Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy
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 compound...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2013-07, Vol.11 (26), p.4397 |
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| creator | Kotelnikov, Alexander I Rybkin, Alexander Yu Khakina, Ekaterina A Kornev, Alexey B Barinov, Alexander V Goryachev, Nikolay S Ivanchikhina, Anastasiya V Peregudov, Alexander S Martynenko, Vyacheslav M Troshin, Pavel A |
| description | 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. |
| doi_str_mv | 10.1039/c3ob40136g |
| format | Article |
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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.</description><subject>Antibiotics, Antineoplastic - chemistry</subject><subject>Daunorubicin - analogs & derivatives</subject><subject>Daunorubicin - chemistry</subject><subject>Fullerenes - chemistry</subject><subject>Nanostructures - chemistry</subject><subject>Photochemotherapy</subject><subject>Photosensitizing Agents - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1Lw0AURQdRbK1u_AGStRB985FMZinFWqHgRnEZJjNvbCTJhJmkmH-vpVpX7_I49y4OIdcU7ihwdW-4rwRQnn-ckDkVUqaQcXV6zAxm5CLGTwCqZC7OyYxxSZmkYk7e11MVapv0Wz94bYZ6h4kbmwYDdphYDPVO759pGCv_NTVJpzsfhzCaYQwYE-fDoWunTre1SYYtBt1Pl-TM6Sbi1e9dkLfV4-tynW5enp6XD5vUsEIOKWPSQg4I6KRWLgPHQQlAWVQabFZwzRgHJipluNJZkVkjHEcJXCubC80X5Pawa4KPMaAr-1C3OkwlhXJvp_y38wPfHOB-rFq0R_RPB_8GZkNiaQ</recordid><startdate>20130714</startdate><enddate>20130714</enddate><creator>Kotelnikov, Alexander I</creator><creator>Rybkin, Alexander Yu</creator><creator>Khakina, Ekaterina A</creator><creator>Kornev, Alexey B</creator><creator>Barinov, Alexander V</creator><creator>Goryachev, Nikolay S</creator><creator>Ivanchikhina, Anastasiya V</creator><creator>Peregudov, Alexander S</creator><creator>Martynenko, Vyacheslav M</creator><creator>Troshin, Pavel A</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130714</creationdate><title>Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy</title><author>Kotelnikov, Alexander I ; Rybkin, Alexander Yu ; Khakina, Ekaterina A ; Kornev, Alexey B ; Barinov, Alexander V ; Goryachev, Nikolay S ; Ivanchikhina, Anastasiya V ; Peregudov, Alexander S ; Martynenko, Vyacheslav M ; Troshin, Pavel A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c287t-227d060e0ef7a9f50f30940e78ba0d583a223024b9c39a585dc4f3e703a9d64a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Antibiotics, Antineoplastic - chemistry</topic><topic>Daunorubicin - analogs & derivatives</topic><topic>Daunorubicin - chemistry</topic><topic>Fullerenes - chemistry</topic><topic>Nanostructures - chemistry</topic><topic>Photochemotherapy</topic><topic>Photosensitizing Agents - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kotelnikov, Alexander I</creatorcontrib><creatorcontrib>Rybkin, Alexander Yu</creatorcontrib><creatorcontrib>Khakina, Ekaterina A</creatorcontrib><creatorcontrib>Kornev, Alexey B</creatorcontrib><creatorcontrib>Barinov, Alexander V</creatorcontrib><creatorcontrib>Goryachev, Nikolay S</creatorcontrib><creatorcontrib>Ivanchikhina, Anastasiya V</creatorcontrib><creatorcontrib>Peregudov, Alexander S</creatorcontrib><creatorcontrib>Martynenko, Vyacheslav M</creatorcontrib><creatorcontrib>Troshin, Pavel A</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kotelnikov, Alexander I</au><au>Rybkin, Alexander Yu</au><au>Khakina, Ekaterina A</au><au>Kornev, Alexey B</au><au>Barinov, Alexander V</au><au>Goryachev, Nikolay S</au><au>Ivanchikhina, Anastasiya V</au><au>Peregudov, Alexander S</au><au>Martynenko, Vyacheslav M</au><au>Troshin, Pavel A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2013-07-14</date><risdate>2013</risdate><volume>11</volume><issue>26</issue><spage>4397</spage><pages>4397-</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><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.</abstract><cop>England</cop><pmid>23712714</pmid><doi>10.1039/c3ob40136g</doi></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2013-07, Vol.11 (26), p.4397 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Antibiotics, Antineoplastic - chemistry Daunorubicin - analogs & derivatives Daunorubicin - chemistry Fullerenes - chemistry Nanostructures - chemistry Photochemotherapy Photosensitizing Agents - chemistry |
| title | Hybrid photoactive fullerene derivative-ruboxyl nanostructures for photodynamic therapy |
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