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dc.contributor.author
Martini, María Florencia
dc.contributor.author
Glisoni, Romina Julieta
dc.contributor.author
Sosnik, Alejandro Dario
dc.contributor.author
Moglioni, Albertina Gladys
dc.contributor.author
Pickholz, Mónica Andrea
dc.date.available
2018-03-28T18:45:10Z
dc.date.issued
2016-10
dc.identifier.citation
Martini, María Florencia; Glisoni, Romina Julieta; Sosnik, Alejandro Dario; Moglioni, Albertina Gladys; Pickholz, Mónica Andrea; Insights on self-aggregation phenomena of 1-indanone thiosemicarbazones and the formation of inclusion complexes with hydroxypropyl-β-cyclodextrin by Molecular Dynamics simulations; Elsevier Science; Journal of Molecular Liquids; 222; 10-2016; 963-971
dc.identifier.issn
0167-7322
dc.identifier.uri
http://hdl.handle.net/11336/40447
dc.description.abstract
1-Indanone thiosemicarbazones (TSCs) display a broad spectrum of pharmacological activities. However, their extremely poor solubility and self-aggregation tendency in water hurdles the reliable evaluation of the activity in vitro. To overcome these drawbacks, the formation of complexes with different natural and chemically modified cyclodextrins (CDs) has been investigated. Aiming to gain further insight into the molecular mechanisms involved in the interaction of these new chemical entities with CDs, this work investigated for the first time the interaction of two types of 1-indanone TSCs with hydroxyl-propyl-β-CD (HPβ-CD) by Molecular Dynamics (MD) simulations. Results were in good agreement with the experimental work and revealed the fundamental contribution of the substituents in the 1-indanone aromatic ring not only to the intrinsic aqueous solubility but also more importantly to the self-aggregation and the ability of the TSC to form stable complexes with the CD. In the particular case of the 5,6-dimethoxy-1-indanone derivative, the increase of the solubility in presence of HPβ-CD stems from a considerable decrease of the TSC-TSC intermolecular interactions and the formation of inclusion complexes that are stable for a short time. Then, the high self-aggregation tendency of this TSC destabilizes the complex and leads to the initial TSC insolubilization and subsequent precipitation.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science
dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.subject
Complex Formation
dc.subject
Cyclodextrins
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Molecular Dynamics
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Thiosemicarbazones of 1-Indanone
dc.subject.classification
Nano-materiales
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Nanotecnología
dc.subject.classification
INGENIERÍAS Y TECNOLOGÍAS
dc.title
Insights on self-aggregation phenomena of 1-indanone thiosemicarbazones and the formation of inclusion complexes with hydroxypropyl-β-cyclodextrin by Molecular Dynamics simulations
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-03-28T16:59:11Z
dc.journal.volume
222
dc.journal.pagination
963-971
dc.journal.pais
Países Bajos
dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Martini, María Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina
dc.description.fil
Fil: Glisoni, Romina Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Nanobiotecnología. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Nanobiotecnología; Argentina
dc.description.fil
Fil: Sosnik, Alejandro Dario. Technion - Israel Institute of Technology; Israel
dc.description.fil
Fil: Moglioni, Albertina Gladys. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina
dc.description.fil
Fil: Pickholz, Mónica Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Nanobiotecnología. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Nanobiotecnología; Argentina
dc.journal.title
Journal of Molecular Liquids
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.molliq.2016.07.109
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0167732216303038


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