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Title 

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

Authors 

Tae Sook JeongJu Ryoung KimKyung Soon KimKyung Hyun ChoK H BaeWoo Song Lee

Publisher 

Elsevier

Issue Date 

2004

Citation 

Bioorganic & Medicinal Chemistry, vol. 12, no. 15, pp. 4017-4023

Keywords 

antioxidant5 (3,4 dihydroxybenzylidene)thiazolidine 2,4 dione5 (3,5 di tert butyl 4 hydroxybenzylidene)thiazolidine 2,4 dione5 (3,5 difluoro 4 hydroxybenzylidene)thiazolidine 2,4 dione5 (4 hydroxy 3,5 diisopropylbenzylidene)thiazolidine 2,4 dione5 (4 hydroxy 3,5 dimethoxybenzylidene)thiazolidine 2,4 dione5 (4 hydroxy 3,5 dimethylbenzylidene)thiazolidine 2,4 dione5 (4 hydroxy 3,5 trimethylbenzylidene)thiazolidine 2,4 dione5 [1 [3,5 bis(1,1 dimethylethyl) 4 hydroxyphenyl]ethylene] 2,4 thiazolidinedioneoxidation

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.

ISSN 

0968-0896

Link 

http://dx.doi.org/10.1016/j.bmc.2004.06.001

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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