메뉴 건너뛰기




Volumn 21, Issue 2, 2008, Pages 295-307

A diazonium ion cascade from the nitrosation of tolazoline, an imidazoline-containing drug

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYETHYL PHENYLACETATE; ACETANILIDE; ACETIC ACID; ALCOHOL DERIVATIVE; AROMATIC COMPOUND; BUFFER; CARCINOGEN; DIAZONIUM COMPOUND; ESTER DERIVATIVE; IMIDAZOLINE DERIVATIVE; ISOPROPYL NITRITE; METHYL CHLORIDE; MUTAGENIC AGENT; N 2 HYDROXYETHYLPHENYLACETAMIDE; N NITROSOTOLAZOLINE; NITRITE; NITROSAMINE; NITROSO DERIVATIVE; OXIME; PHENYLACETIC ACID; PHENYLACETIC ACID DERIVATIVE; TOLAZOLINE; ANTIHYPERTENSIVE AGENT; ION;

EID: 41649100896     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700317g     Document Type: Article
Times cited : (8)

References (58)
  • 1
    • 34547290684 scopus 로고    scopus 로고
    • Wishart, D. (2006) DrugBank, http://redpoll.pharmacy.ualberta.ca/ drugbank/index.html.
    • (2006) DrugBank
    • Wishart, D.1
  • 3
    • 3843115467 scopus 로고    scopus 로고
    • Imidazoline binding sites and their ligands: An overview of the different chemical structures
    • Dardonville, C., and Rozas, I. (2004) Imidazoline binding sites and their ligands: An overview of the different chemical structures. Med. Res. Rev. 24, 639-661.
    • (2004) Med. Res. Rev , vol.24 , pp. 639-661
    • Dardonville, C.1    Rozas, I.2
  • 4
    • 0019513513 scopus 로고
    • Quantitative estimation of endogenous nitrosation in humans by monitoring N-nitrosoproline excreted in the urine
    • Ohshima, H., and Bartsch, H. (1981) Quantitative estimation of endogenous nitrosation in humans by monitoring N-nitrosoproline excreted in the urine. Cancer Res. 41, 3658-3662.
    • (1981) Cancer Res , vol.41 , pp. 3658-3662
    • Ohshima, H.1    Bartsch, H.2
  • 5
    • 0020625977 scopus 로고
    • Metabolic fate of an oral dose of nitrogen-15-labeled nitrate in humans: Effect of diet supplementation with ascorbic acid
    • Wagner, D. A., Schultz, D. S., Deen, W. M., Young, V. R., and Tannenbaum, S. R. (1983) Metabolic fate of an oral dose of nitrogen-15-labeled nitrate in humans: Effect of diet supplementation with ascorbic acid. Cancer Res. 43, 1921-1925.
    • (1983) Cancer Res , vol.43 , pp. 1921-1925
    • Wagner, D.A.1    Schultz, D.S.2    Deen, W.M.3    Young, V.R.4    Tannenbaum, S.R.5
  • 6
    • 0004864311 scopus 로고
    • In-vivo formation of N-nitroso compounds
    • Wagner, D. A., and Tannenbaum, S. R. (1985) In-vivo formation of N-nitroso compounds. Food Technol. 39, 89-90.
    • (1985) Food Technol , vol.39 , pp. 89-90
    • Wagner, D.A.1    Tannenbaum, S.R.2
  • 7
    • 0029071838 scopus 로고
    • Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophogeal, nasopharyngeal and bladder cancer and contribution to cancer known exposures to NOC
    • Mirvish, S. S. (1995) Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophogeal, nasopharyngeal and bladder cancer and contribution to cancer known exposures to NOC. Cancer Lett. 93, 17-45.
    • (1995) Cancer Lett , vol.93 , pp. 17-45
    • Mirvish, S.S.1
  • 9
    • 0014548933 scopus 로고
    • Bacterial reduction of nitrate in the human stomach as a cause of nitrosamine formation
    • Sander, J., and Seif, F. (1969) Bacterial reduction of nitrate in the human stomach as a cause of nitrosamine formation. Arzneim.-Forsch. 19, 1091-1093.
