Hydrophobic Nanoprecipitates of β‑Cyclodextrin/Avermectins Inclusion Compounds Reveal Insecticide Activity against Aedes aegypti Larvae and Low Toxicity against Fibroblasts
In the present work, hydrophobic nanoprecipitates (HNPs) of inclusion complexes formed between β-cyclodextrin (βCD) and the avermectins (AVMs) named eprinomectin (EPRI) and ivermectin (IVER) were synthesized and characterized, and their larvicidal activity against Aedes aegypti and human safety agai...
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Veröffentlicht in: | Journal of agricultural and food chemistry 2018-07, Vol.66 (28), p.7275-7285 |
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creator | dos Santos Moreira, Ana M Bittencourt, Vanessa C. E Costa, Fábio L. S Elena de Lima, Maria Lopes, Miriam T. P Borges, Warley S Martins, Gustavo F Nascimento, Clébio S da Silva, Jeferson G Denadai, Ângelo M. L Borges, Keyller B |
description | In the present work, hydrophobic nanoprecipitates (HNPs) of inclusion complexes formed between β-cyclodextrin (βCD) and the avermectins (AVMs) named eprinomectin (EPRI) and ivermectin (IVER) were synthesized and characterized, and their larvicidal activity against Aedes aegypti and human safety against fibroblasts were evaluated. Initially, thermogravimetric analysis/differential thermal analysis data revealed that inclusion increased the thermal stability of AVMs in the presence of βCD. Nuclear magnetic resonance experiments and density functional theory calculations pointed out the inclusion of the benzofuran ring of the two AVMs in the βCD cavity. Isothermal titration calorimetry experiments allowed identification of different binding constants for EPRI/βCD (K b = 1060) and βCD/IVER (K b = 1700) systems, despite the structural similarity. Dynamic light scattering titrations of AVMs’ dimethyl sulfoxide solution in βCD aqueous solution demonstrated that the formed HNPs have lower sizes in the presence of βCD. Finally, the inclusion of EPRI in βCD increased its larval toxicity and reduced its human cytotoxicity, while for IVER/βCD no beneficial effect was observed upon inclusion. These results were rationalized in terms of structural differences between the two molecules. Finally, the EPRI/βCD complex has great potential as an insecticide against A. aegypti larvae with high human safety. |
doi_str_mv | 10.1021/acs.jafc.8b01300 |
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E ; Costa, Fábio L. S ; Elena de Lima, Maria ; Lopes, Miriam T. P ; Borges, Warley S ; Martins, Gustavo F ; Nascimento, Clébio S ; da Silva, Jeferson G ; Denadai, Ângelo M. L ; Borges, Keyller B</creator><creatorcontrib>dos Santos Moreira, Ana M ; Bittencourt, Vanessa C. E ; Costa, Fábio L. S ; Elena de Lima, Maria ; Lopes, Miriam T. P ; Borges, Warley S ; Martins, Gustavo F ; Nascimento, Clébio S ; da Silva, Jeferson G ; Denadai, Ângelo M. L ; Borges, Keyller B</creatorcontrib><description>In the present work, hydrophobic nanoprecipitates (HNPs) of inclusion complexes formed between β-cyclodextrin (βCD) and the avermectins (AVMs) named eprinomectin (EPRI) and ivermectin (IVER) were synthesized and characterized, and their larvicidal activity against Aedes aegypti and human safety against fibroblasts were evaluated. Initially, thermogravimetric analysis/differential thermal analysis data revealed that inclusion increased the thermal stability of AVMs in the presence of βCD. Nuclear magnetic resonance experiments and density functional theory calculations pointed out the inclusion of the benzofuran ring of the two AVMs in the βCD cavity. Isothermal titration calorimetry experiments allowed identification of different binding constants for EPRI/βCD (K b = 1060) and βCD/IVER (K b = 1700) systems, despite the structural similarity. Dynamic light scattering titrations of AVMs’ dimethyl sulfoxide solution in βCD aqueous solution demonstrated that the formed HNPs have lower sizes in the presence of βCD. Finally, the inclusion of EPRI in βCD increased its larval toxicity and reduced its human cytotoxicity, while for IVER/βCD no beneficial effect was observed upon inclusion. These results were rationalized in terms of structural differences between the two molecules. 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Food Chem</addtitle><description>In the present work, hydrophobic nanoprecipitates (HNPs) of inclusion complexes formed between β-cyclodextrin (βCD) and the avermectins (AVMs) named eprinomectin (EPRI) and ivermectin (IVER) were synthesized and characterized, and their larvicidal activity against Aedes aegypti and human safety against fibroblasts were evaluated. Initially, thermogravimetric analysis/differential thermal analysis data revealed that inclusion increased the thermal stability of AVMs in the presence of βCD. Nuclear magnetic resonance experiments and density functional theory calculations pointed out the inclusion of the benzofuran ring of the two AVMs in the βCD cavity. Isothermal titration calorimetry experiments allowed identification of different binding constants for EPRI/βCD (K b = 1060) and βCD/IVER (K b = 1700) systems, despite the structural similarity. Dynamic light scattering titrations of AVMs’ dimethyl sulfoxide solution in βCD aqueous solution demonstrated that the formed HNPs have lower sizes in the presence of βCD. Finally, the inclusion of EPRI in βCD increased its larval toxicity and reduced its human cytotoxicity, while for IVER/βCD no beneficial effect was observed upon inclusion. These results were rationalized in terms of structural differences between the two molecules. 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Isothermal titration calorimetry experiments allowed identification of different binding constants for EPRI/βCD (K b = 1060) and βCD/IVER (K b = 1700) systems, despite the structural similarity. Dynamic light scattering titrations of AVMs’ dimethyl sulfoxide solution in βCD aqueous solution demonstrated that the formed HNPs have lower sizes in the presence of βCD. Finally, the inclusion of EPRI in βCD increased its larval toxicity and reduced its human cytotoxicity, while for IVER/βCD no beneficial effect was observed upon inclusion. These results were rationalized in terms of structural differences between the two molecules. Finally, the EPRI/βCD complex has great potential as an insecticide against A. aegypti larvae with high human safety.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29925239</pmid><doi>10.1021/acs.jafc.8b01300</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0003-1067-1919</orcidid></addata></record> |
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title | Hydrophobic Nanoprecipitates of β‑Cyclodextrin/Avermectins Inclusion Compounds Reveal Insecticide Activity against Aedes aegypti Larvae and Low Toxicity against Fibroblasts |
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