'In vitro' antioxidant and photoprotective properties and interaction with model membranes of three new quercetin esters

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 56, Issue 2, 2003, Pages 167-174

  Saija, Antonella ^a   Tomaino, Antonio ^a   Trombetta, Domenico ^a   Pellegrino, Maria Luisa ^a   Tita, Beatrice ^b   Messina, Chiara ^c   Bonina, Francesco P ^c   Rocco, Concetta ^d   Nicolosi, Giovanni ^d   Castelli, Francesco ^c  

^a UNIVERSITY OF MESSINA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c UNIVERSITY OF CATANIA   (Italy)

^d CNR   (Italy)

Author keywords

Antioxidant activity; Differential scanning calorimetry; Liposomes; Photoprotection; Quercetin esters

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL RADICAL; ALIPHATIC COMPOUND; DIMYRISTOYLPHOSPHATIDYLCHOLINE; HYDROXIDE; QUERCETIN; QUERCETIN 3 O ACETATE; QUERCETIN 3 O PALMITATE; QUERCETIN 3 O PROPIONATE; QUERCETIN DERIVATIVE; RADICAL; UNCLASSIFIED DRUG; WATER;

ANTIOXIDANT ACTIVITY; ARTICLE; BLEACHING; DIFFERENTIAL SCANNING CALORIMETRY; DRUG EFFECT; DRUG EFFICACY; DRUG SCREENING; DRUG STABILITY; ESTERIFICATION; EXPERIMENTAL MODEL; IN VITRO STUDY; LIPOPHILICITY; MEMBRANE MODEL; PEROXIDATION; PHOSPHOLIPID MEMBRANE; PHYSICAL CHEMISTRY; PROTECTION; RADIATION EXPOSURE; SOLUBILITY; ULTRAVIOLET RADIATION;

EID: 10744227807     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0939-6411(03)00101-2     Document Type: Article

References (35)

