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Xenobiotica
the fate of foreign compounds in biological systems
Volume 7, 1977 - Issue 1-2
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Research Article

Metabolic Fate of N-n-Butyl-N-(4-hydroxybutyl)-nitrosamine and its Analogues: Selective Induction of Urinary Bladder Tumours in the Rat

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Pages 11-24 | Received 03 Jun 1976, Published online: 22 Sep 2008

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JosephE. Saavedra. (1987) RECENT SYNTHETIC APPLICATIONS OF N-NITROSAMINES AND RELATED COMPOUNDS. Organic Preparations and Procedures International 19:2-3, pages 83-159.
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William Lijinsky. (1986) The significance of N‐Nitroso compounds as environmental carcinogens∗ . Environmental Carcinogenesis Reviews 4:1, pages 1-45.
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Joseph L Sottnik, Vandana Mallaredy, Ana Chauca-Diaz, Carolyn Ritterson Lew, Charles Owens, Garrett M Dancik, Serena Pagliarani, Sabrina Lucchiari, Maurizio Moggio, Michela Ripolone, Giacomo P Comi, Henry F FriersonJrJr, David Clouthier & Dan Theodorescu. (2019) Elucidating the role of Agl in bladder carcinogenesis by generation and characterization of genetically engineered mice. Carcinogenesis 40:1, pages 194-201.
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Alessio Crippa, Susanna C. Larsson, Andrea Discacciati, Alicja Wolk & Nicola Orsini. (2016) Red and processed meat consumption and risk of bladder cancer: a dose–response meta-analysis of epidemiological studies. European Journal of Nutrition 57:2, pages 689-701.
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Paula A. Oliveira, Cármen Vasconcelos-Nóbrega, Rui M. Gil da Costa & Regina Arantes-Rodrigues. 2018. Urothelial Carcinoma. Urothelial Carcinoma 155 167 .
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Chelsea E. Catsburg, Manuela Gago-Dominguez, Jian-Min Yuan, J. Esteban Castelao, Victoria K. Cortessis, Malcolm C. Pike & Mariana C. Stern. (2014) Dietary sources of N-nitroso compounds and bladder cancer risk: Findings from the Los Angeles bladder cancer study. International Journal of Cancer 134:1, pages 125-135.
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Jong-Wei Hsu, Iawen Hsu, Defeng Xu, Hiroshi Miyamoto, Liang Liang, Xue-Ru Wu, Chih-Rong Shyr & Chawnshang Chang. (2013) Decreased Tumorigenesis and Mortality from Bladder Cancer in Mice Lacking Urothelial Androgen Receptor. The American Journal of Pathology 182:5, pages 1811-1820.
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Keiko Inami, Hiroki Yasui, Hirotaka Tsugumi, Satoko Ishikawa & Masataka Mochizuki. (2013) Oxidation of N-Alkyl-N-(3-carboxypropyl)nitrosamines by Iron Porphyrin and Oxidant Forms Alkylating Mutagens. Genes and Environment 35:4, pages 99-104.
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Richard Clapp, Molly Jacobs & Willie Lijinsky. 2003. Patty's Toxicology. Patty's Toxicology 401 432 .
Almudena García, Paloma Morales, Nuria Arranz, Eugenia Delgado, Joseph Rafter & Ana I. Haza. (2007) Induction of apoptosis and reactive oxygen species production by N ‐nitrosopiperidine and N ‐nitrosodibutylamine in human leukemia cells . Journal of Applied Toxicology 28:4, pages 455-465.
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Aimee M. Johnson, David L. Conover, Jiaoti Huang, Edward M. Messing, Ruola Ning, Mary J. O’Connell, M. Adrian Rossi, Tung-Tien Sun, Ronald W. Wood, Xue-Ru Wu & Jay E. Reeder. (2006) Early detection and measurement of urothelial tumors in mice. Urology 67:6, pages 1309-1314.
