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Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes

Solubilisation of six polycyclic aromatic hydrocarbons (PAHs) (acenaphthene, anthracene, fluoranthene, fluorene, phenanthrene and pyrene) by three synthetic cyclodextrins (CDs) (2-hydroxypropyl-β-CD, hydroxypropyl-γ-CD and ramdomly methylated-β-CD) was investigated in order to select the CD which pr...

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Autores principales: Morillo, Esmeralda, Sánchez-Trujillo, María Antonia, Moyano, José Ramón, Villaverde, Jaime, Gómez-Pantoja, María Eulalia, Pérez-Martínez, José Ignacio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Public Library of Science 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3446921/
https://www.ncbi.nlm.nih.gov/pubmed/23028493
http://dx.doi.org/10.1371/journal.pone.0044137
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author Morillo, Esmeralda
Sánchez-Trujillo, María Antonia
Moyano, José Ramón
Villaverde, Jaime
Gómez-Pantoja, María Eulalia
Pérez-Martínez, José Ignacio
author_facet Morillo, Esmeralda
Sánchez-Trujillo, María Antonia
Moyano, José Ramón
Villaverde, Jaime
Gómez-Pantoja, María Eulalia
Pérez-Martínez, José Ignacio
author_sort Morillo, Esmeralda
collection PubMed
description Solubilisation of six polycyclic aromatic hydrocarbons (PAHs) (acenaphthene, anthracene, fluoranthene, fluorene, phenanthrene and pyrene) by three synthetic cyclodextrins (CDs) (2-hydroxypropyl-β-CD, hydroxypropyl-γ-CD and ramdomly methylated-β-CD) was investigated in order to select the CD which presents the greatest increase in solubility and better complexation parameters for its use in contaminated scenarios. The presence of the three cyclodextrins greatly enhanced the apparent water solubility of all the PAHs through the formation of inclusion complexes of 1∶1 stoichiometry. Anthracene, fluoranthene, fluorene and phenanthrene clearly presented a higher solubility when β-CD derivatives were used, and especially the complexes with the ramdomly methylated-β-CD were favoured. On the contrary, pyrene presented its best solubility results when using 2-hydroxypropyl-γ-CD, but for acenaphthene the use of any of the three CDs gave the same results. Complementary to experimental phase-solubility studies, a more in-depth estimation of the inclusion process for the different complexes was carried out using molecular modelling in order to find a correlation between the degree of solubilisation and the fit of PAH molecules within the cavity of the different CDs and to know the predominant driving forces of the complexation.
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spelling pubmed-34469212012-10-01 Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes Morillo, Esmeralda Sánchez-Trujillo, María Antonia Moyano, José Ramón Villaverde, Jaime Gómez-Pantoja, María Eulalia Pérez-Martínez, José Ignacio PLoS One Research Article Solubilisation of six polycyclic aromatic hydrocarbons (PAHs) (acenaphthene, anthracene, fluoranthene, fluorene, phenanthrene and pyrene) by three synthetic cyclodextrins (CDs) (2-hydroxypropyl-β-CD, hydroxypropyl-γ-CD and ramdomly methylated-β-CD) was investigated in order to select the CD which presents the greatest increase in solubility and better complexation parameters for its use in contaminated scenarios. The presence of the three cyclodextrins greatly enhanced the apparent water solubility of all the PAHs through the formation of inclusion complexes of 1∶1 stoichiometry. Anthracene, fluoranthene, fluorene and phenanthrene clearly presented a higher solubility when β-CD derivatives were used, and especially the complexes with the ramdomly methylated-β-CD were favoured. On the contrary, pyrene presented its best solubility results when using 2-hydroxypropyl-γ-CD, but for acenaphthene the use of any of the three CDs gave the same results. Complementary to experimental phase-solubility studies, a more in-depth estimation of the inclusion process for the different complexes was carried out using molecular modelling in order to find a correlation between the degree of solubilisation and the fit of PAH molecules within the cavity of the different CDs and to know the predominant driving forces of the complexation. Public Library of Science 2012-09-19 /pmc/articles/PMC3446921/ /pubmed/23028493 http://dx.doi.org/10.1371/journal.pone.0044137 Text en © 2012 Morillo et al http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are properly credited.
spellingShingle Research Article
Morillo, Esmeralda
Sánchez-Trujillo, María Antonia
Moyano, José Ramón
Villaverde, Jaime
Gómez-Pantoja, María Eulalia
Pérez-Martínez, José Ignacio
Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes
title Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes
title_full Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes
title_fullStr Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes
title_full_unstemmed Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes
title_short Enhanced Solubilisation of Six PAHs by Three Synthetic Cyclodextrins for Remediation Applications: Molecular Modelling of the Inclusion Complexes
title_sort enhanced solubilisation of six pahs by three synthetic cyclodextrins for remediation applications: molecular modelling of the inclusion complexes
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3446921/
https://www.ncbi.nlm.nih.gov/pubmed/23028493
http://dx.doi.org/10.1371/journal.pone.0044137
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