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Syntheses and Structure–Activity Relationships in Growth Inhibition Activity against Human Cancer Cell Lines of 12 Substituted Berberine Derivatives

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
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Molecules 2020, 25(8), 1871; https://doi.org/10.3390/molecules25081871
Received: 19 March 2020 / Revised: 2 April 2020 / Accepted: 5 April 2020 / Published: 18 April 2020
In this study, quaternary berberine chloride is used as a lead compound to design and synthesize a series of berberine-12-amine derivatives to evaluate the growth inhibition activity against human cancer cell lines. Forty-two compounds of several series were obtained. The quaternary berberine-12-N,N-di-n-alkylamine chlorides showed the targeted activities with the IC50 values of most active compounds being dozens of times those of the positive control. A significant structure–activity relationship (SAR) was observed. The activities of quaternary berberine-12-N,N-di-n-alkylamine chlorides are significantly stronger than those of the reduced counterparts. In the range of about 6-8 carbon atoms, the activities increase with the elongation of n-alkyl carbon chain of 12-N,N-di-n-alkylamino, and when the carbon atom numbers are more than 6-8, the activities decrease with the elongation of n-alkyl carbon chain. The activities of the tertiary amine structure are significantly higher than that of the secondary amine structure. View Full-Text
Keywords: quaternary berberine chloride; structure modification; berberine-12-amine derivatives; growth inhibition activities against cancer cell lines; structure–activity relationships quaternary berberine chloride; structure modification; berberine-12-amine derivatives; growth inhibition activities against cancer cell lines; structure–activity relationships
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Wang, B.; Deng, A.-J.; Li, Z.-H.; Wang, N.; Qin, H.-L. Syntheses and Structure–Activity Relationships in Growth Inhibition Activity against Human Cancer Cell Lines of 12 Substituted Berberine Derivatives. Molecules 2020, 25, 1871.

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