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Takashi Murai, Yukio Mori, Kenjiro Tatematsu, Akihiro Koide, Akihiro Hagiwara, Susumu Makino, Satoru Mori, Hideki Wanibuchi & Shoji Fukushima. (2005) Differences in susceptibility to N-butyl-N-(4-hydroxybutyl)nitrosamine-induced urinary bladder carcinogenesis between SD/gShi rats with spontaneous hypospermatogenesis and SD/cShi rats with spontaneous hydronephrosis. Cancer Science 96:10, pages 637-644.
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Katsuyuki Iida, Ken Itoh, Yoshito Kumagai, Ryoichi Oyasu, Kazunori Hattori, Koji Kawai, Toru Shimazui, Hideyuki Akaza & Masayuki Yamamoto. (2004) Nrf2 Is Essential for the Chemopreventive Efficacy of Oltipraz against Urinary Bladder Carcinogenesis. Cancer Research 64:18, pages 6424-6431.
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Ji-Yeob Choi, Kyoung-Mu Lee, Soo-Hun Cho, Soo-Woong Kim, Han-Yong Choi, Sang-Yoon Lee, Hyoung-June Im, Ki Jung Yoon, Hwang Choi, Inmi Choi, Ari Hirvonen, Richard B Hayes & Daehee Kang. (2003) CYP2E1 and NQO1 genotypes, smoking and bladder cancer. Pharmacogenetics 13:6, pages 349-355.
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William Lijinsky. 2003. Patty's Toxicology. Patty's Toxicology.
Sidney S. Mirvish. (1995) Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC. Cancer Letters 93:1, pages 17-48.
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Luisa Airoldi, Cinzia Magagnotti, Giovanni De Gregorio, Massimo Moret & Roberto Fanelli. (1992) In vitro metabolism of bladder carcinogenic nitrosamines by rat liver and urothelial cells. Chemico-Biological Interactions 82:2, pages 231-240.
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Seiko Tamano, Tomoyuki Shirai, Mayumi Kawabe, Hiroaki Ni-I, Yukio Mori, Masashi Okada & Shoji Fukushima. (2016) Low Susceptibility of Nude Mice to Induction of Invasive Urinary Bladder Cancers by N -Ethyl- N -(4-hydroxybutyl)nitrosamine . Toxicologic Pathology 20:2, pages 205-211.
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Seiko Tamano, Akihiro Hagiwara, Emako Suzuki, Masashi Okada, Tomoyuki Shirai & Shoji Fukushima. (2005) Time‐ and Dose‐dependent Induction of Invasive Urinary Bladder Cancers by N‐Ethyl‐N‐(4‐hydroxybutyl)nitrosamine in B6C3F 1 Mice . Japanese Journal of Cancer Research 82:6, pages 650-656.
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Rose Anne Boigegrain, Roberto Fanelli, Pierluigi Gariboldi & Luisa Airoldi. (2006) Synthesis of doubly 15‐nitrogen labelled N‐[4‐hydroxybutyl]‐N‐nitrosobutylamine, a potent urinary bladder carcinogen in animals. Journal of Labelled Compounds and Radiopharmaceuticals 25:10, pages 1163-1172.
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Roberta Pastorelli, Annalisa Ancidei, Emilio Benfenati, Roberto Fanelli & Luisa Airoldi. (1988) Effect of butylated hydroxyanisole added in vitro or administered to rats on N,N-dibutylnitrosamine and N-butyl-N-(4-hydroxybutyl)nitrosamine metabolism by post-mitochondrial supernatant of liver homogenates. Toxicology 48:1, pages 71-80.
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Luisa Airoldi, Marina Bonfanti, Cinzia Magagnotti & Roberto Fanelli. 1988. Chemical Carcinogenesis. Chemical Carcinogenesis 137 142 .
Donald L. Nagel, Sidney S. Mirvish, Lawrence Wallcave & Betty Walker. (1987) Alpha-acetoxy derivatives of methyl-2-oxopropylnitrosamine: Synthesis, hydrolysis rate and bacterial mutagenicity. Cancer Letters 36:3, pages 325-332.
