Berberine derivatives, with substituted amino groups linked at the 9-position, as inhibitors of acetylcholinesterase/butyrylcholinesterase

Huang, Ling; Luo, Zonghua; He, Feng; Shi, Anding; Qin, Fangfei; Li, Xingshu

doi:10.1016/j.bmcl.2010.09.013

Cited by 35 publications

(17 citation statements)

References 19 publications

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“…Many studies proved that berberine exerts inhibitory effect against AChE [ 17 , 33 , 34 , 35 , 36 , 37 ]. Jung and co-workers reported that berberine can inhibit AChE with an IC 50 of 0.44 μM [ 17 ] and a close value of 0.58 μM and 0.37 μM was reported by Ingkaninan et al [ 34 ] and Huang et al [ 37 ], respectively. Xiang et al have explored the molecular mechanisms underlying the inhibition of berberine with AChE [ 38 ].…”

Section: Ache and Bche Inhibitory Activitymentioning

confidence: 99%

Berberine: A Potential Multipotent Natural Product to Combat Alzheimer’s Disease

Shen

2011

Molecules

146

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With the accelerated aging of human society Alzheimer’s disease (AD) has become one of the most threatening diseases in the elderly. However, there is no efficient therapeutic agent to combat AD. Berberine is a natural isoquinoline alkaloid that possesses a wide range of pharmacological effects. In the present paper, we review the multiple activities of berberine, including antioxidant, acetylcholinesterase and butyrylcholinesterase inhibitory, monoamine oxidase inhibitory, amyloid-b peptide level-reducing and cholesterol-lowering activities, which suggest that berberine may act as a promising multipotent agent to combat AD.

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Section: Ache and Bche Inhibitory Activitymentioning

confidence: 99%

Berberine: A Potential Multipotent Natural Product to Combat Alzheimer’s Disease

Shen

2011

Molecules

146

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“…200–400 mg/kg berberine daily for six weeks with twice weekly injections of CCL 4 demonstrated hepatoprotective effects in regard to serum liver enzymes and histological examination [ 12 ]. Furthermore, berberine has been found to have an inhibitory potential activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) [ 13 ]. In vitro , berberine reduced β -amyloid levels (APP NL -H4 cells) and downregulate β -secretase in HEK293 cells [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

Berberine Reduces Neurotoxicity Related to Nonalcoholic Steatohepatitis in Rats

Ghareeb

Khalil

Hafez

et al. 2015

Evidence-Based Complementary and Alternative Medicine

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Berberine is a plant alkaloid that has several pharmacological effects such as antioxidant, antilipidemic, and anti-inflammatory effects. Nonalcoholic steatohepatitis (NASH) triggers different aspects of disorders such as impaired endogenous lipid metabolism, hypercholesterolemia, oxidative stress, and neurotoxicity. In this study, we examined the mechanism by which NASH induces neurotoxicity and the protective effect of berberine against both NASH and its associated neurotoxicity. NASH induced rats showed significant impairments in lipid metabolism with increased serum triglycerides, cholesterol, and low-density lipoprotein (LDL). The NASH induced group also demonstrated a significant oxidative stress which is characterized by increased TBARs level and decreased antioxidant capacity such as GSH and SOD levels. Moreover, the NASH induction was associated with inflammation which was demonstrated by increased TNFα and nitric oxide levels. Hyperglycemia and hyperinsulinemia were observed in the NASH induced group. Also, our results showed a significant increase in the expression of the acetylcholine esterase (AChE) and amyloid beta precursor protein (AβPP). These changes were significantly correlated with decreased insulin degrading enzyme (IDE) and beta-amyloid40 (Aβ 40) and increased beta-amyloid42 (Aβ 42) in the hippocampal region. Daily administration of berberine (50 mg/kg) for three weeks ameliorated oxidative stress, inflammation, hyperlipidemia, hyperglycemia, hyperinsulinemia, and the observed neurotoxicity.

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“…Biological assay results Herein, berberine served as the reference compound, and its IC 50 value was 18.87 lM, which is approximately equal to the tested value (18.2 lM) by Li's group (20). Therefore, the experimental errors of the bioassay test between two different sets of compounds were very low, which could provide the high-quality dataset for building models.…”

Section: Resultsmentioning

confidence: 85%

Molecular Modeling on Berberine Derivatives toward BuChE: An Integrated Study with Quantitative Structure–Activity Relationships Models, Molecular Docking, and Molecular Dynamics Simulations

Fang

Pang

et al. 2016

Chem Biol Drug Des

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A dataset of 67 berberine derivatives for the inhibition of butyrylcholinesterase (BuChE) was studied based on the combination of quantitative structure-activity relationships models, molecular docking, and molecular dynamics methods. First, a series of berberine derivatives were reported, and their inhibitory activities toward butyrylcholinesterase (BuChE) were evaluated. By 2D- quantitative structure-activity relationships studies, the best model built by partial least-square had a conventional correlation coefficient of the training set (R(2)) of 0.883, a cross-validation correlation coefficient (Qcv2) of 0.777, and a conventional correlation coefficient of the test set (Rpred2) of 0.775. The model was also confirmed by Y-randomization examination. In addition, the molecular docking and molecular dynamics simulation were performed to better elucidate the inhibitory mechanism of three typical berberine derivatives (berberine, C2, and C55) toward BuChE. The predicted binding free energy results were consistent with the experimental data and showed that the van der Waals energy term (ΔEvdw) difference played the most important role in differentiating the activity among the three inhibitors (berberine, C2, and C55). The developed quantitative structure-activity relationships models provide details on the fine relationship linking structure and activity and offer clues for structural modifications, and the molecular simulation helps to understand the inhibitory mechanism of the three typical inhibitors. In conclusion, the results of this study provide useful clues for new drug design and discovery of BuChE inhibitors from berberine derivatives.

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Berberine derivatives, with substituted amino groups linked at the 9-position, as inhibitors of acetylcholinesterase/butyrylcholinesterase

Cited by 35 publications

References 19 publications

Berberine: A Potential Multipotent Natural Product to Combat Alzheimer’s Disease

Berberine: A Potential Multipotent Natural Product to Combat Alzheimer’s Disease

Berberine Reduces Neurotoxicity Related to Nonalcoholic Steatohepatitis in Rats

Molecular Modeling on Berberine Derivatives toward BuChE: An Integrated Study with Quantitative Structure–Activity Relationships Models, Molecular Docking, and Molecular Dynamics Simulations

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