Abstract
Behavior of nitrosoaromatic compounds in biological systems is of high scientific interest, because these chemical species, as relatively unstable, could easily react with different biomolecules attacking the regular biochemical processes. As xenobiotic agents, arylnitroso derivatives can display mutagenic [1, 2], carcinogenic [3, 4], as well as cytotoxic [5, 6] effects. Since their oxidation state lies in the middle between the stable oxidized form (nitro derivative) and reduced form (amino or hydroxylamino), nitroso compounds may have marked influence on the oxidations and reductions in living cells. As we know from the photochemistry and electrochemistry represented in previous chapters, nitrosoaromatic molecules readily form radicals and radical ions. Such property is especially important for their reactivity in complex biochemical reaction systems. Ability to behave as ligands with more than ten coordination modes in complexes with broad selection of metal atoms makes these molecules very active in reactions with biogenic metals. Biomolecules, which have active centers in which metal ions are included, could be target for the nitrosoaryl ligands. Many examples of interactions of the heme-constituting molecules with nitrosobenzene were discussed in the previous chapter.
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References
Miller JA (1970) Cancer Res 30:559–576
Saito K, Yamazoe Y, Kamataki T, Kato R (1983) Carcinogenesis 4:1547–1550
Mulder GJ, Kadlubar FF, Mays JB, Hinson JA (1984) Mol Pharmacol 26:342–347
Goodall CM, Moore CM, Stephens OB (1986) Xenobiotica 16:587–593
Eyer P, Kampfmeyer H, Maister H, Rosch-Oehme E (1980) Xenobiotica 10:499–516
Eyer P, Kampfmeyer H (1982) Chem Biol Interact 42:209–223
Fujii H, Zhao B, Koscielniak J, Berliner LJ (1994) Magn Res Med 31:77–80
Iwahashi H, Parker CE, Mason RP, Tomer KB (1991) Biochem J 276:447–453
Sridhar R, Floyd RA (1982) Can J Chem 60:1574–1576
Ascherl M, Eyer P, Kampffmeyer H (1985) Biochem Pharmacol 34:3755–3763
Eyer P, Lierheimer E (1980) Xenobiotica 10:517–526
Diepold P, Eyer P, Kampffmeyer H, Reinhardt K (1982) In: Snyder R, Parke VD, Kocsis JJ, Jollow DJ, Gibson CG, Witmer CM (eds) Biological reactive intermediates-II. Chemical mechanism and biological effects. Plenum Press, New York, pp 1173–1181
Eyer P, Schneller M (1983) Biochem Pharmacol 32:1029–1036
Dölle B, Töpner W, Neumann HG (1980) Xenobiotica 10:527–536
Mulder GJ, Unruh LE, Evans FE, Ketterer B, Kadlubar F (1982) Chem-Biol Interact 39:111–127
Klehr H, Eyer P, Schäfer W (1985) Biol Chem Hoppe-Seyler 366:755–760
Neumann HC (1984) Arch Toxicol 57:1–5
Lewalter J, Korallus U (1985) Int Arch Occup Environ Health 56:179–196
Hinson J, Mays JB (1986) J Pharmacol Exp Ther 238:106–112
Eyer P, Ascherl M (1987) Biol Chem Hoppe-Seyler 368:285–294
Eyer P (1979) Chem-Biol Interact 24:227
Saito K, Kato R (1984) Biochem Biophys Res Commun 124:1
Zuman P, Shah B (1994) Chem Rev 94:1621–1641
Montanari S, O'Carroll F, Paradisi C, Scorrano G (1995) Rapid Commun Mass Spectrom 9:1081–1082
Galleman D, Eyer P (1994) Environ Health Perspect 102:137–142
Kazanis S, McClelland RA (1992) J Am Chem Soc 114:3052–3059
Hirota K, Itano HA, Vedvick TS (1978) Biochem J 15:693–697
Halliwel B, Gutteridge JM (1990) Methods Enzymol 186:1–85
Di Girolamo F, Campanella L, Samperi R, Bachi A (2009) Ecotoxicol Environ Safety 72:1601–1608
Liu L, Wagner CR, Hanna PE (2008) Chem Res Toxicol 21:2005–2016
Khan MF, Wu X, Ansari GAS (2000) J Toxicol Environ Health A 60:263–273
Wulferink M, González J, Goebel C, Gleichmann E (2001) Chem Res Toxicol 14:389–397
Barkhan P, Howard AN (1958) Biochem J 70:163–168
Takahashi N, Fischer V, Schreiber J, Mason RP (1988) Free Radic Res Commun 4:351–358
Fujii H, Koscielniak J, Kakinuma K, Berliner LJ (1994) Free Radic Res 21:235–243
Ohkuma Y, Kawanishi S (1999) Biochem Biophys Res Commun 257:555–560
Hiramoto K, Ojima N, Kikugawa K (1997) Free Radic Res 27:409–418
Kim D, Kadlubar FF, Teitel CH, Guengerich FP (2004) Chem Res Toxicol 17:529–536
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Vančik, H. (2013). Biological Systems. In: Aromatic C-nitroso Compounds. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-6337-1_5
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DOI: https://doi.org/10.1007/978-94-007-6337-1_5
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