Stable monolayers and Langmuir-Blodgett films of functionalized fullerenes.

Guldi, Dirk M.; Tian, Yantao; Fendler, János H.; Hungerbuehler, Hartmut; Asmus, K.‐D.

doi:10.1021/j100050a002

Cited by 43 publications

(22 citation statements)

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“…The amphiphilic analytes were synthesized as described in the literature [6] and dissolved in toluene at a ratio of 1 mg analyte per 1 ml of solvent. DCTB (trans-2-[3-{4-tert-Butylphenyl}-2-methyl-2-propenylidene]malononitrile, whose structure is shown in Figure 1c) was supplied by Fluka (Buchs, Switzerland) and used as the matrix.…”

Section: Sample Preparationmentioning

confidence: 99%

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Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization

Fati

Leeman

Vasil’ev

et al. 2002

J. Am. Soc. Mass Spectrom.

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The complexation of alkali metal ions with amphiphilic fullerene derivatives has been investigated by matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometry. The formation of analyte ions occurs via two competing mechanisms including electron transfer from matrix-derived ions and metal ion attachment. The interplay of these processes has been examined by laser fluence dependent sample activation and by variation of the target composition. The attachment of metal ions has been established as the gentler and thus more efficient route towards the formation of intact analyte ions. Investigations into the metal ion complexation have been conducted to reveal the reactivity order of the alkali metals in these reactions and to elucidate the influence of structural differences of the analytes, as well as to unravel effects caused by the anionic counter ion of the metal. The experimental data have been derived by two complementary approaches. Competing reactants were either studied simultaneously, so that the product distribution would provide direct insight into the reactivity pattern, and/or product distributions were obtained in a large variety of separate experiments and normalized for reliable comparison. It has been found that the extent to which complexation is observed follows the charge density order of the alkali metal ions. The structural features of the fullerene-attached ligands were of profound influence on the attachment of the metal ion, inducing enhanced selectivity for the complexation with less reactive metals. The metal ion attachment is reduced with the use of smaller anionic counter ions. Rationalization of these findings is provided within the framework of the mechanisms of ion formation in

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Section: Sample Preparationmentioning

confidence: 99%

“…In these materials the hydrophobic C 60 moiety is methylene-bridged to a long-chained, hydrophilic ligand, which results in molecules with amphiphilic properties. Amphiphilic fullerenes have gained attention as potential biosensors by exploiting their ability to form stable, ordered monomolecular layers and Langmuir-Blodgett films [6,7].…”

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confidence: 99%

Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization

Fati

Leeman

Vasil’ev

et al. 2002

J. Am. Soc. Mass Spectrom.

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“…C 60 derivative 4 ( Figure 1) was prepared according to the literature. 15 LDH (lactic dehydrogenase) assay kit was obtained from Beijing Chemical Kit Company (China). The optical density of each well was measured at 550 nm on a BIO-RAD550 (USA) enzyme-linked analyzer.…”

Section: Methodsmentioning

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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“…DMSO and MTT were obtained from Sigma Chemical Co.(USA). C 60 derivative 4 (Figure 1) was prepared according to the published literature 9 and directly used to compare with C 60 -based ebselen derivative in promoting the activity of mouse thymus cells. The value of optical density of each well was measured at 550 nm by using an enzyme-linked analyzer (BIO-RAD550, USA).…”

Section: Reagents and Instrumentsmentioning

confidence: 99%

C₆₀‐Based Ebselen Derivative: Synthesis and Enhanced Protective Effect on Mouse Thymus Cells

Liu

Guan²,

2008

Chin. J. Chem.

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A C 60 -based ebselen derivative 3 was synthesized through a Bingel cyclopropanation of C 60 with the ebselen malonate 2. It was obtained in a three-step synthesis starting from 2-(chloroseleno)benzoyl chloride and 2-(2-aminoethoxy)ethanol, in a 42% yield (based on consumed C 60 ). Its structure was characterized by 1 H NMR, 13 C NMR, IR, FAB-MS, and elemental analyses techniques. To verify that the C 60 -based ebselen derivative 3 had enhanced effect on viability of mouse thymus cells, the C 60 derivative 4 and ebselen derivative 2 were selected to treat the mouse thymus cells using the same procedures as those with the C 60 -based ebselen derivative 3. The result shows that MTT(OD) values of compound 3 treated groups (0.335±0.021) were all higher than those of compound 4 (0.283±0.031) and compound 2 (0.247±0.025) treated groups, indicating that the compound 3 has an advantage over compounds 2 and 4 in promoting the viability of the mouse thymus cell.

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Stable monolayers and Langmuir-Blodgett films of functionalized fullerenes.

Cited by 43 publications

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Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization

Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization

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

C₆₀‐Based Ebselen Derivative: Synthesis and Enhanced Protective Effect on Mouse Thymus Cells

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Stable monolayers and Langmuir-Blodgett films of functionalized fullerenes.

Cited by 43 publications

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Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization

Alkali cation attachment to derivatized fullerenes studied by matrix-assisted laser desorption/ionization

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

C60‐Based Ebselen Derivative: Synthesis and Enhanced Protective Effect on Mouse Thymus Cells

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C₆₀‐Based Ebselen Derivative: Synthesis and Enhanced Protective Effect on Mouse Thymus Cells