The kinetic study of dediazoniation in an aqueous medium of benzenediazonium tetraflourborate
Keywords:
Aryl cation, kinetics, Genotoxic compounds, Dediazoniation, HPLC, Benzenediazonium ion, Dediazoniation mechanismAbstract
The kinetic analyses carried out at different temperatures (20ºC - 40ºC) indicate that the dediazoniation process of thebenzenediazonium ion (BZ) is of the order of one, with BZ at A = 2,3.1015 s-1 and Ea = 112,5 kJ.mol-1 for the Arrheniusequation, and ΔH‡ = 110,0 kJ.mol-1 and ΔS‡ = 40,7 J.K-1.mol-1 for the Eyring equation. The chromatographic resultsreveal that BZ decomposes through a heterolytic process mediated by the aryl ion. The presence of Cu(I) or Cu(II) saltsand ascorbic acid produce a change in the reaction mechanism. The intermediate compounds produced in these conditionsare stable species that may be transported in the bloodstream. The model studied suggests a possible explanation for thelocalisation of tumours produced by the administration of BZ in rats.Downloads
References
Friederich U, Fischer B., Lüthy J, Hann D, Schlatter C, Würgler FE. The mutagenic activity of agaritine- a constituent
of the cultivated mushroom Agaricus bisporus - and its derivatives detected with the Salmonella/mammalian microsome
assay (Ames Test). Z Lebensm Unters Forsch 1986; 183: 85-89.
Ames BN, Magaw R, Gold LS. Ranking possible carcinogenic hazards Science 1987; 236: 271-280.
Ohta T, Oribe H, Kameyama T, Goto Y, Takitani S. Formation of a diazoquinone-type mutagen from acetaminophen
treated with nitrite under acidic conditions Mut Res 1988; 209: 95-98.
Kikugawa K, Kato T, Takeda Y. Formation of a highly mutagenic diazo compound from the bamethan-nitrite reaction
Mut Res 1987; 172:35-43.
Kikugawa K, Kato T. Formation of a mutagenic diazoquinone by interaction of phenol with nitrite Food Chem Toxicol
; 26, 209-214.
Kikugawa K, Kato T, Takeda Y. Formation of a direct mutagen, diazo-N-nitrosoetilefrin, by interaction of etilefrin with
nitrite Chem. Pharm. Bull 1989; 37:1600-1603.
Lawson T, Gannett PM, Yau WM, Dalal NS, Toth B. Different patterns of mutagenicity of arenediazonium ions in V79
cells and Salmonella typhimurium TA102: Evidence for different mechanisms of actions. J Agric Food Chem 1995;
: 2627-2635.
Furihata C, Yamakoshi A, Matsushima T, Kato T, Kikugawa K. Possible tumour-initiating and –promoting activities of
-diazo-N-nitrosobamethan in rat stomach mucosa Mutagenesis 1988; 3: 299-301.
Ohshima H, Furihata C, Matsushima T, Bartsch H. Formation of direct-acting genotoxic substances in nitrosated smoked
fish and meat products: identification of simple phenolic precursors and phenyldiazonium ions as reactive products
Food Chem Toxicol 1989; 27: 193-203.
Stiborova M, Hansikova H, Schmeiser HH, Frei E. An investigation of the metabolism of N-nitrosodimethylamine and
N-nitrosomethylaniline by horseradish peroxidase in vitro Gen Physiol Biophys 1997; 16: 285-297.
Toth B, Patil K, Jae H-S. Carcinogenesis of 4-(hydroxymethyl)benzene diazonium ion (Tetrafluoroborate) of Agaricus bisporus Cancer Res 1981; 41: 2444-2449.
Toth B, Nagel D, Ross A, Gastric tumorigenesis by a single dose of 4-(hydroxymethyl)benzenediazonium ion of
Agaricus bisporus Br J Cancer 1982; 46: 417-422.
Toth B. Cancer induction by the sulfate form of 4-(hydroxymethyl) benzenediazonium ion of Agaricus bisporus In Vivo
; 1: 39-42.
Toth B, Taylor J, Mattson B, Gannett P. Tumor induction by 4-(methyl)benzenediazonium sulfate in mice. In Vivo
; 3: 17-22.
Toth B, Patil K, Taylor J, Stessman C, Gannett P. Cancer induction in mice by 4-hydroxybenzenediazonium sulfate of
the Agaricus xanthodermus mushroom. In vivo 1989; 3: 301-306.
