title: Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy.
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 (1)H and (13)C 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.
authors.affiliation: IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia. kotel@icp.ac.ru
authors.forename: Alexander I
authors.initials: AI
authors.lastname: Kotelnikov
authors.forename: Alexander Yu
authors.initials: AY
authors.lastname: Rybkin
authors.forename: Ekaterina A
authors.initials: EA
authors.lastname: Khakina
authors.forename: Alexey B
authors.initials: AB
authors.lastname: Kornev
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Barinov
authors.forename: Nikolay S
authors.initials: NS
authors.lastname: Goryachev
authors.forename: Anastasiya V
authors.initials: AV
authors.lastname: Ivanchikhina
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Peregudov
authors.forename: Vyacheslav M
authors.initials: VM
authors.lastname: Martynenko
authors.forename: Pavel A
authors.initials: PA
authors.lastname: Troshin
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000737:chemistry; D037741:Fullerenes / Q000737:chemistry*; D049329:Nanostructures / Q000737:chemistry*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000737:chemistry*
chemical_list: D000903:Antibiotics, Antineoplastic; D037741:Fullerenes; D017319:Photosensitizing Agents; C042480:ruboxyl; D003630:Daunorubicin