Reactivity of 1,4-dihydropyridines toward alkyl, alkylperoxyl radicals, and ABTS radical cation

Chemical Research in Toxicology

Volumn 16, Issue 2, 2003, Pages 208-215

  Lopez Alarcon C ^a   Navarrete, P ^a   Camargo, C ^a   Squella, J A ^a   Nunez Vergara L J ^a  

^a UNIVERSITY OF CHILE   (Chile)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDROPYRIDINE; NISOLDIPINE; NITROGEN; PEROXY RADICAL;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; KINETICS; MASS SPECTROMETRY; PH; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

BENZOTHIAZOLES; CATIONS; CHROMANS; DIHYDROPYRIDINES; FREE RADICAL SCAVENGERS; FREE RADICALS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN-ION CONCENTRATION; KINETICS; NISOLDIPINE; PEROXIDES; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFONIC ACIDS; VITAMIN E;

EID: 0037327931     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025579o     Document Type: Article

References (28)

1. Godfrain, T. (1987) Classification of calcium antagonist. Am. J. Cardiol. 59, 11B-23B.
2. Vanhoutte, P. M. (1987) The expert committee of the World Health Organization on classification of calcium antagonists: the viewpoint of the reporter. Am. J. Cardiol. 59, 3A-SA.
3. Tong, M. I., Boheme, P., and Weglicki, W. B. (1992) Antioxidant protective effects of calcium channel blockers against free radical injury in endothelial cells: Circ. Res. 70, 1099-1103.
4. Aruoma, O. I., Smith, C., Cecchini, R., Evans, P. J., and Halliwell, B. (1991) Free radical scavenging and inhibition of lipid peroxidation by blockers and agents that interfere with calcium metabolism to physiologically significant process? Biochem. Pharmacol. 42, 735-743.
5. Henry, P. D. (1991) Antiperoxidative actions of calcium antagonist and atherogenesis. J. Cardiovasc. Pharmacol. 18, S6-S10.
6. Mak, I. T., Boheme, P., and Weglicki, W. B. (1995) Protective effects of calcium channel blockers against free radical-impaired endothelial cell proliferation. Biochem. Pharmacol. 50, 1531-1534.
7. Mason, R., Mak, T., Trumbore, W., and Masón, P. (1999) Antioxidant properties of calcium antagonists related to membrane biophysical interactions. Am. J. Cardiol. 84, 16L-22L.
8. Velena, A., Zilbers, J., and Durbus, G. (1999) Derivatives of 1,4-dihydropyridines ace modulators of ascorbate-induced lipid peroxidation and high-amplitude swelling of mitochondria, caused by ascorbate, sodium linoleate and sodium pyrophosphate. Cell. Biochem. Funct. 17, 237-252.
9. Belch, J. J. F., Chopra, M., Hutchison, S., Lorimer, R., Sturrock, R. D., Forbes, C. D., and Smith, W. E. (1989) Free radical pathology in chronic arterial disease. Free Radical Biol. Med. 6, 375-378.
10. Prabha, P. S., Das, U. N., Koratkar, R., Sangeetha Sagar, P., and Ramesh, G. (1990) Free radical generation, lipid peroxidation and essential fatty acid in uncontrolled essential hypertension. Prostaglandine, Leukotrienes Essent. Fatty Acids 41, 23-27.
11. Díaz-Araya, G., Godoy, L., Naranjo, L., Squella, A., Letelier, M. E., and Nunez-Vergara, L. J. (1998) Antioxidant Effects of 1,4-Dihydropyridine Nitrous and Aryl Derivatives on the Fe+3/ Ascorbate-Stimulated Lipid Peroxidation in Rat Brain Slices-possible role of endogeneous iron. Gen. Pharmacol. 31, 385-391.
12. Sugawara, H., Tobise, K., and Onodera, S. (1994) Absence of antioxidant effects of nifedipine and diltiazem on myocardial membrane lipid peroxidation in contrast with of nisoldipine and propanolol coughs. Biochem. Pharmacol. 47, 887-892.
13. van Amsterdam, F. Th. M., Roveri, A., Maiorino, M., Ratti, E., and Ursini, F. (1992) Lacidipine: TO dihydropyridine calcium antagonist with antioxidant activity. Free Radical Biol. Med. 12, 183-187.
14. Toniolo, R., Di Narda, F., Bontempelli, G., Ursini, F. (2000) An electroanalytical investigation on the redox properties of lacidipine supporting its anti-oxidant effect. Bioelectrochemistry 51, 193-200.
15. Ortiz, M. E., Núñez-Vergara, L. J., and Squella, J. A. (2002) Cyclic voltammetric behaviour of the O2/O2-redox couple at to HMDE and its interaction with nisoldipine. J. Electroanal. Chem. 519, 46-52.
16. Stout, D. M., and Meyers, A. I. (1982) Recent advances in the chemistry of dihydropyridines. Chem. Rev. 82, 223-243.
17. Ross, L., and Barclay, C. (1988) The cooperative antioxidant role of glutathione with to lipid-soluble and water-soluble antioxidant during peroxidation of liposome's initiated in the aqueous phase and in the lipid phase. J. Biol. Chem. 263, 16138-16142.
18. Halliwell, B., and Gutteridge, J. M. C. (2000) Free Radicals in Biology and Medicine, pp 69-70, Oxford University Press, New York.
19. Niki, E. (1990) Free radical initiators ace source of water or lipidsoluble peroxyl radicals. Methods Enzymol. 186, 100-108.
20. Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., and Ruffle-Evans, C. (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol. Med. 26, 1231-1237.
21. Labudzinska, A., and Gorczynska, K. (1995) The UV difference spectra as a characteristic feature of phenols and aromatic amines. J. Mol. Struct. 349, 469-472.
22. Núñez-Vergara, L. J., López-Alarcón, C., Navarrete-Encina, P. A., Atria, A. M., Camargo, C., and Squella, J. A. (2003) Electrochemical and EPR characterization of 1,4-dihydropyridines. Reactivity towards alkyl radicals. Free Radical Res. 37, 109-120.
23. Collins, C. J., and Bowman, N. S. (1970) Isotope Effects in Chemical Reactions, Van Nostrand-Reinhold Co., New York.
24. More O'Ferrall, R. A. (1975) in Proton-Transfer Reactions (Gold, V., and Caldin, E. F., Eds.) p 201, Chapman and Hall, London.
25. Ludvick, J., Volke, J., and Klima, J. (1987) Electrochemical oxidation mechanisms of different type 1,4-dihydropyridine derivatives in acetonitrile. Electrochim. Acta 32, 1063-1071.
26. Hurvois, J. P., Moinet, C., and Taillec, A. (1993) Anodic oxidation of 4-(o-nitrophenyl)-1,4-dihydropyridines and reductive cyclization of the resulting or-nitrophenyl-pyridines. Electrochim. Acta 38, 1775-1781.
27. Núñez-Vergara, L. J., Sturm, J. C., Alvarez-Lueje, A., Surge-Chance, C., Sunkel, C., and Squella, J. A. (1999) Electrochemical oxidation of 4-methyl-1,4-dihydropyridines in protic and half aprotic. J. Electrochem. Soc. 146, 1478-1485.
28. Ludvik, J., Klima, J., Volke, J., Kurfurst, A., and Kuthan, J. (1982) Electrochemical oxidation of substituted 1,4-dihydropyridines in nonaqueous acetonitrile. J. Electroanal. Chem. 138, 131-138.