Toth B, Gannett P, Rogan E, Williamson J. Bacterial mutagenicity of extracts of the baked and raw Agaricus bisporus
mushroom In Vivo 1992; 6: 487-490.
Toth B, Gannett P. Agaricus bisporus: An assessment of its carcinogenic potency. Mycopathologia. 1993; 124:73-77.
Toth B, Patil K, Erickson J, Gannett P. Carcinogenesis by benzenediazonium sulfate in mice In Vivo 1998; 12: 379-382.
Toth B, Patil K, Erickson J, Gannett P. Cancer induction using different administrations of benzenediazonium sulfate
in mice In Vivo 1999; 13: 125-128.
Toth B. A review of the natural occurrence, synthetic production and use of carcinogenic hydrazines and related
chemicals In Vivo 2000; 14: 299-319.
Chin A, Hung MH, Stock LM. Reactions of benzenediazonium ions with adenine and its derivatives J Org Chem 1981;
: 2203-2207.
Hung M-H, Stock LM. Reactions of benzenediazonium ions with guanine and its derivatives. J Org Chem 1982; 47:
-453.
Koepke SR, Kroeger-Koepke MB. Michejda CJ. Evidence for an unstable DNA adduct from N-nitroso-N-methylaniline
Chem Res Toxicol 1990; 3: 17-20.
Lawson T, Gannett PM, Yau WM, Dalal NS, Toth B. Different patterns of mutagenicity of arenediazonium ions in V79
cells and Salmonella typhimurium TA102: Evidence for different mechanisms of actions. J Agric Food Chem 1995;
: 2627-2635.
Gannett PM, Powell JH, Rao R, Shi X, Lawson T, Kolar C, et al. C8-Arylguanine and C8-aryladenine formation in
calf thymus DNA from arenediazonium ions. Chem Res. Toxicol 1999; 12: 297-304.
Griffiths J, Murphy JA. Cleavage of DNA resulting from exposure to phenyl radicals. J Chem Soc Chem Commun
; 24-26.
Kato T, Kojima K, Hiramoto K, Kikugawa K. DNA strand breakage by hydroxyphenyl radicals generated from
mutagenic diazoquinone compounds Mutation Res 1992; 268: 105-114.
Hazlewood C, Davies MJ, Gilbert BC, Packer JE. Electron paramagnetic resonance studies of the reaction of aryl
radicals with nucleic acids and their components J Chem Soc Perkin Trans 2 1995; 2167-2174.
Hiramoto K, Kaku M, Kato T, Kikugawa K. DNA strand breaking by the carbon-centered radical generated from 4-
(hydroxymethyl)benzene diazonium salt, a carcinogen in mushroom Agaricus bisporus. Chem Biol Interact 1995;
: 21-36.
Gannett PM, Ye J, Ding M, Powell J, Zhang Y, Darian E, et al. Activation of AP-1 through the MAP kinase pathway:
a potential mechanism of the carcinogenic effect of arenediazonium ions. Chem Res Toxicol 2000; 10: 1020-1027.
Berh JP. Photohydrolysis of DNA by polyaminobenzenediazonium salts. J Chem Soc ,Chem Commun 1989; 101-103.
Zollinger H. Diazo Chemistry Vol.I: Aromatic and Heteroaromatic Compounds; Wiley & Sons: New York, 1994.
Bravo Diaz C, González Romero E. Reactivity of arenediazonium ions in micellar and macromolecular systems Current
Topics in Colloid & Interface Science 2001; 58-83 y referencias citadas allí.
Canning PSJ, McCrudden K, Maskill H, Sexton B. Mechanisms of the thermal solvolytic decomposition of arenediazonium
ions J Chem Soc Perkin Trans 2 1999; 2735-2740.
Maskill H, McCrudden K. Croat Chem Acta 1992; 65: 567. Citado en la referencia 34.
Crossley ML, Kienhle RH, Benbrook CH. J Am Chem Soc 1940; 62: 1400. Citado en ref. 38.
Maskill H. The physical basis of Organic Chemistry. Oxford University Press. 1995. Oxford UK.
Pazo Llorente R, Sarabia Rodríguez, MJ, Bravo Diaz C, González Romero E. Hydroxy- and chloro-dediazoniation of
- and 3-methylbenzenediazonium tetrafluorborate in aqueous solution Int J Chem Kinet 1999; 31: 73-82.
