Use of liposomes as membrane models to evaluate the contribution of drug-membrane interactions to antioxidant properties of etodolac

Redox Report

Volumn 13, Issue 5, 2008, Pages 225-236

  Lúcio, Marlene ^a   Ferreira, Helena ^a   Lima, José L F C ^a   Reis, Salette ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Etodolac; Hydroxyl radicals; Lipid peroxidation; Liposome; Peroxyl radicals

Indexed keywords

DIPHENYLHEXATRIENE PROPIONIC ACID; ETODOLAC; FLUORESCEIN; HEXADECANOYL AMINOFLUORESCEIN; HYDROXYL RADICAL; LIPOSOME; PEROXY RADICAL; TROLOX C; UNCLASSIFIED DRUG; (HEXADECANOYL)AMINOFLUORESCEIN; 1 (4' CARBOXYETHYL) 6 DIPHENYL 1,3,5 HEXATRIENE; 1,6 DIPHENYL 1,3,5 HEXATRIENE; 1-(4'-CARBOXYETHYL)-6-DIPHENYL-1,3,5-HEXATRIENE; 6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID; ANTIOXIDANT; CHROMAN DERIVATIVE; DRUG DERIVATIVE; FLUORESCEIN DERIVATIVE; FLUORESCENT DYE; SCAVENGER;

ANISOTROPY; ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CELL MEMBRANE POTENTIAL; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG STRUCTURE; FENTON REACTION; FLUORESCENCE; LIPID BILAYER; LIPID PEROXIDATION; LIPOPHILICITY; MEMBRANE FLUIDITY; PRIORITY JOURNAL; CHEMISTRY; DRUG EFFECT; EVALUATION; METABOLISM;

ANISOTROPY; ANTIOXIDANTS; CHROMANS; DIPHENYLHEXATRIENE; ETODOLAC; FLUORESCEIN; FLUORESCEINS; FLUORESCENT DYES; FREE RADICAL SCAVENGERS; LIPID PEROXIDATION; MEMBRANE FLUIDITY; MEMBRANE POTENTIALS; UNILAMELLAR LIPOSOMES;

EID: 55549103723     PISSN: 13510002     EISSN: None     Source Type: Journal    
DOI: 10.1179/135100008X308939     Document Type: Article

References (46)