    • (1969) Arzneim.-Forsch , vol.19 , pp. 1091-1093
    • Sander, J.1    Seif, F.2
  • 10
    • 0016611279 scopus 로고
    • Formation of N-nitroso compounds: Chemistry, kinetics and in vivo occurrence
    • Mirvish, S. S. (1975) Formation of N-nitroso compounds: Chemistry, kinetics and in vivo occurrence. Toxicol. Appl. Pharmacol. 31, 325-351.
    • (1975) Toxicol. Appl. Pharmacol , vol.31 , pp. 325-351
    • Mirvish, S.S.1
  • 11
    • 0023685375 scopus 로고
    • Mammalian synthesis of nitrite, nitrate, nitric oxide, and N-nitrosating agents
    • Marletta, M. A. (1988) Mammalian synthesis of nitrite, nitrate, nitric oxide, and N-nitrosating agents. Chem. Res. Toxicol. 1, 249-257.
    • (1988) Chem. Res. Toxicol , vol.1 , pp. 249-257
    • Marletta, M.A.1
  • 12
    • 84936046668 scopus 로고
    • The role of N-nitroso compounds in gastric cancer etiology
    • Reed, P. I. (1985) The role of N-nitroso compounds in gastric cancer etiology. Int. Congr. Ser. - Excerpta Med. 685, 97-107.
    • (1985) Int. Congr. Ser. - Excerpta Med , vol.685 , pp. 97-107
    • Reed, P.I.1
  • 13
    • 0030778910 scopus 로고    scopus 로고
    • Approaches to cancer prevention based on an understanding of N-nitrosamine carcinogenesis
    • Hecht, S. S. (1997) Approaches to cancer prevention based on an understanding of N-nitrosamine carcinogenesis. Proc. Soc. Exp. Biol. Med. 216, 181-191.
    • (1997) Proc. Soc. Exp. Biol. Med , vol.216 , pp. 181-191
    • Hecht, S.S.1
  • 14
    • 0025004387 scopus 로고
    • Isolation of an enzyme catalyzing nitrosamine forrriation in Pseudomonas aeruginosa and Neisseria mucosae
    • Calmels, S., Dalla Venezia, N., and Bartsch, H. (1990) Isolation of an enzyme catalyzing nitrosamine forrriation in Pseudomonas aeruginosa and Neisseria mucosae. Biochem. Biophys. Res. Commun. 171, 655-660.
    • (1990) Biochem. Biophys. Res. Commun , vol.171 , pp. 655-660
    • Calmels, S.1    Dalla Venezia, N.2    Bartsch, H.3
  • 15
    • 0023705334 scopus 로고
    • Nitrosamine formation by denitrifying and non-denitrifying bacteria: Implication of nitrite reductase and nitrate reductase in nitrosation catalysis
    • Calmels, S., Ohshima, H., and Bartsch, H. (1988) Nitrosamine formation by denitrifying and non-denitrifying bacteria: Implication of nitrite reductase and nitrate reductase in nitrosation catalysis. J. Gen. Microbiol. 134, 221-226.
    • (1988) J. Gen. Microbiol , vol.134 , pp. 221-226
    • Calmels, S.1    Ohshima, H.2    Bartsch, H.3
  • 16
    • 0024845312 scopus 로고
    • Human exposure to endgenous N-nitroso compounds: Quantitative estimates in subjects at high risk for cancer of the oral cavity, esophpogus, stomach, and urinary bladder
    • Bartsch, H., Ohshima, H., Pignatelli, B., and Calmels, S. (1989) Human exposure to endgenous N-nitroso compounds: Quantitative estimates in subjects at high risk for cancer of the oral cavity, esophpogus, stomach, and urinary bladder. Cancer Surv. 8, 335-362.
    • (1989) Cancer Surv. 8 , pp. 335-362
    • Bartsch, H.1    Ohshima, H.2    Pignatelli, B.3    Calmels, S.4
  • 17
    • 0025935437 scopus 로고
    • Enzyme mechanisms in the metabolism of nitrosamines
    • Yang, C. S., Smith, T., Ishizaki, H., and Hong, J. Y. (1991) Enzyme mechanisms in the metabolism of nitrosamines. IARC Sci. Publ. 105, 265-274.
