Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy

Alexander I. Kotelnikov, Alexander Yu Rybkin, Ekaterina A. Khakina, Alexey B. Kornev, Alexander V. Barinov, Nikolay S. Goryachev, Anastasiya V. Ivanchikhina, Alexander S. Peregudov, Vyacheslav M. Martynenko, Pavel A. Troshin

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Here we report the investigation of photophysical properties and photodynamic action of two novel water soluble hybrid molecular structures based on [60]fullerene dyads bearing covalently attached residues of anthracycline antibiotic "ruboxyl". Molecular structures of the designed compounds were confirmed by IR and UV-VIS absorption spectroscopy, electrospray mass spectrometry (compound 5), and 1H and 13C NMR spectroscopy. Dynamic light scattering, steady-state and kinetic fluorimetry and UV-VIS absorption spectroscopy techniques were used to study the behavior of the synthesized hybrid molecular structures in aqueous solutions. Photodynamic activity of the compounds was evaluated by monitoring the O2 - generation under visible light irradiation using the NBT test. It has been shown that the anthracycline chromophore (ruboxyl moiety possesses no photodynamic activity) behaves as an efficient photosensitizer for the fullerene core operating via the energy and/or the electron transfer pathways. The presented approach opens up wide opportunities for the design of various fullerene-based donor-acceptor systems with enhanced photodynamic properties potentially suitable for biomedicinal applications.

Original languageEnglish
Pages (from-to)4397-4404
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number26
DOIs
Publication statusPublished - 14 Jul 2013
Externally publishedYes

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