Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin
The herbicide terbuthylazine (TBA) is widely used for preemergence or postemergence control of many grass and broadleaf weeds and has, besides other issues, a poor aqueous solubility profile that results in reduced bioavailability. Cyclodextrins and modified cyclodextrins were considered, among othe...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2017-01-01
|
| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2017/8120367 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832563085803520000 |
|---|---|
| author | E. Manuela Garrido Daniela Rodrigues Nuno Milhazes Fernanda Borges Jorge Garrido |
| author_facet | E. Manuela Garrido Daniela Rodrigues Nuno Milhazes Fernanda Borges Jorge Garrido |
| author_sort | E. Manuela Garrido |
| collection | DOAJ |
| description | The herbicide terbuthylazine (TBA) is widely used for preemergence or postemergence control of many grass and broadleaf weeds and has, besides other issues, a poor aqueous solubility profile that results in reduced bioavailability. Cyclodextrins and modified cyclodextrins were considered, among other substances, appropriate agents for improving pesticide water solubility. Therefore, the inclusion complex formation of terbuthylazine with β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied to attain its aqueous solubility enhancement. Their characterization was accomplished with different analytical techniques, namely, by UV-Vis, DSC, FTIR, and 1H NMR. From the analysis of the complexation performance of the herbicide it was concluded that the interaction of terbuthylazine with CDs leads to the formation of inclusion complexes with a stoichiometry of 1 : 1. The association constants of the TBA/β-CD and TBA/HP-β-CD complexes were determined by UV. The mean values obtained for the stability constants are 460.4 ± 26.5 and 532.1 ± 27.6 to TBA/β-CD and TBA/HP-β-CD, respectively. 1H NMR data corroborate the formation of the TBA/β-CD and TBA/HP-β-CD complexes synthesized by the kneading method. A formulation incorporating TBA cyclodextrin complexes might lead to an improvement in terbuthylazine bioavailability. The development of TBA-CD formulations may be interesting since it would enable, through their inclusion into the hydrophobic cavity of CDs, enhancement of solubility, bioavailability, and stability of the herbicide. |
| format | Article |
| id | doaj-art-693bc20f899c4e0081ecd08a5ea930fc |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2017-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-693bc20f899c4e0081ecd08a5ea930fc2025-02-03T01:20:59ZengWileyJournal of Chemistry2090-90632090-90712017-01-01201710.1155/2017/81203678120367Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-CyclodextrinE. Manuela Garrido0Daniela Rodrigues1Nuno Milhazes2Fernanda Borges3Jorge Garrido4Department of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, PortugalDepartment of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, PortugalCIQ/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalCIQ/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, PortugalDepartment of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, PortugalThe herbicide terbuthylazine (TBA) is widely used for preemergence or postemergence control of many grass and broadleaf weeds and has, besides other issues, a poor aqueous solubility profile that results in reduced bioavailability. Cyclodextrins and modified cyclodextrins were considered, among other substances, appropriate agents for improving pesticide water solubility. Therefore, the inclusion complex formation of terbuthylazine with β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied to attain its aqueous solubility enhancement. Their characterization was accomplished with different analytical techniques, namely, by UV-Vis, DSC, FTIR, and 1H NMR. From the analysis of the complexation performance of the herbicide it was concluded that the interaction of terbuthylazine with CDs leads to the formation of inclusion complexes with a stoichiometry of 1 : 1. The association constants of the TBA/β-CD and TBA/HP-β-CD complexes were determined by UV. The mean values obtained for the stability constants are 460.4 ± 26.5 and 532.1 ± 27.6 to TBA/β-CD and TBA/HP-β-CD, respectively. 1H NMR data corroborate the formation of the TBA/β-CD and TBA/HP-β-CD complexes synthesized by the kneading method. A formulation incorporating TBA cyclodextrin complexes might lead to an improvement in terbuthylazine bioavailability. The development of TBA-CD formulations may be interesting since it would enable, through their inclusion into the hydrophobic cavity of CDs, enhancement of solubility, bioavailability, and stability of the herbicide.http://dx.doi.org/10.1155/2017/8120367 |
| spellingShingle | E. Manuela Garrido Daniela Rodrigues Nuno Milhazes Fernanda Borges Jorge Garrido Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin Journal of Chemistry |
| title | Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin |
| title_full | Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin |
| title_fullStr | Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin |
| title_full_unstemmed | Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin |
| title_short | Molecular Encapsulation of Herbicide Terbuthylazine in Native and Modified β-Cyclodextrin |
| title_sort | molecular encapsulation of herbicide terbuthylazine in native and modified β cyclodextrin |
| url | http://dx.doi.org/10.1155/2017/8120367 |
| work_keys_str_mv | AT emanuelagarrido molecularencapsulationofherbicideterbuthylazineinnativeandmodifiedbcyclodextrin AT danielarodrigues molecularencapsulationofherbicideterbuthylazineinnativeandmodifiedbcyclodextrin AT nunomilhazes molecularencapsulationofherbicideterbuthylazineinnativeandmodifiedbcyclodextrin AT fernandaborges molecularencapsulationofherbicideterbuthylazineinnativeandmodifiedbcyclodextrin AT jorgegarrido molecularencapsulationofherbicideterbuthylazineinnativeandmodifiedbcyclodextrin |