1. Gutiérrez ME, Garcia AF, Africa de Mandariaga M, Sagrista ML, Casado FJ, Mora M. Interaction of tocopherols and phenolic compounds with membrane lipid components: evaluation of their antioxidant activity in a liposomal model system. Life Sci 2003; 72: 2337-2360.
2. McMillian M, Nie AY, Parker B et al. A gene expression signature for oxidant stress/reactive metabolites in rat liver. Biochem Pharmacol 2004; 68: 2249-2261.
3. Tomasi A, Özben T, Skulachev VP. Free radicals, nitric oxide, and inflammation: molecular, biochemical and clinical aspects. Ohmaha, NB: IOS, 2003.
4. Behl C. Alzheimer's disease and oxidative stress: implications for novel therapeutic approaches. Prog Neurobiol 1999; 57: 301-323.
5. Cao G, Prior RL. Comparison of different analytical methods for assessing total antioxidant capacity of human serum. Clin Chem 1998; 44: 1309-1315.
6. De Zwart LL, Meerman JHN, Commandeur JNM, Vermeulen NPE. Biomarkers of free radical damage applications in experimental animals and humans. Free Radic Biol Med 1999; 26: 202-226.
7. Fernandes E, Costa D, Toste SA, Lima JLFC, Reis S. In vitro scavenging activity for reactive oxygen and nitrogen species by nonsteroidal anti-inflammatory indole, pyrrole, and oxazole derivative drugs. Free Radic Biol Med 2004; 37: 1895-1905.
8. Halliwell B, Hoult JR, Blake DR. Oxidants, inflammation, and anti-inflammatory drugs. FASEB J 1988; 2 2867-2873.
9. Vapaatalo H. Free radicals and anti-inflammatory drugs. Med Biol 1986; 64: 1-7.
10. Fernandes E, Lima JLFC, Reis S. Involvement of reactive oxygen and nitrogen species in inflammatory processes. Implications for the potential therapeutic use of NSAIDs with antioxidant activity. Curr Top Med Chem 2003; 3: 221-236.
11. Costa D, Gomes A, Reis S, Lima JLFC, Fernandes E. Hydrogen peroxide scavenging activity by non-steroidal anti-inflammatory drugs. Life Sci 2005; 76: 2841-2848.
12. Garcia JB, Saraiva MLMFS, Lima JLFC. Determination and antioxidant activity evaluation of etodolac, an anti-inflammatory drug, by sequential injection analysis. Anal Chim Acta 2006; 573/ 574: 371-375.
13. Ikeda Y, Matsumoto K, Dohi K, Jimbo H, Sasaki K, Satoh K. Direct superoxide scavenging activity of nonsteroidal anti-inflammatory drugs: determination by electron spin resonance using the spin trap method. Headache 2001; 41: 138-141.
14. Aikens J, Dix TA. Hydrodioxyl (perhydroxyl), peroxyl, and hydroxyl radical-initiates lipid peroxidation of large unilamellar vesicles (liposomes): comparative and mechanistic studies. Arch Biochem Biophys 1993; 305: 516-525.
15. Castelli F, Trombetta D, Tomaino A et al. Dipalmitoylphosphatidylcholine/linoleic acid mixed unilamellar vesicles as model membranes for studies on novel free-radical scavengers. J Pharmacol Toxicol Methods 1997; 37: 135-141.
16. Fendler JH. Membrane Mimetic Chemistry. New York: John Wiley, 1983.
17. Paya' M, Halliwell B, Hoult JRS. Interactions of a series of coumarins with reactive oxygen species. Scavenging of super-oxide, hypochlorous acid and hydroxyl radicals. Biochem Pharmacol 1992; 44: 205-214.
18. Kachel K, Asuncion-Punzalan E, London E. The location of fluorescent probes with charged groups in model membranes. Biochim Biophys Acta 1998; 1374: 63-76.
19. Kaiser RD, London E. Location of diphenylhexatriene (DPH) and its derivatives within membranes: comparison of different fluorescence quenching analysis of membrane depth. Biochemistry 1998; 37: 8180-8190.
20. Ou B, Hampsch-Woodill M, Prior RL. Development and validation of an improved oxygen radical absorbance capacity assay using fluorescein as the fluorescent probe. J Agric Food Chem 2001; 49: 4619-4626.
21. Cervato G, Viani P, Masserini M, Di Iorio C, Cestaro B. Studies on peroxidation of arachidonic acid in different liposomes below and above phase transition temperature. Chem Phys Lipids 1988; 49: 135-139.
22. Mclean LR, Hagaman KA. Effect of lipid physical state on the rate of peroxidation of liposomes. Free Radic Biol Med 1992; 12: 113-119.
23. Barclay L, Vinqvist MR. Membrane peroxidation: inhibiting effects of water soluble antioxidants on phospholipids of different charge types. Free Radic Biol Med 1994; 16: 779-788.
24. Saija A, Scalese M, Lanza M, Marzullo D, Bonina F, Castelli F. Flavonoids as antioxidant agents: importance of their interaction with biomembranes. Free Radic Biol Med 1995; 19: 481-486.
25. Gregoriadis G. Liposome technology, 3rd edn (three-volume Set). New York: Informa Healthcare, 2006.
26. McClare CWF. An accurate and convenient organic phosphorus assay. Anal Biochem 1971; 39: 527-530.
27. Lasic DD. Liposomes - from Physics to Applications. New York: Elsevier, 1993.
28. New RRC. Liposomes - a practical approach. New York: Oxford University Press, 1990.
29. Arora A, Strasburg GM. Development and validation of fluorescence spectroscopic assays to evaluate antioxidant efficacy. Application to metal chelators. J Am Oil Chem Soc 1997; 74: 1031-1040.
30. Huang D, Boxin O, Hampsch-Woodill M, Flanagan JA, Prior RL. High-throughput assay of oxygen radical absorbance capacity (ORAC) using a multichannel liquid handling system coupled with a microplate fluorescence reader in 96-well format. J Agric Food Chem 2002; 50: 4437-4444.
31. Huang D, Ou B, Prior RL. The chemistry behind antioxidant capacity assays. J Agric Food Chem 2005; 53: 1841-1856.
32. MacDonald-Wicks LK, Wood LG, Garg ML. Methodology for the determination of biological antioxidant capacity in vitro: a review. J Sci Food Agric 2006; 86: 2046-2056.
33. Poljsak B, Raspor P. The antioxidant and pro-oxidant activity of vitamin C and Trolox in vitro: a comparative study. J Appl Toxicol 2008; 28: 183-188.
34. Lakowicz JR. Principles of fluorescence spectroscopy, 3rd edn. New York: Springer, 2006.
35. Lentz BR. Use of fluorescent probes to monitor molecular order and motions within liposome bilayers. Chem Phys Lipids 1993; 64: 99-116.
36. Kiselev MA, Lesieur P, Kisselev AM, Grabielle-Madelmond C, Ollivon M. DMSO-induced dehydration of DPPC membranes studied by X-ray diffraction, small-angle neutron scattering, and calorimetry. J Alloys Compounds 1999; 286: 195-202.
37. Matos C, Castro B, Gameiro P, Lima JLFC, Reis S. Zeta potential measurements as a tool to quantify the effect of charged drugs on the surface potential of egg phosphatidylcholine liposomes. Langmuir 2004; 20: 369-377.
38. Lucio M, Ferreira H, Lima JLFC, Reis S. Use of liposomes to evaluate the role of membrane interactions on antioxidant activity. Anal Chim Acta 2007; 597: 163-170.
39. Ferreira H, Lucio M, Lima JLFC, Matos c, Reis S. Effects of diclofenac on EPC liposome membrane properties. Anal Bioanal Chem 2005; 382: 1256-1264.
40. Tavares IA, Bennett A. COX-2 inhibitors compared and contrasted. Expert Opin Pharmacother 2001; 2: 1859-1876.
41. Boyd SL, Boyde RJ, Barclay LRC. A theoretical investigation of the structures and properties of peroxyl radicals. J Am Chem Soc 1990; 112: 5724-5730.
42. Fessenden RW, Hitachi A, Nagarajan V. Measurement of the dipole moment of a peroxyl radical by a microwave dielectric absorption. J Phys Chem 1984; 88: 107-110.
43. Saija A, Bonina F, Trombetta D et al. Flavonoid-biomembrane interactions: a calorimetric study on dipalmitoylphosphatidyl-choline vesicles. Int J Pharm 1995; 124: 1-8.
44. Saija A, Tomaino A, Pellegrino M, Giuffrida N, Trombetta D, Castelli F. In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G. Life Sci 2001; 68: 1351-1366.
45. Fukuzawa K, Matsuura K, Tokumura A, Suzuki A, Terao J. Kinetics and dynamics of singlet oxygen scavenging by alpha-tocopherol in phospholipid model membranes. Free Radic Biol Med 1997; 22: 923-930.
46. Weber V, Coudert P, Duroux E, Leal F, Couquelet J, Madesclaire M. Synthesis and in vitro studies of pyran derivatives as scavengers of active oxygen species. Arzneimittelforschung 2001; 51: 877-884.