Effect of complexation with randomly methylated β-cyclodextrin on the aqueous solubility, photostability and antioxidant activity of an indolinonic nitroxide radical

Free Radical Research

Volumn 39, Issue 1, 2005, Pages 41-49

  Damiani, Elisabetta ^a   Tursilli, Rosanna ^b   Casolari, Alberto ^b   Astolfi, Paola ^a   Greci, Lucedio ^a   Scalia, Santo ^b  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

Aqueous solubility; Complexation; Cyclodextrin; Indolinonic nitroxide; Photodegradation; Sntioxidant activity

Indexed keywords

1,2 DIHYDRO 2 METHYL 2 PHENYL 3H INDOLE 3 ONE 1 OXYL; ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; FREE RADICAL; GAMMA CYCLODEXTRIN; NITROXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; FREEZE DRYING; METHYLATION; MICELLE; OXIDATION; PEROXIDATION; PHOTODEGRADATION; PROTECTION; SOLID STATE; SOLUBILIZATION; STRUCTURE ACTIVITY RELATION; THERMAL ANALYSIS; X RAY POWDER DIFFRACTION;

ANTIOXIDANTS; BETA-CYCLODEXTRINS; CHEMISTRY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HEAT; INDOLES; KINETICS; LIGHT; LINOLEIC ACIDS; METHYLATION; MODELS, CHEMICAL; NITROGEN OXIDES; OXYGEN; PHOTOCHEMISTRY; SOLUBILITY; TEMPERATURE; TIME FACTORS; WATER; X-RAY DIFFRACTION;

EID: 14644420298     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760400023689     Document Type: Article

References (45)

