Synthesis and biological evaluation of glycosylated psoralen derivatives |
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Authors: | Chao-Yue Chen Jian-Guo Sun Fei-Yan Liu Kwok-Pui Fung Ping Wu Zhi-Zhen Huang |
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Affiliation: | 1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China;2. Research Centre of Siyuan Natural Pharmacy and Biotoxicology, College of Life Sciences, Zijinggang Campus, Zhejiang University, Hangzhou 310058, PR China;3. Department of Chemistry, Zhejiang University, Hangzhou 310028, PR China;4. Department of Biochemistry, The Chinese University of Hong Kong, Shatin, Hong Kong SAR, PR China |
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Abstract: | A novel route for the efficient synthesis of a target psoralen moiety, 4,4′-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photo-induced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. |
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