Design, Synthesis and Evaluation of Genistein-O-Alkylbenzylamines as Potential Multifunctional Agents for the Treatment of Alzheimer's Disease

Qiang, Xiaoming; Sang, Zhipei; Yuan, Wen; Li, Yan; Liu, Qiang; Bai, Ping; Shi, Yikun; Ang, Wei; Tan, Zhenghuai; Deng, Yong

doi:10.1016/j.ejmech.2014.02.045

Cited by 113Cholinesterase and Neurodegenerative DiseasesAlzheimer's disease research and treatmentsSynthesis and biological activity

Design, Synthesis and Evaluation of Genistein-O-Alkylbenzylamines as Potential Multifunctional Agents for the Treatment of Alzheimer's Disease

Qiang, Xiaoming, Sang, Zhipei, Yuan, Wen, Li, Yan, Liu, Qiang, Bai, Ping, Shi, Yikun, Ang, Wei +2 more·2014·European Journal of Medicinal Chemistry

DOI 10.1016/j.ejmech.2014.02.045

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Abstract

A series of genistein derivatives with carbon spacer-linked alkylbenzylamines were designed, synthesized and tested as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good acetylcholinesterase (AChE) inhibitory activity, with moderate-to-good anti-oxidative activity. Specifically, compounds 10b, 19d and 25d exhibited significant inhibition of β-amyloid (Aβ) aggregation and exhibited metal chelating properties. In particular, 25d inhibited: self-induced Aβ₁₋₄₂ aggregation, Cu(2+)-induced Aβ₁₋₄₂ aggregation, and human AChE-induced Aβ₁₋₄₀ aggregation by 35%, 77.8%, and 36.2%, respectively. Moreover, both kinetic analysis of AChE inhibition and the molecular modeling study suggested that 25d binds simultaneously to catalytic active site and peripheral anionic site of AChE. More importantly, compound 25d disassembled the well-structured Aβ fibrils generated by Cu(2+)-induced Aβ aggregation by 72.1%. Furthermore, the step-down passive avoidance test showed this compound significantly reversed scopolamine-induced memory deficit in mice. These results suggest that 25d may be a promising multifunctional agent for AD treatment.

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In diabetic mice, genistein and some derivatives improve cognitive dysfunction by inhibiting AChE and modulating Ca2+ homeostasis in cholinergic neurons.
“in diabetic mice genistein (Pedersen et al., 1996; Wang et al., 2016), as well as some of its derivatives (Qiang et al., 2014), can improve cognitive dysfunction by inhibiting the activity of AChE and by the modulation of Ca2+ homeostasis in cholinergic neurons (Jhamandas et al., 2001)”
From Exploring the Therapeutic Potential of Phytochemicals in Alzheimer’s Disease: Focus on Polyphenols and Monoterpenes (2022) · cites this paper as Qiang et al., 2014

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Design, synthesis and evaluation of scutellarein-O-alkylamines as multifunctional agents for the treatment of Alzheimer's disease
Sang, Z., Qiang, X., Li, Y., Yuan, W., Liu, Q., Shi, Y., Ang, W., Luo, Y., Tan, Z., & Deng, Y. (2015) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2015.02.063 · Cited by 93 · see citing works
Self-citation
Design, Synthesis, Biological Evaluation and Molecular Dynamics Simulations Study of Genistein‐ O ‐1,3,5‐Triazine Derivatives as Multifunctional Anti‐Alzheimer Agents
Zou, J., Qian, J., Liu, S., Li, R., Zhang, X., Yang, S., Liu, Y., Liu, W., Ma, S., & Shi, D. (2022) · ChemistrySelect · doi:10.1002/slct.202203997 · Cited by 9 · see citing works

Authors: Qiang, X., Sang, Z., Yuan, W., Li, Y., Liu, Q., Bai, P., Shi, Y., Ang, W., Tan, Z., & Deng, Y.
Affiliations: Sichuan University (CN)
Sichuan Academy of Traditional Chinese Medicine (CN)
Corresponding author: Tan, Zhenghuai
Deng, Yong
ORCID: Sang, Zhipei
Li, Yan
Liu, Qiang
Bai, Ping
Ang, Wei
Tan, Zhenghuai
Deng, Yong
Venue: European Journal of Medicinal Chemistry
Publisher: Elsevier BV
Published: 2014-04
Volume: 76
Pages: 314-331
ISSN: 0223-5234 (ISSN-L)
DOI: 10.1016/j.ejmech.2014.02.045
OpenAlex: W2064613096
Cited by: 113
References: 47
Citations by year: 2026: 3 · 2025: 7 · 2024: 7 · 2023: 8 · 2022: 10 · 2021: 9 · 2020: 6 · 2019: 15 · 2018: 14 · 2017: 14 · 2016: 8 · 2015: 9 · 2014: 3
FWCI: 10.41
Type: journal article
Language: en
Open access: closed
Locations: European Journal of Medicinal Chemistry (publishedVersion)
PubMed (publishedVersion)
Funders: National Natural Science Foundation of China
National Science and Technology Major Project
National Key New Drug Creation and Manufacturing Program, Ministry of Science and Technology
Topics: Health Sciences › Medicine › Pharmacology › Cholinesterase and Neurodegenerative Diseases
Health Sciences › Medicine › Physiology › Alzheimer's disease research and treatments
Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
Keywords: genistein derivatives, Alzheimer's disease, acetylcholinesterase inhibition, amyloid-beta aggregation, metal chelation, antioxidant activity, peripheral anionic site, memory impairment, multifunctional agents, structure-activity relationship
MeSH terms: Alzheimer Disease, Animals, Cholinesterase Inhibitors, Kinetics, Models, Molecular, Magnetic Resonance Spectroscopy, Peptide Fragments, Drug Design, Amyloid beta-Peptides, Genistein, Inhibitory Concentration 50, Spectrometry, Mass, Electrospray Ionization, Mice

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