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

Rueda, Andrés G.; Otero, Aurora L. Carreño; Duque, Jonny E.; Kouznetsov, Vladímir V.

doi:10.1016/j.rbe.2018.01.004

Cited by 10 publications

(4 citation statements)

References 45 publications

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“…One of the principal aims of this work was to explore the possible binding mode of selected plant secondary metabolites on relevant targets, trying to explain the observed insecticide activity. For this, some subunits of mitochondrial complexes I, II, III, and IV and acetylcholinesterase, were selected as the main targets due to their relevant role in mosquitoes' bioenergetics and synapsis 2 , 40 , 41 . For this, we first evaluated the ADME properties of these metabolites, finding no violation of rule-of-five and Jorgensen rule as shown in S. Table 3 ; besides, our docking results suggest that secondary metabolites may inhibit the selected Aedes ’ mitochondrial targets as well as acetylcholinesterase (Table 2 ).…”

Section: Resultsmentioning

confidence: 99%

Insecticidal activity of essential oils from American native plants against Aedes aegypti (Diptera: Culicidae): an introduction to their possible mechanism of action

Duque

Urbina

Vesga

et al. 2023

Sci Rep

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Searching for new bioactive molecules to design insecticides is a complex process since pesticides should be highly selective, active against the vector, and bio-safe for humans. Aiming to find natural compounds for mosquito control, we evaluated the insecticidal activity of essential oils (EOs) from 20 American native plants against Aedes aegypti larvae using bioassay, biochemical, and in silico analyses. The highest larvicide activity was exhibited by EOs from Steiractinia aspera (LC50 = 42.4 µg/mL), Turnera diffusa (LC50 = 70.9 µg/mL), Piper aduncum (LC50 = 55.8 µg/mL), Lippia origanoides (chemotype thymol/carvacrol) (LC50 = 61.9 µg/mL), L. origanoides (chemotype carvacrol/thymol) (LC50 = 59.8 µg/mL), Hyptis dilatata (LC50 = 61.1 µg/mL), Elaphandra quinquenervis (LC50 = 61.1 µg/mL), and Calycolpus moritzianus (LC50 = 73.29 µg/mL) after 24 h. This biological activity may be related to the disruption of the electron transport chain through the mitochondrial protein complexes. We hypothesized that the observed EOs' effect is due to their major components, where computational approaches such as homology modeling and molecular docking may suggest the possible binding pose of secondary metabolites that inhibit the mitochondrial enzymes and acetylcholinesterase activity (AChE). Our results provided insights into the possible mechanism of action of EOs and their major compounds for new insecticide designs targeting the mitochondria and AChE activity in A. aegypti for effective and safe insecticide.

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Section: Resultsmentioning

confidence: 99%

Insecticidal activity of essential oils from American native plants against Aedes aegypti (Diptera: Culicidae): an introduction to their possible mechanism of action

Duque

Urbina

Vesga

et al. 2023

Sci Rep

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“…Mosquitocidal results revealed that the synthesized 4,7-dichloroquinoline was highly toxic to developmental stages of malarial and dengue vectors providing LC 50 values ranging from 4.408 µM/mL (larva I) to 7.958 µM/mL (pupa) for the chosen malaria vector and 5.016 µM/mL (larva I) to 10.669 µM/mL (pupa) for the dengue vector (Table 2 ). Recently, Rueda et al 50 demonstrated both adulticidal and larvicidal activity of A. aegypti when exposed to synthesized α-amino nitriles. Shao et al 51 showed for hexahydroimidazo [1,2-α] pyridine derivatives that they had excellent pesticidal properties against aphid species.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of new series of quinoline derivatives with insecticidal effects on larval vectors of malaria and dengue diseases

Murugan

Panneerselvam

Subramaniam

et al. 2022

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Mosquito borne diseases are on the rise because of their fast spread worldwide and the lack of effective treatments. Here we are focusing on the development of a novel anti-malarial and virucidal agent with biocidal effects also on its vectors. We have synthesized a new quinoline (4,7-dichloroquinoline) derivative which showed significant larvicidal and pupicidal properties against a malarial and a dengue vector and a lethal toxicity ranging from 4.408 µM/mL (first instar larvae) to 7.958 µM/mL (pupal populations) for Anopheles stephensi and 5.016 µM/mL (larva 1) to 10.669 µM/mL (pupae) for Aedes aegypti. In-vitro antiplasmodial efficacy of 4,7-dichloroquinoline revealed a significant growth inhibition of both sensitive strains of Plasmodium falciparum with IC50 values of 6.7 nM (CQ-s) and 8.5 nM (CQ-r). Chloroquine IC50 values, as control, were 23 nM (CQ-s), and 27.5 nM (CQ-r). In vivo antiplasmodial studies with P. falciparum infected mice showed an effect of 4,7-dichloroquinoline compared to chloroquine. The quinoline compound showed significant activity against the viral pathogen serotype 2 (DENV-2). In vitro conditions and the purified quinoline exhibited insignificant toxicity on the host system up to 100 µM/mL. Overall, 4,7-dichloroquinoline could provide a good anti-vectorial and anti-malarial agent.

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“…Knowledge of the mechanism of action makes it possible to understand which non-target organisms could be harmed by the use of such products [ 145 , 159 ]. In addition, this information facilitates prospecting other possibly more active materials using biotechnology tools and in silico models [ 160 , 161 , 162 ]. However, in general it is not easy to understand the mechanisms of action of plant natural products.…”

Section: Limitations And/or Expectations Of Plant Natural Product mentioning

confidence: 99%

Plant Natural Products for the Control of Aedes aegypti: The Main Vector of Important Arboviruses

et al. 2020

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The mosquito species Aedes aegypti is one of the main vectors of arboviruses, including dengue, Zika and chikungunya. Considering the deficiency or absence of vaccines to prevent these diseases, vector control remains an important strategy. The use of plant natural product-based insecticides constitutes an alternative to chemical insecticides as they are degraded more easily and are less harmful to the environment, not to mention their lower toxicity to non-target insects. This review details plant species and their secondary metabolites that have demonstrated insecticidal properties (ovicidal, larvicidal, pupicidal, adulticidal, repellent and ovipositional effects) against the mosquito, together with their mechanisms of action. In particular, essential oils and some of their chemical constituents such as terpenoids and phenylpropanoids offer distinct advantages. Thiophenes, amides and alkaloids also possess high larvicidal and adulticidal activities, adding to the wealth of plant natural products with potential in vector control applications.

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

Cited by 10 publications

References 45 publications

Insecticidal activity of essential oils from American native plants against Aedes aegypti (Diptera: Culicidae): an introduction to their possible mechanism of action

Insecticidal activity of essential oils from American native plants against Aedes aegypti (Diptera: Culicidae): an introduction to their possible mechanism of action

Synthesis of new series of quinoline derivatives with insecticidal effects on larval vectors of malaria and dengue diseases

Plant Natural Products for the Control of Aedes aegypti: The Main Vector of Important Arboviruses

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