In Vitro and In Vivo Evaluation of Hydrophilic C 60 (OH) 10 /2-Hydroxypropyl-β-cyclodextrin Nanoparticles as an Antioxidant

Jensen, 1996, Biological applications of fullerenes, Bioorg Med Chem, 4, 767, 10.1016/0968-0896(96)00081-8 Bakry, 2007, Medicinal applications of fullerenes, Int J Nanomed, 2, 639 McEwen, 1992, C60 as a radical sponge, J Am Chem Soc, 114, 4412, 10.1021/ja00037a064 Markovic, 2008, Biomedical potential of the reactive oxygen species generation and quenching by fullerenes (C60), Biomaterials, 29, 3561, 10.1016/j.biomaterials.2008.05.005 Maeda-Mamiya, 2010, In vivo gene delivery by cationic tetraamino fullerene, Proc Natl Acad Sci U S A, 107, 5339, 10.1073/pnas.0909223107 Zakharian, 2005, A fullerene-paclitaxel chemotherapeutic: synthesis, characterization, and study of biological activity in tissue culture, J Am Chem Soc, 127, 12508, 10.1021/ja0546525 Kato, 2009, Highly hydroxylated or γ-cyclodextrin-bicapped water-soluble derivative of fullerene: the antioxidant ability assessed by electron spin resonance method and β-carotene bleaching assay, Bioorg Med Chem Lett, 19, 5293, 10.1016/j.bmcl.2009.07.149 Heymann, 1996, Solubility of fullerenes C60 and C70 in seven normal alcohols and their deduced solubility in water, Fullerene Sci Technol, 4, 509, 10.1080/10641229608001567 Ruoff, 1993, Solubility of fullerene (C60) in a variety of solvents, J Phys Chem, 97, 3379, 10.1021/j100115a049 Nath, 1998, Aggregation of fullerene, C60, in benzonitrile, J Phys Chem B, 102, 10158, 10.1021/jp9824149 Alargova, 2001, Stable colloidal dispersions of fullerenes in polar organic solvents, J Am Chem Soc, 123, 10460, 10.1021/ja010202a Brant, 2006, Characterizing the impact of preparation method on fullerene cluster structure and chemistry, Langmuir, 22, 3878, 10.1021/la053293o Ikeda, 1997, Solution complexes formed from C60 and calixarenes. On the importance of the preorganized structure for cooperative interactions, Tetrahedron Lett, 38, 2107, 10.1016/S0040-4039(97)00318-3 Yoshida, 1994, Molecular recognition of C60 with γ-cyclodextrin, Angew Chem Int Ed Engl, 33, 1597, 10.1002/anie.199415971 Xiao, 2006, The water-soluble fullerene derivative 'Radical Sponge' exerts cytoprotective action against UVA irradiation but not visible-light-catalyzed cytotoxicity in human skin keratinocytes, Bioorg Med Chem Lett, 16, 1590, 10.1016/j.bmcl.2005.12.011 Iwamoto, 2006, A highly water-soluble C60-NVP copolymer: a potential material for photodynamic therapy, Chem Commun (Camb), 4805, 10.1039/B614305A Ikeda, 2010, Photodynamic activity of liposomal photosensitizers via energy transfer from antenna molecules to [60]fullerene, ACS Med Chem Lett, 1, 115, 10.1021/ml100021x Iohara, 2011, Formation of stable hydrophilic C60 nanoparticles by 2-hydroxypropyl-β-cyclodextrin, Mol Pharm, 8, 1276, 10.1021/mp200204v Iohara, 2012, Evaluation of photodynamic activity of C60/2-hydroxypropyl-β-cyclodextrin nanoparticles, J Pharm Sci, 101, 3390, 10.1002/jps.23045 Altaf, 2014, Potential use of C60/2-hydroxypropyl-β-cyclodextrin nanoparticles as a new photosensitizer in the treatment of cancer, Int J Photoenergy, 2014, 570506/1, 10.1155/2014/570506 Umezaki, 2015, Preparation of hydrophilic C60(OH)10/2-hydroxypropyl-β-cyclodextrin nanoparticles for the treatment of a liver injury induced by an overdose of acetaminophen, Biomaterials, 45, 115, 10.1016/j.biomaterials.2014.12.032 Eropkin, 2013, Synthesis and biological