Seleno-analogs of scaffolds resembling natural products a novel warhead toward dual compounds

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dc.contributor.authorAstráin-Redín, Nora
dc.contributor.authorTalavera, Irene
dc.contributor.authorMoreno, Esther
dc.contributor.authorRamírez, María J.
dc.contributor.authorMartínez-Sáez, Nuria
dc.contributor.authorEncío Martínez, Ignacio
dc.contributor.authorSharma, Arun K.
dc.contributor.authorSanmartín, Carmen
dc.contributor.authorPlano, Daniel
dc.contributor.departmentOsasun Zientziakeu
dc.contributor.departmentInstitute for Multidisciplinary Research in Applied Biology - IMABen
dc.contributor.departmentCiencias de la Saludes_ES
dc.date.accessioned2023-05-05T09:49:46Z
dc.date.available2023-05-05T09:49:46Z
dc.date.issued2023
dc.date.updated2023-05-05T09:38:41Z
dc.description.abstractNowadays, oxidative cell damage is one of the common features of cancer and Alzheimer’s disease (AD), and Se-containing molecules, such as ebselen, which has demonstrated strong antioxidant activity, have demonstrated well-established preventive effects against both diseases. In this study, a total of 39 Se-derivatives were synthesized, purified, and spectroscopically characterized by NMR. Antioxidant ability was tested using the DPPH assay, while antiproliferative activity was screened in breast, lung, prostate, and colorectal cancer cell lines. In addition, as a first approach to evaluate their potential anti-Alzheimer activity, the in vitro acetylcholinesterase inhibition (AChEI) was tested. Regarding antioxidant properties, compound 13a showed concentration- and time-dependent radical scavenging activity. Additionally, compounds 14a and 17a showed high activity in the melanoma and ovarian cancer cell lines, with LD50 values below 9.2 µM. Interestingly, in the AChEI test, compound 14a showed almost identical inhibitory activity to galantamine along with a 3-fold higher in vitro BBB permeation (Pe = 36.92 × 10−6 cm/s). Molecular dynamics simulations of the aspirin derivatives (14a and 14b) confirm the importance of the allylic group instead of the propargyl one. Altogether, it is concluded that some of these newly synthesized Se-derivatives, such as 14a, might become very promising candidates to treat both cancer and AD.en
dc.description.sponsorshipThis research was funded by PIUNA (refs 2014-26 and 2018-19) and UNED-Caja Navarra Fundación La Caixa. N.A-R. acknowledges the FPU program from the Spanish Ministry of Universities for a Ph.D. fellowship (FPU20/00175).en
dc.format.mimetypeapplication/pdfen
dc.format.mimetypeapplication/zipen
dc.identifier.citationAstrain-Redin, N., Talavera, I., Moreno, E., Ramírez, M. J., Martínez-Sáez, N., Encío, I., Sharma, A. K., Sanmartín, C., & Plano, D. (2023). Seleno-analogs of scaffolds resembling natural products a novel warhead toward dual compounds. Antioxidants, 12(1), 139. https://doi.org/10.3390/antiox12010139en
dc.identifier.doi10.3390/antiox12010139
dc.identifier.issn2076-3921
dc.identifier.urihttps://academica-e.unavarra.es/handle/2454/45242
dc.language.isoengen
dc.publisherMDPIen
dc.relation.ispartofAntioxidants 2023, 12, 139en
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/FPU20%2F00175/
dc.relation.publisherversionhttps://doi.org/10.3390/antiox12010139
dc.rights© 2023 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.en
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectAcetylcholinesteraseen
dc.subjectAllylen
dc.subjectAlzheimer´s diseaseen
dc.subjectCanceren
dc.subjectGarlicen
dc.subjectNaturalen
dc.subjectNSAIDsen
dc.subjectPropargylen
dc.subjectSeleniumen
dc.subjectSelenoesteren
dc.titleSeleno-analogs of scaffolds resembling natural products a novel warhead toward dual compoundsen
dc.typeinfo:eu-repo/semantics/article
dc.type.versioninfo:eu-repo/semantics/publishedVersion
dspace.entity.typePublication
relation.isAuthorOfPublication599ca381-1fd2-4a23-93ab-4373837eb6e0
relation.isAuthorOfPublication.latestForDiscovery599ca381-1fd2-4a23-93ab-4373837eb6e0

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