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      Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae)

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          Abstract 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.

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          Most cited references 51

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          A new and rapid colorimetric determination of acetylcholinesterase activity

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            Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings.

            Experimental and computational approaches to estimate solubility and permeability in discovery and development settings are described. In the discovery setting 'the rule of 5' predicts that poor absorption or permeation is more likely when there are more than 5 H-bond donors, 10 H-bond acceptors, the molecular weight (MWT) is greater than 500 and the calculated Log P (CLogP) is greater than 5 (or MlogP > 4.15). Computational methodology for the rule-based Moriguchi Log P (MLogP) calculation is described. Turbidimetric solubility measurement is described and applied to known drugs. High throughput screening (HTS) leads tend to have higher MWT and Log P and lower turbidimetric solubility than leads in the pre-HTS era. In the development setting, solubility calculations focus on exact value prediction and are difficult because of polymorphism. Recent work on linear free energy relationships and Log P approaches are critically reviewed. Useful predictions are possible in closely related analog series when coupled with experimental thermodynamic solubility measurements.
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              Guillain-Barré Syndrome outbreak associated with Zika virus infection in French Polynesia: a case-control study.

              Between October, 2013, and April, 2014, French Polynesia experienced the largest Zika virus outbreak ever described at that time. During the same period, an increase in Guillain-Barré syndrome was reported, suggesting a possible association between Zika virus and Guillain-Barré syndrome. We aimed to assess the role of Zika virus and dengue virus infection in developing Guillain-Barré syndrome.

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                Revista Brasileira de Entomologia
                Rev. Bras. entomol.
                Sociedade Brasileira De Entomologia (São Paulo, SP, Brazil )
                June 2018
                : 62
                : 2
                : 112-118
                Santander Santander orgnameUniversidad Industrial de Santander orgdiv1Escuela de Medicina orgdiv2Centro de investigaciones en enfermedades tropicales Colombia
                Santander Santander orgnameUniversidad Industrial de Santander orgdiv1Escuela de Química orgdiv2Laboratorio de Química Orgánica y Biomolecular Colombia

                This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

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