947599-36-2

Upstream product

• 124-13-0 Octanal 
• 483-15-8 7,8-dihydroberberine 

Downstream Products

• 1375475-69-6 2,3-methylenedioxy-9-benzyloxy-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-70-9 2,3-methylenedioxy-9-O-(4-methylbenzoyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-71-0 2,3-methylenedioxy-9-O-(4-methoxylbenzoyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-72-1 2,3-methylenedioxy-9-O-(4-trifluoromethylbenzenesulfonyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-73-2 2,3-methylenedioxy-9-O-(4-cyanobenzenesulfonyl)-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-77-6 2-hydroxy-3-benzyloxy-9,10-dimethoxy-13-n-octylprotoberberine chloride 
• 1375475-81-2 2,3-dibenzyloxy-9,10-dimethoxy-13-n-octylprotoberberine chloride 
• 1375475-85-6 2-hydroxy-3,9-dibenzyloxy-10-methoxy-13-n-octylprotoberberine chloride 
• 1375475-87-8 2,3,9-tribenzyloxy-10-methoxy-13-n-octylprotoberberine chloride 

Relevant academic research and scientific papers

Synthesis and anticancer activity of novel 9,13-disubstituted berberine derivatives

Novel berberine derivatives with disubstituents on positions C9 and C13 were synthesized and evaluated for antiproliferative activities against human prostate cancer cell lines (PC3 and DU145), breast cancer cell line (MDA-MB-231) and human colon cancer cell lines (HT29 and HCT116). All compounds showed significantly enhanced antiproliferative activities compared with berberine. Notably, compound 18e exhibited the strongest cytotoxicity against PC3 cells with an IC50 value of 0.19 μM, and the highest selectivity index (SIPC3 > 20). Further studies showed that 18e could arrest the cell cycle at G1 phase, and significantly inhibit tumor cell colony forming and migration even at low concentrations. Interestingly, 18e could significantly induce cytoplasmic vacuolation, suggesting a different mode of action from berberine.

Synthesis and in vitro photocytotoxicity of 9-/13-lipophilic substituted berberine derivatives as potential anticancer agents

The objective of this study was to synthesize the 9-/13-position substituted berberine derivatives and evaluate their cytotoxic and photocytotoxic effects against three human cancer cell lines. Among all the synthesized compounds, 9-O-dodecyl- (5e), 13-dodecyl- (6e), and 13-O-dodecyl-berberine (7e) exhibited stronger growth inhibition against three human cancer cell lines, (HepG2, HT-29 and BFTC905), in comparison with structurally related berberine (1). These three compounds also showed the photocytotoxicity in human cancer cells in a concentration-dependent and light dose-dependent manner. Through flow cytometry analysis, we found out a lipophilic group at the 9-/13-position of berberine may have facilitated its penetration into test cells and hence enhanced its photocytotoxicity on the human liver cancer cell HepG2. Further, in cell cycle analysis, 5e, 6e, and 7e induced HepG2 cells to arrest at the S phase and caused apoptosis upon irradiation. In addition, photodynamic treatment of berberine derivatives 5e, 6e, and 7e again showed a significant photocytotoxic effects on HepG2 cells, induced remarkable cell apoptosis, greatly increased intracellular ROS level, and the loss of mitochondrial membrane potential. These results over and again confirmed that berberine derivatives 5e, 6e, and 7e greatly enhanced photocytotoxicity. Taken together, the test data led us to conclude that berberine derivatives with a dodecyl group at the 9-/13-position could be great candidates for the anti-liver cancer medicines developments.

Synthesis, structure-activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives

Twenty-eight new 13-n-octylberberine derivatives were synthesized and evaluated for their activities against drug-susceptible Mycobacterium tuberculosis (M. tuberculosis) strain H37Rv. Among these compounds, compound 16e was the most effective anti-tubercular agent with a MIC value of 0.125 μg/mL. Importantly, compound 16e exhibited more potent effect against rifampicin (RIF)- and isoniazid (INH)-resistant M. tuberculosis strains than both RIF and INH, suggesting a new mechanism of action. Therefore, it has been selected as a drug candidate for further investigation, or as a chemical probe for identifying protein target and studying tuberculosis biology. We consider 13-n-octylberberine analogs to be a promising novel class of antituberculars against multi-drug-resistant (MDR) strains of M. tuberculosis.