    • (1991) IARC Sci. Publ , vol.105 , pp. 265-274
    • Yang, C.S.1    Smith, T.2    Ishizaki, H.3    Hong, J.Y.4
  • 18
    • 0025167020 scopus 로고
    • Cytochrome P450IIE1: Roles in nitrosamine metabolism and mechanisms of regulation
    • Yang, C. S., Yoo, J. S. H., Ishizaki, H., and Hong, J. (1990) Cytochrome P450IIE1: Roles in nitrosamine metabolism and mechanisms of regulation. Drug Metab. Rev. 22, 147-159.
    • (1990) Drug Metab. Rev , vol.22 , pp. 147-159
    • Yang, C.S.1    Yoo, J.S.H.2    Ishizaki, H.3    Hong, J.4
  • 19
    • 13944282327 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)1-(3-pyridyl)-1- butanone, a tobacco carcinogen
    • Jalas, J. R., Hecht, S. S., and Murphy, S. E. (2005) Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitrosamino)1-(3-pyridyl)-1- butanone, a tobacco carcinogen. Chem. Res. Toxicol. 18, 95-110.
    • (2005) Chem. Res. Toxicol , vol.18 , pp. 95-110
    • Jalas, J.R.1    Hecht, S.S.2    Murphy, S.E.3
  • 20
    • 2142646454 scopus 로고    scopus 로고
    • Amidine nitrosation
    • Loeppky, R. N., and Yu, H. (2004) Amidine nitrosation. J. Org. Chem. 69, 3015-3024.
    • (2004) J. Org. Chem , vol.69 , pp. 3015-3024
    • Loeppky, R.N.1    Yu, H.2
  • 21
    • 0025375459 scopus 로고
    • Nitrosamines N-nitrosoamides, and diazonium ions from tri-N-substituted amidines
    • Loeppky, R. N., and Yu, L. (1990) Nitrosamines N-nitrosoamides, and diazonium ions from tri-N-substituted amidines. Tetrahedron Lett. 31, 3263-3266.
    • (1990) Tetrahedron Lett , vol.31 , pp. 3263-3266
    • Loeppky, R.N.1    Yu, L.2
  • 22
    • 0032473806 scopus 로고    scopus 로고
    • The nitrosation of imidazolines and oxazolines
    • Loeppky, R. N., and Cui, W. (1998) The nitrosation of imidazolines and oxazolines. Tetrahedron Lett. 39, 1845-1848.
    • (1998) Tetrahedron Lett , vol.39 , pp. 1845-1848
    • Loeppky, R.N.1    Cui, W.2
  • 23
    • 0005916292 scopus 로고
    • Reaction of N-(β- haloethyl)carboxamides with diethylamine
    • Cassebaum, H., and Uhlig, K. (1973) Reaction of N-(β- haloethyl)carboxamides with diethylamine. J. Prak. Chem. 315, 1057-1066.
    • (1973) J. Prak. Chem , vol.315 , pp. 1057-1066
    • Cassebaum, H.1    Uhlig, K.2
  • 24
    • 0010621014 scopus 로고
    • N-Alkyl-N-nitrosoamides. I. Methods of preparation
    • White, E. H. (1955) N-Alkyl-N-nitrosoamides. I. Methods of preparation. J. Am. Chem. Soc. 77, 6608.
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 6608
    • White, E.H.1
  • 25
    • 0000093325 scopus 로고
    • Enantioselective generation and diastereoselective reactions of chiral enolates derived from α-heterosubstituted carboxylic acids
    • Seebach, D., and Naef, R. (1981) Enantioselective generation and diastereoselective reactions of chiral enolates derived from α-heterosubstituted carboxylic acids. Helv. Chim. Acta 64, 2704-2708.
    • (1981) Helv. Chim. Acta , vol.64 , pp. 2704-2708
    • Seebach, D.1    Naef, R.2
  • 26
    • 0000926231 scopus 로고
    • Studies in terpenoids. Part LXXVIII. Synthesis of 3-hydroxy-2,6-dimethyl-1-phenyl- and 3,4-dihydroxy-2,6- dimethyl-1-phenylacetic acids, two potential synthons
    • Raju, B., and Krishna Rao, G. S. (1987) Studies in terpenoids. Part LXXVIII. Synthesis of 3-hydroxy-2,6-dimethyl-1-phenyl- and 3,4-dihydroxy-2,6- dimethyl-1-phenylacetic acids, two potential synthons. Indian J. Chem. 26B, 469-470.