1. Longstreth J., de Gruijl F.R., Kripke M.L., Arnold F., Slaper H.I., Velders G., Takizawa Y., van der Leun J.C. Health risks. J. Photochem. Photobiol. B Biol. 46:1998;20-39.
2. Rettberg P., Horneck G. Intrinsic and extrinsic biomarkers for the assessment of risks from environmental UV radiation. J. Epidemiol. 9:1999;S78-S83.
3. Schwarz T.J., light U.V. affects cell membrane and cytoplasmic targets. Photochem. Photobiol. B Biol. 44:1998;91-96.
4. Beissert S., Schwarz T. Mechanisms involved in ultraviolet light-induced immunosuppression. J. Invest. Dermatol. Symp. Proc. 4:1999;61-64.
5. Sarasin A. The molecular pathways of ultraviolet-induced carcinogenesis. Mutat. Res. 428:1999;5-10.
6. Balasubramanian D.J. Ultraviolet radiation and cataract. Ocul. Pharmacol. Ther. 16:2000;285-297.
7. Bickers D.R., Athar M. Novel approaches to chemoprevention of skin cancer. J. Dermatol. 27:2000;691-695.
8. Eberlein-Konig B., Placzek M., Przybilla B. Phototoxic lysis of erythrocytes from humans is reduced after oral intake of ascorbic acid and d-alpha-tocopherol. Photodermatol. Photoimmunol. Photomed. 13:1997;173-177.
9. Inal M.E., Kahraman A. The protective effect of flavonol quercetin against ultraviolet A induced oxidative stress in rats. Toxicology. 154:2000;21-29.
10. Fyer M.J. Evidence for the photoprotective effects of vitamin E. Photochem. Photobiol. 58:1993;304-312.
11. Reddy G.B., Bhat K.S. Protection against UVB inactivation (in vitro) of rat lens enzymes by natural antioxidants. Mol. Cell Biochem. 194:1999;41-45.
12. Saliou C., Kitazawa M., McLaughlin L., Yang J.-P., Lodge J.K., Tesuka T., Iwasaki K., Cillard J., Okamoto T., Packer L. Antioxidants modulate acute solar ultraviolet radiation NF-Kappa-B activation in a human keratinocyte cell line. Free Radic. Biol. Med. 26:1999;174-183.
13. Dreher F., Maibach H. Protective effects of topical antioxidants in humans. Curr. Probl. Dermatol. 29:2001;157-164.
14. Grundmann J.U., Gollnick H. Prevention of ultraviolet ray damage: external and internal sunscreens. Ther. Umsch. 56:1999;225-232.
15. Hertog M.G.L., Feskens E.J.M., Hollman P.C.H., Kafan M.B., Kromhout D. Dietary antioxidant flavonoids and risk of coronary heart disease. The Zutphen Elderly Study. Lancet. 342:1993;1007-1111.
16. Stavric B. Quercetin in our diet: from potent mutagen to probable anticarcinogen. Clin. Biochem. 27:1994;2456-2458.
17. Arora A., Nair M.G., Strasburg G.M. Structure-activity relationship for antioxidant activities of a series of flavonoids in a liposomal system. Free Radic. Biol. Med. 24:1998;1355-1363.
18. Silva M.M., Santos M.R., Caroco G., Rocha R., Justino G., Mira L. Structure-antioxidant relationships of flavonoids: a re-examination. Free Radic. Res. 36:2002;1219-1227.
19. Formica J.V., Regelson W. Review of the biology of quercetin and related bioflavonoids. Food Chem. Toxicol. 33:1995;1061-1080.
20. Gordon M.H., Roedig-Penman A. Antioxidant activity of quercetin and myricetin in liposomes. Chem. Phys. Lipids. 97:1998;79-85.
21. Bonina F., Lanza M., Montenegro L., Puglisi C., Tomaino A., Trombetta D., Castelli F., Saija A. Flavonoids as potential agents against photo-oxidative skin damage. Int. J. Pharm. 145:1996;87-94.
22. Skaper S.D., Fabris M., Ferrari V., Dalle Carbonare M., Leon A. Quercetin protects cutaneous tissue-associated cell types including sensory neurons from oxidative stress induced by glutathione depletion: cooperative effects of ascorbic acid. Free Radic. Biol. Med. 22:1997;669-679.
23. Erden Inal M., Kahraman A., Köken T. Beneficial effects of quercetin on oxidative stress induced by ultraviolet A. Clin. Exp. Dermatol. 26:2001;536-542.
24. Steerenberg P.A., Garssen J., Dortant P.M., van der Vliet H., Geerse E., Verlaan A.P., Goettsch W.G., Sontag Y., Bueno-de-Mesquita H.B., van Loveren H. The effect of oral quercetin on UVB-induced tumor growth and local immunosuppression in SKH-1. Cancer Lett. 114:1997;187-189.
25. Lambusta D., Nicolosi G., Patti A., Piattelli M. Enzyme-mediated regioprotection deprotection of hydroxyl-groups in (+)-catechin. Synthesis-Stuttgart. 11:1993;1155-1158.
26. Rapisarda P., Tomaino A., Lo Cascio R., Bonina F., De Pasquale A., Saija A. Antioxidant effectiveness as influenced by phenolic content of fresh orange juices. J. Agric. Food Chem. 47:1999;4718-4723.
27. Saija A., Tomaino A., Lo Cascio R., Trombetta D., Proteggente A., De Pasquale A., Uccella N., Bonina F. Ferulic and caffeic acids as potential protective agents against photooxidative skin damage. J. Sci. Food Agric. 79:1999;476-480.
28. Castelli F., Uccella N., Trombetta D., Saija A. Difference between coumaric and cinnamic acids in membrane permeation as evidenced by time-dependent calorimetry. J. Agric. Food Chem. 47:1999;991-995.
29. Rouser G., Fleicher S., Yamamoto A. Two dimensional then layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots. Lipids. 5:1970;494-496.
30. Raudino A., Castelli F. Modeling specific-heat transient anomalies during permeation of liposomes by water-soluble substances. J. Colloid Interf. Sci. 200:1998;52-58.
31. Hope M.J., Bally M.B., Webb G., Cullis P.R. Production of large unilamellar vesicles by a rapid extrusion procedure. Characterization of size distribution, trapped ability to maintain a membrane potential. Biochim. Biophys. Acta. 812:1985;55-65.
32. Bonina F.P., Montenegro L., De Capraris P., Bousquet E., Tirendi S. 1-Alkylazacycloalkan-2-one esters as prodrugs of indomethacin for improved delivery through human skin. Int. J. Pharm. 77:1991;21-29.
33. Castelli F., Puglisi G., Giammona G., Ventura C.A. Effect of the complexation of some nonsteroidal antiinflammatory drugs with beta-cyclodextrin on the interaction with phosphatidylcholine liposomes. Int. J. Pharm. 88:1992;1-3.
34. Jorgensen K., Ipsen J.H., Mouritsen O.G., Bennet D., Zuckermann M.J. A general model for the interaction of foreign molecules with lipid membranes: drugs and anaesthetics. Biochim. Biophys. Acta. 1062:1991;227-238.
35. Mouritsen O.G., Bloom M. Mattress model of lipid-protein interactions in membranes. Biophys. J. 46:1984;141-153.