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

References

• Berliner LJ, Reuben J. Spin labeling I and II, theory and applications. Vols. 1 and 2 New York: Clarendon Press; 1976 and 1979.
   Google Scholar
• Krishna MC, Samuni A. Nitroxides as antioxidants. Methods Enzymol 1994;234:580–589.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• Greci L. Homolytic substitution in indolinone nitroxide radicals. Part 3. Reactions with terbutoxy and methyl radical. Tetrahedron 1982;38:2435–2439.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• Damiani E, Greci L, Rizzoli C. Reaction of indolinonic aminoxyls with nitric oxide. J Chem Soc, Perkin Trans 2001;2:1139–1144.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• Damiani E, Paganga G, Greci L, Rice-Evans C. Inhibition of copper mediated low-density lipoprotein peroxidation by quinoline and indolinone nitroxide radicals. Biochem Phar-macol 1994;48:1155–1161.
   Google Scholar
• Buschmann HJ, Schollmayer L. Application of cyclodextrins in cosmetic products: A review. J Cosmet Sci 2002;53:185–191.
   PubMed Web of Science ®Google Scholar
• Szente L, Mikuni K, Hashimoto H, Szejtli J. Stabilization and solubilization of lipophilic natural colorants with cyclodex-trins. J Inclusion Phenom Mol Recognit Chem 1998;32:81–89.
   Web of Science ®Google Scholar
• Loftsson T, Brewster ME. Pharmaceutical application of cylcodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 1996;85:1017–1025.
   PubMed Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodex-trins. 2. In vivo drug delivery. J Pharm Sci 1996;85:1142–1169.
   PubMed Web of Science ®Google Scholar
• Uekama K, Hirayama F, Irie T. Cyclodextrin drug carrier systems. Chem Rev 1998;98:2045–2076.
   PubMed Web of Science ®Google Scholar
• Berti C, Colonna M, Greci L, Marchetti L. Stable nitroxide radicals from phenylisatogen and arylimino derivatives with organometallic compounds. Tetrahedron 1975;31:1745–1753.
   Web of Science ®Google Scholar
• Danek S, Kelly DP, Serelis AK, Steel PJ. A stereospecific synthesis of azonitriles. J Org Chem 1987;52:2911–2919.
   Google Scholar
• Higuchi T, Connors KA. Phase-Solubility techniques. advances in analytical chemistry instrumentation. 4 New York: Wiley Interscience; 1965. p 117–212.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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.
   Google Scholar
• Moyano J, Gines J, Arias M, Rabasco A. Study of the dissolution characteristics of oxazepam via complexation with 3-cyclodextrin. Int J Pharm 1995;114:95–102.
   Web of Science ®Google Scholar
• Hedges AR. Industrial applications of cyclodextrins. Chem Rev 1998;98:2035–2044.
   PubMed Web of Science ®Google Scholar
• Kotake Y, Janzen EG. Electron nuclear double resonance detection of distinct multimoldal inclusion complexes of 3-cyclodextrin with a nitroxide spin adduct probe. J Am Chem Soc 1992;114:2872–2874.
   Google Scholar
• Franchi P, Lucarini M, Pedulli G-F. Detection of paramag-netic pH-dependent inclusion complexes between B-cyclodex-trin dimers and nitroxide radicals. Angew. Chem. Int. Ed. 2003;42:1842–1845.
   Google Scholar
• Niki E. Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol. 1990;186: 100–108.
   PubMed Web of Science ®Google Scholar
• 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 3-cyclodextrin as the solubility enhancer. J Agric Food Chem 2002;50: 1815–1821.
   Google Scholar
• Iaconinoto A, Chicca M, Pinamonti S, Casolari A, Bianchi A, Scalia S. Influcence of cyclodextrin complexation on the photodegradation and antioxidant activity of alpha-toco-pherol. Pharmazie 2004;59:30–33.
   PubMed Web of Science ®Google Scholar
• Polyakov NE, Leshina TV, Konovalova TA, Hand OE, Kispert LD. Inclusion complexes of carotenoids with cyclodextrins: NMR, EPR, and optical studies. Free Radic Biol Med 2004;36:872–880.
   Google Scholar
• Calabro ML, Tommasini S, Donato P, Raneri D, Stancanelli R, Ficarra P, Ficarra R, Costa C, Catania S, Rustichelli C, Gamberini G. Effects of a- and 3-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones. J Pharm Biomed Anal 2004;35: 365–377.
   Google Scholar
• Karoui H, Tordo P. ESR-spin trapping in the presence of cyclodextrins. Detection of PBN-superoxide spin adduct. Tetrahedron Lett. 2004;45:1043–1045.
   Web of Science ®Google Scholar
• 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.
   Google Scholar
• Stella VJ, Rao MV, Zannou EA, Zia V. Mechanisms of drug release from cyclodextrin complexes. Adv Drug Deliv Rev 1999;36:3–16.
   PubMed Web of Science ®Google Scholar
• Beckwith AU, Bowry VW, Ingold KU. Kinetics of nitroxyl radical trapping. 1. Solvent effects. J Am Chem Soc 1992;114: 4983–4992.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar