Biodiversity Literature Repository

Submit to community
Liberated Data
Published February 12, 2018 | Version v1
Journal article Open

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

Authors/Creators

  • 1. Universidad Industrial de Santander, Escuela de Química, Laboratorio de Química Orgánica y Biomolecular, Santander, Colombia
  • 2. Universidad Industrial de Santander, Escuela de Medicina, Centro de investigaciones en enfermedades tropicales, Santander, Colombia

Description

Rueda, Andrés G., Carreño Otero, Aurora L., Duque, Jonny E., Kouznetsov, Vladimir V. (2018): Synthesis of new α-amino nitriles with insecticidal action on Aedes aegypti (Diptera: Culicidae). Revista Brasileira de Entomologia 62 (2): 112-118, DOI: 10.1016/j.rbe.2018.01.004, URL: http://dx.doi.org/10.1016/j.rbe.2018.01.004

Files

source.pdf

Files (797.0 kB)

Name Size Download all
md5:1851f47cab02d0d154609415d2b1dcde
797.0 kB Preview Download

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:1851F47CAB02FFD154609415FFB1FFDE

Related works

Cites
Publication: 10.1016/B978-0-12-417010-0.00006-9 (DOI)
Publication: 10.1016/j.antiviral.2016.03.010 (DOI)
Has part
Figure: 10.5281/zenodo.13197867 (DOI)

