In vitro evaluation of the antioxidant activity of liposomal flavonols by the HRP-H2O2-luminol system

Journal of Microencapsulation

Volumn 28, Issue 4, 2011, Pages 258-267

  Landi Librandi, Ana Paula ^a   De Oliveira, Carlos Alberto ^b   Caleiro Seixas Azzolini, Ana Elisa ^a   Mariko Kabeya, Luciana ^a   Del Ciampo, José Orestes ^a   Lopes Badra Bentley, Maria Vitria ^a   Lucisano Valim, Yara Maria ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

encapsulation; flavonols; horseradish peroxidase; liposome; reactive oxygen species

Indexed keywords

ALCOHOL; FLAVONOL DERIVATIVE; GALANGIN; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; KAEMPFEROL; LIPOSOME; LUMINOL; MYRICETIN; QUERCETIN; REACTIVE OXYGEN METABOLITE;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; EVALUATION; IN VITRO STUDY; OXIDATIVE STRESS; TECHNIQUE; ZETA POTENTIAL;

ANTIOXIDANTS; DRUG EVALUATION, PRECLINICAL; FLAVONOLS; HORSERADISH PEROXIDASE; HUMANS; HYDROGEN PEROXIDE; LIPOSOMES; LUMINOL;

EID: 79955834322     PISSN: 02652048     EISSN: 14645246     Source Type: Journal    
DOI: 10.3109/02652048.2011.559283     Document Type: Article

References (50)

1. Alexopoulou E, Georgopoulos A, Kagkadis KA, Demetzos C. Preparation and characterization of lyophilized liposomes with incorporated quercetin. J Liposome Res, 2006;16:17-25.
2. Arora A, Nair MG, Strasburg GM. Structure-activity relationships for antioxidant activities of a series of flavonoids in a liposomal system. Free Radical Biol Med, 1998;24:1355-63. (Pubitemid 28270336)
3. Aruoma OI. Free radicals, oxidative strees, and antioxidants in human health and disease. JAOCS, 1998;75:199-212. (Pubitemid 128607978)
4. Batzri S, Korn ED. Single bilayer liposomes prepared without sonication. Biochim Biophys Acta, 1973;298:1015-9.
5. Beckman KB, Ames BN. The free radical theory of aging matures. Physiol Rev, 1998;78:547-81. (Pubitemid 28182903)
6. Betageri GV, Parsons DL. Drug encapsulation and release from multilamellar and unilamellar liposomes. Int J Pharm, 1992;81:235-41.
7. Cos P, Ying L, Calomme M, Hu JP, Cimanga K, Van Poel B, Pieters L, Vlietinck AJ, Vanden Berghe D. Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers. J Nat Prod, 1998;61(1):71-6. (Pubitemid 28086977)
8. Cruz ME, Gaspar MM, Bárbara M, Martins F, Corvo ML. Liposomal superoxide dismutases and their use in the treatment of experimental arthritis. Methods Enzymol, 2005;391:395-413. (Pubitemid 40254047)
9. Dipali SR, Kulkarni SB, Betageri GV. Comparative study of separation of non-encapsulated drug from unilamellar liposomes by various methods. J Pharm Pharmacol, 1996;48:1112-15. (Pubitemid 126449478)
10. Edeas M. Anti-oxidants, controversies and perspectives: How can the failure of clinical studies using anti-oxidants be explained? J Soc Biol, 2009;203:271-80.
11. Gulati M, Bajad S, Singh S, Ferdous AJ, Singh M. Development of liposomal amphotericin B formulation. J Microencapsul, 1998;15:137-51. (Pubitemid 28105130)
12. Harigai T, Hagiwara H, Ogawa Y, Ishizuka T, Kaneda S, Kimura J. Prednisolone phosphate-containing TRX-20 liposomes inhibit cytokine and chemokine production in human fibroblast-like synovial cells: A novel approach to rheumatoid arthritis therapy. J Pharm Pharmacol, 2007;59:137-43. (Pubitemid 46133053)
13. Harman D. Aging - A theory based on free-radical and radiation-chemistry. J Gerontol, 1956;11:298-300.
14. Havsteen B. Flavonoids, a class of natural products of high pharmacological potency. Biochem Pharmacol, 1983;32:1141-8. (Pubitemid 13135620)
15. Hu JP, Calomme M, Lasure A, De Bruyne T, Pieters L, Vlietinck A, Vanden Berghe DA. Structure-activity relationship of flavonoids with superoxide scavenging activity. Biol Trace Elem Res, 1995; 47(1-3):327-31.
16. Jadot G, Michelson AM, Puget K. Anti-inflammatory activity of superoxide dismutases: Studies on adjuvant induced polyarthritis in rats. Free Radical Res Commun, 1986;2(1-2):27-42.
17. Janoff AS, 1999. Liposomes: Rational design. New York: Marcel Dekker. Kamps JA, Scherphof GL. Receptor versus non-receptor mediated clearance of liposomes. Adv Drug Delivery Rev, 1998;32:81-97.
18. Krol W, Czuba Z, Scheller S, Paradowski Z, Shani J. Structure-activity relationship in the ability of flavonols to inhibit chemiluminescence. J Ethnopharmacol, 1994;41:121-6. (Pubitemid 24053238)
19. Limasset B, Ojasoo T, le Doucen C, Doré JC. Inhibition of chemiluminescence in human PMNs by monocyclic phenolic acids and flavonoids. Planta Med, 1999;65:23-9. (Pubitemid 29077423)
20. Lopes LB, Scarpa MV, Silva GV, Rodrigues DC, Santilli CV, Oliveira AG. Studies on the encapsulation of diclofenac in small unilamellar liposomes of soya phosphatidylcholine. Colloids Surf B: Biointerfaces, 2004;39:151-8. (Pubitemid 39536237)
21. López-Pinto JM, González-Rodrćguez ML, Rabasco AM. Effect of cholesterol and ethanol on dermal delivery from DPPC liposomes. Int J Pharm, 2005;298:1-12. (Pubitemid 40828324)
22. Mandal AK, Das N. Sugar coated liposomal flavonoid: A unique formulation in combating carbontetrachloride induced hepatic oxidative damage. J Drug Target, 2005;13:305-15. (Pubitemid 41283164)
23. Mandal AK, Das S, Mitra M, Chakrabarti RN, Chatterjee M, Das N. Vesicular flavonoid in combating diethylnitrosamine induced hepatocarcinoma in rat model. J Exp Ther Oncol, 2008;7:123-33.
24. McCord MM, Fridovich I. Superoxide dismutase an enzymic function for erythrocuprein Hemocuprein. J Biol Chem, 1969;244:6049-55.
25. Metselaar JM, Wauben MH, Wagenaar-Hilbers JP, Boerman OC, Storm G. Complete remission of experimental arthritis by joint targeting of glucocorticoids with long-circulating liposomes. Arthritis Rheum, 2003;48:2059-66. (Pubitemid 36828702)
26. Metselaar JM, van den Berg WB, Holthuysen AE, Waube MH, Storm G, van Lent PL. Liposomal targeting of glucocorticoids to synovial lining cells strongly increases therapeutic benefit in collagen type II arthritis. Ann Rheum Dis, 2004;63:348-53. (Pubitemid 38453298)