    • (1987) Indian J. Chem , vol.26 B , pp. 469-470
    • Raju, B.1    Krishna Rao, G.S.2
  • 27
    • 37049085971 scopus 로고
    • N-Nitroso compounds. Part 1. Structure and decomposition of N-nitroso-2-arylimidazolines in aqueous acidic media
    • Iley, J., Norberto, F., and Rosa, E. (1989) N-Nitroso compounds. Part 1. Structure and decomposition of N-nitroso-2-arylimidazolines in aqueous acidic media. J. Chem. Soc., Perkin Trans. 2, 1471-1475.
    • (1989) J. Chem. Soc., Perkin Trans , vol.2 , pp. 1471-1475
    • Iley, J.1    Norberto, F.2    Rosa, E.3
  • 28
    • 48249088843 scopus 로고    scopus 로고
    • The Griess test, which is based on the nitrosative diazotization of an aromatic amine and subsequent diazo coupling to generate a dye, involves the liberation of the NO moiety from the N- or O-nitroso compound by means of either UV radiation or acid under conditions where it produces a nitrosating agent. It has been extensively used to visualize N-nitroso compounds on TLC plates. It is reliable, sensitive, and well-tested when used in this way.
    • The Griess test, which is based on the nitrosative diazotization of an aromatic amine and subsequent diazo coupling to generate a dye, involves the liberation of the NO moiety from the N- or O-nitroso compound by means of either UV radiation or acid under conditions where it produces a nitrosating agent. It has been extensively used to "visualize" N-nitroso compounds on TLC plates. It is reliable, sensitive, and well-tested when used in this way.
  • 29
    • 0000771277 scopus 로고
    • N-Alkyl-N-nitrosoamides. III. Mechanism of the nitrogen-elimination reaction
    • White, E. H. (1955) N-Alkyl-N-nitrosoamides. III. Mechanism of the nitrogen-elimination reaction. J. Am. Chem. Soc. 77, 6014-6022.
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 6014-6022
    • White, E.H.1
  • 30
    • 84913505204 scopus 로고
    • Rapid nitrosamine formation from tertiary nitrogen compounds: An overview
    • Eisenbrand, G, Bolzer, G, and Nicolai, H. V, Eds, Gustav Fischer Verlag, New York
    • Loeppky, R. N., Shevlin, G., and Yu, L. (1990) Rapid nitrosamine formation from tertiary nitrogen compounds: An overview. In Significance of N-Nitrosation of Drugs (Drug Dev. Eval.) (Eisenbrand, G., Bolzer, G., and Nicolai, H. V., Eds.) Gustav Fischer Verlag, New York.
    • (1990) Significance of N-Nitrosation of Drugs (Drug Dev. Eval.)
    • Loeppky, R.N.1    Shevlin, G.2    Yu, L.3
  • 31
    • 0030741105 scopus 로고    scopus 로고
    • Further ab initio studies on the reactivity of nitrosoketene
    • Ham, S., and Birney, D. M. (1997) Further ab initio studies on the reactivity of nitrosoketene. Tetrahedron Lett. 38, 5925-5928.
    • (1997) Tetrahedron Lett , vol.38 , pp. 5925-5928
    • Ham, S.1    Birney, D.M.2
  • 32
    • 41649094212 scopus 로고    scopus 로고
    • Loeppky, R. N., and Shi, J. (2008) N-Nitrosotolazoline: Decomposition studies of a typical N-nitrosoimidazoline. Chem. Res. Toxicol. 21, 0000.
    • Loeppky, R. N., and Shi, J. (2008) N-Nitrosotolazoline: Decomposition studies of a typical N-nitrosoimidazoline. Chem. Res. Toxicol. 21, 0000.