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Joseph B. Guttenplan. (1987) N-nitrosamines: bacterial mutagenesis and in vitro metabolism. Mutation Research/Reviews in Genetic Toxicology 186:2, pages 81-134.
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R. Preussmann & M. Wiessler. (1987) The enigma of the organspecificity of carcinogenic nitrosamines. Trends in Pharmacological Sciences 8:5, pages 185-189.
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Rose-Anne Boigegrain, Marina Bonfanti, Roberto Fanelli & Luisa Airoldi. (1986) N-Nitrosobutyl-N-(4-hydroxybutyl)amine glucuronide in vitro synthesis, characterization by mass spectrometry and determination by gas chromatography—thermal energy analysis. Journal of Chromatography B: Biomedical Sciences and Applications 383, pages 172-178.
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D.E. Hathway. 1986. Mechanisms of Chemical Carcinogenesis. Mechanisms of Chemical Carcinogenesis 85 99 .
Hiroshi Ohshima, Jagadeesan Nair, Marie-Christine Bourgade, Marlin Friesen, Liliane Garren & Helmut Bartsch. (1985) Identification and occurrence of two new N-nitrosamino acids in tobacco products: 3-(N-nitroso-N-methylamino) propionic acid and 4-(N-nitroso-N-methylamino) butyric acid. Cancer Letters 26:2, pages 153-162.
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E. Richter, X. Feng & M. Wiessler. (1985) Biotransformation of symmetric dialkylnitrosamines in the rat intestine. Biochemical Pharmacology 34:3, pages 445-446.
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Luisa Airoldi, Marina Bonfanti, Roberto Fanelli, Bruno Bove, Emilio Benfenati & Pierluigi Gariboldi. (1984) Identification of a nitrosamino aldehyde and a nitrosamino acid resulting from β-oxidation of N-nitrosodiethanolamine. Chemico-Biological Interactions 51:1, pages 103-113.
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Anna M. Tacchi, Dietrich Schmähl & Michael Habs. (1984) Delay of bladder cancer induction in rats treated with N-nitroso-N-butyl-N-(4-hydroxybutyl)amine by administration of sodium-2-mercaptoethanesulfonate (Mesna). Cancer Letters 22:1, pages 89-94.
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Hiroshi Ohshima, Marlin Friesen, Ian O'Neill & Helmut Bartsch. (1983) Presence in human urine of a new N-nitroso compound, N-nitrosothiazolidine 4-carboxylic acid. Cancer Letters 20:2, pages 183-190.
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L. Airoldi, M. Bonfanti, E. Benfenati, P. Tavecchia & R. Fanelli. (1983) Identification of an acidic metabolite ofN-nitrosodiethanolamine isolated from rat urine. Biological Mass Spectrometry 10:5, pages 334-337.
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Luisa Airold, Claudio Spagone, Marina Bonfanti, Claudio Pantarotto & Roberto Fanelli. (1983) Rapid method for quantitative analysis of N,N-dibutylnitrosamine, N-butyl-N-(4-hydroxybutyl)nitrosamine and N-butyl-N-(3-carboxypropyl)nitrosamine in rat urine by gas chromatography—thermal energy analysis. Journal of Chromatography B: Biomedical Sciences and Applications 276, pages 402-407.
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William Lijinsky. 1983. Organ and Species Specificity in Chemical Carcinogenesis. Organ and Species Specificity in Chemical Carcinogenesis 63 75 .
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D. Kühne. (1982) Analyse von flüchtigen Nitrosaminen (NA): Nichtcarcinogenes N-Nitroso-n-butyl-tert.-butyl-amin als Standard für die gas-chromatographische BestimmungAnalysis of volatile nitrosamines: Non-carcinogenic N-nitroso-n-butyl-tert.-butyl-amine as standard for the gas-chromatographic determination. Fresenius' Zeitschrift für analytische Chemie 312:3, pages 241-241.
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Emerich S. Fiala. 1981. Inhibition of Tumor Induction and Development. Inhibition of Tumor Induction and Development 23 69 .

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