In silico models for predicting vector control chemicals targeting Aedes aegypti

SAR and QSAR in Environmental Research

Volumn 25, Issue 10, 2014, Pages 805-835

  Devillers, J ^a   Lagneau, C ^b   Lattes, A ^c   Garrigues, J C ^c   Clemente M M ^d   Yebakima A ^d  

^a CTIS   (France)

^b Entente Interdepartementale pour la Demoustication du Littoral Mediterraneen   (France)

^c Université Paul Sabatier   (France)

^d Centre de Démoustication LAV ARS Conseil Général de la Martinique   (France)

Author keywords

adulticide; Aedes aegypti; homology modelling; larvicide; QSAR

Indexed keywords

CLIMATE CHANGE; COMPUTATIONAL CHEMISTRY; CONTROLLED DRUG DELIVERY; INSECTICIDES; VECTOR CONTROL (ELECTRIC MACHINERY);

% REDUCTIONS; ADULTICIDE; AEDES AEGYPTI; HOMOLOGY MODELING; IN-SILICO MODELS; LARVICIDE; NUMBER OF FACTORS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP MODELING; VACCINE DEVELOPMENT;

VECTORS;

AEDES AEGYPTI;

INSECTICIDE;

AEDES; ANIMAL; CHEMISTRY; COMPUTER SIMULATION; DISEASE CARRIER; DRUG EFFECTS; PHYSIOLOGY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

AEDES; ANIMALS; COMPUTER SIMULATION; INSECT VECTORS; INSECTICIDES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84907708217     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2014.958291     Document Type: Article

References (157)

1. WHO, Dengue and severe dengue, Fact sheet n°117, World Health Organisation, 2013. Available at http://www.who.int/mediacentre/factsheets/fs117/en/ (accessed 2 December 2013).
2. D.J. Gubler, Epidemic dengue/dengue hemorrhagic fever as a public health, social and economical problem in the 21st century, Trends Microbiol. 10 (2002), pp. 100–103.10.1016/S0966-842X(01)02288-0
3. N.E.A. Murray, M.B. Quam, and A. Wilder-Smith, Epidemiology of dengue: Past, present and future prospects, Clin. Epidemiol. 5 (2013), pp. 299–309.
4. L. Su, L. Fu, J. He, W. Qin, L. Sheng, M.H. Abraham, and Y.H. Zhao, Comparison of Tetrahymena pyriformis toxicity based on hydrophobicity, polarity, ionization and reactivity of class-based compounds, SAR QSAR Environ. Res. 23 (2012), pp. 537–552.10.1080/1062936X.2012.666567
5. Y. Sakuratani, H.Q. Zhang, S. Nishikawa, K. Yamazaki, T. Yamada, J. Yamada, and M. Hayashi, Categorization of nitrobenzenes for repeated dose toxicity based on adverse outcome pathways, SAR QSAR Environ. Res. 24 (2013), pp. 35–46.10.1080/1062936X.2012.728995
6. A. Yan, H. Liang, Y. Chong, X. Nie, and C. Yu, In-silico prediction of blood–brain barrier permeability, SAR QSAR Environ. Res. 24 (2013), pp. 61–74.10.1080/1062936X.2012.729224
7. Y. Brito-Sánchez, J.A. Castillo-Garit, H. Le-Thi-Thu, Y. González-Madariaga, F. Torrens, Y. Marrero-Ponce, and J.E. Rodríguez-Borges, Comparative study to predict toxic modes of action of phenols from molecular structures, SAR QSAR Environ. Res. 24 (2013), pp. 235–251.10.1080/1062936X.2013.766260
8. E. Papa, S. Kovarich, and P. Gramatica, QSAR prediction of the competitive interaction of emerging halogenated pollutants with human transthyretin, SAR QSAR Environ. Res. 24 (2013), pp. 333–349.10.1080/1062936X.2013.773374
9. N. Kireeva, S.L. Kuznetsov, A.A. Bykov, and A. Yu Tsivadze, Towards in silico identification of the human ether-a-go-go-related gene channel blockers: Discriminative vs. generative classification models, SAR QSAR Environ. Res. 24 (2013), pp. 103–117.10.1080/1062936X.2012.742135
10. S. Gharaghani, T. Khayamian, and M. Ebrahimi, Molecular dynamics simulation study and molecular docking descriptors in structure-based QSAR on acetylcholinesterase (AChE) inhibitors, SAR QSAR Environ. Res. 24 (2013), pp. 773–794.10.1080/1062936X.2013.792877
11. N. Marchand-Geneste and J. Devillers, Comparative modeling review of nuclear receptor superfamily, in Endocrine Disruption Modeling, J. Devillers, ed., CRC Press, Boca Raton, FL, pp. 97–142.
12. M. Saxena, S.S. Bhunia, and A.K. Saxena, Docking studies of novel pyrazinopyridoindoles class of antihistamines with the homology modelled H1-receptor, SAR QSAR Environ. Res. 23 (2012), pp. 311–325.10.1080/1062936X.2012.664561
13. A.K. Saxena and K.K. Roy, Hierarchical virtual screening: Identification of potential high-affinity and selective β3-adrenergic receptor agonists, SAR QSAR Environ. Res. 23 (2012), pp. 389–407.10.1080/1062936X.2012.664824
14. B. Vyas, O. Silakari, M. Singh Bahia, and B. Singh, Glutamine: Fructose-6-phosphate amidotransferase (GFAT): Homology modelling and designing of new inhibitors using pharmacophore and docking based hierarchical virtual screening protocol, SAR QSAR Environ. Res. 24 (2013), pp. 733–752.10.1080/1062936X.2013.797493
15. D.G. Heckel, L.J. Gahan, J.C. Daly, and S. Trowell, A genomic approach to understanding Heliothis and Helicoverpa resistance to chemical and biological insecticides, Phil. Trans. R. Soc. Lond. B 353 (1998), pp. 1713–1722.10.1098/rstb.1998.0323
16. W. Tan, X. Wang, P. Cheng, L. Liu, H. Wang, M. Gong, X. Quan, H. Gao, and C. Zhu, Cloning and overexpression of transferrin gene from cypermethrin-resistant Culex pipiens pallens, Parasitol. Res. 110 (2012), pp. 939–959.10.1007/s00436-011-2580-4
17. T. Yang and N. Liu, Genome analysis of cytochrome P450s and their expression profiles in insecticide resistant mosquitoes, Culex quinquefasciatus, PLoS One 6 (2011),12,e29418. doi: 10.1371/journal.pone.0029418.
18. Y. Gong, T. Li, L. Zhang, X. Gao, and N. Liu, Permethrin induction of multiple cytochrome P450 genes in insecticide resistant mosquitoes, Culex quinquefasciatus, Int. J. Biol. Sci. 9 (2013), pp. 863–871.10.7150/ijbs.6744
19. M. Paris and L. Despres, Identifying insecticide resistance genes in mosquito by combining AFLP genome scans and 454 pyrosequencing, Mol. Ecol. 21 (2012), pp. 1672–1686.10.1111/mec.2012.21.issue-7
20. A. Bonin, M. Paris, G. Tetreau, J.P. David, and L. Després, Candidate genes revealed by a genome scan for mosquito resistance to a bacterial insecticide: Sequence and gene expression variations, BMC Genomics 21, 10 (2009) 551. doi: 10.1186/1471-2164-10-551.10.1186/1471-2164-10-551
21. A.R. Katritzky, D.A. Dobchev, I. Tulp, M. Karelson, and D.A. Carlson, QSAR study of mosquito repellents using Codessa Pro, Bioorg. Med. Chem. Lett. 16 (2006), pp. 2306–2311.10.1016/j.bmcl.2005.11.113
22. J.B. Bhonsle, A.K. Bhattacharjee, and R.K. Gupta, Novel semi-automated methodology for developing highly predictive QSAR models: Application for development of QSAR models for insect repellent amides, J. Mol. Model. 13 (2007), pp. 179–208.
23. R. Natarajan, S.C. Basak, D. Mills, J.J. Kraker, and D.M. Hawkins, Quantitative structure-activity relationship modeling of mosquito repellents using calculated descriptors, Croat. Chem. Acta 81 (2008), pp. 333–340.
24. U.R. Bernier and M. Tsikolia, Development of novel repellents using structure–activity modeling of compounds in the USDA Archival Database, in Recent Developments in Invertebrate Repellents, G.E. Paluch and J.R. Coats, eds., American Chemical Society, ACS Symposium Series, volume 1090, 2011, pp. 21–46.
25. P.V. Oliferenko, A.A. Oliferenko, G.I. Poda, D.I. Osolodkin, G.G. Pillai, U.R. Bernier, M. Tsikolia, N.M. Agramonte, G.G. Clark, K.J. Linthicum, and A.R. Katritzky, Promising Aedes aegypti repellent chemotypes identified through integrated QSAR, virtual screening, synthesis, and bioassay, PLoS ONE 8 (2013) 9, e64547. doi: 10.1371/journal.pone.0064547.10.1371/journal.pone.0064547
26. K. Hartfelder, Insect juvenile hormone: From “status quo” to high society, Braz. J. Med. Biol. Res. 33 (2000), pp. 157–177.10.1590/S0100-879X2000000200003
27. L.I. Gilbert, N.A. Granger, and R.M. Roe, The juvenile hormones: Historical facts and speculations on future research directions, Insect Biochem. Mol. Biol. 30 (2000), pp. 617–644.10.1016/S0965-1748(00)00034-5
28. S.R. Palli, Recent advances in the mode of action of juvenile hormones and their analogs, in Biorational Control of Arthropod Pests, I. Ishaaya and A.R. Horowitz, eds., Springer, New York, 2009, pp. 111–129.10.1007/978-90-481-2316-2
29. S.G. Kamita and B.D. Hammock, Juvenile hormone esterase: Biochemistry and structure, J. Pestic. Sci. 35 (2010), pp. 265–274.10.1584/jpestics.R10-09
30. S.G. Kamita, A.C. Hinton, C.E. Wheelock, M.D. Wogulis, D.K. Wilson, N.M. Wolf, J.E. Stok, B. Hock, and B.D. Hammock, Juvenile hormone (JH) esterase: Why are you so JH specific?, Insect Biochem. Mol. Biol. 33 (2003), pp. 1261–1273.10.1016/j.ibmb.2003.08.004
31. A.B. Shapiro, G.D. Wheelock, H.H. Hagedorn, F.C. Baker, L.W. Tsai, and D.A. Schooley, Juvenile hormone and juvenile hormone esterase in adult females of the mosquito Aedes aegypti, J. Insect Physiol. 32 (1986), pp. 867–877.10.1016/0022-1910(86)90102-2
32. Y. Li, S. Hernandez-Martinez, G.C. Unnithan, R. Feyereisen, and F.G. Noriega, Activity of the corpora allata of adult female Aedes aegypti: Effects of mating and feeding, Insect Biochem. Molec. Biol. 33 (2003), pp. 1307–1315.10.1016/j.ibmb.2003.07.003
33. J. Devillers, Juvenile hormones and juvenoids: A historical survey, in Juvenile Hormones and Juvenoids. Modeling Biological Effects and Environmental Fate, J. Devillers, ed., CRC Press, Boca Raton, 2013, pp. 1–14.10.1201/CRCQSARENVHEA
34. C.A. Henrick, W.E. Willy, and G.B. Staal, Insect juvenile hormone activity of alkyl (2E,4E)-3,7,11-trimethyl-2,4-dodecadienoates. Variations in the ester function and in the carbon chain, J. Agric. Food Chem. 24 (1976), pp. 207–218.10.1021/jf60204a018
35. A. Nakayama, H. Iwamura, and T. Fujita, Quantitative structure-activity relationship of insect juvenile hormone mimetic compounds, J. Med. Chem. 27 (1984), pp. 1493–1502.10.1021/jm00377a019
36. H. Iwamura, K. Nishimura, and T. Fujita, Quantitative structure-activity relationships of insecticides and plant growth regulators: Comparative studies toward understanding the molecular mechanism of action, Environ. Health Perspect. 61 (1985), pp. 307–320.10.1289/ehp.8561307
37. C. Hansch and A. Leo, Exploring QSAR. Fundamentals and Applications in Chemistry and Biology, ACS Professional Reference Book Series, Washington, DC, 1995.
38. S. Bintein, J. Devillers, and W. Karcher, Nonlinear dependence of fish bioconcentration on n-octanol/water partition coefficient, SAR QSAR Environ. Res. 1 (1993), pp. 29–39.10.1080/10629369308028814
39. J. Devillers, SAR and QSAR modeling of juvenile hormone mimics, in Juvenile Hormones and Juvenoids. Modeling Biological Effects and Environmental Fate, J. Devillers, ed., CRC Press, Boca Raton, 2013, pp. 145–174.10.1201/CRCQSARENVHEA
40. J. Devillers, Neural Networks in QSAR and Drug Design, Academic Press, London, U.K., 1996.
41. S.C. Basak, R. Natarajan, D. Mills, D.M. Hawkins, and J.J. Kraker, Quantitative structure-activity relationship modeling of insect juvenile hormone activity of 2,4-dienoates using computed molecular descriptors, SAR QSAR Environ. Res. 16 (2005), pp. 581–606.10.1080/10659360500468526
42. J. Devillers and A.T. Balaban, Topological Indices and Related Descriptors in QSAR and QSPR, Gordon and Breach Science Publishers, Amsterdam, the Netherlands, 1999.
43. A.E. Hoerl and R.W. Kennard, Ridge regression: Applications to nonorthogonal problems, Technometrics 12 (1970), pp. 69–82.10.1080/00401706.1970.10488635
44. J. Devillers, D. Zakarya, M. Chastrette, and J.C. Doré, The stochastic regression analysis as a tool in ecotoxicological QSAR studies, Biomed. Environ. Sci. 2 (1989), pp. 385–393.
45. H. Abdi, Partial least squares regression and projection on latent structure regression (PLS Regression), WIREs Comput. Stat. 2010, doi: 10.1002/wics.051.
46. S.S. Young and D.M. Hawkins, Using recursive partitioning to analyze a large SAR data set, SAR QSAR Environ. Res. 8 (1998), pp. 183–193.10.1080/10629369808039140
47. A. Székács, B. Bordás, and B.D. Hammock, Transition state analog enzyme inhibitors: Structure–activity relationships of trifluoromethyl ketones, in Rational Approaches to Structure, Activity, and Ecotoxicology of Agrochemicals, W. Draber and T. Fujita, eds., ACS Symp. Ser, American Chemical Society, Washington, DC, 1992, pp. 219–249.
48. C.E. Wheelock, Y. Nakagawa, M. Akamatsu, and B.D. Hammock, Use of classical and 3-D QSAR to examine the hydration state of juvenile hormone esterase inhibitors, Bioorg. Med. Chem. 11 (2003), pp. 5101–5116.10.1016/j.bmc.2003.08.023
49. J. Devillers, J.P. Doucet, A. Doucet-Panaye, A. Decourtye, and P. Aupinel, Linear and non-linear QSAR modelling of juvenile hormone esterase inhibitors, SAR QSAR Environ. Res. 23 (2012), pp. 357–369.10.1080/1062936X.2012.664562
50. J. Devillers, A. Doucet-Panaye, and J.P. Doucet, Predicting highly potent juvenile hormone esterase inhibitors from 2D QSAR modeling, in Juvenile Hormones and Juvenoids. Modeling Biological Effects and Environmental Fate, J. Devillers, ed., CRC Press, Boca Raton, 2013, pp. 241–266.10.1201/CRCQSARENVHEA
51. J. Caballero, Receptor-guided structure–activity modeling of inhibitors of juvenile hormone epoxide hydrolases, in Juvenile Hormones and Juvenoids. Modeling Biological Effects and Environmental Fate, J. Devillers, ed., CRC Press, Boca Raton, 2013, pp. 267–289.
52. J.P. Doucet, A. Doucet-Panaye, and J. Devillers, Structure–activity relationship study of trifluoromethylketones: Inhibitors of insect juvenile hormone esterase, SAR QSAR Environ. Res. 24 (2013), pp. 481–499.10.1080/1062936X.2013.792499
53. J. Zhu, K. Miura, L. Chen, and A.S. Raikhel, AHR38, a homolog of NGFI-B, inhibits formation of the functional ecdysteroid receptor in the mosquito Aedes aegypti, EMBO J. 19 (2000), pp. 253–262.10.1093/emboj/19.2.253
54. L. Swevers and K. Iatrou, Ecdysteroids and ecdysteroid signaling pathways during insect oogenesis, in Ecdysone: Structures and Functions, G. Smagghe, ed., Springer, New York, 2009, pp. 127–164.
55. K.D. Spindler, C. Hönl, C. Tremmel, S. Braun, H. Ruff, and M. Spindler-Barth, Ecdysteroid hormone action, Cell. Mol. Life Sci. 66 (2009), pp. 3837–3850.10.1007/s00018-009-0112-5
56. M.Y. Song, J.D. Stark, and J.J. Brown, Comparative toxicity of four insecticides, including imidacloprid and tebufenozide, to four aquatic arthropods, Environ. Toxicol. Chem. 16 (1997), pp. 2494–2500.10.1002/etc.v16:12
57. J. Cruz, D.H. Sieglaff, P. Arensburger, P.W. Atkinson, and A.S. Raikhel, Nuclear receptors in the mosquito Aedes aegypti, Annotation, hormonal regulation and expression profiling, FEBS J. 276 (2009), pp. 1233–1254.
58. H.C. Smith, C.K. Cavanaugh, J.L. Friz, C.S. Thompson, J.A. Saggers, E.L. Michelotti, J. Garcia, and C.M. Tice, Synthesis and SAR of cis-1-benzoyl-1,2,3,4-tetrahydroquinoline ligands for control of gene expression in ecdysone responsive systems, Bioorg. Med. Chem. Lett. 13 (2003), pp. 1943–1946.10.1016/S0960-894X(03)00317-2
59. S. Lapenna, J. Friz, A. Barlow, S.R. Palli, L. Dinan, and R.E. Hormann, Ecdysteroid ligand-receptor selectivity-exploring trends to design orthogonal gene switches, FEBS J. 275 (2008), pp. 5785–5809.10.1111/j.1742-4658.2008.06687.x
60. N. Awang, N.A. Kosnon, and H. Othman, The effectiveness of organotin (IV) benzylisopropyldithiocarbamate compounds as insecticide against Aedes aegypti Linn. (Diptera: Culicidae) in laboratory, Middle-East, J. Sci. Res. 13 (2013), pp. 907–912.
61. X. Song, A. Zapata, J. Hoerner, A.C. de Dios, L. Casabianca, and G. Eng, Synthesis, larvicidal, QSAR and structural studies of some triorganotin 2,2,3,3-tetramethylcyclopropanecarboxylates, Appl. Organomet. Chem. 21 (2007), pp. 545–550.10.1002/(ISSN)1099-0739
62. C. Hansch and R.P. Verma, Larvicidal activities of some organotin compounds on mosquito larvae: A QSAR study, Eur. J. Med. Chem. 44 (2009), pp. 260–273.10.1016/j.ejmech.2008.02.040
63. Q. Duong, X. Song, E. Mitrojorgji, S. Gordon, and G. Eng, Larvicidal and structural studies of some triphenyl- and tricyclohexyltin para-substituted benzoates, J. Organomet. Chem. 691 (2006), pp. 1775–1779.10.1016/j.jorganchem.2005.12.005
64. X. Song, Q. Duong, E. Mitrojorgji, A. Zapata, N. Nguyen, D. Strickman, J. Glass, and G. Eng, Synthesis, structure characterization and larvicidal activity of some tris-(para-substitutedphenyl)tins, Appl. Organomet. Chem. 18 (2004), pp. 363–368.10.1002/(ISSN)1099-0739
65. M.P. Freitas, T.C. Ramalho, E.F.F. da Cunha, and R.A.Cormanich, Multivariate image analysis applied to QSAR as a tool for mosquitoes control: Dengue and yellow Fever, in Chemoinformatics: Directions Toward Combating Neglected Diseases, T.C. Ramalho, M.P. Freitas, and E.F.F. da Cunha, eds., Bentham Science Publishers Ltd. 2010, pp. 172–182.
66. A. Aronson, Sporulation and δ-endotoxin synthesis by Bacillus thuringiensis, Cell. Mol. Life Sci. 59 (2002), pp. 417–425.10.1007/s00018-002-8434-6
67. N. Crickmore, D.R. Zeigler, J. Feitelson, E. Schnepf, J. van Rie, D. Lereclus, J. Baum, and D.H. Dean, Revision of the nomenclature for the Bacillus thuringiensis pesticidal crystal proteins, Microbiol. Mol. Biol. Rev. 62 (1998), pp. 807–813.
68. C. Berry, S. O’Neil, E. Ben-Dov, A.F. Jones, L. Murphy, M.A. Quail, M.T.G. Holden, D. Harris, A. Zaritsky, and J. Parkhill, Complete sequence and organization of pBtoxis, the toxin-coding plasmid of Bacillus thuringiensis subsp. israelensis, Appl. Environ. Microbiol. 68 (2002), pp. 5082–5095.10.1128/AEM.68.10.5082-5095.2002
69. C. Stein, G.W. Jones, T. Chalmers, and C. Berry, Transcriptional analysis of the toxin-coding plasmid pBtoxis from Bacillus thuringiensis subsp. israelensis, Appl. Environ. Microbiol. 72 (2006), pp. 1771–1776.10.1128/AEM.72.3.1771-1776.2006
70. V. Guidi, N. Patocchi, P. Lüthy, and M. Tonolla, Distribution of Bacillus thuringiensis subsp. israelensis in soil of a Swiss wetland reserve after 22 years of mosquito control, Appl. Environ. Microbiol. 77 (2011), pp. 3663–3668.10.1128/AEM.00132-11
71. L. Després, C. Lagneau, and R. Frutos, Using the bio-insecticide Bacillus thuringiensis israelensis in mosquito control, in Pesticides in the Modern World – Pests Control and Pesticides Exposure and Toxicity Assessment, M. Stoytcheva, ed., InTech, Rijeka, Croatia 2011, pp. 93–126.
72. J. Chen, K.G. Aimanova, L.E. Fernandez, A. Bravo, M. Soberon, and S.S. Gill, Aedes aegypti cadherin serves as a putative receptor of the Cry11Aa toxin from Bacillus thuringiensis subsp. israelensis, Biochem. J. 424 (2009), pp. 191–200.10.1042/BJ20090730
73. V. Vachon, R. Laprade, and J.L. Schwartz, Current models of the mode of action of Bacillus thuringiensis insecticidal crystal proteins: A critical review, J. Invert. Pathol. 111 (2012), pp. 1–12.10.1016/j.jip.2012.05.001
74. V.N. Jisha, R.B. Smitha, and S. Benjamin, An overview of the crystal toxins from Bacillus thuringiensis, Adv. Microbiol. 3 (2013), pp. 462–472.10.4236/aim.2013.35062
75. L. Pardo-López, C. Muñoz-Garay, H. Porta, C. Rodriguez-Almazán, M. Soberón, and A. Bravo, Strategies to improve the insecticidal activity of Cry toxins from Bacillus thuringiensis, Peptides 30 (2009), pp. 589–595.10.1016/j.peptides.2008.07.027
76. P. Boonserm, M. Mo, C. Angsuthanasombat, and J. Lescar, Structure of the functional form of the mosquito larvicidal Cry4Aa toxin from Bacillus thuringiensis at a 2.8-angstom resolution, J. Bacteriol. 188 (2006), pp. 3391–3401.10.1128/JB.188.9.3391-3401.2006
77. P. Boonserm, P. Davis, D.J. Ellar, and J. Li, Crystal structure of the mosquito-larvicidal toxin Cry4Ba and its biological implications, J. Mol. Biol. 348 (2005), pp. 363–382.10.1016/j.jmb.2005.02.013
78. R.A. de Maagd, A. Bravo, and N. Crickmore, How Bacillus thuringiensis has evolved specific toxins to colonize the insect world, Trends Genet. 17 (2001), pp. 193–199.10.1016/S0168-9525(01)02237-5
79. C.R. Pigott, M.S. King, and D.J. Ellar, Investigating the properties of Bacillus thuringiensis Cry proteins with novel loop replacements created using combinatorial molecular biology, Appl. Environ. Microbiol. 74 (2008), pp. 3497–3511.10.1128/AEM.02844-07
80. S. Likitvivatanavong, J. Chen, A.M. Evans, A. Bravo, M. Soberon, and S.S. Gill, Multiple receptors as targets of Cry toxins in mosquitoes, J Agric Food Chem. 59 (2011), pp. 2829–2838.10.1021/jf1036189
81. L.E. Fernández, C. Pérez, L. Segovia, M.H. Rodriguez, S.S. Gill, A. Bravo, and M. Soberón, Cry11Aa toxin from Bacillus thuringiensis binds its receptor in Aedes aegypti mosquito larvae through loop α-8 of domain II, FEBS Letters 579 (2005), pp. 3508–3514.10.1016/j.febslet.2005.05.032
82. M.A.F. Abdullah and D.H. Dean, Enhancement of Cry19Aa mosquitocidal activity against Aedes aegypti by mutations in the putative loop regions of domain II, Appl. Environ. Microbiol. 70 (2004), pp. 3769–3771.10.1128/AEM.70.6.3769-3771.2004
83. M.L. Rosso and A. Delécluse, Contribution of the 65-kilodalton protein encoded by the cloned gene cry19A to the mosquitocidal activity of Bacillus thuringiensis subsp. jegathesan, Appl. Environ. Microbiol. 63 (1997), pp. 4449–4455.
84. C.N. Dias and D.F.C. Moraes, Essential oils and their compounds as Aedes aegypti L. (Diptera: Cilicidae) larvicides: Review, Parasitol. Res. 113 (2014), pp. 565–592.10.1007/s00436-013-3687-6
85. N. Kishore, B.B. Mishra, V.K. Tiwari, and V. Tripathi, A review on natural products with mosquitosidal potentials, in Opportunity, Challenge and Scope of Natural Products in Medicinal Chemistry, V.K. Tiwari and B.B. Mishra, eds., Research Signpost, Kerala, India, 2011, pp. 335–365.
86. N. Kishore, B.B. Mishra, V.K. Tiwari, V. Tripathi, and N. Lall, Natural products as leads to potential mosquitocides, Phytochem. Rev. (2013), pp. 1–41.
87. C.L. Cantrell, J.W. Pridgeon, F.R. Fronczek, and J. Becnel, Structure-activity relationship studies on derivatives of Eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults, Chem. Biodiv. 7 (2010), pp. 1681–1697.10.1002/cbdv.201000031
88. C.P. Kiprono, J.O. Midiwo, P.K. Kipkemboi, and S. Ladogana, Larvicidal benzoquinone from Embelia schimperi, Bull. Chem. Soc. Ethiop. 18 (2004), pp. 45–49.
89. J.O. Midiwo, Y. Ghebremeskel, and R.W. Mwangi, Insect antifeedant, growth-inhibiting and larvicidal compounds from Rapanea melanophloes (Myrsinaceae), Insect Sci. Appl. 16 (1995), pp. 163–166.
90. D.P. de Sousa, Y.W. Viera, M.P. Uliana, M.A. Melo, T.J. Brocksom, and S.C.H. Cavalcanti, Larvicidal activity of para-benzoquinone, Parasitol. Res. 107 (2010), pp. 741–745.10.1007/s00436-010-1942-7
91. S.R.L. Santos, M.A. Melo, A.V. Cardoso, R.L.C. Santos, D.P. de Sousa, and S.C.H. Cavalcanti, Structure-activity relationships of larvicidal monoterpenes and derivatives against Aedes aegypti Linn, Chemosphere 84 (2011), pp. 150–153.10.1016/j.chemosphere.2011.02.018
92. A. Lucia, E. Zerba, and H. Masuh, Knockdown and larvicidal activity of six monoterpenes against Aedes aegypti (Diptera: Culicidae) and their structure-activity relationships, Parasitol. Res. 112 (2013), pp. 4267–4272.10.1007/s00436-013-3618-6
93. B. Khanikor, P. Parida, R.N.S. Yadav, and D. Bora, Comparative mode of action of some terpene compounds against octopamine receptor and acetyl cholinesterase of mosquito and human system by the help of homology modeling and docking studies, J. Appl. Pharm. Sci. 3 (2013), pp. 6–12.
94. L. Scotti, M.T. Scotti, V.B. Silva, S.R.L. Santos, S.C.H. Cavalcanti, and F.J.B. Mendonça Jr, Chemometric studies on potential larvicidal compounds against Aedes aegypti, Med. Chem. 10 (2014), pp. 201–210.10.2174/15734064113099990005
95. A.C.S. Pinto, K.L. Nogueira, F.C.M. Chaves, L.V. Souza da Silva, W.P. Tadei, and A.M. Pohlit, Adulticidal activity of dillapiol and semi-synthetic derivatives of dillapiol against Aedes aegypti (L.) (Culicidae), J. Mosqu. Res. 2 (2012), pp. 1–7.
96. J.W. Pridgeon, K.M. Meepagala, J.J. Becnel, G.G. Clark, R.M. Pereira, and K.J. Linthicum, Structure-activity relationships of 33 piperidines as toxicants against female adults of Aedes aegypti (Diptera: Culicidae), J. Med. Entomol. 44 (2007), pp. 263–269.10.1603/0022-2585(2007)44[263:SROPAT]2.0.CO;2
97. J. Devillers, L. Lagadic, O. Yamada, F. Darriet, R. Delorme, X. Deparis, J.P. Jaeg, C. Lagneau, B. Lapied, F. Quiniou, and A. Yébakima, Use of multicriteria analysis for selecting candidate insecticides for vector control, in, Juvenile Hormones and Juvenoids. Modeling Biological Effects and Environmental Fate, J. Devillers, ed., CRC Press, Boca Raton, 2013, pp. 341–381.
98. M. Vaillant, J.M. Jouany, and J. Devillers, A multicriteria estimation of the environmental risk of chemicals with the SIRIS method, Toxicol. Model. 1 (1995), pp. 57–72.
99. D. Filmore, It’s a GPCR world, Mod. Drug Discov. 7 (2004), pp. 24–28.
100. V. Nene, J.R. Wortman, D. Lawson, B. Haas, C. Kodira, Z.J. Tu, B. Loftus, Z. Xi, K. Megy, M. Grabherr, Q. Ren, E.M. Zdobnov, N.F. Lobo, K.S. Campbell, S.E. Brown, M.F. Bonaldo, J. Zhu, S.P. Sinkins, D.G. Hogenkamp, P. Amedeo, P. Arensburger, P.W. Atkinson, S. Bidwell, J. Biedler, E. Birney, R.V. Bruggner, J. Costas, M.R. Coy, J. Crabtree, M. Crawford, B. Debruyn, D. Decaprio, K. Eiglmeier, E. Eisenstadt, H. El-Dorry, W.M. Gelbart, S.L. Gomes, M. Hammond, L.I. Hannick, J.R. Hogan, M.H. Holmes, D. Jaffe, J.S. Johnston, R.C. Kennedy, H. Koo, S. Kravitz, E.V. Kriventseva, D. Kulp, K. Labutti, E. Lee, S. Li, D.D. Lovin, C. Mao, E. Mauceli, C.F. Menck, J.R. Miller, P. Montgomery, A. Mori, A.L. Nascimento, H.F. Naveira, C. Nusbaum, S. O’leary, J. Orvis, M. Pertea, H. Quesneville, K.R. Reidenbach, Y.H. Rogers, C.W. Roth, J.R. Schneider, M. Schatz, M. Shumway, M. Stanke, E.O. Stinson, J.M. Tubio, J.P. Vanzee, S. Verjovski-Almeida, D. Werner, O. White, S. Wyder, Q. Zeng, Q. Zhao, Y. Zhao, C.A. Hill, A.S. Raikhel, M.B. Soares, D.L. Knudson, N.H. Lee, J. Galagan, S.L. Salzberg, I.T. Paulsen, G. Dimopoulos, F.H. Collins, B. Birren, C.M. Fraser-Liggett, and D.W. Severson, Genome sequence of Aedes aegypti, a major arbovirus vector, Science 316 (2007), pp. 1718–1723.10.1126/science.1138878
101. C.A. Hill, A.N. Fox, R.J. Pitts, L.B. Kent, P.L. Tan, M.A. Chrystal, A. Cravchik, F.H. Collins, H.M. Robertson, and L.J. Zwiebel, G protein-coupled receptors in Anopheles gambiae, Science 298 (2002), pp. 176–178.10.1126/science.1076196
102. J.P. Andersen, A. Schwartz, J.B. Gramsbergen, and V. Loeschcke, Dopamine levels in the mosquito Aedes aegypti during adult development, following blood feeding and in response to heat stress, J. Insect Physiol. 52 (2006), pp. 1163–1170.10.1016/j.jinsphys.2006.08.004
103. J.M. Meyer, K.F.K. Ejendal, L.V. Avramova, E.E. Garland-Kuntz, G.I. Giraldo-Calderón, T.F. Brust, V.J. Watts, and C.A. Hill, A ‘‘genome-to-lead’’ approach for insecticide discovery: Pharmacological characterization and screening of Aedes aegypti D1-like dopamine receptors, PLoS Negl. Trop. Dis. 6 (2012), p. e1478.10.1371/journal.pntd.0001478
104. C.A. Hill, J.M. Meyer, K.F.K. Ejendal, D.F. Echeverry, E.G. Lang, L.V. Avramova, J.M. Conley, and V.J. Watts, Re-invigorating the insecticide discovery pipeline for vector control: GPCRs as targets for the identification of next gen insecticides, Pest. Biochem. Physiol. 106 (2013), pp. 141–146.10.1016/j.pestbp.2013.02.008
105. H.W. Tedford, B.A. Steinbaugh, L. Bao, B.D. Tait, A. Tempczyk-Russell, W. Smith, G.L. Benzon, C.A. Finkenbinder, and R.M. Kennedy, In silico screening for compounds that match the pharmacophore of omega-hexatoxin-Hv1a leads to discovery and optimization of a novel class of insecticides, Pest. Biochem. Physiol. 106 (2013), pp. 124–140.10.1016/j.pestbp.2013.01.009
106. D. Borovsky, Biosynthesis and control of mosquito gut proteases, Life 55 (2003), pp. 435–441.
107. J. Isoe, J. Collins, H. Badgandi, W.A. Day, and R.L. Miesfeld, Defects in coatomer protein I (COPI) transport cause blood feeding-induced mortality in yellow fever mosquitoes, Proc. Natl. Acad. Sci. USA 108 (2011), pp. E211–217.10.1073/pnas.1102637108
108. J.B. Sáenz, W.J. Sun, J.W. Chang, J. Li, B. Bursulaya, N.S. Gray, and D.B. Haslam, Golgicide A reveals essential roles for GBF1 in Golgi assembly and function, Nat. Chem. Biol. 5 (2009), pp. 157–165.10.1038/nchembio.144
109. D.J. Mack, J. Isoe, R.L. Miesfeld, and J.T. Njardarson, Distinct biological effects of golgicide A derivatives on larval and adult mosquitoes, Bioorg. Med. Chem. Lett. 22 (2012), pp. 5177–5181.10.1016/j.bmcl.2012.06.076
110. J.S. Li and J. Li, Major chorion proteins and their crosslinking during chorion hardening in Aedes aegypti mosquitoes, Insect Biochem. Mol. Biol. 36 (2006), pp. 954–964.10.1016/j.ibmb.2006.09.006
111. J. Li, B.A. Hodgeman, and B.M. Christensen, Involvement of peroxidase in chorion hardening in Aedes aegypti, Insect Biochem. Mol. Biol. 26 (1996), pp. 309–317.10.1016/0965-1748(95)00099-2
112. J.S. Li, S.R. Kim, and J. Li, Molecular characterization of a novel peroxidase involved in Aedes aegypti chorion protein crosslinking, Insect Biochem. Mol. Biol. 34 (2004), pp. 1195–1203.10.1016/j.ibmb.2004.08.001
113. E.P. Alcantara, In silico identification of potential inhibitors of dengue mosquito, Aedes aegypti chorion peroxidase, Comput. Biol. Bioinform. 2 (2014), pp. 38–42.
114. D.R. Koes and C.J. Camacho, ZINCPharmer: Pharmacophore search of the ZINC database, Nuc. Acids Res. 40 (2012), pp. W409–W414.10.1093/nar/gks378
115. J.J. Irwin and B.K. Shoichet, ZINC – A free database of commercially available compounds for virtual screening, J. Chem. Inf. Model. 45 (2005), pp. 177–182.10.1021/ci049714+
116. D.W. Severson and S.K. Behura, Mosquito genomics: Progress and challenges, Annu. Rev. Entomol. 57 (2012), pp. 143–166.10.1146/annurev-ento-120710-100651
117. B. Bryant, C.D. Blair, K.E. Olson, and R.J. Clem, Annotation and expression profiling of apoptosis-related genes in the yellow fever mosquito, Aedes aegypti, Insect Biochem. Molec. Biol. 38 (2008), pp. 331–345.
118. Z. Xi, J.L. Ramirez, and G. Dimopoulos, The Aedes aegypti toll pathway controls dengue virus infection, PLoS Pathog. 4 (2008), e1000098. doi: 10.1371/journal.ppat.1000098.10.1371/journal.ppat.1000098
119. L.L. Drake, D.Y. Boudko, O. Marinotti, V.K. Carpenter, A.L. Dawe, and I.A. Hansen, The aquaporin gene family of the yellow fever mosquito, Aedes aegypti, PLoS One 5 (2010), p. e15578. doi: 10.1371/journal.pone.0015578.10.1371/journal.pone.0015578
120. A.A. Ptitsyn, G. Reyes-Solis, K. Saavedra-Rodriguez, J. Betz, E.L. Suchman, J.O. Carlson, and W.C. Black, Rhythms and synchronization patterns in gene expression in the Aedes aegypti mosquito, BMC Genomics 12, 153 (2011), pp. 1–16.
121. O.J.T. Briët and N. Chitnis, Effects of changing mosquito host searching behaviour on the cost effectiveness of a mass distribution of long-lasting, insecticidal nets: A modelling study, Malaria J. 12 (2013), pp. 1–11.
122. C. Sokhna, M.O. Ndiath, and C. Rogier, The changes in mosquito vector behaviour and the emerging resistance to insecticides will challenge the decline of malaria, Clin. Microbiol. Infect. 19 (2013), pp. 902–907.10.1111/1469-0691.12314
123. H. Pates and C. Curtis, Mosquito behavior and vector control, Annu. Rev. Entomol. 50 (2005), pp. 53–70.10.1146/annurev.ento.50.071803.130439
124. T.E. Nkya, I. Akhouayri, W. Kisinza, and J.P. David, Impact of environment on mosquito response to pyrethroid insecticides: Facts, evidences and prospects, Insect Biochem. Molec. Biol. 43 (2013), pp. 407–416.10.1016/j.ibmb.2012.10.006
125. J. Hemingway and H. Ranson, Insecticide resistance in insect vectors of human disease, Annu. Rev. Entomol. 45 (2000), pp. 371–391.10.1146/annurev.ento.45.1.371
126. G. Bingham, C. Strode, and L. Tran, PT Khoa, and H.P. Jamet, Can piperonyl butoxide enhance the efficacy of pyrethroids against pyrethroid-resistant Aedes aegypti? Trop. Med. Int. Health 16 (2011), pp. 492–500.10.1111/tmi.2011.16.issue-4
127. C. Strode, C.S. Wondji, J.P. David, N.J. Hawkes, N. Lumjuan, D.R. Nelson, D.R. Drane, S.H.P. Karunaratne, J. Hemingway, W.C. Black 4th, and H. Ranson, Genomic analysis of detoxification genes in the mosquito Aedes aegypti, Insect Biochem. Mol. Biol. 38 (2008), pp. 113–123.10.1016/j.ibmb.2007.09.007
