE: Prostaglandin endoperoxide synthetase-dependent cooxidation of acetaminophen to intermediates which covalently bind in vitro to rabbit renal medullary microsomes. J Pharmacol Exp Ther (219): 659–664, 1981.
Egan RW, Gale PH, Kuehl Jr FA: Reduction of hydroperoxides in the prostaglandin biosynthetic pathway by a microsomal peroxidase. J Biol Chem (254):3295–3302, 1979.
Egan RW, Gale PH, VandenHeuvel WJA, Baptista EM, Kuehl Jr FA: Mechanism of oxygen transfer by prostaglandin hydroperoxidase. J Biol Chem (255): 323–326, 1980.
Reed GA, Brooks EA, Eling TE: Phenylbutazone-dependent epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene. J Biol Chem (259): 5591–5595, 1984.
Siedlik PH, Marnett LJ: Oxidizing radical generation by prostaglandin H synthase. Methods Enzymol (105): 412–417, 1984.
Boyd JA, Harvan DJ, Eling TE: The oxidation of 2-aminofluorene by prostaglandin endoperoxide synthetase. J Biol Chem (258): 8246–8254, 1983.
Nelson RF: Anodic oxidation pathways of aliphatic and aromatic nitrogen functions. In: Weinberg N (ed) Techniques of electro-organic synthesis. Wiley, New York, 1974.
Ross SD, Finkelstein M, Rudd EJ: Anodic Oxidations. Academic Press, New York, 1975.
Adams RN: Electrochemistry at Solid Electrodes. Dekker, New York, 1969.
Flaks A, Flaks B: Induction of liver cell tumours in Fmice by paracetamol. Carcinogenesis (4): 363–368, 1983.
Hinson JA, Pohl LR, Monks TJ, Gillette JR: Minireview: Acetaminophen-induced hepatotoxicity. Life Sci (29): 107–116, 1981.
Volans GN: Self-poisoning and suicide due toparacetamol. Int Med Res (4): 7–13, 1976.
McMurtry RJ, Snodgrass WR, Mitchell JR: Renal necrosis, glutathione depletion, and covalent binding after acetaminophen. Toxicol Appl Pharmacol (46): 87–100, 1978.
Newton JF, Braselton Jr WE, Kuo C-H, Kluwe WM, Gemborys MW, Mudge GH, Hook JB: Metabolism of acetaminophen by the isolated perfused kidney. J Pharmacol Exp Ther (221): 76–79, 1982.
Armbrecht HJ, Birnbaum LS, Zenser TV, Mattammal MB, Davis BB: Renal cytochrome P-450’s — electrophoretic and electron paramagnetic resonance studies. Arch Biochem Biophys (197): 277–284, 1979.
Saker BM, Kincaid-Smith P: Papillary necrosis in experimental analgesic nephropathy. Brit Med J (1): 161–162, 1969.
Josephy PD, Fling TE, Mason RP: Oxidation of p-aminophenol catalyzed by horseradish peroxidase and prostaglandin synthase. Mol Pharmacol (23): 461–466, 1983.
Andersson B, Larsson R, Rahimtula A, Moldeus P: Hydroperoxide-dependent activation of p-phenetidine catalyzed by prostaglandin synthase and other peroxidases. Biochem Pharmacol (32): 1045–1050, 1983.
Nelson SD, Dahlin DC, Rauckman EJ, Rosen GM: Peroxidase-mediated formation of reactive metabolites of acetaminophen. Mol Pharmacol (20): 195–199, 1981.
Moldeus P, Rahimtula A: Metabolism of paracetamol to a glutathione conjugate catalyzed by prostaglandin synthetase. Biochem Biophys Res Comm (96): 469–475, 1980.
Moldeus P, Andersson B, Rahimtula A, Berggren M: Prostaglandin synthetase catalyzed activation of paracetamol. Biochem Pharmacol (31): 1363–1368, 1982.
Hinson JA, Mitchell JR: N-hydroxylation of phenacetin by hamster liver microsomes. Drug Metab Dispos (4): 430–435, 1976.
Calder IC, Creek MJ, Williams PJ: N-hydroxyphenacetin as a precursor of 3-substituted 4-hydroxyacetanilide metabolites of phenacetin. Chem-Biol Interact (8): 87–90, 1974.
Miner DJ, Kissinger PT: Evidence for the involvement of N-acetyl-p-quinoneimine in acetaminophen metabolism. Biochem Pharmacol (28): 3285–3290, 1979.
Hinson JA, Pohl LR, Gillette JR: N-hydroxyacetaminophen: A microsomal metabolite of N-hydroxyphenacetain but apparently not of acetaminophen. Life Sci (24): 2133–2138, 1979.
