Antioxidant properties of novel lipophilic ascorbic acid analogues

Journal of Pharmacy and Pharmacology

Volumn 52, Issue 5, 2000, Pages 523-530

  Weber, Valerie ^a   Coudert, Pascal ^a   Rubat, Catherine ^b   Duroux, Eliane ^b   Leal, Fernand ^a   Couquelet, Jacques ^a,b  

^a Laboratoire de Pharmacochimie   (France)

^b UNIVERSITÉ CLERMONT AUVERGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 4 ACETYL 3,4 DIHYDROFURAN 2(5H)ONE DERIVATIVE; 4 BENZOYL 3 HYDROXYFURAN 2(5H)ONE; ANION; ASCORBIC ACID DERIVATIVE; LIPID; SUPEROXIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG SYNTHESIS; LIPID PEROXIDATION; LIPOPHILICITY; LIVER MICROSOME; MALE; MOUSE; NONHUMAN; RAT; TOXICITY TESTING;

EID: 0342748415     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/0022357001774318     Document Type: Article

References (29)

1. Andreadou, I., Rekka, E. A., Demopoulos, V. J., Bijloo, G. J., Kourounakis, P. N. (1997) Synthesis, antioxidant and anti-inflammatory activity of novel substituted ethylenediamines and ethanolamines. Arzneim. Forsch. 47: 643-647
2. Bast, A., Haenen, G., Doelman, C. (1991) Oxidants and antioxidants: state of the art. Am. J. Med. 91 (Suppl. 3C): 2S-13S
3. Bechalany, A., Rothlisberger, T., El Tayar, N., Testa, B. (1989) Comparison of various non-polar stationary phases used for assessing lipophilicity. J. Chromatogr. 473: 115-124
4. Bulkley, G. B. (1993) Free radicals and other reactive oxygen metabolites: clinical relevance and the therapeutic efficacity of antioxidant therapy. Surgery 113: 479-483
5. Coudert, P., Leal, F., Duroux, E., Rubat, C., Couquelet, J. (1996) Effect on free radical processes of some ascorbic acid analogues. Biol. Pharm. Bull. 19: 220-223
6. Couquelet, J. M., Taoufik, J., Couquelet, J. D., Tronche, P. (1983) Nouveaux dérivés des dihydro-4,5 (3H) acetyl-4-furannones-2: étude chimique et pharmacologique. Eur. J. Med. Chem. (Chim. Ther.) 18: 301-305
7. Diplock, A. T. (1994) Antioxidants and free radical scavengers.In: Rice-Evans, C. A., Burdon, R. H. (eds) Free Radical Damage and its Control. Elsevier Science B.V. (Amsterdam), pp 113-130
8. Dix, T. A., Aikens, J. (1993) Mechanisms and biological relevance of lipid peroxidation initiation. Chem. Res. Toxicol. 6: 2-18
9. Durantin, G., Boyer, J. B., Couquelet, J., Bastide, P. (1972) Hydroxy-2 benzoyl-3 butène-2-olides-4 affectant le système nerveux central. Chim. Ther. 6: 472-475
10. El Tayar, N., Van de Waterbeemd, H., Testa, B. (1985) Lipophilicity measurements of protonated basic compounds by reversed-phase high-performance liquid chromatography. I. Relationship between capacity factors and the methanol concentration in methanol-water eluents. J. Chromatogr. 320: 293-304
11. Halliwell, B. (1990) How to characterize a biological antioxidant. Free Rad. Res. Comm. 9: 1-32
12. Halliwell, B. (1991) Drug antioxidant effects. A basis for drug selection. Drugs 42: 569-605
13. Halliwell, B. (1994) Free radicals, antioxidants and human disease: curiosity, cause or consequence? Lancet 344: 721-724
14. Kato, K., Terao, S., Shimamoto, N., Hirata, M. (1988) Studies on scavengers of active oxygen species. 1. Synthesis and biological activity of 2-O-alkylascorbic acids. J. Med. Chem. 31: 793-798
15. May, H. E., McCay, P. B. (1968) Reduced triphosphopyridine nucleotide oxidase-catalysed alterations of membrane phospholipids. I: Nature of the lipid alterations. J. Biol. Chem. 243: 2288-2295
16. Meunier, M. T., Duroux, E., Bastide, P. (1989) Activité antiradicalaire d'oligomères procyanidotiques et d'anthocyanosides vis-à-vis de l'anion superoxyde et vis-à-vis de la lipoperoxydation. Plantes Médicinales et Phytothérapie 23: 267-274
17. Morisaki, K., Ozaki, S. (1996) Design of novel hybrid Vitamin C derivatives: thermal stability and biological activity. Chem. Pharm. Bull. 44: 1647-1655
18. Müller, A., Cadenas, E., Graf, P., Sies, H. (1984) A novel biologically active seleno-organic compound. I. Glutathion peroxidase-like activity in-vitro and antioxidant capacity of PZ 51 (Ebselen). Biochem. Pharmacol. 33: 3235-3239
19. Nihro, Y., Miyataka, H., Sudo, T., Miki, T., Matsumoto, H., Satoh, T. (1991) 3-O-alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation. J. Med. Chem. 34: 2152-2157
20. Niki, E. (1991) Action of ascorbic acid as a scavenger of active and stable oxygen radicals. Am. J. Clin. Nutr. 54: 1119S-1124S
21. Niki, E., Kawakami, A., Saito, M., Yamamoto, Y., Tsuchiya, J., Kamuja, Y. (1985) Effect of phytyl side chain of vitamin E on its antioxidant activity. J. Biol. Chem. 260: 2191-2196
22. 2 synthase and 5-lipoxygenase with scavenging activity of active oxygen species. Synthesis of a novel series of (3-pyridymethyl) benzoquinone derivatives. J. Med. Chem. 34: 267-276
23. Point, D., Coudert, P., Leal, F., Rubat, C., Sautou-Miranda, V., Chopineau, J., Couquelet, J. (1998) Antioxidant activity of some ascorbic acid and cinnamic acids derivatives. II Farmaco: 85-88
24. Ratty, A. K., Sunammoto, J., Das, N. P. (1988) Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochem. Pharmacol. 37: 989-995
25. Rose, R. C., Bode, A. M. (1993) Biology of free radical scavengers: an evaluation of ascorbate. FASEB J. 7: 1135-1142
26. Schmid, E., Figala, V., Roth, D., Ullrich, V. (1993) Antioxidant and neutrophil-inhibiting properties of new 2-O-methyl-6-(alkylthio)ascorbic acid derivatives. J. Med. Chem. 36: 4021-4029
27. Slater, T. F., Eakins, M. N. (1974) Interactions of (+)-cyanidanol-3 with free radical generating systems. Int. Symp. Tirrenia, Karger, Basel pp 84-89
28. Yamagami, C., Masaki, Y. (1995) Hydrophobicity parameters determined by reversed-phase liquid chromatography. X. Relationship between capacity factor and octanol-water partition coefficients of monosubstituted thiophenes. Chem. Pharm. Bull. 43: 2238-2242
29. Yu, M. J., McCowan, J. R., Phebus, L. A., Towner, R. D., Ho, P. P. K., Keith, P. T., Luttman, C. A., Saunders, R. D., Ruterbories, K. J., Lindstrom, T. D., Wikel, J. H., Morgan, E., Hahn, R. A. (1993) Benzylamine antioxidants: relationships between structure, peroxyl radical scavenging, lipid peroxidation inhibition, and cytoprotection. J. Med. Chem. 36: 1262-1271