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Article

Covalent Attachment of Aggregation-Induced Emission Molecules to the Surface of Ultrasmall Gold Nanoparticles to Enhance Cell Penetration

by
Kai Klein
1,
Matthias Hayduk
2,
Sebastian Kollenda
1,
Marco Schmiedtchen
2,
Jens Voskuhl
2,* and
Matthias Epple
1,*
1
Inorganic Chemistry and Center for Nanointegration Duisburg-Essen (CeNIDE), University of Duisburg-Essen, Universitätsstr. 5-7, 45117 Essen, Germany
2
Organic Chemistry and Center for Nanointegration Duisburg-Essen (CeNIDE), University of Duisburg-Essen, Universitätsstr. 5-7, 45117 Essen, Germany
*
Authors to whom correspondence should be addressed.
Molecules 2022, 27(6), 1788; https://doi.org/10.3390/molecules27061788
Submission received: 18 February 2022 / Revised: 7 March 2022 / Accepted: 7 March 2022 / Published: 9 March 2022
(This article belongs to the Special Issue Aggregation-Induced Emission: Commemorative Issue of the 20th Anniversary of AIE Research and the 65th Birthday of Professor Ben Zhong Tang)
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Abstract

Three different alkyne-terminated aggregation-induced emission molecules based on a para-substituted di-thioether were attached to the surface of ultrasmall gold nanoparticles (2 nm) by copper-catalyzed azide–alkyne cycloaddition (click chemistry). They showed a strong fluorescence and were well water-dispersible, in contrast to the dissolved AIE molecules. The AIE-loaded nanoparticles were not cytotoxic and easily penetrated the membrane of HeLa cells, paving the way for an intracellular application of AIE molecules, e.g., for imaging.
Keywords: gold; nanoparticles; click chemistry; aggregation-induced emission; bioavailability gold; nanoparticles; click chemistry; aggregation-induced emission; bioavailability

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MDPI and ACS Style

Klein, K.; Hayduk, M.; Kollenda, S.; Schmiedtchen, M.; Voskuhl, J.; Epple, M. Covalent Attachment of Aggregation-Induced Emission Molecules to the Surface of Ultrasmall Gold Nanoparticles to Enhance Cell Penetration. Molecules 2022, 27, 1788. https://doi.org/10.3390/molecules27061788

AMA Style

Klein K, Hayduk M, Kollenda S, Schmiedtchen M, Voskuhl J, Epple M. Covalent Attachment of Aggregation-Induced Emission Molecules to the Surface of Ultrasmall Gold Nanoparticles to Enhance Cell Penetration. Molecules. 2022; 27(6):1788. https://doi.org/10.3390/molecules27061788

Chicago/Turabian Style

Klein, Kai, Matthias Hayduk, Sebastian Kollenda, Marco Schmiedtchen, Jens Voskuhl, and Matthias Epple. 2022. "Covalent Attachment of Aggregation-Induced Emission Molecules to the Surface of Ultrasmall Gold Nanoparticles to Enhance Cell Penetration" Molecules 27, no. 6: 1788. https://doi.org/10.3390/molecules27061788

APA Style

Klein, K., Hayduk, M., Kollenda, S., Schmiedtchen, M., Voskuhl, J., & Epple, M. (2022). Covalent Attachment of Aggregation-Induced Emission Molecules to the Surface of Ultrasmall Gold Nanoparticles to Enhance Cell Penetration. Molecules, 27(6), 1788. https://doi.org/10.3390/molecules27061788

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