Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae)
Aedes aegypti is the principal vector of arboviral pathogens that may cause diseases as dengue fever, chikungunya and zika. The harmful environmental effects of commercial pesticides coalesced with the development of insecticide-resistant populations encourage the discovery and generation of new alt...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Entomologia
2018-04-01
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| Series: | Revista Brasileira de Entomologia |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S0085562617301401 |
| _version_ | 1828237793292189696 |
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| author | Andrés G. Rueda Aurora L. Carreño Otero Jonny E. Duque Vladimir V. Kouznetsov |
| author_facet | Andrés G. Rueda Aurora L. Carreño Otero Jonny E. Duque Vladimir V. Kouznetsov |
| author_sort | Andrés G. Rueda |
| collection | DOAJ |
| description | Aedes aegypti is the principal vector of arboviral pathogens that may cause diseases as dengue fever, chikungunya and zika. The harmful environmental effects of commercial pesticides coalesced with the development of insecticide-resistant populations encourage the discovery and generation of new alternative products as a tool to reduce the incidence of vector-borne diseases. In this work, through the classic three component Strecker reaction of commercial benzaldehydes, cyclic secondary amines and KCN, a new series of nine α-amino nitriles, girgensohnine analogs, has been synthetized and screened for larvicide and adulticide properties against A. aegypti, one of the dominant vectors of dengue, chikungunya and zika in tropical and subtropical areas all over the world. Molecules 3 and 4 were identified as potential larvicidal agents with LC50 values of 50.55 and 69.59 ppm, respectively. Molecule 3 showed 100% of mortality after 2 h of treatment when a concentration of 30 ppm in adulticidal assays was evaluated. Additionally, in order to elucidate the mode of action of these molecules, their acetylcholinesterase (AChE) inhibitory properties were evaluated using the Ellman assay. It was found that the molecules possess a weak AChE inhibitory activity with IC50 values between 148.80 and 259.40 μM, indicating that AChE could not be a principal target for insecticide activity. Keywords: Arthropod-borne diseases, Girgensohnine analogs, Strecker reaction, Insecticidal activity, Vector control |
| first_indexed | 2024-04-12T20:53:47Z |
| format | Article |
| id | doaj.art-af70d93c8db54588b03aee5c56c7c528 |
| institution | Directory Open Access Journal |
| issn | 0085-5626 |
| language | English |
| last_indexed | 2024-04-12T20:53:47Z |
| publishDate | 2018-04-01 |
| publisher | Sociedade Brasileira de Entomologia |
| record_format | Article |
| series | Revista Brasileira de Entomologia |
| spelling | doaj.art-af70d93c8db54588b03aee5c56c7c5282022-12-22T03:17:03ZengSociedade Brasileira de EntomologiaRevista Brasileira de Entomologia0085-56262018-04-01622112118Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae)Andrés G. Rueda0Aurora L. Carreño Otero1Jonny E. Duque2Vladimir V. Kouznetsov3Universidad Industrial de Santander, Escuela de Química, Laboratorio de Química Orgánica y Biomolecular, Santander, ColombiaUniversidad Industrial de Santander, Escuela de Química, Laboratorio de Química Orgánica y Biomolecular, Santander, ColombiaUniversidad Industrial de Santander, Escuela de Medicina, Centro de investigaciones en enfermedades tropicales, Santander, Colombia; Corresponding authors.Universidad Industrial de Santander, Escuela de Química, Laboratorio de Química Orgánica y Biomolecular, Santander, Colombia; Corresponding authors.Aedes aegypti is the principal vector of arboviral pathogens that may cause diseases as dengue fever, chikungunya and zika. The harmful environmental effects of commercial pesticides coalesced with the development of insecticide-resistant populations encourage the discovery and generation of new alternative products as a tool to reduce the incidence of vector-borne diseases. In this work, through the classic three component Strecker reaction of commercial benzaldehydes, cyclic secondary amines and KCN, a new series of nine α-amino nitriles, girgensohnine analogs, has been synthetized and screened for larvicide and adulticide properties against A. aegypti, one of the dominant vectors of dengue, chikungunya and zika in tropical and subtropical areas all over the world. Molecules 3 and 4 were identified as potential larvicidal agents with LC50 values of 50.55 and 69.59 ppm, respectively. Molecule 3 showed 100% of mortality after 2 h of treatment when a concentration of 30 ppm in adulticidal assays was evaluated. Additionally, in order to elucidate the mode of action of these molecules, their acetylcholinesterase (AChE) inhibitory properties were evaluated using the Ellman assay. It was found that the molecules possess a weak AChE inhibitory activity with IC50 values between 148.80 and 259.40 μM, indicating that AChE could not be a principal target for insecticide activity. Keywords: Arthropod-borne diseases, Girgensohnine analogs, Strecker reaction, Insecticidal activity, Vector controlhttp://www.sciencedirect.com/science/article/pii/S0085562617301401 |
| spellingShingle | Andrés G. Rueda Aurora L. Carreño Otero Jonny E. Duque Vladimir V. Kouznetsov Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae) Revista Brasileira de Entomologia |
| title | Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae) |
| title_full | Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae) |
| title_fullStr | Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae) |
| title_full_unstemmed | Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae) |
| title_short | Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae) |
| title_sort | synthesis of new α amino nitriles with insecticidal action on aedes aegypti diptera culicidae |
| url | http://www.sciencedirect.com/science/article/pii/S0085562617301401 |
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