What is it about?

In this work, we describe the synthesis of a particular class of fullerene derivatives, fulleropyrrolidines, endowed with polyethylene glycol tails to enhance their solubility in water. The synthetic method we use ensures exclusive formation of only one type of possible stereoisomeric fulleropyrrolidines -- trans-isomers.

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Why is it important?

Fullerene is a spherical all-carbon molecule, which has a potential as an antiviral or antibacterial agent. The particular fulleropyrrolidine structural fragment constructed by our method appears in compounds with reported antiviral activity. The medical applications of fullerene derivatives is often hampered by their low solubility in water. Additional prerequisite to the development of fullerene-based pharmaceuticals is the ability to afford high degree of control over the molecular structure of the potential pharmaceutical agent. Both these tasks are addressed in our work.

Perspectives

The reported compounds might be good candidates for the developement of efficient antiviral agents. Also, their evaluation in antibacterial and antitumor photodynamic therapy can be suggested due to the known ability of fullerenes to generate singlet oxygen upon irradiation with visible light on the one hand and their ability to form nanosized aggregates in aqueous medium allowing for passive tumor targeting on the other.

Alexander S. Konev
Saint Petersburg State University

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This page is a summary of: PEG-modified aziridines for stereoselective synthesis of water-soluble fulleropyrrolidines, Organic & Biomolecular Chemistry, January 2019, Royal Society of Chemistry,
DOI: 10.1039/c9ob01949a.
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