Novel Rivastigmine Derivatives as Promising Multi-Target Compounds for Potential Treatment of Alzheimer’s Disease
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Alzheimer’s disease (AD) is the most serious and prevalent neurodegenerative disorder still without cure. Since its aetiology is diverse, recent research on anti-AD drugs has been focused on multi-target compounds. In this work, seven novel hybrids (RIV–BIM) conjugating the active moiety of the drug rivastigmine (RIV) with 2 isomeric hydroxyphenylbenzimidazole (BIM) units were developed and studied. While RIV assures the inhibition of cholinesterases, BIM provides further appropriate properties, such as inhibition of amyloid β-peptide (Aβ) aggregation, antioxidation and metal chelation. The evaluated biological properties of these hybrids included antioxidant activity; inhibition of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and Aβ42 aggregation; as well as promotion of cell viability and neuroprotection. All the compounds are better inhibitors of AChE than rivastigmine (IC50 = 32.1 µM), but compounds of series 5 are better inhibitors of BChE (IC50 = 0.9−1.7 µM) than those of series 4. Series 5 also showed good capacity to inhibit self- (42.1−58.7%) and Cu(II)-induced (40.3−60.8%) Aβ aggregation and also to narrow (22.4−42.6%) amyloid fibrils, the relevant compounds being 5b and 5d. Some of these compounds can also prevent the toxicity induced in SH-SY5Y cells by Aβ42 and oxidative stress. Therefore, RIV–BIM hybrids seem to be potential drug candidates for AD with multi-target abilities.
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Rivastigmine is authorized for use in mild-to-moderate Parkinson's disease dementia and mild-to-moderate AD.
“It is authorized for use in mild-to-moderate Parkinson’s disease dementia and mild-to-moderate AD [116,117,118].”
From Recent Advances in Therapeutics for the Treatment of Alzheimer’s Disease (2024) · cites this paper as [117]
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Self-citation
- Authors
- Vicente-Zurdo, D., Rosales-Conrado, N., León-González, M. E., Brunetti, L., Piemontese, L., Pereira-Santos, A. R., Cardoso, S. M., Madrid, Y., Chaves, S., & Santos, M. A.
- Affiliations
- Universidad Complutense de Madrid (ES)
- Department of Analytical Chemistry, Faculty of Chemistry, Complutense University of Madrid, Avenida Complutense s/n, 28040 Madrid, Spain
- University of Lisbon (PT)
- University of Bari Aldo Moro (IT)
- University of Coimbra (PT)
- Centro de Química Estrutural, Institute of Molecular Sciences, Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais 1, 1049-001 Lisboa, Portugal
- Corresponding author
- Santos, M. Amélia
- ORCID
- Venue
- Biomedicines
- Publisher
- MDPI AG
- Published
- 2022-06-26
- Volume
- 10
- Issue
- 7
- Pages
- 1510
- ISSN
- 2227-9059 (ISSN-L)
- PMC
- PMC9313321
- OpenAlex
- W4283522325
- Cited by
- 47
- References
- 61
- Citations by year
- 2026: 12 · 2025: 12 · 2024: 13 · 2023: 9 · 2022: 1
- FWCI
- 5.39
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Licence
- Locations
- Biomedicines (publishedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- CINECA IRIS Institutional Research Information System (University of Bari Aldo Moro) (submittedVersion, cc-by)
- BURJC Digital (King Juan Carlos University) (submittedVersion, cc-by)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion)
- Hispana (submittedVersion, cc-by)
- Funders
- Portuguese Fundação para a Ciência e Tecnologia (FCT) (UIDB/00100/2020, UIDP/00100/2020, UIDB/04539/2020, UIDP/04539/2020, LA/P/0058/2020, PID2020-114714RB-I00, S2018/BAA-4393, AVANSECAL-II-CM, FPU18/00573, PD/BD/2020.06543.BD)
- Spanish Ministry of Science and Innovation (UIDB/00100/2020, UIDP/00100/2020, UIDB/04539/2020, UIDP/04539/2020, LA/P/0058/2020, PID2020-114714RB-I00, S2018/BAA-4393, AVANSECAL-II-CM, FPU18/00573, PD/BD/2020.06543.BD)
- Community of Madrid and European funding from FSE and FEDER programs for financial support (UIDB/00100/2020, UIDP/00100/2020, UIDB/04539/2020, UIDP/04539/2020, LA/P/0058/2020, PID2020-114714RB-I00, S2018/BAA-4393, AVANSECAL-II-CM, FPU18/00573, PD/BD/2020.06543.BD)
- Spanish Ministry of Science, Innovation and Universities (UIDB/00100/2020, UIDP/00100/2020, UIDB/04539/2020, UIDP/04539/2020, LA/P/0058/2020, PID2020-114714RB-I00, S2018/BAA-4393, AVANSECAL-II-CM, FPU18/00573, PD/BD/2020.06543.BD)
- Erasmus+ program for an international fellowship (UIDB/00100/2020, UIDP/00100/2020, UIDB/04539/2020, UIDP/04539/2020, LA/P/0058/2020, PID2020-114714RB-I00, S2018/BAA-4393, AVANSECAL-II-CM, FPU18/00573, PD/BD/2020.06543.BD)
- PhD fellowship (UIDB/00100/2020, UIDP/00100/2020, UIDB/04539/2020, UIDP/04539/2020, LA/P/0058/2020, PID2020-114714RB-I00, S2018/BAA-4393, AVANSECAL-II-CM, FPU18/00573, PD/BD/2020.06543.BD)
- 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
- Alzheimer's disease, multi-target drugs, acetylcholinesterase inhibition, butyrylcholinesterase inhibition, amyloid-beta aggregation, antioxidant activity, metal chelation, neuroprotection, SH-SY5Y cells, oxidative stress, hybrid drug design
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