Novel structural features increase the antioxidant effect of estrogen analogues on low density lipoprotein
| Autor: | A. F. Fidarov, Alexander G. Shavva, Roman P. Bogautdinov, S. N. Morozkina, Matti J. Tikkanen, Veera Vihma |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
Male
Antioxidant Double bond medicine.drug_class Stereochemistry Endocrinology Diabetes and Metabolism medicine.medical_treatment Clinical Biochemistry Conjugated system Biochemistry Antioxidants chemistry.chemical_compound Endocrinology medicine Organic chemistry Humans Molecular Biology chemistry.chemical_classification Molecular Structure Estrogens Cell Biology In vitro Lipoproteins LDL chemistry Estrogen Low-density lipoprotein Molecular Medicine Methyl group Lipoprotein |
| Zdroj: | The Journal of steroid biochemistry and molecular biology. 154 |
| ISSN: | 1879-1220 |
| Popis: | Many known estrogens, both natural and synthetic, may act as antioxidants. We designed and synthesized 22 novel estrogen analogues with different ring junctions or substitutions, such as fluorine. We studied the antioxidant capacity in vitro of 35 synthetic estrogen analogues in aqueous lipoprotein solution by monitoring the formation of conjugated dienes. In addition to a free C-3 hydroxyl group, the two most active antioxidants had either a methyl group at C-4 and a six-carbon D-ring, or a fluorine atom at C-2 and an unsaturated B-ring. Extension of the D-ring increased the antioxidant capacity of 6-oxa estrogens. Compounds with a fluorine atom at C-2 were similar or more potent antioxidants compared with the principal endogenous estrogen, 17β-estradiol. In compounds with a substituted C-3 hydroxyl group, the antioxidant capacity could be significantly increased by additional double bonds in the C- or D-rings. In conclusion, we show that the antioxidant capacity of estrogen analogues could be increased by structural changes. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect