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Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase.
Bioorg Med Chem. 2010 Jun 15; 18(12):4475-84.BM

Abstract

A series of novel berberine derivatives were designed, synthesized, and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among these derivatives, compound 48a, berberine linked with 3-methylpyridinium by a 2-carbon spacer, was found to be a potent inhibitor of AChE, with an IC(50) value of 0.048 microM and compound 40c, berberine linked with 2-thionaphthol by a 4-carbon spacer, acted as the most potent inhibitor for BuChE with an IC(50) value of 0.078 microM. Kinetic studies and molecular modeling simulations of the AChE-inhibitor complex indicated that a mixed-competitive binding mode existed for these berberine derivatives.

Authors+Show Affiliations

The Industrial Institute of Fine Chemicals and Synthetic Drugs, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20471843

Citation

Huang, Ling, et al. "Synthesis and Biological Evaluation of a New Series of Berberine Derivatives as Dual Inhibitors of Acetylcholinesterase and Butyrylcholinesterase." Bioorganic & Medicinal Chemistry, vol. 18, no. 12, 2010, pp. 4475-84.
Huang L, Luo Z, He F, et al. Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase. Bioorg Med Chem. 2010;18(12):4475-84.
Huang, L., Luo, Z., He, F., Lu, J., & Li, X. (2010). Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase. Bioorganic & Medicinal Chemistry, 18(12), 4475-84. https://doi.org/10.1016/j.bmc.2010.04.063
Huang L, et al. Synthesis and Biological Evaluation of a New Series of Berberine Derivatives as Dual Inhibitors of Acetylcholinesterase and Butyrylcholinesterase. Bioorg Med Chem. 2010 Jun 15;18(12):4475-84. PubMed PMID: 20471843.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase. AU - Huang,Ling, AU - Luo,Zonghua, AU - He,Feng, AU - Lu,Jing, AU - Li,Xingshu, Y1 - 2010/04/27/ PY - 2010/02/21/received PY - 2010/04/20/revised PY - 2010/04/21/accepted PY - 2010/5/18/entrez PY - 2010/5/18/pubmed PY - 2010/10/15/medline SP - 4475 EP - 84 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 18 IS - 12 N2 - A series of novel berberine derivatives were designed, synthesized, and biologically evaluated as inhibitors of both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among these derivatives, compound 48a, berberine linked with 3-methylpyridinium by a 2-carbon spacer, was found to be a potent inhibitor of AChE, with an IC(50) value of 0.048 microM and compound 40c, berberine linked with 2-thionaphthol by a 4-carbon spacer, acted as the most potent inhibitor for BuChE with an IC(50) value of 0.078 microM. Kinetic studies and molecular modeling simulations of the AChE-inhibitor complex indicated that a mixed-competitive binding mode existed for these berberine derivatives. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/20471843/Synthesis_and_biological_evaluation_of_a_new_series_of_berberine_derivatives_as_dual_inhibitors_of_acetylcholinesterase_and_butyrylcholinesterase_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(10)00375-5 DB - PRIME DP - Unbound Medicine ER -