  • 33
    • 0000136410 scopus 로고    scopus 로고
    • Theoretical study of the mechanism of the addition of diazomethane to ethylene and formaldehyde. Comparison of conventional ab initio and density functional methods
    • Branchadell, V., Muray, E., Oliva, A., Ortuno, R. M., and Rodriguez-Garcia, C. (1998) Theoretical study of the mechanism of the addition of diazomethane to ethylene and formaldehyde. Comparison of conventional ab initio and density functional methods. J. Phys. Chem. A 102, 10106-10112.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 10106-10112
    • Branchadell, V.1    Muray, E.2    Oliva, A.3    Ortuno, R.M.4    Rodriguez-Garcia, C.5
  • 34
    • 0005471227 scopus 로고
    • Theoretical investigation of reaction pathways of 3-methyl-oxadiazolinium ion and 1,2,3-oxadiazoline: Correlation with experimental findings
    • Kroeger Koepke, M. B., Schmiedekamp, A. M., and Michejda, C. J. (1994) Theoretical investigation of reaction pathways of 3-methyl-oxadiazolinium ion and 1,2,3-oxadiazoline: Correlation with experimental findings. J. Org. Chem. 59, 3301-3306.
    • (1994) J. Org. Chem , vol.59 , pp. 3301-3306
    • Kroeger Koepke, M.B.1    Schmiedekamp, A.M.2    Michejda, C.J.3
  • 35
    • 0029133586 scopus 로고
    • Thiol oxidation by 1,2,3-oxadiazolinium ions, presumed carcinogens
    • Loeppky, R. N., and Srinivasan, A. (1995) Thiol oxidation by 1,2,3-oxadiazolinium ions, presumed carcinogens. Chem. Res. Toxicol. 8, 817-820.
    • (1995) Chem. Res. Toxicol , vol.8 , pp. 817-820
    • Loeppky, R.N.1    Srinivasan, A.2
  • 36
    • 0019256029 scopus 로고
    • Chemistry of nitrosoureas. Intermediacy of 4,5-dihydro-1,2,3-oxadiazole in 1,3-bis(2-chloroethyl)-1-nitrosourea decomposition
    • Brundrett, R. B. (1980) Chemistry of nitrosoureas. Intermediacy of 4,5-dihydro-1,2,3-oxadiazole in 1,3-bis(2-chloroethyl)-1-nitrosourea decomposition. J. Med. Chem. 23, 1245-1247.
    • (1980) J. Med. Chem , vol.23 , pp. 1245-1247
    • Brundrett, R.B.1
  • 37
    • 0019505209 scopus 로고
    • Mechanism of action of (2-haloethyl)nitrosoureas on DNA. Isolation and reactions of postulated 2-(alkylimino)-3-nitrosooxazolidine intermediates in the decomposition of 1,3-bis(2-chloroethyl)-, 1-(2-chloroethyl)-3-cyclohexyl-, and 1-(2-chloroethyl)-3-(4′-trans-methylcyclohexyl)-1-nitrosourea
    • Lown, J. W., and Chauhan, S. M. S. (1981) Mechanism of action of (2-haloethyl)nitrosoureas on DNA. Isolation and reactions of postulated 2-(alkylimino)-3-nitrosooxazolidine intermediates in the decomposition of 1,3-bis(2-chloroethyl)-, 1-(2-chloroethyl)-3-cyclohexyl-, and 1-(2-chloroethyl)-3-(4′-trans-methylcyclohexyl)-1-nitrosourea. J. Med. Chem. 24, 270-279.
    • (1981) J. Med. Chem , vol.24 , pp. 270-279
    • Lown, J.W.1    Chauhan, S.M.S.2
  • 38
    • 0001373384 scopus 로고
    • Kinetics of N-nitrosation in oxygenated nitric oxide solutions at physiological ph: Role of nitrous anhydride and effects of phosphate and chloride
    • Lewis, R. S., Tannenbaum, S. R., and Deen, W. M. (1995) Kinetics of N-nitrosation in oxygenated nitric oxide solutions at physiological ph: role of nitrous anhydride and effects of phosphate and chloride. J. Am. Chem. Soc. 117, 3933-3939.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 3933-3939
    • Lewis, R.S.1    Tannenbaum, S.R.2    Deen, W.M.3
  • 39
    • 24944449498 scopus 로고    scopus 로고
    • Carbon-bound diazeniumdiolates from the reaction of nitric oxide with amidines
    • Hrabie, J. A., Citro, M. L., Chmurny, G. N., and Keefer, L. K. (2005) Carbon-bound diazeniumdiolates from the reaction of nitric oxide with amidines. J. Org. Chem. 70, 7647-7653.
