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dc.contributor.author
Solórzano, Eliana Rita
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dc.contributor.author
Pastore, Paolo
dc.contributor.author
Dolmella, Alessandro
dc.contributor.author
Cazorla, Silvia Ines
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dc.contributor.author
Arias Cassará, María Lucrecia
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dc.contributor.author
Sankaran, Sankaran Venkatachalam
dc.contributor.author
Thamotharan, Subbiah
dc.contributor.author
Gil, Diego Mauricio
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dc.date.available
2023-07-27T19:02:10Z
dc.date.issued
2022-10
dc.identifier.citation
Solórzano, Eliana Rita; Pastore, Paolo; Dolmella, Alessandro; Cazorla, Silvia Ines; Arias Cassará, María Lucrecia; et al.; Importance of R-CH3⋯O tetrel bonding and vinyl⋯aryl stacking interactions in stabilizing the crystal packing of 2’,4’-dihydroxy-3’-methoxychalcone: Exploration of antileishmanial activity and molecular docking studies; Elsevier Science; Journal of Molecular Structure; 1265; 10-2022; 1-14
dc.identifier.issn
0022-2860
dc.identifier.uri
http://hdl.handle.net/11336/205856
dc.description.abstract
A detailed experimental and theoretical investigation of a chalcone derivative 2’,4’-dihydroxy-3’-methoxychalcone (DHMC) isolated from Argentinean type-Zuccagnia propolis has been performed. The isolated compound was characterized by 1H and 13C Nuclear Magnetic Resonance (NMR), infrared (IR) and Raman spectroscopies and its crystal structure was solved by single-crystal X-ray diffraction (XRD). The molecular geometry of the title compound was investigated theoretically and a very good agreement between experimental and computed geometrical parameters and vibrational frequencies have been observed. The substance crystallized in the orthorhombic Pbcn crystal system, with Z= 8 molecules per unit cell. The molecular geometry of the molecule is mainly stabilized by intramolecular O-H⋯O(keto) hydrogen bonds. The structure reveals that the crystal packing is mainly governed by O-H⋯O and C-H⋯O hydrogen bonds. The supramolecular assembly of the compound in solid state is also stabilized by σ-hole tetrel bonding interactions (O⋯C) involving the O-atom of the hydroxyl and the carbon atom of the methoxy group. Other interactions such as C-H⋯π and vinyl⋯π stacking interactions are also relevant in the stabilization of the solid structure of DHMC. The interaction energies of the different self-assembled dimers have been estimated using DFT calculations and various computational tools including MEP surfaces, QTAIM, NBO and NCI plot analysis. The antileishmanial activity of DHMC indicates that the compound was active against the main specie that cause tegumentary leishmaniosis in Argentina. The computational molecular docking simulation was used to predict the binding potential of the title chalcone derivative against six different leishmanial protein targets.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier Science
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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
ANTILEISHMANIAL ACTIVITY
dc.subject
CHALCONE
dc.subject
DOCKING STUDIES
dc.subject
HIRSHFELD SURFACES
dc.subject
QTAIM
dc.subject
Σ-HOLE INTERACTIONS
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Importance of R-CH3⋯O tetrel bonding and vinyl⋯aryl stacking interactions in stabilizing the crystal packing of 2’,4’-dihydroxy-3’-methoxychalcone: Exploration of antileishmanial activity and molecular docking studies
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2023-07-07T19:00:55Z
dc.identifier.eissn
1872-8014
dc.journal.volume
1265
dc.journal.pagination
1-14
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Solórzano, Eliana Rita. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia; Argentina. Università di Padova; Italia
dc.description.fil
Fil: Pastore, Paolo. Università di Padova; Italia
dc.description.fil
Fil: Dolmella, Alessandro. Università di Padova; Italia
dc.description.fil
Fil: Cazorla, Silvia Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Centro de Referencia para Lactobacilos; Argentina
dc.description.fil
Fil: Arias Cassará, María Lucrecia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucuman. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Organica. Cátedra de Química Organica I; Argentina
dc.description.fil
Fil: Sankaran, Sankaran Venkatachalam. Sastra Deemed University; India
dc.description.fil
Fil: Thamotharan, Subbiah. Sastra Deemed University; India
dc.description.fil
Fil: Gil, Diego Mauricio. Universidad Nacional de Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Biotecnología Farmacéutica y Alimentaria; Argentina
dc.journal.title
Journal of Molecular Structure
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286022010134
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1016/j.molstruc.2022.133357
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