Alkylating Potential of Oxetanes
Chem. Res. Toxicol., Vol. 23, No. 7, 2010 1281
(
12) Pritchard, J. G., and Long, F. A. (1958) The kinetics of the hydrolysis
of trimethylene oxide in water, deuterium oxide and 40% aqueous
dioxane. J. Am. Chem. Soc. 80, 4162–4165.
13) Searles, S., and Gregory, V. P. (1954) The reaction of trimethylene
oxide with amines. J. Am. Chem. Soc. 76, 2789–2790.
(33) Manso, J. A., et al. (2009) Alkylating potential of N-phenyl-N-
nitrosourea. J. Phys. Org. Chem. 22, 386–389.
(34) P e´ rez-Prior, M. T., Manso, J. A., Garc ´ı a-Santos, M. D., Calle, E., and
Casado, J. (2005) Alkylating potential of potassium sorbate. J. Agric.
Food Chem. 53, 10244–10247.
(
(
14) Yan, D., Hou, J., Zhu, X., Kosman, J., and Wu, H. (2000) A new
approach to control crystallinity of resulting polymers: Self-condensing
ring opening polymerization. Macromol. Rapid Commun. 21, 557–
(35) P e´ rez-Prior, M. T., Manso, J. A., Garc ´ı a-Santos, M. D., Calle, E., and
Casado, J. (2008) Sorbic acid as an alkylating agent. J. Solution Chem.
37, 459–466.
(36) C e´ spedes, I. F., Manso, J. A., P e´ rez-Prior, M. T., G o´ mez-Bombarelli,
R., Gonz a´ lez-P e´ rez, M., Calle, E., and Casado, J. (2010) Reactivity
of acrylamide as an alkylating agent: A kinetic approach. J. Phys.
Org. Chem. 23, 171–175.
5
61.
(
(
15) Moussa, K., and Decker, C. (1993) Light-induced polymerization of
new highly reactive acrylic-monomers. J. Polym. Sci., Part A: Polym.
Chem. 31, 2197–2203.
16) Bayerl, M., Braig, T., Nuyken, O., Muller, D., Gross, M., and
Meerholz, K. (1999) Crosslinkable hole-transport materials for prepa-
ration of multilayer organic light emitting devices by spin-coating.
Macromol. Rapid Commun. 20, 224–228.
(
37) Fern a´ ndez-Rodr ´ı guez, E., Manso, J. A., P e´ rez-Prior, M. T., Garc ´ı a-
Santos, M. D. P., Calle, E., and Casado, J. (2007) The unusual ability
of R-angelicalactone to form adducts: A kinetic approach. Int. J. Chem.
Kinet. 39, 591–594.
(38) G o´ mez-Bombarelli, R., Gonz a´ lez-P e´ rez, M., P e´ rez-Prior, M. T., Manso,
J. A., Calle, E., and Casado, J. (2008) Chemical reactivity and
biological activity of diketene. Chem. Res. Toxicol. 21, 1964–1969.
(39) Manso, J. A., P e´ rez-Prior, M. T., Garc ´ı a-Santos, M. P., Calle, E., and
Casado, J. (2008) Steric effect in alkylation reactions by N-alkyl-N-
nitrosoureas: a kinetic approach. J. Phys. Org. Chem. 21, 932–938.
(40) P e´ rez-Prior, M. T., G o´ mez-Bombarelli, R., Gonz a´ lez-P e´ rez, M., Manso,
J. A., Garc ´ı a-Santos, M. P., Calle, E., and Casado, J. (2009) Sorbate-
nitrite interactions: acetonitrile oxide as an alkylating agent. Chem.
Res. Toxicol. 22, 1320–1324.
(
17) Yang, X., Muller, D., Neher, D., and Meerholz, K. (2006) Highly
efficient polymeric electrophosphorescent diodes. AdV. Mater. 18, 948–
9
54.
(
18) Muller, C., et al. (2003) Multi-colour organic light-emitting displays
by solution processing. Nature 421, 829–833.
(
19) Rademann, J., Grotli, M., Meldal, M., and Bock, K. (1999) SPOCC:
A resin for solid-phase organic chemistry and enzymatic reactions on
solid phase. J. Am. Chem. Soc. 121, 5459–5466.
(
20) Correa, A., Gray, R. H., Cohen, R., Rothman, N., Shah, F., Seacat,
H., and Corn, M. (1996) Ethylene glycol ethers and risks of
spontaneous abortion and subfertility. Am. J. Epidemiol. 143, 707–
(
41) P e´ rez-Prior, M. T., G o´ mez-Bombarelli, R., Gonz a´ lez-P e´ rez, M., Manso,
J. A., Garc ´ı a-Santos, M. P., Calle, E., and Casado, J. (2010) Reactivity
of the mutagen 1,4-dinitro-2-methylpyrrole as an alkylating agent. J.
Org. Chem. 75, 1444–1449.
7
17.
(
21) Corthals, S. M., Kamendulis, L. M., and Klaunig, J. E. (2006)
Mechanisms of 2-butoxyethanol-induced hemangiosarcomas. Toxicol.
Sci. 92, 378–386.
(
42) Mortelmans, K., and Zeiger, E. (2000) The Ames Salmonella/
microsome mutagenicity assay. Mutat. Res. 455, 29–60.
(
22) Foster, P. M. D., Creasy, D. M., Foster, J. R., Thomas, L. V., Cook,
M. W., and Gangolli, S. D. (1983) Testicular toxicity of ethylene-
glycol monomethyl and monoethyl ethers in the rat. Toxicol. Appl.