activity of fullerenols with various contents of hydroxyl groups, Pharm Chem J, 47, 87, 10.1007/s11094-013-0901-x Fileti, 2008, Effects of hydroxyl group distribution on the reactivity, stability and optical properties of fullerenols, Nanotechnology, 19, 365703/1, 10.1088/0957-4484/19/36/365703 Kokubo, 2008, Facile synthesis of highly water-soluble fullerenes more than half-covered by hydroxyl groups, ACS Nano, 2, 327, 10.1021/nn700151z Mirkov, 2004, Nitric oxide-scavenging activity of polyhydroxylated fullerenol, C60(OH)24, Nitric Oxide, 11, 201, 10.1016/j.niox.2004.08.003 Jin, 2000, Polyhydroxylated C60, fullerenols, as glutamate receptor antagonists and neuroprotective agents, J Neurosci Res, 62, 600, 10.1002/1097-4547(20001115)62:4<600::AID-JNR15>3.0.CO;2-F Chen, 2004, Fullerene derivatives protect against oxidative stress in RAW 264.7 cells and ischemia-reperfused lungs, Am J Physiol Regul Integr Comp Physiol, 287, R21, 10.1152/ajpregu.00310.2003 Injac, 2009, Protective effects of fullerenol C60(OH)24 against doxorubicin-induced cardiotoxicity and hepatotoxicity in rats with colorectal cancer, Biomaterials, 30, 1184, 10.1016/j.biomaterials.2008.10.060 Injac, 2008, Potential hepatoprotective effects of fullerenol C60(OH)24 in doxorubicin-induced hepatotoxicity in rats with mammary carcinomas, Biomaterials, 29, 3451, 10.1016/j.biomaterials.2008.04.048 Squadrito, 1998, Oxidative chemistry of nitric oxide: the roles of superoxide, peroxynitrite, and carbon dioxide, Free Radic Biol Med, 25, 392, 10.1016/S0891-5849(98)00095-1 Quideau, 2011, Plant polyphenols: chemical properties, biological activities, and synthesis, Angew Chem Int Ed Engl, 50, 586, 10.1002/anie.201000044 Rice-Evans, 1996, Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free Radic Biol Med, 20, 933, 10.1016/0891-5849(95)02227-9 Husebo, 2004, Fullerenols revisited as stable radical anions, J Am Chem Soc, 126, 12055, 10.1021/ja047593o Satoh, 2002, Edarabone scavenges nitric oxide, Redox Rep, 7, 219, 10.1179/135100002125000587 Yamamoto, 1996, Antioxidant activity of 3-methyl-1-phenyl-2-pyrazolin-5-one, Redox Rep, 2, 333, 10.1080/13510002.1996.11747069 Watanabe, 2004, Research and development of the free radical scavenger edaravone as a neuroprotectant, Yakugaku Zasshi, 124, 99, 10.1248/yakushi.124.99 Archer, 1990, Effects of ascorbate on myogenesis in micromass culture, In Vitro Cell Dev Biol, 26, 259, 10.1007/BF02624455 Hata, 1989, L-Ascorbic acid 2-phosphate stimulates collagen accumulation, cell proliferation, and formation of a three-dimensional tissuelike substance by skin fibroblasts, J Cell Physiol, 138, 8, 10.1002/jcp.1041380103 Nakagawa, 2011, Cytotoxic effects of hydroxylated fullerenes on isolated rat hepatocytes via mitochondrial dysfunction, Arch Toxicol, 85, 1429, 10.1007/s00204-011-0688-z Hinson, 1998, Nitrotyrosine-protein adducts in hepatic centrilobular areas following toxic doses of acetaminophen in mice, Chem Res Toxicol, 11, 604, 10.1021/tx9800349 LoGuidice, 2011, Acetaminophen overdose-induced liver injury in mice is mediated by peroxynitrite independently of the cyclophilin d-regulated permeability transition, Hepatology, 54, 969, 10.1002/hep.24464 Ji, 2006, Biodistribution and tumor uptake of C60(OH)x in mice, J Nanopart Res, 8, 53, 10.1007/s11051-005-9001-5 Qingnuan, 2002, Preparation of 99mTc-C60(OH)x and its biodistribution studies, Nucl Med Biol, 29, 707, 10.1016/S0969-8051(02)00313-X