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Synthesis and ABTS Radical, MMP‐1 Inhibitory Activity of CAPE Analogues
Author(s) -
Chiang ChihChia,
Hsu LingYih,
Chang TsuChung,
Tsai HouJen
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800105
Subject(s) - chemistry , caffeic acid phenethyl ester , abts , matrix metalloproteinase , polyphenol , photoaging , antioxidant , reactive oxygen species , caffeic acid , dermal fibroblast , cytotoxicity , biochemistry , radical , in vitro , fibroblast , dpph , genetics , biology
In the photoaging process of skin, the ultraviolet (UV)‐induced reactive oxygen species (ROS) is the key regulator of matrix metalloproteinase (MMPs) expression. In this study, a series of Caffeic acid phenethyl ester (CAPE) analogues were synthesized by conjugating the group VI elements (selenium, sulfur, oxygen)‐containing aliphatic alcohols to polyphenolic acids. Their biological activities were evaluated by in vitro testing of their radical scavenging activity the of ABTS [2,2′‐azinobis‐(3‐ethyl‐benzothiazoline‐6‐sulfonic acid)] radical and inhibitory effect against the matrix metalloproteinase‐1 (MMP‐1) activity of collagen degradation and cytotoxicity of a human dermal fibroblast skin cell. Our results suggest these compounds displayed moderate anti‐free radical, potent MMP‐1 inhibitory, and low cytotoxic activities.