Effect of [60] Fullerene on the Chondrogenesis in Mouse Embryonic Limb Bud Cell Culture System

Tsuchiya, Toshie; Oguri, Ikuko; Yamakoshi, Yoko; Miyata, Naoki

doi:10.1080/10641229608001157

Cited by 19 publications

(5 citation statements)

References 9 publications

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“…To realize the potential of these promising compounds, we have sought to overcome both of these limitations. In particular, our discovery of a novel approach to the effective solubilization of fullerenes in aqueous, physiologically relevant media 8 has enabled the study of the mechanism and biological activity of photoexcited fullerenes, leading to the discovery of DNA strand cleaving activity, 9 hemolytic activity, 10 antimicrobial photodynamic therapy 11 and cytotoxicity, 12,13 and, in the absence of irradiation, a chondrogenesis-promoting effect 14,15 and glutathione S-transferase-inhibitory activity. 16 The readily availability of aqueous fullerene solutions also led to the first mechanistic study of active oxygen generation by underivatized photoexcited fullerenes in aqueous media, leading to the † National Institute of Health Sciences, Japan.…”

Section: Introductionmentioning

confidence: 99%

Active Oxygen Species Generated from Photoexcited Fullerene (C₆₀) as Potential Medicines: O₂^-^•versus¹O₂

et al. 2003

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To characterize fullerenes (C(60) and C(70)) as photosensitizers in biological systems, the generation of active oxygen species, through energy transfer (singlet oxygen (1)O(2)) and electron transfer (reduced active oxygen radicals such as superoxide anion radical O(2)(-)* and hydroxyl radical *OH), was studied by a combination of methods, including biochemical (DNA-cleavage assay in the presence of various scavengers of active oxygen species), physicochemical (EPR radical trapping and near-infrared spectrometry), and chemical methods (nitro blue tetrazolium (NBT) method). Whereas (1)O(2) was generated effectively by photoexcited C(60) in nonpolar solvents such as benzene and benzonitrile, we found that O(2)(-)* and *OH were produced instead of (1)O(2) in polar solvents such as water, especially in the presence of a physiological concentration of reductants including NADH. The above results, together with those of a DNA cleavage assay in the presence of various scavengers of specific active oxygen species, indicate that the active oxygen species primarily responsible for photoinduced DNA cleavage by C(60) under physiological conditions are reduced species such as O(2)(-)* and *OH.

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Section: Introductionmentioning

confidence: 99%

Active Oxygen Species Generated from Photoexcited Fullerene (C₆₀) as Potential Medicines: O₂^-^•versus¹O₂

et al. 2003

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“…Fullerenes, such as C 60 and C 70 , are known to have strong photosensitizing activities , and the potential utility of fullerenes as pharmaceuticals has been extensively explored in recent years. , Fullerenes, which are sensitive to light at wavelengths longer than 500 nm, are expected to be an effective photodynamic therapy agent because bodily tissues are most transparent in this region of wavelengths . C 60 and its derivatives are reported to promote chondrogenesis, exhibiting enzyme-inhibiting activity and radical-quenching activity . In particular, the DNA-cleaving and lipid peroxidation activities of fullerenes have attracted considerable attention. − At first, it was presumed that the mechanism of DNA cleavage involves photoexcitation of the fullerene group followed by sensitized formation of singlet oxygen ( 1 O 2 ) which would then cleave DNA. , Photoirradiation of C 60 results in the formation of the singlet excited state 1 C 60 *, which undergoes efficient intersystem crossing (ISC) to give the triplet excited state 3 C 60 * (Scheme ) .…”

Section: Introductionmentioning

confidence: 99%

DNA Cleavage via Superoxide Anion Formed in Photoinduced Electron Transfer from NADH to γ-Cyclodextrin-Bicapped C₆₀ in an Oxygen-Saturated Aqueous Solution

et al. 2002

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γ-Cyclodextrin-bicapped C 60 (C 60 /γ-CyD) shows an efficient DNA cleaving-activity in the presence of NADH (β-nicotinamide adenine dinucleotide, reduced form) in an O 2 -saturated aqueous solution under visible-light irradiation. No DNA cleavage has been observed without NADH under experimental conditions that are otherwise the same, although singlet oxygen ( 1 O 2 ) has been detected by the ESR spin-trapping of the C 60 / γ-CyD-O 2 system. This indicates that neither triplet excited state of C 60 /γ-CyD ( 3 C 60 */γ-CyD) nor 1 O 2 produced via an energy transfer from 3 C 60 */γ-CyD to O 2 is an actual reactive species, which is responsible for the DNA damage under the present experimental conditions. In the presence of NADH, photoinduced electron transfer from NADH to 3 C 60 */γ-CyD occurs to yield two equivalents of the radical anion (C 60 •-/γ-CyD), which exhibits its characteristic NIR band at 1080 nm. The dynamics of the photoinduced electron transfer have been examined by monitoring the decay of triplet-triplet absorption band at 740 nm and concomitant rise of the NIR absorption band at 1080 nm due to C 60 •-/γ-CyD with use of the laser flash photolysis for the C 60 /γ-CyD-NADH system. In the presence of O 2 , C 60 •-/γ-CyD disappears via the electron transfer to O 2 and an electron transfer from NADH to 1 O 2 to produced O 2 •-. The formation of O 2 •has been confirmed by the spin trap with DEPMPO (5-diethoxyphosphoryl-5-methyl-1-pyrroline-N-oxide), which is an efficient O 2 •-trapping agent. The reorganization energy for the reduction of O 2 to O 2 •is evaluated as 43.4 kcal mol -1 , which agrees with the literature value determined directly for the self-exchange between 36 O 2 •and 32 O 2 . This indicates that the electron transfer from C 60 •-/γ-CyD to O 2 proceeds via an outer-sphere pathway. The O 2 •thus produced gives H 2 O 2 , ultimately yielding hydroxyl radical, which is shown to be an actual DNAcleaving reagent.

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“…The biological activity of fullerenes has attracted considerable attention with regard to the development of novel pharmaceuticals . C 60 and its derivatives have been reported to promote chondrogenesis, and to exhibit enzyme-inhibiting activity and radical-quenching activity . These activities may be useful in some pharmaceutical applications.…”

mentioning

confidence: 99%

•OH and O₂^•- Generation in Aqueous C₆₀ and C₇₀ Solutions by Photoirradiation: An EPR Study

Yamakoshi¹,

Sueyoshi²,

Fukuhara³

et al. 1998

J. Am. Chem. Soc.

149

101

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Effect of [60] Fullerene on the Chondrogenesis in Mouse Embryonic Limb Bud Cell Culture System

Cited by 19 publications

References 9 publications

Active Oxygen Species Generated from Photoexcited Fullerene (C₆₀) as Potential Medicines: O₂^-^•versus¹O₂

Active Oxygen Species Generated from Photoexcited Fullerene (C₆₀) as Potential Medicines: O₂^-^•versus¹O₂

DNA Cleavage via Superoxide Anion Formed in Photoinduced Electron Transfer from NADH to γ-Cyclodextrin-Bicapped C₆₀ in an Oxygen-Saturated Aqueous Solution

•OH and O₂^•- Generation in Aqueous C₆₀ and C₇₀ Solutions by Photoirradiation: An EPR Study

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Effect of [60] Fullerene on the Chondrogenesis in Mouse Embryonic Limb Bud Cell Culture System

Cited by 19 publications

References 9 publications

Active Oxygen Species Generated from Photoexcited Fullerene (C60) as Potential Medicines: O2-•versus1O2

Active Oxygen Species Generated from Photoexcited Fullerene (C60) as Potential Medicines: O2-•versus1O2

DNA Cleavage via Superoxide Anion Formed in Photoinduced Electron Transfer from NADH to γ-Cyclodextrin-Bicapped C60 in an Oxygen-Saturated Aqueous Solution

•OH and O2•- Generation in Aqueous C60 and C70 Solutions by Photoirradiation: An EPR Study

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Active Oxygen Species Generated from Photoexcited Fullerene (C₆₀) as Potential Medicines: O₂^-^•versus¹O₂

Active Oxygen Species Generated from Photoexcited Fullerene (C₆₀) as Potential Medicines: O₂^-^•versus¹O₂

DNA Cleavage via Superoxide Anion Formed in Photoinduced Electron Transfer from NADH to γ-Cyclodextrin-Bicapped C₆₀ in an Oxygen-Saturated Aqueous Solution

•OH and O₂^•- Generation in Aqueous C₆₀ and C₇₀ Solutions by Photoirradiation: An EPR Study