Synthesis and antioxidant properties of fullero-steroidal covalent conjugates
Abstract
Four new fullero-steroids were synthesized starting from gamma-aminobutyric acid (GABA)-incorporated fulleropyrrolidine and corresponding sterols. The synthesis, characterization, preliminary study on in vitro antioxidant activity as well as the steady state photophysical properties are presented. All synthesized compounds showed antioxidant activity 2-3-fold higher than the parent fullerene. The most active compound appeared to be as potent as standard antioxidant BHT (2,6-di-tert-butyl-4-methylphenol). Also, all of them fluoresce 6-8-fold stronger than C-60, thus representing potential irradiation assisted pro-oxidants. With significantly increased lipophilicity, it could be expected that attached steroidal subunit enables better penetration Of C60 to living cell membranes, thus facilitating its antioxidant activity. Based on all obtained results, newly synthesized covalent fullero-steroidal conjugates represent good candidates for potential antioxidants as well as pro-oxidants. (c) ...2007 Elsevier Ltd. All rights reserved.
Source:
Carbon, 2007, 45, 11, 2260-2265Publisher:
- Pergamon-Elsevier Science Ltd, Oxford
Funding / projects:
- Sinteza, karakterizacija i primena novih derivata fulerena (RS-MESTD-MPN2006-2010-142049)
DOI: 10.1016/j.carbon.2007.06.027
ISSN: 0008-6223
WoS: 000250185900019
Scopus: 2-s2.0-34548500386
Collections
Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Bjelaković, Mira S. AU - Godjevac, Dejan AU - Milić, Dragana PY - 2007 UR - https://cherry.chem.bg.ac.rs/handle/123456789/883 AB - Four new fullero-steroids were synthesized starting from gamma-aminobutyric acid (GABA)-incorporated fulleropyrrolidine and corresponding sterols. The synthesis, characterization, preliminary study on in vitro antioxidant activity as well as the steady state photophysical properties are presented. All synthesized compounds showed antioxidant activity 2-3-fold higher than the parent fullerene. The most active compound appeared to be as potent as standard antioxidant BHT (2,6-di-tert-butyl-4-methylphenol). Also, all of them fluoresce 6-8-fold stronger than C-60, thus representing potential irradiation assisted pro-oxidants. With significantly increased lipophilicity, it could be expected that attached steroidal subunit enables better penetration Of C60 to living cell membranes, thus facilitating its antioxidant activity. Based on all obtained results, newly synthesized covalent fullero-steroidal conjugates represent good candidates for potential antioxidants as well as pro-oxidants. (c) 2007 Elsevier Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Carbon T1 - Synthesis and antioxidant properties of fullero-steroidal covalent conjugates VL - 45 IS - 11 SP - 2260 EP - 2265 DO - 10.1016/j.carbon.2007.06.027 ER -
@article{ author = "Bjelaković, Mira S. and Godjevac, Dejan and Milić, Dragana", year = "2007", abstract = "Four new fullero-steroids were synthesized starting from gamma-aminobutyric acid (GABA)-incorporated fulleropyrrolidine and corresponding sterols. The synthesis, characterization, preliminary study on in vitro antioxidant activity as well as the steady state photophysical properties are presented. All synthesized compounds showed antioxidant activity 2-3-fold higher than the parent fullerene. The most active compound appeared to be as potent as standard antioxidant BHT (2,6-di-tert-butyl-4-methylphenol). Also, all of them fluoresce 6-8-fold stronger than C-60, thus representing potential irradiation assisted pro-oxidants. With significantly increased lipophilicity, it could be expected that attached steroidal subunit enables better penetration Of C60 to living cell membranes, thus facilitating its antioxidant activity. Based on all obtained results, newly synthesized covalent fullero-steroidal conjugates represent good candidates for potential antioxidants as well as pro-oxidants. (c) 2007 Elsevier Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Carbon", title = "Synthesis and antioxidant properties of fullero-steroidal covalent conjugates", volume = "45", number = "11", pages = "2260-2265", doi = "10.1016/j.carbon.2007.06.027" }
Bjelaković, M. S., Godjevac, D.,& Milić, D.. (2007). Synthesis and antioxidant properties of fullero-steroidal covalent conjugates. in Carbon Pergamon-Elsevier Science Ltd, Oxford., 45(11), 2260-2265. https://doi.org/10.1016/j.carbon.2007.06.027
Bjelaković MS, Godjevac D, Milić D. Synthesis and antioxidant properties of fullero-steroidal covalent conjugates. in Carbon. 2007;45(11):2260-2265. doi:10.1016/j.carbon.2007.06.027 .
Bjelaković, Mira S., Godjevac, Dejan, Milić, Dragana, "Synthesis and antioxidant properties of fullero-steroidal covalent conjugates" in Carbon, 45, no. 11 (2007):2260-2265, https://doi.org/10.1016/j.carbon.2007.06.027 . .