Next Article in Journal
Indatraline: Synthesis and Effect on the Motor Activity of Wistar Rats
Next Article in Special Issue
Inhibitors of Testosterone Biosynthetic and Metabolic Activation Enzymes
Previous Article in Journal
Chemical Constituents of the Mexican Mistletoe (Psittacanthus calyculatus)
Previous Article in Special Issue
Stigmasterol-Based Novel Low Molecular Weight/Mass Organic Gelators
Molecules 2011, 16(11), 9404-9420; doi:10.3390/molecules16119404

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

1,2,3,* , 1
, 2,3
, 2,3
, 2,3
, 3
, 3,4
, 5
, 5
 and 1
Received: 29 September 2011 / Revised: 2 November 2011 / Accepted: 7 November 2011 / Published: 10 November 2011
(This article belongs to the Special Issue Steroids)
Download PDF [397 KB, uploaded 18 June 2014]
Abstract: 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. Their low toxicity towards mice fibroblasts at maximal concentrations, their antioxidant activity, comparable or even higher than that of ascorbic acid as determined by direct quenching of the DPPH radical, and their potential for significantly altering total and LDL cholesterol levels, suggest that these conjugates merit further studies in the treatment of cardiovascular or other related diseases. A brief discussion of succinobucol’s ability to quench the radicals, supported with a computational model of the electrostatic potential mapped on the electron density surface of the drug, is also presented.
Keywords: succinobucol; phytosterol; atherosclerosis; cholesterol; probucol succinobucol; phytosterol; atherosclerosis; cholesterol; probucol
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |

MDPI and ACS Style

Jurček, O.; Ikonen, S.; Buřičová, L.; Wimmerová, M.; Wimmer, Z.; Drašar, P.; Horníček, J.; Galandáková, A.; Ulrichová, J.; Kolehmainen, E.T. Succinobucol’s New Coat — Conjugation with Steroids to Alter Its Drug Effect and Bioavailability. Molecules 2011, 16, 9404-9420.

AMA Style

Jurček O, Ikonen S, Buřičová L, Wimmerová M, Wimmer Z, Drašar P, Horníček J, Galandáková A, Ulrichová J, Kolehmainen ET. Succinobucol’s New Coat — Conjugation with Steroids to Alter Its Drug Effect and Bioavailability. Molecules. 2011; 16(11):9404-9420.

Chicago/Turabian Style

Jurček, Ondřej; Ikonen, Satu; Buřičová, Lucie; Wimmerová, Martina; Wimmer, Zdeněk; Drašar, Pavel; Horníček, Jan; Galandáková, Adéla; Ulrichová, Jitka; Kolehmainen, Erkki T. 2011. "Succinobucol’s New Coat — Conjugation with Steroids to Alter Its Drug Effect and Bioavailability." Molecules 16, no. 11: 9404-9420.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert