Synthesis and characterization of IMPY derivatives that regulate metal-induced amyloid-β aggregation

Choi, Jung-Suk; Braymer, Joseph J.; Park, Se Kyung; Mustafa, Shaik; Chae, Junghyun; Lim, Mi Hee

doi:10.1039/c0mt00077a

Cited by 41Alzheimer's disease research and treatmentsMolecular Sensors and Ion DetectionCholinesterase and Neurodegenerative Diseases

Synthesis and characterization of IMPY derivatives that regulate metal-induced amyloid-β aggregation

Choi, Jung-Suk, Braymer, Joseph J., Park, Se Kyung, Mustafa, Shaik, Chae, Junghyun, Lim, Mi Hee·2011·Metallomics

DOI 10.1039/c0mt00077a

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Abstract

Metal ions associated with amyloid-β (Aβ) species have been suggested to be involved in neurodegeneration leading to the progression of Alzheimer's disease (AD). The role of metal-involved Aβ species in AD neuropathogenesis, however, is not fully elucidated. In order to advance this understanding and contribute to the therapeutic development for AD, the rational structure-based design of small molecules that specifically target metal ions surrounded by Aβ species has recently received increased attention. To date, only a few compounds have been fashioned for this purpose. Herein, we report the design strategy, synthesis, characterization, and reactivity of new bifunctional IMPY derivatives K1 and K2. Using UV-vis and high-resolution two-dimensional (2D) NMR spectroscopy, the bifunctionality of K1 and K2 (metal chelation and Aβ interaction) was confirmed. These bifunctional IMPY derivatives showed preferential reactivity toward metal-induced Aβ aggregation over metal-free conditions in both in vitro inhibition and disaggregation experiments. Taken together, this study provides another example of a bifunctional small molecule framework that can target metal ions associated with Aβ species.

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Two approaches have been pursued in BFC design: direct incorporation of metal-binding atom donors into the structural framework of an Aβ-interacting compound, and linking the metal-chelating and Aβ-binding molecular fragments.
“In this context, two approaches have been pursued in BFC design. 31,49–58 One strategy is based on the direct incorporation of metal-binding atom donors into the structural framework of an Aβ-interacting compoud (Scheme 1, approach A), and the other involves linking the metal-chelating and Aβ-binding molecular fragments (Scheme 1, approach B).”
From Bifunctional Compounds for Controlling Metal-Mediated Aggregation of the Aβ42Peptide (2012) · cites this paper as [56]

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Authors: Choi, J.-S., Braymer, J. J., Park, S. K., Mustafa, S., Chae, J., & Lim, M. H.
Affiliations: University of Michigan (US)
Sungshin Women's University (KR)
Corresponding author: Chae, Junghyun
Lim, Mi Hee
ORCID: Braymer, Joseph J.
Chae, Junghyun
Lim, Mi Hee
Venue: Metallomics
Publisher: Oxford University Press (OUP)
Published: 2011
Volume: 3
Issue: 3
Pages: 284
ISSN: 1756-5901 (ISSN-L)
1756-591X
DOI: 10.1039/c0mt00077a
OpenAlex: W2045704153
Cited by: 41
References: 45
Citations by year: 2025: 1 · 2024: 4 · 2022: 2 · 2020: 3 · 2019: 2 · 2018: 2 · 2017: 1 · 2016: 2 · 2015: 2 · 2014: 6 · 2013: 4 · 2012: 7
FWCI: 4.80
Type: journal article
Language: en
Open access: closed
Locations: Metallomics (publishedVersion)
PubMed (publishedVersion)
Scholarworks@UNIST (Ulsan National Institute of Science and Technology) (submittedVersion)
Topics: Health Sciences › Medicine › Physiology › Alzheimer's disease research and treatments
Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
Health Sciences › Medicine › Pharmacology › Cholinesterase and Neurodegenerative Diseases
Keywords: amyloid-beta aggregation, metal ions, Alzheimer's disease, metal chelation, bifunctional small molecules, structure-based drug design
MeSH terms: Alzheimer Disease, Chelating Agents, Humans, Metals, Pyrazoles, Pyridines, Drug Design, Amyloid beta-Peptides

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Synthesis and characterization of IMPY derivatives that regulate metal-induced amyloid-β aggregation

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