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Molecules 2012, 17(10), 11294-11302;

Synthesis and Cytotoxicity Evaluation of 13-n-Alkyl Berberine and Palmatine Analogues as Anticancer Agents

School of Pharmacy, China Pharmaceutical University, Nanjing 210009, Jiangsu, China
Oil Crops Research Institute, Chinese Academy of Agricultural Sciences, Wuhan 430062, Hubei, China
Key Laboratory of Biology and Genetic Improvement of Oil Crops, Ministry of Agriculture, Wuhan 430062, Hubei, China
Wuxi JC Pharmaceutical Technology Inc., Wuxi 214036, Jiangsu, China
School of Pharmacy, Nanjing Medical University, Nanjing 210029, Jiangsu, China
Author to whom correspondence should be addressed.
Received: 30 August 2012 / Revised: 11 September 2012 / Accepted: 17 September 2012 / Published: 25 September 2012
(This article belongs to the Section Medicinal Chemistry)
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By introducing long carbon-chain alkyl groups at the C-13 position of berberine and palmatine, 13-n-hexyl/13-n-octyl berberine and palmatine chloride analogues 4ad were synthesized and examined by MTT assays for cytotoxic activity in seven human cancer cell lines (7701QGY, SMMC7721, HepG2, CEM, CEM/VCR, KIII, Lewis), yielding IC50 values of 0.02 ± 0.01–13.58 ± 2.84 μM. 13-n-Octyl palmatine (compound 4d) gave the most potent inhibitor activity, with an IC50 of 0.02 ± 0.01 μM for SMMC7721. In all cases, the 13-n-alkyl berberine and palmatine analogues 4ad were more cytotoxic than berberine and palmatine. In addition, compounds 4ad also exhibited more potent cytotoxicity than berberine and palmatine in mice with S180 sarcoma xenografted in vivo. The primary screening results indicated that the 13-n-hexyl/13-n-octyl berberine and palmatine analogues might be valuable source for new potent anticancer drug candidates. View Full-Text
Keywords: berberine; palmatine; alkylation; cytotoxicity; antitumor berberine; palmatine; alkylation; cytotoxicity; antitumor

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Zhang, L.; Li, J.; Ma, F.; Yao, S.; Li, N.; Wang, J.; Wang, Y.; Wang, X.; Yao, Q. Synthesis and Cytotoxicity Evaluation of 13-n-Alkyl Berberine and Palmatine Analogues as Anticancer Agents. Molecules 2012, 17, 11294-11302.

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