Radical Reactions of C
            <sub>60</sub>

Krusic, Paul J.; Wasserman, E.; Keizer, P. N.; Morton, J. R.; Preston, K. F.

doi:10.1126/science.254.5035.1183

Cited by 896 publications

(512 citation statements)

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“…C60 fullerene, as a radical sponge, inactivates multiple circulating free radicals, thus having the potential to stop free radical injury and to halt the progression of diseases caused by excess free radical production (33)(34)(35). It is well known that C60 can effectively protect against all of the principal damaging forms of ROS: hydrogen peroxide, hydroxyl radical, and superoxide (35).…”

Section: Discussionmentioning

confidence: 99%

“…It is well known that C60 can effectively protect against all of the principal damaging forms of ROS: hydrogen peroxide, hydroxyl radical, and superoxide (35).…”

Section: Discussionmentioning

confidence: 99%

“…This compound has high reactivity with oxygen-derived free radicals and functions potentially as a free-radical scavenger. It has been reported that the antioxidant level of C60 fullerene is several hundred-fold higher than that of other antioxidants (35).…”

mentioning

confidence: 89%

“…Fullerene (C60) is known as a spheric carbon molecule with a unique cage structure (33,34), and is characterized as a strong radical sponge (35). This compound has high reactivity with oxygen-derived free radicals and functions potentially as a free-radical scavenger.…”

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confidence: 99%

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Water‐soluble C60 fullerene prevents degeneration of articular cartilage in osteoarthritis via down‐regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development

Yudoh

Shishido

Murayama

et al. 2007

Arthritis & Rheumatism

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Objective. Studies have shown the roles of oxidative stress in the pathogenesis of osteoarthritis (OA) and induction of chondrocyte senescence during OA progression. The aim of this study was to examine the potential of a strong free-radical scavenger, watersoluble fullerene (C60), as a protective agent against catabolic stress-induced degeneration of articular cartilage in OA, both in vitro and in vivo.Methods. In the presence or absence of C60 (100 M), human chondrocytes were incubated with interleukin-1␤ (10 ng/ml) or H 2 O 2 (100 M), and chondrocyte activity was analyzed. An animal model of OA was produced in rabbits by resection of the medial meniscus and medial collateral ligament. Rabbits were divided into 5 subgroups: sham operation or treatment with C60 at 0.1 M, 1 M, 10 M, or 40 M. The left knee joint was injected intraarticularly with watersoluble C60 (2 ml), while, as a control, the right knee joint received 50% polyethylene glycol (2 ml), once weekly for 4 weeks or 8 weeks. Knee bone and cartilage tissue were prepared for histologic analysis. In addition, in the OA rabbit model, the effect of C60 (10 M) on degeneration of articular cartilage was compared with that of sodium hyaluronate (HA) (5 mg/ml).Results. C60 (100 M) inhibited the catabolic stress-induced production of matrix-degrading enzymes (matrix metalloproteinases 1, 3, and 13), downregulation of matrix production, and apoptosis and premature senescence in human chondrocytes in vitro.In rabbits with OA, treatment with water-soluble C60 significantly reduced articular cartilage degeneration, whereas control knee joints showed progression of cartilage degeneration with time. This inhibitory effect was dose dependent, and was superior to that of HA. Combined treatment with C60 and HA yielded a significant reduction in cartilage degeneration compared with either treatment alone. Conclusion.The results indicate that C60 fullerene is a potential therapeutic agent for the protection of articular cartilage against progression of OA.During the development of osteoarthritis (OA), mechanical and chemical stresses on articular cartilage change the stable cellular activities of chondrocytes and stimulate the production of growth factors and matrix proteins as well as inflammation mediators (1-4). It is well known that catabolic-stressed chondrocytes produce excess amounts of reactive oxygen species (ROS) (superoxide, nitric oxide, hydrogen peroxide, and peroxynitrite) as well as proinflammatory cytokines and chemokines (4-9).Studies have provided ample confirmation of the generation of ROS and the depletion of cellular antioxidants in degenerated articular cartilage (8-10). Numerous reports have indicated that the degeneration of articular cartilage is partially mediated by oxygenderived free radicals (8-12). Kurz et al reported that the extent of mechanical stress on articular cartilage is sufficient to stimulate an excess production of ROS from chondrocytes, leading to depolymerization of hyaluronic acid and chondrocyte death (11,12). Similarly, Gree...