1. Berliner LJ, Reuben J. Spin labeling I and II, theory and applications. Vols. 1 and 2 New York: Clarendon Press; 1976 and 1979.
2. Krishna MC, Samuni A. Nitroxides as antioxidants. Methods Enzymol 1994;234:580-589.
3. Mitchell JB, Krishna MC, Samuni A. Nitroxides as protectors against oxidative stress. In: Colton C, Gilbert D, editors. Reactive Oxygen Species in Biological Systems. New York: Plenum Press; 1999. p 293-313.
4. Samuni A, Krishna MC. Antioxidant properties of nitroxides and nitroxide SOD mimics. In: Packer L, Cadenas E, editors. Handbook of synthetic antioxidants. New York: Marcel Dekker; 1997. p 351-373.
5. Carloni P, Greci L, Stipa P, Eberson L. Electron-transfer reactions. Oxidation of Grignard reagents in the presence of aminoxyl as a radical trapping agent. J Org Chem 1991;56:4733-4737.
6. Damiani E, Carloni P, Iacussi M, Stipa P, Greci L. Reactivity of sulfur-centered radicals with indolinonic and quinolinic aminoxyls. Eur J Org Chem 1999;1:2405-2412.
7. Carloni P, Cardellini L, Greci L, Stipa P, Faucitano A. Homolytic substitution in indolinone nitroxide radicals. Part 5. Reactions with tert-butylperoxy radicals. Gazz Chim Ital 1989;119:621-625.
8. Greci L. Homolytic substitution in indolinone nitroxide radicals. Part 3. Reactions with terbutoxy and methyl radical. Tetrahedron 1982;38:2435-2439.
9. Damiani E, Carloni P, Stipa P, Greci L. Reactivity of an indolinonic aminoxyl with superoxide anion and hydroxyl radicals. Free Radic Res 1999;31:113-121.
10. Carloni P, Damiani E, Greci L, Stipa P, Marrosu G, Petrucci R, Trazza A. Chemical and electrochemical study on the interactions of aminoxyls with superoxide anion. Tetrahedron 1996;52:11257-11264.
11. Damiani E, Greci L, Rizzoli C. Reaction of indolinonic aminoxyls with nitric oxide. J Chem Soc, Perkin Trans 2001;2:1139-1144.
12. Damiani E, Belaid C, Carloni P, Greci L. Comparison of antioxidant activity between aromatic indolinonic nitroxides and natural and synthetic antioxidants. Free Radic Res 2003;37:731-741.
13. Fedeli D, Damiani E, Greci L, Littarru GP, Falcioni G. Nitroxide radicals protect against DNA damage in rat epithelial cells induced by nitric oxide, nitroxyl anion and peroxynitrite. Mutation Res 2003;535:117-125.
14. Damiani E, Carloni P, Biondi C, Greci L. Increased oxidative modification of albumin when illuminated in vitro in the presence of a common sunscreen ingredient; protection by nitroxide radicals. Free Radic Biol Med 2001;28:193-201.
15. Damiani E, Kalinska B, Canapa A, Canestrari S, Wozniak M, Olmo E, Greci L. The effects of nitroxide radicals on oxidative DNA damage. Free Radic Biol Med 2000;28:1257-1265.
16. Gabbianelli R, Falcioni G, Santroni AM, Caulini G, Greci L, Damiani E. Effect of aromatic nitroxides on hemolysis of human erythrocytes entrapped with isolated hemoglobin chains. Free Radic Biol Med 1997;23:278-281.
17. Antosiewicz J, Popinigis J, Wozniak M, Damiani E, Carloni P, Greci L. Effects of indolinic and quinolinic and indolinonic aminoxyls on protein and lipid peroxidation of rat liver microsomes. Free Radic Biol Med 1995;22:249-255.
18. Damiani E, Paganga G, Greci L, Rice-Evans C. Inhibition of copper mediated low-density lipoprotein peroxidation by quinoline and indolinone nitroxide radicals. Biochem Pharmacol 1994;48:1155-1161.
19. Buschmann HJ, Schollmayer L. Application of cyclodextrins in cosmetic products: A review. J Cosmet Sci 2002;53:185-191.
20. Szente L, Mikuni K, Hashimoto H, Szejtli J. Stabilization and solubilization of lipophilic natural colorants with cyclodextrins. J Inclusion Phenom Mol Recognit Chem 1998;32:81-89.
21. Loftsson T, Brewster ME. Pharmaceutical application of cylcodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 1996;85:1017-1025.
22. Szente L, Szejtli J, Szeman J, Kato L. Fatty-acid cyclodextrin complexes - properties and applications. J. Inclusion Phenom. Mol. Recognit. Chem. 1993;16:339-354.
23. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci 1996;85:1142-1169.
24. Uekama K, Hirayama F, Irie T. Cyclodextrin drug carrier systems. Chem Rev 1998;98:2045-2076.
25. Berri C, Colonna M, Greci L, Marchetti L. Stable nitroxide radicals from phenylisatogen and arylimino derivatives with organometallic compounds. Tetrahedron 1975;31:1745-1753.
26. Danek S, Kelly DP, Serelis AK, Steel PJ. A stereospecific synthesis of azonitriles. J Org Chem 1987;52:2911-2919.
27. Higuchi T, Connors KA. Phase-Solubility techniques. advances in analytical chemistry instrumentation. 4 New York: Wiley Interscience; 1965. p 117-212.
28. Foti M, Piattelli M, Baratta MT, Ruberto G. Flavonoids, Coumarins and Cinnamic acids as antioxidants in a micellar system. Structure - Activity Relationships. J Agric Food Chem 1996;44:497-501.
29. Levine RL, Garland K, Oliver CN, Amici A, Climent I, Lenz AG, Ahn BW, Shaltiel S, Stadtman ER. Determination of carbonyl content in oxidatively modified proteins. Methods Enzymol. 1990;186:464-478.
30. Liu X, Lin H-S, Thenmozhiyal JC, Chan SY, Ho PC. Inclusion of acitrein into cyclodextrins: Phase solubility, photostability and physicochemical characterization. J Pharm Sci 2003;92:2449-2457.
31. Moyano J, Gines J, Arias M, Rabasco A. Study of the dissolution characteristics of oxazepam via complexation with β-cyclodextrin. Int J Pharm 1995;114:95-102.
32. Hedges AR. Industrial applications of cyclodextrins. Chem Rev 1998;98:2035-2044.
33. Kotake Y, Janzen EG. Electron nuclear double resonance detection of distinct multimoldal inclusion complexes of β-cyclodextrin with a nitroxide spin adduct probe. J Am Chem Soc 1992;114:2872-2874.
34. Franchi P, Lucarini M, Pedulli G-F. Detection of paramagnetic pH-dependent inclusion complexes between β-cyclodextrin dimers and nitroxide radicals. Angew. Chem. Int. Ed. 2003;42:1842-1845.
35. Niki E. Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol. 1990;186: 100-108.
36. Huang D, Ou B, Woodill-Hampsch M, Flanagan JA, Deemer EK. Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated β-cyclodextrin as the solubility enhancer. J Agric Food Chem 2002; 50:1815-1821.
37. Iaconinoto A, Chicca M, Pinamonti S, Casolari A, Bianchi A, Scalia S. Influcence of cyclodextrin complexation on the photodegradation and antioxidant activity of alpha-tocopherol. Pharmazie 2004;59:30-33.
38. 1H NMR, EPR, and optical studies. Free Radic Biol Med 2004;36:872-880.
39. Calabrò ML, Tommasini S, Donato P, Raneri D, Stancanelli R, Ficarra P, Ficarra R, Costa C, Catania S, Rustichelli C, Gamberini G. Effects of α- and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones. J Pharm Biomed Anal 2004;35:365-377.
40. Karoui H, Tordo P. ESR-spin trapping in the presence of cyclodextrins. Detection of PBN-superoxide spin adduct. Tetrahedron Lett. 2004;45:1043-1045.
41. Scalia S, Casolari A, Iaconinoto A, Simeoni S. Comparative studies of the influence of cyclodextrins on the stability of the sunscreen agent 2-ethylhexyl-p-methoxycinnamate. J Pharm Biomed Anal 2002;20:1181-1189.
42. Stella VJ, Rao MV, Zannou EA, Zia V. Mechanisms of drug release from cyclodextrin complexes. Adv Drug Deliv Rev 1999;36:3-16.
43. Beckwith ALJ, Bowry VW, Ingold KU. Kinetics of nitroxyl radical trapping. 1. Solvent effects. J Am Chem Soc 1992;114:4983-4992.
44. Goldstein S, Merenyi G, Russo A, Samuni A. The role of oxoammonium cation in the SOD-mimic activity of cyclic nitroxides. J Am Chem Soc 2003;125:789-795.
45. Samuni A, Goldstein S, Russo A, Mitchell JB, Krishna MC, Neta P. Kinetics and mechanism of hydroxyl radical and OH-adduct radical reactions with nitroxides and with their hydroxylamines. J Am Chem Soc 2002;124:8719-8724.