Bioinorganic Chemistry and Applications
Volume 2007 (2007), Article ID 92145, 7 pages
doi:10.1155/2007/92145
Research Article

Organosilicon-Containing Thiazole Derivatives as Potential Lipoxygenase Inhibitors and Anti-Inflammatory Agents

Athina Geronikaki,1 Dimitra Hadjipavlou-Litina,1 Alla Zablotskaya,2 and Izolda Segal2

1Department of Pharmaceutical Chemistry, School of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece
2Laboratory of Organometallic Chemistry, Latvian Institute of Organic Synthesis, Latvian Academy of Sciences, 21 Aizkraukles Street, Riga 1006, Latvia

Received 24 December 2006; Revised 12 March 2007; Accepted 3 May 2007

Academic Editor: Guillermo Mendoza-Diaz

Copyright © 2007 Athina Geronikaki et al. 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.

Abstract

A number of trimethylsiloxyalkyl and trialkylsilylalkyl thiazole derivatives have been evaluated for their anti-inflammatory activity, lipoxygenase inhibiting properties, and cytotoxicity. The investigated compounds have been found to protect in vivo against carrageenin-induced edema, especially 3-(4-trimethylsiloxypiperidin-1-yl)-N-(thiazol-2-yl)-propionamide (21) and 2-amino-3-(γ-trimethylsilylpropyl)thiazolium iodide (22), which exhibited good anti-inflammatory activity: 57.2% CPE inhibition in dose of 0.2 mmol/kg for compound 21 and 55.0% in dose of 0.01 mmol/kg for compound 22. All the compounds tested inhibited soybean lipoxygenase activity. 2-(4-Trimethylsilyloxypiperidin-1-yl)-N-[4-(p-methoxyphenyl)-thiazol-2-yl]-acetamide (19) was the most potent displaying inhibition against lipoxygenase (ID50=0.01 mmol). It also possessed moderate cytotoxic effect (LC50=13 μg/mL, 3×10−8 mmol/mL) concerning MG-22A cell lines.