Pharmacol. 69, 385–399.
(43) Kranendonk, M., Mesquita, P., Laires, A., Vermeulen, N. P. E., and
Rueff, J. (1998) Expression of human cytochrome P450 1A2 in
Escherichia coli: a system for biotransformation and genotoxicity
studies of chemical carcinogens. Mutagenesis 3, 263–269.
(
(
(
23) Johnson, W., and Cosmetic Ingredient Review, E. (2002) Final report
on the safety assessment of ethoxyethanol and ethoxyethanol acetate.
Int. J. Toxicol. 21, 9–62.
24) IARC (2006) Formaldehyde, 2-Butoxyethanol and 1-tert-Butoxypro-
pan-2-ol, In IARC Monographs on the EValuation of Carcinogenic
Risks to Humans, IARC, Vol. 88, Lyon, France.
(44) Duarte, M. P., Palma, B. B., Laires, A., Oliveira, J. S., Rueff, J., and
Kranendonk, M. (2005) Escherichia coli BTC, a human cytochrome
P450 competent tester strain with a high sensitivity towards alkylat-
ingagents: involvement of alkyltransferases in the repair of DNA
damage induced by aromatic amines. Mutagenesis 20, 199–208.
(45) Duarte, M. P., et al. (2007) The stimulatory role of human cytochrome
b(5) in the bioactivation activities of human CYP1A2, 2A6 and 2E1:
a new cell expression system to study cytochrome P450-mediated
biotransformation (a corrigendum report on Duarte et al. (2005)
Mutagenesis 20, 93-100). Mutagenesis 22, 75–81.
25) Chen, C. S., Hseu, Y. C., Liang, S. H., Kuo, J. Y., and Chen, S. C.
(
2008) Assessment of genotoxicity of methyl-tert-butyl ether, benzene,
toluene, ethylbenzene, and xylene to human lymphocytes using comet
assay. J. Hazard. Mater. 153, 351–356.
(
46) Carmichael, J., DeGraff, W. G., Gazdar, A. F., Minna, J. D., and
Mitchell, J. B. (1987) Evaluation of a tetrazolium-based semiautomated
colorimetric assay: assessment of chemosensitivity testing. Cancer Res.
(
26) Goldsworthy, T., Monticello, T., Morgan, K., Bermudez, E., Wilson,
D., Jackh, R., and Butterworth, B. (1991) Examination of potential
mechanisms of carcinogenicity of 1,4-dioxane in rat nasal epithelial-
cells and hepatocytes. Arch. Toxicol. 65, 1–9.
4
7, 936–941.
(
(
(
47) Wilson, A. P. (2000) Cytotoxicity and Viability Assays, in Animal
Cell Culture: A Practical Approach (Masters, J. R. W., Ed.) Oxford
University Press, Oxford, U.K.
48) Martins, C., et al. (2007) Cytogenetic damage induced by acrylamide
and glycidamide in mammalian cells: correlation with specific gly-
cidamide-DNA adducts. Toxicol. Sci. 95, 383–390.
49) Casado, J., L o´ pez-Quintela, M. A., and Lorenzo-Barral, F. M. (1986)
The initial rate method in chemical kinetics: evaluation and experi-
mental illustration. J. Chem. Educ. 63, 450.
(
27) Stickney, J. A., et al. (2003) An updated evaluation of the carcinogenic
potential of 1,4-dioxane. Regul. Toxicol. Pharmacol. 38, 183–195.
28) Kano, H., et al. (2009) Carcinogenicity studies of 1,4-dioxane
administered in drinking-water to rats and mice for 2 years. Food
Chem. Toxicol. 47, 2776–2784.
(
(
29) IARC (1995) Dry Cleaning: Some Chlorinated Solvents and Other
Industrial Chemicals, in IARC Monographs on the EValuation of
Carcinogenic Risks to Humans, Vol. 63, pp 393-407, IARC, Lyon,
France.
(
50) Rao, C. (1967) Ultra-Violet and Visible Spectroscopy, Chapter 4,
Butterworth, London.
(
30) Epstein, J., Rosenthal, R. W., and Ess, R. J. (1955) Use of p-(4-
nitrobenzyl)-pyridine as analytical reagent for ethylenimines and
alkylating agents. Anal. Chem. 27, 1435–1439.
(
51) Guegenrich, F. (2005) Cytochrome P450 Structure, Mechanism and
Biochemistry (Montellano, P. O. D., Ed.) Kluwer, Academic/Plenum
Publishers, New York.
(
31) Kim, J. H., and Thomas, J. J. (1992) Use of 4-(nitrobenzyl)pyridine
(
4-Nbp) to test mutagenic potential of slow-reacting epoxides, their
(
52) Duarte, M. P., et al. (2005) The stimulatory role of human cytochrome
b5 in the bioactivation activities of human CYP1A2, 2A6 and 2E1: a
new cell expression system to study cytochrome P450 mediated
biotransformation. Mutagenesis 20, 93–100.
corresponding olefins, and other alkylating-agents. Bull. EnViron.
Contam. Toxicol. 49, 879–885.
(
32) Manso, J. A., P e´ rez-Prior, M. T., Garc ´ı a-Santos, M. D., Calle, E., and
Casado, J. (2005) A kinetic approach to the alkylating potential of
carcinogenic lactones. Chem. Res. Toxicol. 18, 1161–1166.
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