Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide
Currently, controlled release formulations (CRFs) of pesticides in response to biotic and/or abiotic stimuli have shown great potential for providing “on-demand” smart release of loaded active ingredients. In this study, amphiphilic biopolymers were prepared by introducing hydrophobic (7-diethylamin...
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| Format: | Article |
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MDPI AG
2020-10-01
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| Series: | Polymers |
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| Online Access: | https://www.mdpi.com/2073-4360/12/10/2268 |
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| author | Song Feng Junqin Wang Lihua Zhang Qin Chen Wang Yue Ni Ke Haibo Xie |
| author_facet | Song Feng Junqin Wang Lihua Zhang Qin Chen Wang Yue Ni Ke Haibo Xie |
| author_sort | Song Feng |
| collection | DOAJ |
| description | Currently, controlled release formulations (CRFs) of pesticides in response to biotic and/or abiotic stimuli have shown great potential for providing “on-demand” smart release of loaded active ingredients. In this study, amphiphilic biopolymers were prepared by introducing hydrophobic (7-diethylaminocoumarin-4-yl)methyl succinate (DEACMS) onto the main chain of hydrophilic carboxymethylchitosan (CMCS) via the formation of amide bonds which were able to self-assemble into spherical micelles in aqueous media and were utilized as light-responsive nanocarriers for the controlled release of pesticides. FTIR and NMR characterizations confirmed the successful synthesis of the CMCS-DEACMS conjugate. The critical micelle concentration (CMC) decreased with the increase in the substitution of DEACMS on CMCS, which ranged from 0.013 to 0.042 mg/mL. Upon irradiation under simulated sunlight, the hydrodynamic diameter, morphology, photophysical properties and photolysis were researched by means of dynamic light scattering (DLS), transmission electron microscopy (TEM), UV-vis absorption spectroscopy and fluorescence spectroscopy. Moreover, 2,4-dichlorophenoxyacetic acid (2,4-D) was used as a model pesticide and encapsulated into the CMCS-DEACMS micelles. In these micelle formulations, the release of 2,4-D was promoted upon simulated sunlight irradiation, during which the coumarin moieties were cleaved from the CMCS backbone, resulting in a shift of the hydrophilic–hydrophobic balance and destabilization of the micelles. Additionally, bioassay studies suggested that this 2,4-D contained which micelles showed good bioactivity on the target plant without harming the nontarget plant. Thereby, the light-responsive CMCS-DEACMS micelles bearing photocleavable coumarin moieties provide a smart delivery platform for agrochemicals. |
| first_indexed | 2024-03-10T15:53:47Z |
| format | Article |
| id | doaj.art-4247efc0150a4cf38339ef94b00e2d7a |
| institution | Directory Open Access Journal |
| issn | 2073-4360 |
| language | English |
| last_indexed | 2024-03-10T15:53:47Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Polymers |
| spelling | doaj.art-4247efc0150a4cf38339ef94b00e2d7a2023-11-20T15:51:58ZengMDPI AGPolymers2073-43602020-10-011210226810.3390/polym12102268Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of PesticideSong Feng0Junqin Wang1Lihua Zhang2Qin Chen3Wang Yue4Ni Ke5Haibo Xie6Department of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaDepartment of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaDepartment of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaDepartment of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaDepartment of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaDepartment of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaDepartment of Polymer Materials and Engineering, College of Materials and Metallurgy, Guizhou University, Guiyang 550025, ChinaCurrently, controlled release formulations (CRFs) of pesticides in response to biotic and/or abiotic stimuli have shown great potential for providing “on-demand” smart release of loaded active ingredients. In this study, amphiphilic biopolymers were prepared by introducing hydrophobic (7-diethylaminocoumarin-4-yl)methyl succinate (DEACMS) onto the main chain of hydrophilic carboxymethylchitosan (CMCS) via the formation of amide bonds which were able to self-assemble into spherical micelles in aqueous media and were utilized as light-responsive nanocarriers for the controlled release of pesticides. FTIR and NMR characterizations confirmed the successful synthesis of the CMCS-DEACMS conjugate. The critical micelle concentration (CMC) decreased with the increase in the substitution of DEACMS on CMCS, which ranged from 0.013 to 0.042 mg/mL. Upon irradiation under simulated sunlight, the hydrodynamic diameter, morphology, photophysical properties and photolysis were researched by means of dynamic light scattering (DLS), transmission electron microscopy (TEM), UV-vis absorption spectroscopy and fluorescence spectroscopy. Moreover, 2,4-dichlorophenoxyacetic acid (2,4-D) was used as a model pesticide and encapsulated into the CMCS-DEACMS micelles. In these micelle formulations, the release of 2,4-D was promoted upon simulated sunlight irradiation, during which the coumarin moieties were cleaved from the CMCS backbone, resulting in a shift of the hydrophilic–hydrophobic balance and destabilization of the micelles. Additionally, bioassay studies suggested that this 2,4-D contained which micelles showed good bioactivity on the target plant without harming the nontarget plant. Thereby, the light-responsive CMCS-DEACMS micelles bearing photocleavable coumarin moieties provide a smart delivery platform for agrochemicals.https://www.mdpi.com/2073-4360/12/10/2268carboxymethyl chitosan micelleslight-responsivecoumarin2,4-Dcontrolled releasepesticide |
| spellingShingle | Song Feng Junqin Wang Lihua Zhang Qin Chen Wang Yue Ni Ke Haibo Xie Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide Polymers carboxymethyl chitosan micelles light-responsive coumarin 2,4-D controlled release pesticide |
| title | Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide |
| title_full | Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide |
| title_fullStr | Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide |
| title_full_unstemmed | Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide |
| title_short | Coumarin-Containing Light-Responsive Carboxymethyl Chitosan Micelles as Nanocarriers for Controlled Release of Pesticide |
| title_sort | coumarin containing light responsive carboxymethyl chitosan micelles as nanocarriers for controlled release of pesticide |
| topic | carboxymethyl chitosan micelles light-responsive coumarin 2,4-D controlled release pesticide |
| url | https://www.mdpi.com/2073-4360/12/10/2268 |
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