    • (2005) J. Org. Chem , vol.70 , pp. 7647-7653
    • Hrabie, J.A.1    Citro, M.L.2    Chmurny, G.N.3    Keefer, L.K.4
  • 40
    • 48249141034 scopus 로고    scopus 로고
    • Eisenbrand, G., Bozler, G., and Nicolai, H. v. (1990) The Significance of N-Nitrosation of Drugs, 16, Drug Development and Evaluation, Gustav Fischer Verlag, Stuttgart.
    • Eisenbrand, G., Bozler, G., and Nicolai, H. v. (1990) The Significance of N-Nitrosation of Drugs, Vol. 16, Drug Development and Evaluation, Gustav Fischer Verlag, Stuttgart.
  • 41
    • 0343351898 scopus 로고
    • Endogenous nitrosation - Findings and problems
    • Eisenbrand, G, Bozler, G, and Nicolai, H. v, Eds, pp, Gustav Fischer Verlag, Stuttgart
    • Eisenbrand, G. (1990) Endogenous nitrosation - Findings and problems. In The Significance of N-Nitrosation of Drugs (Eisenbrand, G., Bozler, G., and Nicolai, H. v., Eds.) pp 47-68, Gustav Fischer Verlag, Stuttgart.
    • (1990) The Significance of N-Nitrosation of Drugs , pp. 47-68
    • Eisenbrand, G.1
  • 42
  • 43
    • 0004206788 scopus 로고
    • Cambridge University Press, Cambridge, United Kingdom
    • Williams, D. L. H. (1988) Nitrosation, Cambridge University Press, Cambridge, United Kingdom.
    • (1988) Nitrosation
    • Williams, D.L.H.1
  • 44
    • 37049070667 scopus 로고
    • Nitration and oxidation of 4-methoxyphenol by nitrous acid in aqueous acid solution
    • Beake, B. D., Constantine, J., and Moodie, R. B. (1994) Nitration and oxidation of 4-methoxyphenol by nitrous acid in aqueous acid solution. J. Chem. Soc., Perkin Trans. 2 335-340.
    • (1994) J. Chem. Soc., Perkin Trans , vol.2 , pp. 335-340
    • Beake, B.D.1    Constantine, J.2    Moodie, R.B.3
  • 45
    • 23444436373 scopus 로고    scopus 로고
    • Apples increase nitric oxide production by human saliva at the acidic pH of the stomach: A new biological function for polyphenols with a catechol group?
    • Peri, L., Pietraforte, D., Scorza, G., Napolitano, A., Fogliano, V., and Minetti, M. (2005) Apples increase nitric oxide production by human saliva at the acidic pH of the stomach: A new biological function for polyphenols with a catechol group? Free Radical Biol. Med. 39, 668-681.
    • (2005) Free Radical Biol. Med , vol.39 , pp. 668-681
    • Peri, L.1    Pietraforte, D.2    Scorza, G.3    Napolitano, A.4    Fogliano, V.5    Minetti, M.6
  • 46
    • 41649094413 scopus 로고    scopus 로고
    • Nucleoside and DNA adducts from N-nitrosotolazoline
    • Loeppky, R. N., and Shi, J. (2008) Nucleoside and DNA adducts from N-nitrosotolazoline. Chem. Res. Toxicol. 21, 319-329.
    • (2008) Chem. Res. Toxicol , vol.21 , pp. 319-329
    • Loeppky, R.N.1    Shi, J.2
  • 47
    • 0001847614 scopus 로고
    • Blocking nitrosamine formation: Understanding the chemistry of nitrosamine formation
    • Loeppky, R. N, and Michejda, C. J, Eds, pp, American Chemical Society, Washington, DC
    • Loeppky, R. N., Bao, Y. T., Bae, J. Y., Yu, L., and Shevlin, G. (1994) Blocking nitrosamine formation: Understanding the chemistry of nitrosamine formation. In Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry (Loeppky, R. N., and Michejda, C. J., Eds.) pp 52-65, American Chemical Society, Washington, DC.