Nelson SD, Forte AJ, Dahlin DC: Lack of evidence for N-hydroxyacetaminophen as a reactive metabolite of acetaminophen in vitro. Biochem Pharmacol (29): 1617–1620, 1980.
Rosen GM, Singletary Jr WV, Rauckman EJ, Killenherg PG: Acetaminophen hepatotoxicity: An alternative mechanism. Biochem Pharmacol (32): 2053–2059, 1983.
Rosen GM, Rauckman EJ, Ellington SP, Dahlin DC, Christie JL, Nelson SD: Reduction and glutathione conjugation reactions of N-acetyl-p-benzoquinone imine and two dimethylated analogues. Mol Pharmacol (25): 151–157, 1983.
Miller MG, Jollow DJ: Effect of L-ascorbic acid on acetaminophen-induced hepatotoxicity and covalent binding in hamsters. Drug Metab Dispos (12): 271–279, 1984.
Devalia JL, McLean AEM: Covalent binding and the mechanism of paracetamol toxicity. Biochem Pharmacol (32): 2602–2603, 1983.
de Vries J: Hepatotoxic metabolic activation of paracetamol and its derivatives phenacetin and benorilate: Oxygenation or electron transfer9 Biochem Pharmacol (30): 399–402, 1981.
Porter KE, Dawson AG: Inhibition of respiration and gluconeogenesis by paracetamol in rat kidney preparations. Biochem Pharmacol (28): 3057–3062, 1979.
Trager WF: The postenzymatic chemistry of activated oxygen. Drug Metab Rev (13): 51–69, 1982.
Kadlubar FF, Miller, JA, Miller EC: Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res (37): 805–814, 1977.
Radomski JL: The primary aromatic amines: Their biological properties and structure-activity relationships. Ann Rev Pharmacol Toxicol (19): 129–157, 1979.
Zenser TV, Mattamnal MB, Davis BB: Demonstration of separate pathways for the metabolism of organic compounds in rabbit kidney. J Pharmacol Exp Ther (208): 418–421, 1979.
Mattammal MB, Zenser TV, Brown WW, Herman CA, Davis BB: Mechanism of inhibition of renal prostaglandin production by acetaminophen. J Pharmacol Exp Ther (210): 405–409, 1979.
Zenser TV, Mattanmal MB, Davis BB: Cooxidation of benzidine by renal medullary prostaglandin cyclooxygenase. J Pharmacol Exp Ther (211): 460–464, 1979.
Zenser TV, Mattamnal MB, Armbrecht HJ, Davis BB: Benzidine binding to nucleic acids mediated by the peroxidative activity of prostaglandin endoperoxide synthetase. Cancer Res (40): 2839–2845, 1980.
Rice JR, Kissinger PT: Cooxidation of benzidine by horseradish peroxidase and subsequent formation of possible thioether conjugates of benzidine. Biochem Biophys Res Comm (104): 1312–1318, 1982.
Wise RW, Zenser TV, Davis BB: Peroxidase metabolism of the urinary bladder carcinogen 2-amino-4-(5-nitro-2-furyl)thiazole. Cancer Res (43): 1518–1522, 1983.
Josephy PD, Eling TE, Mason RP: An electron spin resonance study of the activation of benzidine by peroxidases. Mol Pharmacol (23): 766–770, 1982.
Martin CN, Beland FA, Roth RW, Kadlubar FF: Covalent binding of benzidine and N-acetylbenzidine to DNA at the C-8 atom of deoxyguanosine in vivo and in vitro. Cancer Res (42): 2678–2696, 1982.
Gemhorys MW, Gribble GW, Mudge GH: Synthesis of N-hydroxyacetaminophen, a postulated toxic metabolite of acetaminophen, and its phenolic sulfate conjugate. J Med Chem (21): 649–652, 1978.
Miner DJ, Rice JR, Riggin RM, Kissinger PT: Voltammetry of acetaminophen and its metabolites. Anal Chem (53): 2258–2263, 1981.
Rice JR, Kissinger PT: Determination of benzidine and its acetylated metabolites in urine by liquid chromatography. J Anal Toxicol (3): 64–66, 1979.
Zenser TV, Mattamnal MB, Wise RW, Rice JR, Davis RB: Prostaglandin H synthase-catalyzed activation of benzidine: A model to assess pharmacologie intervention of the initiation of chemical carcinogenesis. J Pharmacol Exp Ther (227): 545–550, 1983.
Josephy PD, Fling T, Mason RP: The horseradish peroxidase-catalyzed oxidation of 3,5,3’,5’tetramethylbenzidine. J Biol Chem (257): 3669–3675, 1982.
Josephy PD, Fling TE, Mason RP: Co-oxidation of benzidine by prostaglandin synthase and comparison with the action of horseradish peroxidase. J Biol Chem (258): 5561–5569, 1983.
