Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins
Polychlorinated dibenzo-p-dioxins (PCDD) are persistent organic pollutants which result as byproducts in industrial or combustion processes and induce toxicity in both wildlife and humans. In this study, all seven PCDD, tetrachlorinated dibenzo-p-dioxins (TCDD), pentachlorinated dibenzo-p-dioxins (P...
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MDPI AG
2023-08-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/17/13214 |
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| author | Maria-Cristina Ghetu Marian Virgolici Alina Tirsoaga Ioana Stanculescu |
| author_facet | Maria-Cristina Ghetu Marian Virgolici Alina Tirsoaga Ioana Stanculescu |
| author_sort | Maria-Cristina Ghetu |
| collection | DOAJ |
| description | Polychlorinated dibenzo-p-dioxins (PCDD) are persistent organic pollutants which result as byproducts in industrial or combustion processes and induce toxicity in both wildlife and humans. In this study, all seven PCDD, tetrachlorinated dibenzo-p-dioxins (TCDD), pentachlorinated dibenzo-p-dioxins (P5CDD), hexachlorinated dibenzo-p-dioxins (H6CDD), heptachlorinated dibenzo-p-dioxins (H7CDD), and octachlorinated dibenzo-p-dioxins (OCDD) were studied in interaction with two cyclodextrins, β-CD and γ-CD, resulting in a total of 40 host–guest complexes. The flexibility of the cyclodextrins was given by the number of glucose units, and the placement of the chlorine groups on the dioxins structure accounted for the different complex formed. Various geometries of interaction obtained by guided docking were studied, and the complexation and binding energy were calculated in the frame of MM+ and OPLS force fields. The results show that the recognition of the PCDD pollutants by the CD may be possible through the formation of PCDD:CD inclusion complexes. This recognition is based on the formation of Coulombic interactions between the chlorine atom of the PCDD and the primary and secondary hydroxyl groups of the CD and van der Waals interaction of the CD hydrophobic cavity with PCDD aromatic structures. Both MM+ and OPLS calculus resulted in close values for the complexation and binding energies. Molecular mechanics calculations offer a proper insight into the molecular recognition process between the PCDD compounds and CD molecules, proved by a good description of the C-H···O bonds formed between the guest and host molecules. It was shown for the first time that CD may efficiently trap PCCDs, opening the way for their tremendous potential use in environmental remediation. |
| first_indexed | 2024-03-10T23:21:24Z |
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| language | English |
| last_indexed | 2024-03-10T23:21:24Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-5fd0a5cd11644f39b737403bfa0d61982023-11-19T08:14:03ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-08-0124171321410.3390/ijms241713214Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-CyclodextrinsMaria-Cristina Ghetu0Marian Virgolici1Alina Tirsoaga2Ioana Stanculescu3Faculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta Bd., 030018 Bucharest, RomaniaHoria Hulubei National Institute of Research and Development for Physics and Nuclear Engineering, 30 Reactorului Str., 077125 Magurele, RomaniaFaculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta Bd., 030018 Bucharest, RomaniaFaculty of Chemistry, University of Bucharest, 4-12 Regina Elisabeta Bd., 030018 Bucharest, RomaniaPolychlorinated dibenzo-p-dioxins (PCDD) are persistent organic pollutants which result as byproducts in industrial or combustion processes and induce toxicity in both wildlife and humans. In this study, all seven PCDD, tetrachlorinated dibenzo-p-dioxins (TCDD), pentachlorinated dibenzo-p-dioxins (P5CDD), hexachlorinated dibenzo-p-dioxins (H6CDD), heptachlorinated dibenzo-p-dioxins (H7CDD), and octachlorinated dibenzo-p-dioxins (OCDD) were studied in interaction with two cyclodextrins, β-CD and γ-CD, resulting in a total of 40 host–guest complexes. The flexibility of the cyclodextrins was given by the number of glucose units, and the placement of the chlorine groups on the dioxins structure accounted for the different complex formed. Various geometries of interaction obtained by guided docking were studied, and the complexation and binding energy were calculated in the frame of MM+ and OPLS force fields. The results show that the recognition of the PCDD pollutants by the CD may be possible through the formation of PCDD:CD inclusion complexes. This recognition is based on the formation of Coulombic interactions between the chlorine atom of the PCDD and the primary and secondary hydroxyl groups of the CD and van der Waals interaction of the CD hydrophobic cavity with PCDD aromatic structures. Both MM+ and OPLS calculus resulted in close values for the complexation and binding energies. Molecular mechanics calculations offer a proper insight into the molecular recognition process between the PCDD compounds and CD molecules, proved by a good description of the C-H···O bonds formed between the guest and host molecules. It was shown for the first time that CD may efficiently trap PCCDs, opening the way for their tremendous potential use in environmental remediation.https://www.mdpi.com/1422-0067/24/17/13214non-covalent interactionmolecular modellingdioxinscyclodextrins |
| spellingShingle | Maria-Cristina Ghetu Marian Virgolici Alina Tirsoaga Ioana Stanculescu Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins International Journal of Molecular Sciences non-covalent interaction molecular modelling dioxins cyclodextrins |
| title | Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins |
| title_full | Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins |
| title_fullStr | Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins |
| title_full_unstemmed | Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins |
| title_short | Molecular Modelling of Polychlorinated Dibenzo-p-Dioxins Non-Covalent Interactions with β and γ-Cyclodextrins |
| title_sort | molecular modelling of polychlorinated dibenzo p dioxins non covalent interactions with β and γ cyclodextrins |
| topic | non-covalent interaction molecular modelling dioxins cyclodextrins |
| url | https://www.mdpi.com/1422-0067/24/17/13214 |
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