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Synthesis and biological evaluation of berberine-thiophenyl hybrids as multi-functional agents: Inhibition of acetylcholinesterase, butyrylcholinesterase, and Aβ aggregation and antioxidant activity.
Bioorg Med Chem. 2013 Sep 15; 21(18):5830-40.BM

Abstract

A series of berberine-thiophenyl hybrids were designed, synthesised, and evaluated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and β-amyloid (Aβ) aggregation and as antioxidants. Among these hybrids, compounds 4f and 4i, berberine linked with o-methylthiophenyl and o-chlorothiophenyl by a 2-carbon spacer, were observed to be potent inhibitors of AChE, with IC50 values of 0.077 and 0.042 μM, respectively. Of the tested compounds, 4i was also the most potent inhibitor of BuChE, with an IC50 value of 0.662 μM. Kinetic studies and molecular modelling simulations of the AChE-inhibitor complex indicated that a mixed-competitive binding mode existed for these berberine derivatives. The biological studies also demonstrated that these hybrids displayed interesting activities, including Aβ aggregation inhibition and antioxidant properties.

Authors+Show Affiliations

Institute of Drug Synthesis and Pharmaceutical Process, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23932451

Citation

Su, Tao, et al. "Synthesis and Biological Evaluation of Berberine-thiophenyl Hybrids as Multi-functional Agents: Inhibition of Acetylcholinesterase, Butyrylcholinesterase, and Aβ Aggregation and Antioxidant Activity." Bioorganic & Medicinal Chemistry, vol. 21, no. 18, 2013, pp. 5830-40.
Su T, Xie S, Wei H, et al. Synthesis and biological evaluation of berberine-thiophenyl hybrids as multi-functional agents: Inhibition of acetylcholinesterase, butyrylcholinesterase, and Aβ aggregation and antioxidant activity. Bioorg Med Chem. 2013;21(18):5830-40.
Su, T., Xie, S., Wei, H., Yan, J., Huang, L., & Li, X. (2013). Synthesis and biological evaluation of berberine-thiophenyl hybrids as multi-functional agents: Inhibition of acetylcholinesterase, butyrylcholinesterase, and Aβ aggregation and antioxidant activity. Bioorganic & Medicinal Chemistry, 21(18), 5830-40. https://doi.org/10.1016/j.bmc.2013.07.011
Su T, et al. Synthesis and Biological Evaluation of Berberine-thiophenyl Hybrids as Multi-functional Agents: Inhibition of Acetylcholinesterase, Butyrylcholinesterase, and Aβ Aggregation and Antioxidant Activity. Bioorg Med Chem. 2013 Sep 15;21(18):5830-40. PubMed PMID: 23932451.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and biological evaluation of berberine-thiophenyl hybrids as multi-functional agents: Inhibition of acetylcholinesterase, butyrylcholinesterase, and Aβ aggregation and antioxidant activity. AU - Su,Tao, AU - Xie,Shishun, AU - Wei,Hui, AU - Yan,Jun, AU - Huang,Ling, AU - Li,Xingshu, Y1 - 2013/07/24/ PY - 2013/05/14/received PY - 2013/07/04/revised PY - 2013/07/05/accepted PY - 2013/8/13/entrez PY - 2013/8/13/pubmed PY - 2014/3/29/medline KW - Alzheimer’s disease KW - Antioxidants KW - Inhibitors of AChE KW - berberine–thiophenyl hybrids KW - β-Amyloid aggregation SP - 5830 EP - 40 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 21 IS - 18 N2 - A series of berberine-thiophenyl hybrids were designed, synthesised, and evaluated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and β-amyloid (Aβ) aggregation and as antioxidants. Among these hybrids, compounds 4f and 4i, berberine linked with o-methylthiophenyl and o-chlorothiophenyl by a 2-carbon spacer, were observed to be potent inhibitors of AChE, with IC50 values of 0.077 and 0.042 μM, respectively. Of the tested compounds, 4i was also the most potent inhibitor of BuChE, with an IC50 value of 0.662 μM. Kinetic studies and molecular modelling simulations of the AChE-inhibitor complex indicated that a mixed-competitive binding mode existed for these berberine derivatives. The biological studies also demonstrated that these hybrids displayed interesting activities, including Aβ aggregation inhibition and antioxidant properties. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/23932451/Synthesis_and_biological_evaluation_of_berberine_thiophenyl_hybrids_as_multi_functional_agents:_Inhibition_of_acetylcholinesterase_butyrylcholinesterase_and_Aβ_aggregation_and_antioxidant_activity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(13)00622-6 DB - PRIME DP - Unbound Medicine ER -