Novel polyhydroxylated fullerene suppresses intracellular oxidative stress together with repression of intracellular lipid accumulation during the differentiation of OP9 preadipocytes into adipocytes

References

• Yin JJ, Lao F, Fu PP, Wamer WG, Zhao Y, Wang PC, Qiu Y, Sun B, Xing G, Dong J, Liang XJ, Chen C. The scavenging of reactive oxygen species and the potential for cell protection by functionalized fullerene materials. Biomaterials 2009;30:611–621.
   PubMed Web of Science ®Google Scholar
• Yamawaki H, Iwai N. Cytotoxicity of water-soluble fullerene in vascular endothelial cells. Am J Physiol Cell Physiol 2006;290:1495–1502.
   PubMed Web of Science ®Google Scholar
• Tsai MC, Chen YH, Chiang LY. Polyhydroxylated C60, fullerenol, a novel free-radical trapper, prevented hydrogen peroxide- and cumene hydroperoxide-elicited changes in rat hippocampus in vitro. J Pharm Pharmacol 1997;49: 438–445.
   PubMed Web of Science ®Google Scholar
• Chiang LY, Lu F-J, Lin J-T. Free radical scavenging activity of water-soluble fullerenols. J Chem Soc Chem Commun 1995; 12:1283–1284.
   Google Scholar
• Lai HS, Chen Y, Chen WJ, Chang J, Chiang LY. Free radical scavenging activity of fullerenol on grafts after small bowel transplantation in dogs. Transplant Proc 2000;32:1272–1274.
   PubMedGoogle Scholar
• Lai HS, Chen WJ, Chiang LY. Free radical scavenging activity of fullerenol on the ischemia-reperfusion intestine in dogs. World J Surg 2000;24:450–454.
   PubMedGoogle Scholar
• Kato S, Aoshima H, Saitoh Y, Miwa N. Highly hydroxylated or gamma-cyclodextrin-bicapped water-soluble derivative of fullerene: the antioxidant ability assessed by electron spin resonance method and beta-carotene bleaching assay. Bioorg Med Chem Lett 2009;19:5293–5296.
   Google Scholar
• Kamat JP, Devasagayam TP, Priyadarsini KI, Mohan H. Reactive oxygen species mediated membrane damage induced by fullerene derivatives and its possible biological implications. Toxicology 2000;155:55–61.
   PubMed Web of Science ®Google Scholar
• Isakovic A, Markovic Z, Todorovic-Markovic B, Nikolic N, Vranjes-Djuric S, Mirkovic M, Dramicanin M, Harhaji L, Raicevic N, Nikolic Z, Trajkovic V. Distinct cytotoxic mechanisms of pristine versus hydroxylated fullerene. Toxicol Sci 2006;91:173–183.
   PubMed Web of Science ®Google Scholar
• Dugan LL, Gabrielsen JK, Yu SP, Lin TS, Choi DW. Buckminsterfullerenol free radical scavengers reduce excitotoxic and apoptotic death of cultured cortical neurons. Neurobiol Dis 1996;3:129–135.
   PubMed Web of Science ®Google Scholar
• Djordjevic A, Bogdanovic G, Dobric S. Fullerenes in biomedicine. J BUON 2006;11:391–404.
   PubMedGoogle Scholar
• Lai YL, Chiang LY. Water-soluble fullerene derivatives attenuate exsanguination-induced bronchoconstriction of guinea-pigs. J Auton Pharmacol 1997;17:229–235.
   PubMedGoogle Scholar
• Jin H, Chen WQ, Tang XW, Chiang LY, Yang CY, Schloss JV, Wu JY. Polyhydroxylated C60, fullerenols, as glutamate receptor antagonists and neuroprotective agents. J Neurosci Res 2000;62:600–607.
   PubMed Web of Science ®Google Scholar
• Chen YW, Hwang KC, Yen CC, Lai YL. Fullerene derivatives protect against oxidative stress in RAW 264.7 cells and ischemia-reperfused lungs. Am J Physiol Regul Integr Comp Physiol 2004;287:21–26.
