Succinobucol’s New Coat - Conjugation with Steroids to Alter Its Drug Effect and Bioavailability

0368252 - ÚEB 2012 RIV CH eng J - Journal Article
Jurček, Ondřej - Ikonen, S. - Buřičová, Lucie - Wimmerová, Martina - Wimmer, Zdeněk - Drašar, P. - Horníček, Jan - Galandáková, A. - Ulrichová, J. - Kolehmainen, E. T.
Succinobucol’s New Coat - Conjugation with Steroids to Alter Its Drug Effect and Bioavailability.
Molecules. Roč. 16, č. 11 (2011), s. 9404-9420. E-ISSN 1420-3049
R&D Projects: GA MŠMT 2B06024; GA MŠMT(CZ) OC10001; GA ČR GA203/09/2037
Institutional research plan: CEZ:AV0Z50380511; CEZ:AV0Z40550506
Keywords : succinobucol * phytosterol * atherosclerosis
Subject RIV: CC - Organic Chemistry
Impact factor: 2.386, year: 2011

Synthesis, detailed structural characterization (X-ray, NMR, MS, IR, elemental analysis), and studies of toxicity, antioxidant activity and bioavailability of unique potent anti-atherosclerotic succinobucol-steroid conjugates are reported. The conjugates consist of, on one side, the therapeutically important drug succinobucol ([4-{2,6-di-tert-butyl-4-[(1-{[3-tert-butyl-4-hydroxy-5-(propan-2-yl)phenyl]sulfanyl}ethyl)sulfanyl]phenoxy}-4-oxo-butanoic acid]) possessing an antioxidant and anti-inflammatory activity, and on the other side, plant stanol/sterols (stigmastanol, β-sitosterol and stigmasterol) possessing an ability to lower the blood cholesterol level. A cholesterol-succinobucol prodrug was also prepared in order to enhance the absorption of succinobucol through the intestinal membrane into the organism and to target the drug into the place of lipid metabolism—The enterohepatic circulation system.
Permanent Link: http://hdl.handle.net/11104/0202647