References

  • Aguirre-obando, O.A., Bona, A.C.D., Duque, J.E.L., Navarro-silva, M.A., 2015. Insecticide resistance and genetic variability in natural populations of Aedes (Stegomyia) aegypti (Diptera: Culicidae) from Colombia. Zoologia 32, 14-22, Insecticide.
  • Ashford, J., Sowden, R.R., 1970.Multi-variate probit analysis.Biometrics 26, 535-546.
  • Bona, A.C.D., Chitolina, R.F., Fermino, M.L., de Castro Poncio, L., Weiss, A., Lima, J.B.P., Paldi, N., Bernardes, E.S., Henen, J., Maori, E., 2016. Larval application of sodium channel homologous dsRNA restores pyrethroid insecticide susceptibility in a resistant adult mosquito population. Parasit. Vectors 9, 397-410.
  • Braga, I.A., Valle, D., 2007. Aedes aegypti: inseticidas, mecanismos de acao e resistencia. Epidemiol. Serv. Saude 16, 279-293.
  • Brahmachari, G., 2016. Design of organic transformations at ambient conditions: our sincere efforts to the cause of green chemistry practice. Chem. Rec. 16, 98-123.
  • Brogdon, W.G., Rojanapremsuk, J., Suvannadabba, S., Pandii, W., Jones, J.W., Sithiprasasna, R., Provincial, P., Health, P., Biology, V., Sciences, M., 2005. Bottle and biochemical assays on temephos. Southeast Asian J. Trop. Med. Public Heal. 36, 417-425.
  • Cao-Lormeau, V.-M., Blake, A., Mons, S., Lastere, S., Roche, C., Vanhomwegen, J., Dub, T., Baudouin, L., Teissier, A., Larre, P., Vial, A.-L., Decam, C., Choumet, V., Halstead, S.K., Willison, H.J., Musset, L., Manuguerra, J.-C., Despres, P., Fournier, E., Mallet, H.-P., Musso, D., Fontanet, A., Neil,J., Ghawche, F., 2016.Guillain-Barre syndrome outbreak associated with Zika virus infection in French Polynesia:a case-control study. Lancet 387, 1531-1539.
  • Carreno, A.L., Vargas Mendez, L.Y., Duque, L.J.E., Kouznetsov, V.V., 2014. Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever. Eur. J. Med. Chem. 78, 392-400.
  • Carreno Otero, A.L., Palacio-Cortes, A.M., Navarro-Silva, M.A., Kouznetsov, V.V., Duque, L J.E., 2018. Behavior of detoxifying enzymes of Aedes aegypti exposed to girgensohnine alkaloid analog and Cymbopogon flexuosus essential oil. Comp. Biochem. Physiol. Part C: Toxicol. Pharmacol. 204, 14-25.
  • Dias, C.N., Moraes, D.F.C., 2013. Essential oils and their compounds as Aedes aegypti L (Diptera: Culicidae) larvicides: review. Parasitol. Res. 113, 565-592.
  • Ellman, G., Courtney, D., Valentino, A., Featherstone, M., 1961. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7, 88-95.
  • Erturk, E., Tezeren, M.A., Atalar, T., Tilki, T., 2012. Regioselective ring-opening of epoxides with ortho-lithioanisoles catalyzed by BF 3-OEt 2. Tetrahedron 68, 6463-6471.
  • Flores-Conde,M.I., Reyes, L., Herrera, R., Rios, H., Vazquez,M.A., Miranda, R., Tamariz, J., Delgado, F., 2012.Highly regio- and stereoselective Diels-Alder cycloadditions via two-step and multicomponent reactions promoted by infrared irradiation under solvent-free conditions. Int. J. Mol. Sci. 13, 2590-2617.
  • Grisales, N., Poupardin, R., Gomez, S., Fonseca-Gonzalez, I., Ranson, H., Lenhart, A., 2013. Temephos resistance in Aedes aegypti in Colombia compromises dengue vector control. PLoS Negl. Trop. Dis. 7, e2438.
  • Guedes, R.N.C., Walse, S.S., Throne, J.E., 2017. Sublethal exposure, insecticide resistance, and community stress. Curr. Opin. Insect Sci. 21, 47-53.
  • Guzman, M.G., Harris, E., 2015. Dengue. Lancet 385, 453-465.
  • Harris, A.F., Rajatileka, S., Ranson, H., 2010. Pyrethroid resistance in Aedes aegypti from Grand Cayman. Am. J. Trop. Med. Hyg. 83, 277-284.
  • Hayes, E.B., 2009. Zika virus outside Africa. Emerg. Infect. Dis. 15, 1347-1350.
  • Hemingway, J., 2005. Guidelines for laboratory and field testing of mosquito larvicides. World Health Organization.
  • Hemingway, J., Hawkes, N.J., McCarroll, L., Ranson, H., 2004. The molecular basis of insecticide resistance in mosquitoes. Insect Biochem. Mol. Biol. 34, 653-665.
  • Instituto Nacional de Salud INS, 2017. Boletin epidemiologico semana 43 de 2017.
  • Ioos, S., Mallet, H.P., Leparc Goffart, I., Gauthier, V., Cardoso, T., Herida, M., 2014. Current Zika virus epidemiology and recent epidemics. Med. Mal. Infect. 44, 302-307.
  • Kawada, H., Ohashi, K., Dida, G.O., Sonye, G., Njenga, S.M., Mwandawiro, C., Minakawa, N., 2014. Preventive effect of permethrin-impregnated long-lasting insecticidal nets on the blood feeding of three major pyrethroid-resistant malaria vectors in western Kenya. Paras. Vectors 7, 1-9.
  • Lima, E.P., Paiva, M.H.S., de Araujo, A.P., da Silva, E.V.G., da Silva, U.M., de Oliveira, L.N., Santana, A.E.G., Barbosa, C.N., de Paiva Neto, C.C., Goulart, M.O.F., Wilding, C.S., Ayres, C.F.J., de Melo Santos, M.A.V., 2011. Insecticide resistance in Aedes aegypti populations from Ceara. Brazil. Parasit. Vectors 4, 5.
  • Lipinski, C.A., 2001. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 44, 235-249.
  • Lipinski, C.A., Lombardo, F., Dominy, B.W., Feeney, P.J., 2001. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46, 3-26.
  • Liu, X.C., Lai, D., Liu, Q.Z., Zhou, L., Liu, Q., Liu, Z.L., 2016. Bioactivities of a new pyrrolidine alkaloid from the root barks of Orixa japonica. Molecules 21, 1-8.
  • Low, V.L., Vinnie-Siow, W.Y., Lim,Y.A.L., Tan, T.K., Leong, C.S., Chen, C.D., Azidah, A.A., Sofian-Azirun, M., 2015. First molecular genotyping of A302S mutation in the gamma aminobutyric acid (GABA) receptor in Aedes albopictus from Malaysia. Trop. Biomed. 32, 554-556.
  • Musso, D., Gubler, D.J., 2016. Zika virus. Clin. Microbiol. Rev. 29, 488-524.
  • Nahrstedt, A., Lechtenberg, M., Brinker, A., Seigler, D.S., Hegnauer, R., 1993. 4- Hidroximandelonitrile glucosides, dhurrin in Sucleya suckleyana and taxiphillin in Girgensohnia oppositiflora (chenopodiaceae). Phytochemistry 33, 847-850.
  • Otto, N., Opatz, T., 2014. Heterocycles from α- Aminonitriles. Chem. - Eur. J. 20, 13065-13077.
  • Pacelli, G., De Lima, G.P., De Souza, T.M., Freire, G.D.P., Farias, D.F., Cunha, A.P., Maria, N., Silva, P., De Morais, S.M., 2013. Further insecticidal activities of essential oils from Lippia sidoides and Croton species against Aedes aegypti L. Parasitol. Res. 112, 1953-1958.
  • Pang, Y.P., 2014. Insect acetylcholinesterase as a target for effective and environmentally safe insecticides. In: Advances in Insect Physiology, 1st ed. Elsevier Inc., http://dx.doi.org/10.1016/B978-0-12-417010-0.00006-9.
  • Prajapati, V., Tripathi, A.K., Aggarwal, K.K., Khanuja, S.P.S., 2005. Insecticidal, repellent and oviposition-deterrent activity of selected essential oils against Anopheles stephensi, Aedes aegypti and Culex quinquefasciatus. Bioresour.Technol. 96, 1749-1757.
  • Rashad, A.A., Mahalingam, S., Keller,P.A.,2014.Chikungunya virus: emerging targets and new opportunities for medicinal chemistry. J. Med. Chem. 57, 1147-1166.
  • Rasmussen, S.A., Jamieson, D.J., Honein, M.A., Petersen, L.R., 2016. Zika virus and birth defects - reviewing the evidence for causality. N. Engl. J. Med. 374, 1-7.
  • Rodriguez-Morales, A.J., 2015. Zika: the new arbovirus threat for Latin America. J. Infect. Dev. Ctries 9, 684-685.
  • Russell, R.J., Claudianos, C., Campbell, P.M., Horne, I., Sutherland, T.D., Oakeshott, J.G., 2004. Two major classes of target site insensitivity mutations confer resistance to organophosphate and carbamate insecticides. Pestic. Biochem. Physiol. 79, 84-93.
  • Seo, S.M., Jung, C.S., Kang, J., Lee, H.R., Kim, S.W., Hyun, J., Park, I.K., 2015. Larvicidal and acetylcholinesterase inhibitory activities of apiaceae plant essential oils and their constituents against Aedes albopictus and formulation development. J. Agric. Food Chem. 63, 9977-9986.
  • Shafer, T.J., Meyer, D.A., Crofton, K.M., 2005. Developmental neurotoxicity of pyrethroid insecticides: critical review and future research needs. Environ. Health Perspect. 113, 123-136.
  • Shafran, Y.M., Bakulev, V.A., Mokrushin, V.S., 1989. Synthesis and properties of aaminonitriles. Russ. Chem. Rev. 58, 148-162.
  • Shan, C., Xie, X., Barrett, A.D.T., Garcia-Blanco, M.A., Tesh, R.B., Vasconcelos, P.F.D.C., Vasilakis, N., Weaver, S.C., Shi, P.Y., 2016. Zika virus: diagnosis therapeutics, and vaccine. ACS Infect. Dis. 2, 170-172.
  • Simmons, et al., 2012. Current concepts, Dengue. N. Engl. J. Med. 366, 1423-1432.
  • Smith, L.B., Kasai,S., Scott, J.G., 2016. Pyrethroid resistance in Aedes aegypti and Aedes albopictus: important mosquito vectors of human diseases. Pestic. Biochem. Physiol. 133, 1-59.
  • Sparks, T.C., Nauen, R., 2015. IRAC: mode of action classification and insecticide resistance management. Pestic. Biochem. Physiol. 121, 122-128.
  • Staples, J.E., Fischer, M., 2014. Chikungunya virus in the Americas - what a vector-borne pathogen can do. N. Engl. J. Med. 371, 887-889.
  • Stevens, A.J., Gahan, M.E., Mahalingam, S., Keller, P.A., 2009. The medicinal chemistry of dengue fever. J. Med. Chem. 52, 7911-7926.
  • Strecker, A., 1850. Ueber die kunstliche Bildung der Milchsaure und einen neuen, dem Glycocoll homologen Korper. Eur. J. Org. Chem. 75, 27-45.
  • Vargas, L.Y., Kouznetsov, V.V., 2013. First girgensohnine analogs prepared through InCl3-catalyzed strecker reaction and their bioprospection. Curr. Org. Synth. 10, 969-973.
  • Wang, J., Liu, X., Feng, X., 2011. Asymmetric strecker reactions. Chem. Rev. 111, 6947-6983.
  • Weaver, S.C., Costa, F., Garcia-Blanco, M.A., Ko, A.I., Ribeiro, G.S., Saade, G., Shi, P.Y., Vasilakis, N., 2016. Zika virus: history, emergence, biology, and prospects for control. Antiviral Res., http://dx.doi.org/10.1016/j.antiviral.2016.03.010.
  • Weaver, S.C., Reisen, W.K., 2010. Present and future arboviral threats. Antiviral Res. 85, 328-345.
  • World Health Organisation, 2012. Report of a WHO Technical Working Group Meeting on Dengue Prevention and Control, Meeting Report.
  • Zanluca, C., De Melo, V.C.A., Mosimann, A.L.P., Dos Santos, G.I.V., dos Santos, C.N.D., Luz, K., 2015. First report of autochthonous transmission of Zika virus in Brazil. Mem. Inst. Oswaldo Cruz 110, 569-572.