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dc.contributor.author
Carvalho, Alessandra
dc.contributor.author
Barbosa, Barbara Marinho
dc.contributor.author
Flores, Jesica Soledad
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dc.contributor.author
Do Carmo Goncalves, Phelippe
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Diniz, Renata
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Cordeiro, Yraima
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Fernández, Claudio O.
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Cukierman, Daphne S.
dc.contributor.author
Rey, Nicolás A.
dc.date.available
2024-01-22T15:45:39Z
dc.date.issued
2023-01
dc.identifier.citation
Carvalho, Alessandra; Barbosa, Barbara Marinho; Flores, Jesica Soledad; Do Carmo Goncalves, Phelippe; Diniz, Renata; et al.; New mescaline-related N-acylhydrazone and its unsubstituted benzoyl derivative: Promising metallophores for copper-associated deleterious effects relief in Alzheimer's disease; Elsevier Science Inc.; Journal of Inorganic Biochemistry; 238; 1-2023; 1-12
dc.identifier.issn
0162-0134
dc.identifier.uri
http://hdl.handle.net/11336/224485
dc.description.abstract
Alzheimer's disease (AD) is related to the presence of extracellular aggregated amyloid-β peptide (Aβ), which binds copper(II) with high affinity in its N-terminal region. In this sense, two new 1-methylimidazole-containing N-acylhydrazonic metallophores, namely, X1TMP and X1Benz, were synthesized as hydrochlorides and characterized. The compound X1TMP contains the 3,4,5-trimethoxybenzoyl moiety present in the structure of mescaline, a natural hallucinogenic protoalkaloid that occurs in some species of cacti. Single crystals of X1Benz, the unsubstituted derivative of X1TMP, were obtained. The experimental partition coefficients of both compounds were determined, as well as their apparent affinity for Cu2+ in aqueous solution. Ascorbate consumption assays showed that these N-acylhydrazones are able to lessen the production of ROS by the Cu(Aβ)-system, and a short-time scale aggregation study, measured through turbidity and confirmed by TEM images, revealed their capacity in preventing Aβ fibrillation at equimolar conditions in the presence and absence of copper. 1H[sbnd]15N HSQC NMR experiments demonstrated a direct interaction between Aβ and X1Benz, the most soluble of the compounds. The Cu2+ sequestering potential of this hydrazone towards Aβ was explored by 1H NMR. Although increasing amounts of X1Benz were unexpectedly not efficient at removing the metal-induced perturbations in Aβ backbone amides, the broadening effects observed on the compound's signals indicate the formation of a ternary Aβ‑copper-X1Benz species, which can be responsible for the observed ROS-lessening and aggregation-preventing activities. Overall, the N-acylhydrazones X1TMP and X1Benz have shown promising prospects as agents for the treatment of AD.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science Inc.
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dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
ALZHEIMER'S DISEASE
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COPPER(II)
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MESCALINE
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METALLOPHORES
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N-ACYLHYDRAZONES
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ROS
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Otros Tópicos Biológicos
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dc.subject.classification
Ciencias Biológicas
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CIENCIAS NATURALES Y EXACTAS
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dc.subject.classification
Biofísica
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dc.subject.classification
Ciencias Biológicas
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CIENCIAS NATURALES Y EXACTAS
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dc.title
New mescaline-related N-acylhydrazone and its unsubstituted benzoyl derivative: Promising metallophores for copper-associated deleterious effects relief in Alzheimer's disease
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2024-01-22T12:08:47Z
dc.journal.volume
238
dc.journal.pagination
1-12
dc.journal.pais
Estados Unidos
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dc.description.fil
Fil: Carvalho, Alessandra. Pontifícia Universidade Católica do Rio de Janeiro; Brasil
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Fil: Barbosa, Barbara Marinho. Pontifícia Universidade Católica do Rio de Janeiro; Brasil
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Fil: Flores, Jesica Soledad. Universidad Nacional de Rosario. Centro de Estudios Interdisciplinarios; Argentina
dc.description.fil
Fil: Do Carmo Goncalves, Phelippe. Universidad Nacional de Rosario. Centro de Estudios Interdisciplinarios; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
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Fil: Diniz, Renata. Universidade Federal de Minas Gerais; Brasil
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Fil: Cordeiro, Yraima. Universidade Federal do Rio de Janeiro; Brasil
dc.description.fil
Fil: Fernández, Claudio O.. Universidad Nacional de Rosario. Centro de Estudios Interdisciplinarios; Argentina
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Fil: Cukierman, Daphne S.. Universidade Federal do Rio de Janeiro; Brasil. Pontifícia Universidade Católica do Rio de Janeiro; Brasil
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Fil: Rey, Nicolás A.. Pontifícia Universidade Católica do Rio de Janeiro; Brasil
dc.journal.title
Journal of Inorganic Biochemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.jinorgbio.2022.112033
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