27. Michelson AM, Puget K. Medical aspects of superoxide dismutases. C R Seances Soc Biol Fil, 1979;173(2):380-93.
28. Michelson AM, Puget K. Cell penetration by exogenous superoxide dismutase. Acta Physiol Scand Suppl, 1980;492:67-80.
29. Middleton Jr E, Kandaswami C, Theoharides TC. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol Rev, 2000;52:673-751.
30. Miller CR, Bondurant B, McLean SD, McGovern KA, O'Brien DF. Liposome-cell interactions in vitro: Effect of liposome surface charge on the binding and endocytosis of conventional and sterically stabilized liposomes. Biochemistry, 1998;37:12875-83. (Pubitemid 28433520)
31. Mitall CK, Murad F. Activation of guanylate cyclase by superoxide-dismutase and hydroxyl radical - Physiological regulator of guanosine 30,50- monophosphate formation. Proc Natl Acad Sci USA, 1977;74:4360-4. (Pubitemid 8225122)
32. Moreira MR, Kanashiro A, Kabeya LM, Polizello AC, Azzolini AE, Curti C, Oliveira CA, T-do Amaral A, Lucisano-Valim YM. Neutrophil effector functions triggered by Fc-gamma and/or complement receptors are dependent on B-ring hydroxylation pattern and physicochemical properties of flavonols. Life Sci, 2007;81:317-26. (Pubitemid 47033898)
33. Moribe K, Maruyama K, Iwatsuru M. Encapsulation characteristics of nystatin in liposomes: Effects of cholesterol and polyethylene glycol derivatives. Int J Pharm, 1999;188:193-202. (Pubitemid 29486722)
34. Mura P, Maestrelli F, González-Rodr;́guez ML, Michelacci I, Ghelardini C, Rabasco AM. Development, characterization and in vivo evaluation of benzocaine-loaded liposomes. Eur J Pharm Biopharm, 2007;67:86-95. (Pubitemid 46991345)
35. Navas-D?́az A, Garc?́a-Sánchez F, González- Garcia JA. Phenol derivatives as enhancers and inhibitors of luminol-H2O2-horseradish peroxidase chemiluminescence. J Biolumin Chemilumin, 1998;13:75-84.
36. New RRC. 1997. Liposomes: A practical approach. Oxford: IRL Press. Okawa M, Kinjo J, Nohara T, Ono M. DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity of flavonoids obtained from some medicinal plants. Biol Pharm Bull, 2001;24(10):1202-5.
37. Ostrakhovitch EA, Afanas'ev IB. Oxidative stress in rheumatoid arthritis leukocytes: Suppression by rutin and other antioxidants and chelators. Biochem Pharmacol, 2001;62:743-6. (Pubitemid 32816991)
38. Oteiza PI, Erlejman AG, Verstraeten SV, Keen CL, Fraga CG. Flavonoidmembrane interactions: A protective role of flavonoids at the membrane surface? Clin Dev Immunol, 2005;12:19-25. (Pubitemid 41647026)
39. Pannala AS, Chan TS, O0brien PJ, Rice-Evans CA. Flavonoid B-ring chemistry and antioxidant activity: Fast reaction kinetics. Biochem Biophys Res Commun, 2001;282:1161-8. (Pubitemid 32912847)
40. Rackova L, Firakova S, Kostalova D, Stefek M, Sturdik E, Majekova M. Oxidation of liposomal membrane suppressed by flavonoids: Quantitative structure-activity relationship. Bioorg Med Chem, 2005;13:6477-84. (Pubitemid 41539311)
41. Ratnam DV, Ankola DD, Bhardwaj V, Sahana DK, Kumar MN. Role of antioxidants in prophylaxis and therapy: A pharmaceutical perspective. J Control Release, 2006;113:189-207. (Pubitemid 43983041)
42. Saija A, Scalese M, Lanza M, Marzullo D, Bonina F, Castelli F. Flavonoids as antioxidant agents: Importance of their interaction with biomembranes. Free Radical Bio Med, 1995;19:481-6.
43. Scherphof GL, Velinova M, Kamps J, Donga J, Want H, Kuipers F, Haveke L, Daemen T. Modulation of pharmacolinetic behavior of liposomes. Adv Drug Delivery Rev, 1997;24:179-91.
44. Stone WL, Smith M. Therapeutic uses of antioxidant liposomes. Mol Biotechnol, 2004;27:217-30. (Pubitemid 41490590)
45. Tarner IH, Müller-Ladner U. Drug delivery systems for the treatment of rheumatoid arthritis. Expert Opin Drug Deliv, 2008;5:1027-37.
46. Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol, 2007;39:44-84. (Pubitemid 44566469)
47. van Dijk C, Driessen AJ, Recourt K. The uncoupling efficiency and affinity of flavonoids for vesicles. Biochem Pharmacol, 2000;60:1593-600.
48. Verstraeten SV, Keen CL, Schmitz HH, Fraga CG, Oteiza PI. Flavan-3-ols and procyanidins protect liposomes against lipid oxidation and disruption of the bilayer structure. Free Radical Biol Med, 2003;34:84-92. (Pubitemid 36043889)
49. Yang H, Paromov V, Smith M, Stone WL. Preparation, characterization, and use of antioxidant-liposome. Methods Mol Biol, 2008;477:277-92.
50. Yokozawa T, Chen CP, Dong E, Tanaka T, Nonaka GI, Nishioka I. Study on the inhibitory effect of tannins and flavonoids against the 1,1-diphenyl-2 picrylhydrazyl radical. Biochem Pharmacol, 1998;56(2):213-22. (Pubitemid 28479829)