   PubMed Web of Science ®Google Scholar
• Bogdanovic G, Kojic V, Dordevic A, Canadanovic-Brunet J, Vojinovic-Miloradov M, Baltic VV. Modulating activity of fullerol C60(OH)22 on doxorubicin-induced cytotoxicity. Toxicol In Vitro 2004;18:629–637.
   PubMed Web of Science ®Google Scholar
• Lu LH, Lee YT, Chen HW, Chiang LY, Huang HC. The possible mechanisms of the antiproliferative effect of fullerenol, polyhydroxylated C60, on vascular smooth muscle cells. Br J Pharmacol 1998;123:1097–1102.
   PubMedGoogle Scholar
• Roursgaard M, Poulsen SS, Kepley CL, Hammer M, Nielsen GD, Larsen ST. Polyhydroxylated C60 fullerene (fullerenol) attenuates neutrophilic lung inflammation in mice. Basic Clin Pharmacol Toxicol 2008;103:386–388.
   PubMed Web of Science ®Google Scholar
• Cai X, Jia H, Liu Z, Hou B, Luo C, Feng Z, Li W, Liu J. Polyhydroxylated fullerene derivative C(60)(OH)(24) prevents mitochondrial dysfunction and oxidative damage in an MPP(+) -induced cellular model of Parkinson’s disease. J Neurosci Res 2008;86:3622–3634.
   PubMed Web of Science ®Google Scholar
• Kopelman PG. Obesity as a medical problem. Nature-. 2000;404:635–643.
   PubMed Web of Science ®Google Scholar
• Furukawa S, Fujita T, Shimabukuro M, Iwaki M, Yamada Y, Nakajima Y, Nakayama O, Makishima M, Matsuda M, Shimomura I. Increased oxidative stress in obesity and its impact on metabolic syndrome. J Clin Invest. 2004;114:1752-1761.
   PubMed Web of Science ®Google Scholar
• Urakawa H, Katsuki A, Sumida Y, Gabazza EC, Murashima S, Morioka K, Maruyama N, Kitagawa N, Tanaka T, Hori Y, Nakatani K, Yano Y, Adachi . Oxidative stress is associated with adiposity and insulin resistance in men. J Clin Endocrinol Metab 2003;88:4673–4676.
   PubMed Web of Science ®Google Scholar
• Matsuzawa-Nagata N, Takamura T, Ando H, Nakamura S, Kurita S, Misu H, Ota T, Yokoyama M, Honda M, Miyamoto K, Kaneko S. Increased oxidative stress precedes the onset of high-fat diet-induced insulin resistance and obesity. Metabolism 2008;57:1071–1077.
   PubMed Web of Science ®Google Scholar
• Diniz YS, Rocha KK, Souza GA, Galhardi CM, Ebaid GM, Rodrigues HG, Novelli Filho JL, Cicogna AC, Novelli EL. Effects of N-acetylcysteine on sucrose-rich diet-induced hyperglycaemia, dyslipidemia and oxidative stress in rats. Eur J Pharmacol 2006;543:151–157.
   PubMed Web of Science ®Google Scholar
• Wolins NE, Quaynor BK, Skinner JR, Tzekov A, Park C, Choi K, Bickel PE. OP9 mouse stromal cells rapidly differentiate into adipocytes: characterization of a useful new model of adipogenesis. J Lipid Res 2006;47:450–460.
   PubMed Web of Science ®Google Scholar
• Kokubo K, Matsubayashi K, Tategaki H, Takada H, Oshima T. Facile synthesis of highly water-soluble fullerenes more than half-covered by hydroxyl groups. ACS Nano 2008;2: 327–333.
   PubMed Web of Science ®Google Scholar
• Ramirez-Zacarias JL, Castro-Munozledo F, Kuri-Harcuch W. Quantitation of adipose conversion and triglycerides by staining intracytoplasmic lipids with Oil red O. Histochemistry 1992;97:493–497.
   PubMedGoogle Scholar
• Schrenzel J, Serrander L, Bánfi B, Nüsse O, Fouyouzi R, Lew DP, Demaurex N, Krause . Electron currents generated by the human phagocyte NADPH oxidase. Nature 1998;392: 734–737.
