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Synthesis of novel fluorescently labeled water-soluble fullerenes and their application to its cellar uptake and distribution properties

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Abstract

Fullerene is a well-known carbon nanomaterial, which can be potentially used for drug manufacture or delivery. Despite several successful examples of utilizing fullerene derivatives as drug candidate materials, their low water solubility under physiological conditions negatively affects the cell penetration efficiency after treatment. In this work, we successfully synthesized two fullerene derivatives with covalently attached fluorescein and boron dipyrromethene (BODIPY) fluorophore moieties, which exhibited cellular uptake and intracellular localization. While both fluorophores decreased their fluorescence intensity in the vicinity of fullerene, the cellar uptake of the fluorescein-modified fullerene was detected via fluorescence microscopy observations. Moreover, decreases in the fluorescence intensities of the intact fluorescein and BODIPY species were observed when both fluorophores and fullerene coexisted in aqueous media.

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Funding

This work was partially supported by the Grants-in-Aid for Scientific Research grant awarded to a doctoral student from the Kanagawa Institute of Technology.

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Correspondence to Takeji Takamura-Enya.

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The authors declare that they have no conflict of interest.

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Hashimoto, A., Yamanaka, T. & Takamura-Enya, T. Synthesis of novel fluorescently labeled water-soluble fullerenes and their application to its cellar uptake and distribution properties. J Nanopart Res 19, 402 (2017). https://doi.org/10.1007/s11051-017-4098-x

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  • DOI: https://doi.org/10.1007/s11051-017-4098-x

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