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Synthesis and antioxidant properties of fullero-steroidal covalent conjugates

Authorized Users Only
2007
Authors
Bjelaković, Mira
Gođevac, Dejan
Milić, Dragana
Article (Published version)
Metadata
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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.

Keywords:
steroids / fullerenes / fullero-steroids / synthesis / characterization / antioxidant activity
Source:
Carbon, 2007, 45, 11, 2260-2265
Publisher:
  • Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
  • Sinteza, karakterizacija i primena novih derivata fulerena (RS-142049)

DOI: 10.1016/j.carbon.2007.06.027

ISSN: 0008-6223

WoS: 000250185900019

Scopus: 2-s2.0-34548500386
[ Google Scholar ]
29
27
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4183
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Bjelaković, Mira
AU  - Gođevac, Dejan
AU  - Milić, Dragana
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4183
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  - Oxford : Pergamon-Elsevier Science Ltd
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
UR  - Kon_1836
ER  - 
@article{
author = "Bjelaković, Mira and Gođevac, 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 = "Oxford : Pergamon-Elsevier Science Ltd",
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",
url = "Kon_1836"
}
Bjelaković, M., Gođevac, D.,& Milić, D.. (2007). Synthesis and antioxidant properties of fullero-steroidal covalent conjugates. in Carbon
Oxford : Pergamon-Elsevier Science Ltd., 45(11), 2260-2265.
https://doi.org/10.1016/j.carbon.2007.06.027
Kon_1836
Bjelaković M, Gođevac 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
Kon_1836 .
Bjelaković, Mira, Gođevac, 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 .,
Kon_1836 .

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