   PubMed Web of Science ®Google Scholar
• Emmons C, Peterson DM. Antioxidant activity and phenolic contents of oat groats and hulls. Cereal Chemistry 1999;76: 902–906.
   Web of Science ®Google Scholar
• Lin Y, Berg AH, Iyengar P, Lam TK, Giacca A, Combs TP, . The hyperglycemia-induced inflammatory response in adipocytes: the role of reactive oxygen species. J Biol Chem 2005;280:4617–4626.
   PubMed Web of Science ®Google Scholar
• Aoshima H, Kokubo K, Shirakawa S, Ito M, Yamana S, Oshima T. Antimicrobial activity of fullerenes and their hydroxylated derivatives. Biocontrol Sci 2009;14:69–72.
   PubMedGoogle Scholar
• Chiang LY, Wang LY, Swirczewski JW, Soled S, Cameron S. Efficient synthesis of polyhydroxylated fullerene derivatives via hydrolysis of polycyclosulfated precursors. J Org Chem 1994;59:3960–3968.
   Web of Science ®Google Scholar
• Wang S, He P, Zhang J-M, Jiang H, Zhu S-Z. Novel and efficient synthesis of water-soluble [60] fullerenol by solvent-free reaction. Synth Commun 2005;35:1803–1807.
   Web of Science ®Google Scholar
• Sayes C, Fortner JD, Guo W, Lyon D, Boyd AM, Ausman KD, Tao YJ, Sitharaman B, Wilson LJ, Hughes J, West JL, Colvin VL. The differential cytotoxicity of water-soluble fullerenes. Nano Letters 2004;4:1881–1887.
   Web of Science ®Google Scholar
• Sayes CM, Gobin AM, Ausman KD, Mendez J, West JL, Colvin VL. Nano-C60 cytotoxicity is due to lipid peroxidation. Biomaterials 2005;26:7587–7595.
   PubMed Web of Science ®Google Scholar
• Wolfram S, Wang Y, Thielecke F. Anti-obesity effects of green tea: from bedside to bench. Mol Nutr Food Res 2006;50:176–187.
   PubMed Web of Science ®Google Scholar
• Moon HS, Chung CS, Lee HG, Kim TG, Choi YJ, Cho CS. Inhibitory effect of (-)-epigallocatechin-3-gallate on lipid accumulation of 3T3-L1 cells. Obesity (Silver Spring) 2007; 15:2571–2582.
   PubMed Web of Science ®Google Scholar
• Morikawa K, Ikeda C, Nonaka M, Pei S, Mochizuki M, Mori A, Yamada S. Epigallocatechin gallate-induced apoptosis does not affect adipocyte conversion of preadipocytes. Cell Biol Int 2007;31:1379–1387.
   Google Scholar
• Morikawa K, Nonaka M, Mochizuki H, Handa K, Hanada H, Hirota K. Naringenin and hesperetin induce growth arrest, apoptosis, and cytoplasmic fat deposit in human preadipocytes. J Agric Food Chem 2008;56:11030–11037.
   Google Scholar
• Yang JY, Della-Fera MA, Rayalam S, Ambati S, Hartzell DL, Park HJ, Baile CA. Enhanced inhibition of adipogenesis and induction of apoptosis in 3T3-L1 adipocytes with combinations of resveratrol and quercetin. Life Sci 2008;82:1032–1039.
   PubMed Web of Science ®Google Scholar
• Rayalam S, Yang JY, Ambati S, Della-Fera MA, Baile CA. Resveratrol induces apoptosis and inhibits adipogenesis in 3T3-L1 adipocytes. Phytother Res 2008;22:1367–1371.
   PubMed Web of Science ®Google Scholar
• Xiao Y, Yuan T, Yao W, Liao K. 3T3-L1 adipocyte apoptosis induced by thiazolidinediones is peroxisome proliferator- activated receptor-gamma-dependent and mediated by the caspase-3-dependent apoptotic pathway. FEBS J 2010;277: 687–696.
   Google Scholar