Powell JH, Gannett PM. Mechanisms of carcinocenicity of aryl hydrazines, aryl hidrazides and arenediazonium ions
J Environ Pathol Toxicol Oncol. 2002; 21: 1-31.
Galli C. Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical Chem Rev 1988;
: 765-792.
Jiménez A, Planells E, Aranda P, Sánchez-Viñas M, Llopis J. Changes in bioavailability and tissue distribution of
copper caused by magenesium deficiency in rats J Agric Food Chem 1997; 45: 4023-4027.
Linder MC, Wooten P, Cerveza S, Cotton R, Shulze R, Lomeli N. Copper transport Am J Clin Nutr 1998; 67: 965S-
S.
Inagaki K, Mikuriya N, Morita H, Haraguchi Y, Nakahara M, Hattori M, Kinosita T, Sayto H. Speciation of proteinbinding
zinc and copper in human blood serum by chelating resin pre-treatment and inductively coupled plasma
mass spectrometry. Analyst 2000; 125: 197-203.
Gutteridge JMC, Halliwell B. Antioxidants in nutrition, health, and disease. Oxford University Press. 1994 Oxford UK
pp 36-37.
Majors AK, Sengupta S, Willard B, Kinter MT, Pyeritz RE, Jacobsen DW. Homocysteine binds to human plasma
fibronectin and inhibits its interaction with fibrin Arterioescler Thromb Vasc Biol 2002; 22: 1354-1359.
Sengupta S, Chen H, Togawa T, DiBello PM, Majors AK, Budy B, Katterer ME, Jacobsen DW. Albumin thiolate anion
is an intermediate in the formation of albumin-S-S-homocysteine J Biol Chem 2001; 276: 30111-30117.
Bourdon E, Loreau N, Blache D. Glucose and free radicals impair the antioxidant properties of serum albumin FASEB
J 1999; 13: 233-244.
Eaton JW, Qian M. Interactions of copper with glycated proteins: possible involvement in the etiology of diabetic
neuropathy Mol Cell Biochem 2002; 234-235: 135-142.
Gryzunov YA, Arroyo A, Vigne JL, Zhao Q, Tyurin VA, Hubel CA, Gandley RE, Vladimorov YA, Taylor RN, Kagan
VE. Binding of fatty acids facilitates oxidation of cysteine-34 and converts copper-albunmin complexes from
antioxidants to prooxidants Arch Biochem Biophys 2003; 413: 53-66.
Llopis J. (comunicación personal).
Hanson P., Jones JR, Gilbert BC, Timms A.W. Sansmeyer reactions. Part 1. A comparative study of the transfer of
halide and water ligands from complexes of Cu(II) to aryl radicals J Chem Soc Perkin Trans 2 1991; 1009-1017.
Malik S, Parmar VS, Kohli E, Tyagi YK, Rohil V, Dwarakanath BS, Adhikari JS, Bose M, Jain SC, Olsen CE
Chemoprevention of benzene-induced bone marrow and pulmonary genotoxicity. J Teratogarcinog Mutagen 2001;
: 181-187.
Mullin AH, Nataraj D, Ren JJ, Mullin DA. Inhaled benzene increases the frequency and length of lacI deletion
mutations in lung tissues of mice J Carcinogenesis 1998; 19: 1723-1733.
Huff JE, Haseman JK, DeMarini DM, Eustis S, Maronpot RR, Peters AC Persing RL, Chrisp CE, Jacobs AC. Multiplesite
carcinogenicity of benzene in Fischer 344 rats and B6C3F1 mice.J Environ Health Perspect 1989; 82: 125-163.
Downloads
Published
How to Cite
Issue
Section
License
The articles, which are published in this journal, are subject to the following terms in relation to the rights of patrimonial or exploitation:
- The authors will keep their copyright and guarantee to the journal the right of first publication of their work, which will be distributed with a Creative Commons BY-NC-SA 4.0 license that allows third parties to reuse the work whenever its author, quote the original source and do not make commercial use of it.
b. The authors may adopt other non-exclusive licensing agreements for the distribution of the published version of the work (e.g., deposit it in an institutional telematic file or publish it in a monographic volume) provided that the original source of its publication is indicated.
c. Authors are allowed and advised to disseminate their work through the Internet (e.g. in institutional repositories or on their website) before and during the submission process, which can produce interesting exchanges and increase citations of the published work. (See The effect of open access).