Claiborne A, Fridovich I: Chemical and enzymatic intermediates in the peroxidation of o-dianisidine by horseradish peroxidase. 1. Spectral properties of the products of dianisidine oxidation. Biochemistry (18): 2324–2328, 1979.
Wise RW, 7enser TV, Davis BB: Prostaglandin H synthase metabolism of the urinary bladder carcinogens benzidine and ANFT. Carcinogenesis (3): 285–289, 1983.
Frederick CB, Mays JB, Ziegler DM, Guengerich FP, Kadlubar FF: Cytochrome P-450- and flavin-containing monooxygenase-catalyzed formation of the carcinogen N-hydroxy-2-aminofluorene and its covalent binding to nuclear DNA. Cancer Res (42): 2671–2677, 1982.
Saunders BC, Holmes-Siedle AG, Stark BP: Peroxidase. Washington, Butterworths, 1964, p 9.
Josephy PD, Mason RP, Fling T: Chemical structure of the adducts formed by the oxidation of benzidine in the presence of phenols. Carcinogenesis (3): 1227–1230, 1982.
Josephy PD, Damne AV: Reaction of 4-substituted phenols with benzidine in a peroxidase system. Biochem Pharmacol (33): 1155–1156, 1984.
McKee RH, Tometsko AM: Inhibition of promutagen activation by the antioxidants butylated hydroxyanisole and butylated hydroxytoluene. J Natl Cancer Inst (63): 473–477, 1979.
Maeura Y, Weisburger JH, Williams GH: Dose-dependent reduction of N-2-fluorenylacetamide-induced liver cancer and enhancement of bladder cancer in rats by butylated hydroxytoluene. Cancer Res (44): 1604–1610, 1984.
Weber WW: Acetylation pharmacogenetics: Experimental models for human toxicity. Fed Proc (43): 2332–2337, 1984.
Lower Jr GM, Nilsson T, Nelson CE, Wolf H, Gamsky TE, Bryan GT: N-Acetyltransferase phenotype and risk in urinary bladder cancer: Approaches in molecular epidemiology. Preliminary results in Sweden and Denmark. Environ Health Perspect (29): 71–79, 1979.
Lower Jr GM, Bryan GT: Enzymatic N-acetylation of carcinogenic aromatic amines by liver cytosol of species displaying different organ susceptibilities. Biochem Pharmacol (22): 1581–1588, 1973.
Morton KC, King CM, Vaught JB, Wang CY, Lee M-S, Marnett LJ: Prostaglandin H synthase-mediated reaction of carcinogenic arylamines with tRNA and homopolyribonucleotides. Biochem Riophys Res Comm (111): 96–103, 1983.
Kadlubar FF, Frederick CR, Weis CC, Tenser TV:Prostaglandin endoperoxide synthetase-mediated metabolism of carcinogenic aromatic amines and their binding to DNA and protein. Biochem Biophys Res Comm (108): 253–258, 1982.
Radomski JL, Rey AA, Brill F: Evidence for a glucuronic acid conjugate of N-hydroxy-4-aminohiphenyi in the urine of dogs given 4-aminobiphenvl. Cancer Res (33): 1284–1289, 1973.
Radomski JL, Hearn WL, Randomski T, Moreno H, Scott WE: Isolation of the glucuronic acid conjugate of N-hydroxy-4-aminohiphenyi from dog urine and its mutagenic activity. Cancer Res (37): 1757–1762, 1977.
Miller JA: Carcinogenesis by chemicals: Anoverview—G.H.A. Clowes Memorial Lecture. Cancer Res (30): 559–576, 1970.
Vaught JB, Lee M-S, Shayman MA, Thissen MP, King CM: Arylhydroxylamine-induced ribonucleic acid chain cleavage and chromatographic analysis of arylamine-ribonucleic acid adducts. Chem-Biol Interact (34): 109–124, 1981.
Nitrofurans: Chemistry, Metabolism, Mutagenesis, and Carcinogenesis. Bryan GT (ed) Carcinogenesis-A comprehensive survey, Vol. 4. New York, Raven Press, 1978.
Jacobs JB, Arai M, Cohen SM, Friedell GH: A long-term study of reversible and progressive urinary bladder lesions in rats fed N-[4-(5-nitro-2-furyl)-2-thiazolyl] formamide. Cancer Res (37): 2817–2821, 1977.
Cohen SM, Lower Jr CM, Erturk F, Bryan CT: Comparative carcinogenicity in Swiss mice of N-[4-(5-nitro-2-furyl)2-thiazolyl]acetamide and structurally related 5-nitrofurans and 4-nitrobenzenes. Cancer Res (33): 1593–1597, 1973.