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Section: Discussionmentioning

confidence: 99%

“…It is well known that C60 can effectively protect against all of the principal damaging forms of ROS: hydrogen peroxide, hydroxyl radical, and superoxide (35).…”

Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 89%

mentioning

confidence: 99%

See 2 more Smart Citations

Water‐soluble C60 fullerene prevents degeneration of articular cartilage in osteoarthritis via down‐regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development

Yudoh

Shishido

Murayama

et al. 2007

Arthritis & Rheumatism

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“…C 60 -fullerenes, owing to their electronic structure as electron-poor polyolefines, are highly reactive towards various organic radicals 3 and have drawn considerable attention in the area of antioxidant research. An electron paramagnetic resonance analysis has shown that C 60 derivatives, such as carboxyfullerene, fullerenol and hexa(sulfobutyl)fullerene, have excellent capabilities to scavenge deleterious reactive oxygen species.…”

Section: Introductionmentioning

confidence: 99%

C60-based ebselen derivative: synthesis by bingel cyclopropanation and enhanced antioxidative and neuroprotective activity

Liu¹,

Guan

2007

J. Braz. Chem. Soc.

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Um derivado de ebselen baseado em C 60 , 3, foi sintetizado pela reação de ciclopropanação de Bingel envolvendo C 60 e manolato de ebselen, 2. O produto foi sintetizado em três etapas, partindo de cloreto de 2-cloro-selenobenzoila e 2-(2-aminoetoxietanol), com rendimento de 42% (baseado no consumo de C 60 ). O composto 3 foi caracterizado estruturalmente por análises espectroscópicas de RMN de 1 H e de 13 C, IV, UV e FAB-MS. Com o objetivo de verificar um possível aumento na atividade antioxidante e neuroprotetora do derivado 3, um derivado de C 60 (4), um derivado de ebselen (2) e sua mistura (4 + 2 em razão equimolar) foram selecionados para o tratamento de células neurais pelo mesmo procedimento adotado para 3 e na mesma concentração final (30 µmol L -1 ). As viabilidades celulares dos quatro grupos de tratamento foram estimadas por ensaios de LDH (desidrogenase láctica) e MTT (brometo de 3-[4,5-dimetil-tiazol-2-il]-2,5-difenil-tetrazólio). Os resultados mostraram que a atividade antioxidante e neuroprotetora de 3 frente à lesão neural mediada por H 2 O 2 (MTT(OD) 0,364 ± 0,028; LDH liberado (UL -1 ) 4,66 ± 0,28) foi significativamente mais alta que a do derivado de C 60 4 (MTT(OD) 0,324 ± 0,025; LDH liberado (UL -1 ) 5,39 ± 0,17), do derivado de ebselen 2 (MTT(OD) 0,294 ± 0,021; LDH liberado (UL -1 ) 5,71 ± 0,27), e da sua mistura (4 + 2) (MTT(OD) 0,310 ± 0,018; LDH liberado (UL -1 ) 5,54 ± 0,39). Esses resultados mostram que a combinação de dois componentes moleculares com atividades biológicas similares (C 60 e ebselen) pode ser uma forma desejável de preparação de novos compostos biologicamente efetivos derivados de C 60 .C 60 -based ebselen derivative 3 was synthesized through Bingel cyclopropanation of C 60 with the ebselen malonate 2. Compound 3 was obtained in 42% yield (based on consumed C 60 ) in a three-step synthesis starting from 2-(chloroseleno)benzoyl chloride and 2-(2-aminoethoxy)ethanol. Its structure was confirmed by 1 H NMR, 13 C NMR, IR, UV and FAB-MS spectroscopy analyses. In order to verify the enhanced antioxidative and neuroprotective activity of 3, a C 60 derivative (4), an ebselen derivative (2), and their mixture (4 plus 2 in equimolar ratio) were employed to treat cortical neuronal cells, following the same procedure used with 3 and at the same final concentration (30 µmol L -1 ). Cell viabilities of the four treated groups were estimated by LDH (lactic dehydrogenase) leakage and MTT (3-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide) assays. Results showed that the antioxidative and protective activities of C 60 -based ebselen derivative 3 against H 2 O 2 -mediated neuronal injury (MTT(OD) 0.364 ± 0.028; LDH release (UL -1 ) 4.66 ± 0.28) were significantly higher than those of C 60 derivative 4 (MTT(OD) 0.324 ± 0.025; LDH release (UL -1 ) 5.39 ± 0.17), ebselen derivative 2 (MTT(OD) 0.294 ± 0.021; LDH release (UL -1 ) 5.71 ± 0.27), and the mixture of 4 and 2 (MTT(OD) 0.310 ± 0.018; LDH release (UL -1 ) 5.54 ± 0.39). These findings demonstrated that the combination of t...

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Syntheses and properties of macromolecular fullerenes, a review

1999

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Radical Reactions of C ₆₀

Cited by 896 publications

References 8 publications

Water‐soluble C60 fullerene prevents degeneration of articular cartilage in osteoarthritis via down‐regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development

Water‐soluble C60 fullerene prevents degeneration of articular cartilage in osteoarthritis via down‐regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development

C60-based ebselen derivative: synthesis by bingel cyclopropanation and enhanced antioxidative and neuroprotective activity

Syntheses and properties of macromolecular fullerenes, a review

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Radical Reactions of C 60

Cited by 896 publications

References 8 publications

Water‐soluble C60 fullerene prevents degeneration of articular cartilage in osteoarthritis via down‐regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development

Water‐soluble C60 fullerene prevents degeneration of articular cartilage in osteoarthritis via down‐regulation of chondrocyte catabolic activity and inhibition of cartilage degeneration during disease development

C60-based ebselen derivative: synthesis by bingel cyclopropanation and enhanced antioxidative and neuroprotective activity

Syntheses and properties of macromolecular fullerenes, a review

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Radical Reactions of C ₆₀