Reactivity of the mutagen l,4-dinitro-2-methylpyrrole as an alkylating agent

Journal of Organic Chemistry

Volumn 75, Issue 5, 2010, Pages 1444-1449

  Teresa Perez Prior M ^a   Gómez Bombarelli, Rafael ^a   González Pérez, Marina ^a   Manso, José A ^a   Pilar Garcia Santos M ^a   Calle, Emilio ^a   Casado, Julio ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENTS; AQUEOUS MEDIUM; BACTERIAL TESTS; CHEMICAL SPECIES; DNA BASIS; GENOTOXIC; HYDROXIDE IONS; MUTAGENIC ACTIVITY; MUTAGENIC PROPERTIES; MUTAGENICITY; SORBIC ACID;

ACIDS; CARBOXYLIC ACIDS; HYDROCARBONS;

MUTAGENS;

2 METHYL 1,4 DINITROPYRROLE; 4 (4 NITROBENZYL)PYRIDINE; 5 METHYL 3 NITRO 1H PYRROL 2 OL; 5-METHYL-3-NITRO-1H-PYRROL 2(5H) ONE; ALKYLATING AGENT; HYDROXIDE; NITRITE; PYRROLE DERIVATIVE; SORBIC ACID; UNCLASSIFIED DRUG; 2-METHYL-1,4-DINITROPYRROLE; DNA; MUTAGENIC AGENT;

ALKYLATION; ARTICLE; GENOTOXICITY; MUTAGENIC ACTIVITY; MUTAGENICITY; CHEMISTRY; DNA DAMAGE; DRUG EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MICROBIOLOGICAL EXAMINATION; MUTATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALMONELLA; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROPHOTOMETRY;

ALKYLATING AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DNA DAMAGE; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MICROBIAL SENSITIVITY TESTS; MUTAGENS; MUTATION; NITRITES; PYRROLES; SALMONELLA; SORBIC ACID; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77949293101     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo902329q     Document Type: Article

References (33)

1. U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition. FDA List of Food Additives that are Generally Recognized as Safe (GRAS); U.S. Government Printing Office: Washington, DC, 2005.
2. Hartman, P. E. E. Environ. Mutagen, 1983, 5, 217.
3. Thakur, B. R.; Singh, K.; Arya, S. S. Food Rev. Int. 1994, 10, 71.
4. Hasegawa, M. M.; Nishi, Y.; Ohkawa, Y.; Inui, N. Food. Chem. Toxicol. 1984, 22, 501.
5. Münzer, R.; Guigas, C.; Renner, H. W. Food Chem. Toxicol. 1990, 28, 397.
6. Würgler, F. E.; Schlatter, J.; Maier, P. Multar. Res. 1992, 283, 107.
7. Mpountoukas, P.; Vantarakis, A.; Sivridis, E.; Lialiaris, T. Food Chem. Toxicol. 2008, 46, 2390.
8. Pérez-Prior, M. T.; Manso, J. A.; García-Santos, M. P.; Calle, E.; Casado, J. J. Agric Food Chem. 2005, 53, 10244.
9. Pérez-Prior, M. T.; Manso, J. A.; García-Santos, M. P.; Calle, E.; Casado, J. J. Solution Chem. 2008, 37, 459.
10. Adams, J. B. Food Chem. 1997, 59, 401.
11. Namiki, M.; Udaka, S.; Osawa, T.; Tsuji, K.; Kada, T. Mutat, Res. 1980, 73, 21.
12. Namiki, M.; Osawa, T.; Ishibashi, H.; Namiki, K.; Tsuji, K.; Agric. Food Chem. 1981, 29, 407.
13. Hartman, P. E. Emiron. Mutagen. 1983, 5, 217.
14. Osawa, T; Namiki, M. Agric. Biol. Chem. 1982, 46, 2299.
15. Kito, Y.; Namiki, M.; Tsuji, K. Tetrahedron 1978, 34, 505.
16. Osawa, T.; Kito, Y.; Namiki, M.; K. Tetrahedron Lett. 1979, 45, 4399.
17. Namiki, M.; Kada, T. Agric. Biol. Chem. 1975, 39, 1335.
18. Hansen, T. J.; Tannenbaum, S. R.; Archer, M. C. J. Agric. Food Chem. 1981, 29, 1008.
19. Pérez-Prior, M. T.; Manso, J. A.; Gómez-Bombarelli, R.; GonzálezPérez, M.; García-Santos, M. P.; Calle, E.; Caballero, M. C.; Casado, J. J. Agric. Food Chem. 2008, 56, 11824.
20. Pérez-Prior, M. T.; Manso, J. A.; Gómez-Bombarelli, R.; GonzálezPérez, M.; Céspedes, I. F.; García-Santos, M. P.; Calle, E.; Casado, J. J. Phys. Org. Chem. 2009, 22, 418.
21. Pérez-Prior, M. T.; Gómez-Bombarelli, R.; González-Pérez, M.; Manso, J. A.; García-Santos, M. P.; Calle, E.; Casado, J. Chem. Res. Toxicol. 2009, 22, 1320.
22. Kim, J. H.;Thomas, J.J. Bull. Environ. Contam. Toxicol. 1992, 49, 879.
23. Shephard, S. E.; Lutz, W. K. Cancer Surv. 1989, 8, 401.
24. Norman, R.; Coxon, J. M. Principles of Organic Synthesis; 3rd ed.; CRC Press: Boca Raton, FL, 1993; Chapter 21.
25. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317.
26. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842.
27. Manso, J. A.; Pérez-Prior, M. T.; García-Santos, M. P.; Calle, E.; Casado, J. Chem. Res. Toxicol, 2005, 18, 1161.
28. Gómez-Bombarelli, R.; González-Pérez, M.; Pérez-Prior, M. T.; Manso, J. A.; Calle, E.; Casado, J. Chem. Res. Toxicol. 2008, 21, 1964.
29. Céspedes-Camacho, I. F.; Manso, J. A.; Pérez-Prior, M. T.; Gómez-Bombarelli, R.; González-Pérez M.; Calle, E.; Casado, J. J. Phys. Org. Chem. 2010, 23, 171
30. Connors, K. A. Chemical Kinetics. The Study of Reaction Rates in Solution; VCH: New York, 1990; Chapter 3.
31. Kada, T.; Tutikawa, K.; Sadaie, Y. Mutat. Res. 1972, 16, 165.
32. McCann, J.; Choi, E.; Yamasaki, E.; Ames, B. N. Proc. Natl. Acad. Sci. U.S.A. 1915, 72, 5135.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Kudin, T. V. Jr., K. N.; Buran t, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.