Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: A lipophilic substitute role |
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Authors: | Chih-Yu Lo Lin-Chen Hsu Min-Shin Chen Yi-Jing Lin Lih-Geeng Chen Cheng-Deng Kuo Jin-Yi Wu |
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Institution: | 1. Department of Food Science, College of Life Sciences, National Chiayi University, Taiwan, ROC;2. St. Martin De Porres Hospital Laboratory, Chiayi, Taiwan, ROC;3. Department of Microbiology, Immunology and Biopharmaceutics, College of Life Sciences, National Chiayi University, 300 University Road, Chiayi 60004, Taiwan, ROC;4. Department of Medical Research and Education, Taipei Veterans General Hospital, Taipei, Taiwan, ROC |
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Abstract: | To alter its hydrophobicity, a series of compounds bearing 9-O-alkyl- or 9-O-terpenyl- substituted berberine were synthesized and evaluated for anticancer activity against human cancer HepG2 and HT29 cell lines. We found that the lipophilic substitute of 9-O-alkyl- and 9-O-terpenyl berberine derivatives plays a role in inhibiting the human cancer cell growth and its activity could be maximized with the optimized substitute type and chain length. Most strikingly, nonetheless, of the six compounds prepared, sample 8, a farnesyl 9-O-substituted berberine, showed either comparable or better cytotoxic activity against human cancer HepG2 cell line than that of berberine. Compound 8 had also shown a 104-fold antiproliferation activity in compare with berberine against human hepatoma HepG2 cell lines after 48 incubation hours. Further, in Hoechst 33258 and annexin V-FITC/PI staining analyses it induced apoptosis in HepG2 cells at lower concentration than that of berberine for 24 h. Take all; farnesyl 9-O-substituted berberine could be a potential candidate for new anticancer drug development. |
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