Wang CY, Kamiryo Y, Croft WA: Carcinogenicity of 2-amino-4-(5-nitro-2-furyl)thiazole in rats by oral and subcutaneous administration. Carcinogenesis (3): 275–277, 1982.
Erturk E, Cohen SM, Bryan GT: Carcinogenicity of N-[4(5-nitro-2-furyl)-2-thiazoly1]acetamide in female rats. Cancer Res (30): 936–941, 1970.
Croft WA, Bryan GT: Production of urinary bladder carcinomas in male hamsters by N-[4-(5-nitro-2-furyll-2thiazolyl]formamide, N-[4-(5-nitro-2-fury11-2-thiazolyl] acetamide, or formic acid 2-[4-(5-nitro-2-furyl)-2thiazolyl]hydrazide. J Natl Cancer Inst (51): 941–949, 1973.
Wang CY, Behrens BC, Ichikawa M, Bryan GT: Nitroreduction of 5-nitrofuran derivatives by rat liver xanthine oxidase and reduced nicotinamide adenine dinucleotide phosphate-cytochrome c reductase. Biochem Pharmacol (23): 3395–3404, 1974.
Mattanmal MB, Zenser TV, Davis BB: Anaerobic metabolism and nuclear binding of the carcinogen 2-amino-4(5-nitro-2-furyl)thiazole (ANFT). Carcinogenesis (3): 1339–1344, 1982.
Swaminathan S, Bryan GT: Biotransformation of the bladder carcinogen N-[4-(5-nitro-2-fury1)-2-thiazolyl] formamide in mice. Cancer Res (44): 2331–2338, 1984.
Wang CY, Hayashida S, Pamukcu AM, Bryan GT: Enhancing effect of allopurinol on the induction of bladder cancer in rats by N-[4-(5-nitro-2-fury1)-2-thiazolyl]formamide (FANFT). Proc Am Assoc Cancer Res (18): 100, 1976.
Zenser TV, Palmier MO, Mattammal MB, Bolla RI, Davis BB: Comparative effects of prostaglandin H synthase-catalyzed binding of two 5-nitrofuran urinary bladder carcinogens. J Pharmacol Exp Ther (227): 139–143, 1983.
Wang CY, Bryan GT: Deacylation of carcinogenic 5-nitrofuran derivatives by mammalian tissues. Chem-Biol Interact (9): 423–428, 1974.
Zenser TV, Palmier MO, Mattanmal MB, Davis RB: Metabolic activation of the carcinogen N-[4-(5-nitro-2-fury])-2thiazolyljacetamide by prostaglandin H synthase. Carcinogenesis, in press.
Rice JR, Kissinger PT: Liquid chromatography with precolumn sample preconcentration and electrochemical detection: Determination of aromatic amines in environmental samples. Environ Sci Technol (16): 263–268, 1982.
Zenser TV, Mattanmal MB, Rapp NS, Davis BB: Effect of aspirin on metabolism of acetaminophen and benzidine by renal inner medulla prostaglandin hydroperoxidase. J Lab Clin Med (101): 58–65, 1983.
Murasaki G, Zenser TV, Davis BB, Cohen SM: Inhibition by aspirin of N-[4-(5-nitro-2-fury11–2-thiazolyl]formamideinduced bladder carcinogenesis and enhancement of fore-stomach carcinogenesis. Carcinogenesis (5): 53–55, 1984.
Cramer JW, Miller JA, Miller EC: N-hydroxylation: A new metabolic reaction observed in the rat with carcinogen 2-acetylaminofluorene. J Biol. Chem (235): 885–888, 1960.
Miller EC, Miller JA: Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer (47): 2327–2345, 1981.
Yamazoe Y, Miller DW, Gupta RC, Zenser TV, Weis CC, Kadlubar FF: DNA adducts formed by prostaglandin H synthase-mediated activation of carcinogenic arylamines. Proc Am Assoc Cancer Res (25): 91, 1984.
Tateiski M: Methylthiolated metabolites. Drug Metab Rev (14): 1207–1234, 1983.
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1985 Martinus Nijhoff Publishing, Boston
About this chapter
Cite this chapter
Rice, J.R., Zenser, T.V., Davis, B.B. (1985). Prostaglandin Synthase-Dependent Cooxidation and Aromatic Amine Carcinogenesis. In: Marnett, L.J. (eds) Arachidonic Acid Metabolism and Tumor Initiation. Prostaglandins, Leukotrienes, and Cancer, vol 2. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-2611-3_4
Download citation
DOI: https://doi.org/10.1007/978-1-4613-2611-3_4
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4612-9634-8
Online ISBN: 978-1-4613-2611-3
eBook Packages: Springer Book Archive