A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems

Panagiota Zygouri; Konstantinos Spyrou; Efstratia Mitsari; Maria Barrio; Roberto Macovez; Michaela Patila; Haralambos Stamatis; Ioannis I. Verginadis; Anastasia P. Velalopoulou; Angelos M. Evangelou; Zili Sideratou; Dimitrios Gournis; Petra Rudolf

doi:10.1038/s41598-020-65117-7

A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems

Panagiota Zygouri^*, Konstantinos Spyrou, Efstratia Mitsari, Maria Barrio, Roberto Macovez, Michaela Patila, Haralambos Stamatis, Ioannis I. Verginadis, Anastasia P. Velalopoulou, Angelos M. Evangelou, Zili Sideratou, Dimitrios Gournis, Petra Rudolf

^*Corresponding author for this work

Surfaces and Thin Films

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Abstract

A facile, environment-friendly, versatile and reproducible approach to the successful oxidation of fullerenes (oxC(60)) and the formation of highly hydrophilic fullerene derivatives is introduced. This synthesis relies on the widely known Staudenmaier's method for the oxidation of graphite, to produce both epoxy and hydroxy groups on the surface of fullerenes (C-60) and thereby improve the solubility of the fullerene in polar solvents (e.g. water). The presence of epoxy groups allows for further functionalization via nucleophilic substitution reactions to generate new fullerene derivatives, which can potentially lead to a wealth of applications in the areas of medicine, biology, and composite materials. In order to justify the potential of oxidized C-60 derivatives for bio-applications, we investigated their cytotoxicity in vitro as well as their utilization as support in biocatalysis applications, taking the immobilization of laccase for the decolorization of synthetic industrial dyes as a trial case.

Original language	English
Article number	8244
Number of pages	13
Journal	Scientific Reports
Volume	10
Issue number	1
DOIs	https://doi.org/10.1038/s41598-020-65117-7
Publication status	Published - 19-May-2020

Keywords

GRAPHENE OXIDE
AZOMETHINE YLIDES
RAMAN-SPECTRA
C-60
WATER
CHEMISTRY
C60
BUCKMINSTERFULLERENE
OXIDATION
FUNCTIONALIZATION

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A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systemsFinal publisher's version, 2.51 MBLicence: CC BY

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Zygouri, P., Spyrou, K., Mitsari, E., Barrio, M., Macovez, R., Patila, M., Stamatis, H., Verginadis, I. I., Velalopoulou, A. P., Evangelou, A. M., Sideratou, Z., Gournis, D., & Rudolf, P. (2020). A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems. Scientific Reports, 10(1), Article 8244. https://doi.org/10.1038/s41598-020-65117-7

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title = "A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems",

abstract = "A facile, environment-friendly, versatile and reproducible approach to the successful oxidation of fullerenes (oxC(60)) and the formation of highly hydrophilic fullerene derivatives is introduced. This synthesis relies on the widely known Staudenmaier's method for the oxidation of graphite, to produce both epoxy and hydroxy groups on the surface of fullerenes (C-60) and thereby improve the solubility of the fullerene in polar solvents (e.g. water). The presence of epoxy groups allows for further functionalization via nucleophilic substitution reactions to generate new fullerene derivatives, which can potentially lead to a wealth of applications in the areas of medicine, biology, and composite materials. In order to justify the potential of oxidized C-60 derivatives for bio-applications, we investigated their cytotoxicity in vitro as well as their utilization as support in biocatalysis applications, taking the immobilization of laccase for the decolorization of synthetic industrial dyes as a trial case.",

keywords = "GRAPHENE OXIDE, AZOMETHINE YLIDES, RAMAN-SPECTRA, C-60, WATER, CHEMISTRY, C60, BUCKMINSTERFULLERENE, OXIDATION, FUNCTIONALIZATION",

author = "Panagiota Zygouri and Konstantinos Spyrou and Efstratia Mitsari and Maria Barrio and Roberto Macovez and Michaela Patila and Haralambos Stamatis and Verginadis, {Ioannis I.} and Velalopoulou, {Anastasia P.} and Evangelou, {Angelos M.} and Zili Sideratou and Dimitrios Gournis and Petra Rudolf",

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month = may,

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doi = "10.1038/s41598-020-65117-7",

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Zygouri, P, Spyrou, K, Mitsari, E, Barrio, M, Macovez, R, Patila, M, Stamatis, H, Verginadis, II, Velalopoulou, AP, Evangelou, AM, Sideratou, Z, Gournis, D & Rudolf, P 2020, 'A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems', Scientific Reports, vol. 10, no. 1, 8244. https://doi.org/10.1038/s41598-020-65117-7

TY - JOUR

T1 - A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems

AU - Zygouri, Panagiota

AU - Spyrou, Konstantinos

AU - Mitsari, Efstratia

AU - Barrio, Maria

AU - Macovez, Roberto

AU - Patila, Michaela

AU - Stamatis, Haralambos

AU - Verginadis, Ioannis I.

AU - Velalopoulou, Anastasia P.

AU - Evangelou, Angelos M.

AU - Sideratou, Zili

AU - Gournis, Dimitrios

AU - Rudolf, Petra

PY - 2020/5/19

Y1 - 2020/5/19

N2 - A facile, environment-friendly, versatile and reproducible approach to the successful oxidation of fullerenes (oxC(60)) and the formation of highly hydrophilic fullerene derivatives is introduced. This synthesis relies on the widely known Staudenmaier's method for the oxidation of graphite, to produce both epoxy and hydroxy groups on the surface of fullerenes (C-60) and thereby improve the solubility of the fullerene in polar solvents (e.g. water). The presence of epoxy groups allows for further functionalization via nucleophilic substitution reactions to generate new fullerene derivatives, which can potentially lead to a wealth of applications in the areas of medicine, biology, and composite materials. In order to justify the potential of oxidized C-60 derivatives for bio-applications, we investigated their cytotoxicity in vitro as well as their utilization as support in biocatalysis applications, taking the immobilization of laccase for the decolorization of synthetic industrial dyes as a trial case.

AB - A facile, environment-friendly, versatile and reproducible approach to the successful oxidation of fullerenes (oxC(60)) and the formation of highly hydrophilic fullerene derivatives is introduced. This synthesis relies on the widely known Staudenmaier's method for the oxidation of graphite, to produce both epoxy and hydroxy groups on the surface of fullerenes (C-60) and thereby improve the solubility of the fullerene in polar solvents (e.g. water). The presence of epoxy groups allows for further functionalization via nucleophilic substitution reactions to generate new fullerene derivatives, which can potentially lead to a wealth of applications in the areas of medicine, biology, and composite materials. In order to justify the potential of oxidized C-60 derivatives for bio-applications, we investigated their cytotoxicity in vitro as well as their utilization as support in biocatalysis applications, taking the immobilization of laccase for the decolorization of synthetic industrial dyes as a trial case.

KW - GRAPHENE OXIDE

KW - AZOMETHINE YLIDES

KW - RAMAN-SPECTRA

KW - C-60

KW - WATER

KW - CHEMISTRY

KW - C60

KW - BUCKMINSTERFULLERENE

KW - OXIDATION

KW - FUNCTIONALIZATION

U2 - 10.1038/s41598-020-65117-7

DO - 10.1038/s41598-020-65117-7

M3 - Article

SN - 2045-2322

VL - 10

JO - Scientific Reports

JF - Scientific Reports

IS - 1

M1 - 8244

ER -

A facile approach to hydrophilic oxidized fullerenes and their derivatives as cytotoxic agents and supports for nanobiocatalytic systems

Abstract

Keywords

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