    • (1994) Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry , pp. 52-65
    • Loeppky, R.N.1    Bao, Y.T.2    Bae, J.Y.3    Yu, L.4    Shevlin, G.5
  • 48
    • 0021804272 scopus 로고
    • Pharmacokinetics of nitrate in humans: Role of gastrointestinal absorption and metabolism
    • Schultz, D. S., Deen, W. M., Karel, S. F., Wagner, D. A., and Tannenbaum, S. R. (1985) Pharmacokinetics of nitrate in humans: role of gastrointestinal absorption and metabolism. Carcinogenesis 6, 847-852.
    • (1985) Carcinogenesis , vol.6 , pp. 847-852
    • Schultz, D.S.1    Deen, W.M.2    Karel, S.F.3    Wagner, D.A.4    Tannenbaum, S.R.5
  • 50
    • 0023851276 scopus 로고
    • Use of ascorbic acid to inhibit nitrosation: Kinetic and mass transfer considerations for an in vitro system
    • Licht, W. R., Tannenbaum, S. R., and Deen, W. M. (1988) Use of ascorbic acid to inhibit nitrosation: kinetic and mass transfer considerations for an in vitro system. Carcinogenesis 9, 365-372.
    • (1988) Carcinogenesis , vol.9 , pp. 365-372
    • Licht, W.R.1    Tannenbaum, S.R.2    Deen, W.M.3
  • 51
    • 0023856171 scopus 로고
    • Effects of ascorbic acid and thiocyanate on nitrosation of proline in the dog stomach
    • Licht, W. R., Fox, J. G., and Deen, W. M. (1988) Effects of ascorbic acid and thiocyanate on nitrosation of proline in the dog stomach. Carcinogenesis 9, 373-377.
    • (1988) Carcinogenesis , vol.9 , pp. 373-377
    • Licht, W.R.1    Fox, J.G.2    Deen, W.M.3
  • 54
    • 84959839939 scopus 로고
    • Nitrite in human saliva. Its possible relation to nitrosamine formation
    • Tannenbaum, S. R., Sinskey, A. J., Weisman, M., and Bishop, W. (1974) Nitrite in human saliva. Its possible relation to nitrosamine formation. J. Natl. Cancer Inst. 53, 79-84.
    • (1974) J. Natl. Cancer Inst , vol.53 , pp. 79-84
    • Tannenbaum, S.R.1    Sinskey, A.J.2    Weisman, M.3    Bishop, W.4
  • 55
    • 0017046438 scopus 로고
    • Influence of dietary nitrate on nitrite content in human saliva: Possible relevance to in vivo formation of N-nitroso compounds
    • Spiegelhalder, B., Eisenbrand, G., and Preussmann, R. (1976) Influence of dietary nitrate on nitrite content in human saliva: Possible relevance to in vivo formation of N-nitroso compounds. Food Cosmet. Toxicol. 14, 545-548.
    • (1976) Food Cosmet. Toxicol , vol.14 , pp. 545-548
    • Spiegelhalder, B.1    Eisenbrand, G.2    Preussmann, R.3
  • 57
    • 0018889162 scopus 로고
    • Are nitrite and N-nitroso compounds in gastric juice risk factors for carcinoma in the operated stomach?
    • Schlag, P., Ulrich, H., Merkle, P., Boeckler, R., Peter, M., and Herfarth, C. (1980) Are nitrite and N-nitroso compounds in gastric juice risk factors for carcinoma in the operated stomach? Lancet 1, 727-729.
    • (1980) Lancet , vol.1 , pp. 727-729
    • Schlag, P.1    Ulrich, H.2    Merkle, P.3    Boeckler, R.4    Peter, M.5    Herfarth, C.6
  • 58
    • 0021252415 scopus 로고
    • Susceptibilities of drugs to nitrosation under standardized chemical conditions
    • Gillatt, P. N., Hart, R. J., Walters, C. L., and Reed, P. I. (1984) Susceptibilities of drugs to nitrosation under standardized chemical conditions. Food Chem. Toxicol. 22, 269-274.
    • (1984) Food Chem. Toxicol , vol.22 , pp. 269-274
    • Gillatt, P.N.1    Hart, R.J.2    Walters, C.L.3    Reed, P.I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.