Inhibitory effects of multi-substituted benzylidenethiazolidine-2,4-diones on LDL oxidation

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Title
Inhibitory effects of multi-substituted benzylidenethiazolidine-2,4-diones on LDL oxidation
Author(s)
Tae Sook Jeong; Ju Ryoung Kim; Kyung Soon Kim; Kyung Hyun Cho; K H Bae; Woo Song Lee
Bibliographic Citation
Bioorganic & Medicinal Chemistry, vol. 12, no. 15, pp. 4017-4023
Publication Year
2004
Abstract
Multi-substituted benzylidenethiazolidine-2,4-diones 3a-h were synthesized by Knoevenagel condensation of di- or tri-substituted 4-hydroxybenzaldehydes [or 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone] 1 with thiazolidine-2,4-dione (2) and evaluated for antioxidant activities of Cu2+-induced oxidation of human low-density lipoproteins (LDL). Among compounds 3a-h, 3a was superior to probucol in LDL-antioxidant activities and found to be ninefold more active than probucol. Due to its potency, compound 3a was tested for complementary in vitro investigations, such as TBARS assay (IC 50=0.1μM), lag time (240min at 1.5μM), relative electrophoretic mobility (REM) of ox-LDL (inhibition of 83% at 10μM), fragmentation of apoB-100 (inhibition of 61% at 5μM), and radical DPPH scavenging activity on copper-mediated LDL oxidation. In macrophage-mediated LDL oxidation, the TBARS formation was also inhibited by compound 3a.
Keyword
antioxidant
ISSN
0968-0896
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.bmc.2004.06.001
Type
Article
Appears in Collections:
Division of Biomaterials Research > Industrial Bio-materials Research Center > 1. Journal Articles
Jeonbuk Branch Institute > Functional Biomaterial Research Center > 1. Journal Articles
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