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dc.contributor.author Ravetti, Soledad
dc.contributor.author de Candia, Cristian Ariel
dc.contributor.author Gualdesi, María Soledad
dc.contributor.author Pampuro, Sandra Esther
dc.contributor.author Turk, Gabriela Julia Ana
dc.contributor.author Quevedo, Mario Alfredo
dc.contributor.author Briñon, Margarita Cristina
dc.date.available 2017-12-21T19:49:04Z
dc.date.issued 2014-02
dc.identifier.citation Biological evaluation and molecular modelling of didanosine derivatives; Royal Society of Chemistry; MedChemComm; 5; 2-2014; 622-631
dc.identifier.issn 2040-2503
dc.identifier.uri http://hdl.handle.net/11336/31271
dc.description.abstract Five carbonate derivatives of 50-O-20,30-dideoxyinosine (DDI, 1) have been synthesized by combination with aliphatic alcohols, with their in vitro anti-HIV activity and cytotoxicity being evaluated afterward in human peripheral blood mononuclear cells (PBMCs). One particular compound, namely DDI-Penta, exhibited an outstanding performance because it was found to have both a higher inhibitory potency and a lower cytotoxicity than the lead compound, resulting in a 100 enhancement in its selectivity index. In order to further study this phenomenon, the ability of these derivatives to bind to the cytoplasmatic nucleotidase (ncN-II) was studied by in silico methods. Also, the higher calculated lipophilicity of the synthesized compounds was proposed to improve their permeability through the cell membrane since said lipophilicity would allow a higher concentration of the corresponding prodrug inside the infected cell. Overall, a combination of an optimal lipophilicity and the ability of DDI-Penta to bind to ncN-II is suggested due to the higher potency and lower cytotoxicity observed for this compound. Based on the reported findings, we believe that the combination of certain aliphatic alcohols and DDI through a carbonate linkage could significantly increase the performance of this class of therapeutic compounds; therefore, it merits further evaluations.
dc.format application/pdf
dc.language.iso eng
dc.publisher Royal Society of Chemistry
dc.rights info:eu-repo/semantics/openAccess
dc.rights.uri https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject DIDANOSINE CARBONATES
dc.subject PRODRUGS
dc.subject ANTI HIV ACTIVITY
dc.subject CYTOTOXICITY
dc.subject MOLECULAR DOCKING
dc.subject MOLECULAR DYNAMICS
dc.subject.classification Otras Ciencias Químicas
dc.subject.classification Ciencias Químicas
dc.subject.classification CIENCIAS NATURALES Y EXACTAS
dc.title Biological evaluation and molecular modelling of didanosine derivatives
dc.type info:eu-repo/semantics/article
dc.type info:ar-repo/semantics/artículo
dc.type info:eu-repo/semantics/publishedVersion
dc.date.updated 2017-12-11T16:43:34Z
dc.journal.number 5
dc.journal.pagination 622-631
dc.journal.pais Reino Unido
dc.description.fil Fil: Ravetti, Soledad. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil Fil: de Candia, Cristian Ariel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Investigaciones Biomédicas en Retrovirus y Sida. Universidad de Buenos Aires. Facultad de Medicina. Instituto de Investigaciones Biomédicas en Retrovirus y Sida; Argentina
dc.description.fil Fil: Gualdesi, María Soledad. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
dc.description.fil Fil: Pampuro, Sandra Esther. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Investigaciones Biomédicas en Retrovirus y Sida. Universidad de Buenos Aires. Facultad de Medicina. Instituto de Investigaciones Biomédicas en Retrovirus y Sida; Argentina
dc.description.fil Fil: Turk, Gabriela Julia Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Investigaciones Biomédicas en Retrovirus y Sida. Universidad de Buenos Aires. Facultad de Medicina. Instituto de Investigaciones Biomédicas en Retrovirus y Sida; Argentina
dc.description.fil Fil: Quevedo, Mario Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
dc.description.fil Fil: Briñon, Margarita Cristina. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Farmacia; Argentina
dc.journal.title MedChemComm
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/C4MD00003J
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2014/md/c4md00003j#!divAbstract


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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)