128. S. Marcombe, R. Poupardin, F. Darriet, S. Reynaud, J. Bonnet, C. Strode, C. Brengues, A. Yébakima, H. Ranson, V. Corbel, and J.P. David, Exploring the molecular basis of insecticide resistance in the dengue vector Aedes aegypti: A case study in Martinique Island (French West Indies), BMC Genomics 10 494 (2009), pp. 1–14.
129. S. Marcombe, R.B. Mathieu, N. Pocquet, M.A. Riaz, R. Poupardin, S. Sélior, F. Darriet, S. Reynaud, A. Yébakima, V. Corbel, J.P. David, and F. Chandre, Insecticide resistance in the dengue vector Aedes aegypti from Martinique: Distribution, mechanisms and relations with environmental factors, PLoS ONE 7 (2012), p. e30989. (doi: 10.1371/journal.pone.0030989).10.1371/journal.pone.0030989
130. J.P. David, E. Coissac, C. Melodelima, R. Poupardin, M.A. Riaz, A. Chandor-Proust, and S. Reynaud, Transcriptome response to pollutants and insecticides in the dengue vector Aedes aegypti using next-generation sequencing technology, BMC Genomics 11, 216 (2010), pp. 1–12.
131. J.P. David, H.M. Ismail, A. Chandor-Proust, and M.J.I. Paine, Role of cytochrome P450s in insecticide resistance: Impact on the control of mosquito-borne diseases and use of insecticides on Earth, Phil. Trans. R. Soc. B 368 (2013), 20120429.10.1098/rstb.2012.0429
132. A. Chandor-Proust, J. Bibby, M. Régent-Kloeckner, J. Roux, E. Guittard-Crilat, R. Poupardin, M.A. Riaz, C. Dauphin-Villemant, S. Reynaud, and J.P. David, The central role of mosquito cytochrome P450 CYP6Zs in insecticide detoxification revealed by functional expression and structural modelling, Biochem. J. 455 (2013), pp. 75–85.10.1042/BJ20130577
133. P. Lertkiatmongkol, E. Jenwitheesuk, and P. Rongnoparut, Homology modeling of mosquito cytochrome P450 enzymes involved in pyrethroid metabolism: Insights into differences in substrate selectivity, BMC Res. Notes 4 (2011), p. 321.10.1186/1756-0500-4-321
134. T.L. Chiu, Z. Wen, S.G. Rupasinghe, and M.A. Schuler, Comparative molecular modeling of Anopheles gambiae CYP6Z1, a mosquito P450 capable of metabolizing DDT, Proc. Natl Acad. Sci. USA 105 (2008), pp. 8855–8860.10.1073/pnas.0709249105
135. R.J. Marles, R.L. Compadre, C.M. Compadre, C. Soucy-Breau, R.W. Redmond, F. Duval, B. Mehta, P. Morand, J.C. Scaiano, and J.T. Arnason, Thiophenes as mosquito larvicides: Structure–toxicity relationship analysis, Pest. Biochem. Physiol. 41 (1991), pp. 89–100.10.1016/0048-3575(91)90063-R
136. D.G. Hammond and I. Kubo, Structure-activity relationship of alkanols as mosquito larvicides with novel findings regarding their mode of action, Bioorg. Med. Chem. 7 (1999), pp. 271–278.10.1016/S0968-0896(98)00248-X
137. S.C. Basak, R. Natarajan, D. Mills, D.M. Hawkins, and J.J. Kraker, Quantitative structure-activity relationship modeling of juvenile hormone mimetic compounds for Culex pipiens larvae, with a discussion of descriptor-thinning methods, J. Chem. Inf. Model. 46 (2006), pp. 65–77.10.1021/ci050215y
138. N.A. Begum, N. Roy, R.A. Laskar, and K. Roy, Mosquito larvicidal studies of some chalcone analogues and their derived products: Structure–activity relationship analysis, Med. Chem. Res. 20 (2011), pp. 184–191.10.1007/s00044-010-9305-6
139. R. Sun, Y. Li, M. Lü, L. Xiong, and Q. Wang, Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group, Bioorg. Med. Chem. Lett. 20 (2010), pp. 4693–4699.10.1016/j.bmcl.2010.04.144
140. H.E.D.M. Zahran and S.A.M. Abdelgaleil, Insecticidal and developmental inhibitory properties of monoterpenes on Culex pipiens L. (Diptera: Culicidae), J. Asia-Pacific Entomol. 14 (2011), pp. 46–51.10.1016/j.aspen.2010.11.013
141. J. Devillers, N. Marchand-Geneste, A. Carpy, and J.M. Porcher, SAR and QSAR modeling of endocrine disruptors, SAR QSAR Environ. Res. 17 (2006), pp. 393–412.10.1080/10629360600884397
142. J. Devillers, H. Devillers, A. Decourtye, J. Fourrier, P. Aupinel, and D. Fortini, Agent-based modeling of the long term effects of pyriproxyfen on honey bee population, in In Silico Bees, J. Devillers, ed., CRC Press, Boca Raton, 2014, pp. 179–208.10.1201/b16453
143. R. Carbó-Dorca and E. Besalú, Construction of coherent nano quantitative structure–properties relationships (nano-QSPR) models and catastrophe theory, SAR QSAR Environ. Res. 22 (2011), pp. 661–665.10.1080/1062936X.2011.623319
144. L. Lubinski, P. Urbaszek, A. Gajewicz, M.T.D. Cronin, S.J. Enoch, J.C. Madden, D. Leszczynska, J. Leszczynski, and T. Puzyn, Evaluation criteria for the quality of published experimental data on nanomaterials and their usefulness for QSAR modelling, SAR QSAR Environ. Res. 24 (2013), pp. 995–1008.10.1080/1062936X.2013.840679
145. D.A. Winkler, F.R. Burden, B. Yan, R. Weissleder, C. Tassa, S. Shaw, and V.C. Epa, Modelling and predicting the biological effects of nanomaterials, SAR QSAR Environ. Res. 25 (2014), pp. 161–172.10.1080/1062936X.2013.874367
146. J.E. Riviere and C.L. Tran, Pharmacokinetics of nanomaterials, in Nanotoxicology. Characterization, Dosing, and Health Effects, N.A. Monteiro-Riviere and C.L. Tran, eds., Informa, NY, 2007, pp. 127–140.10.3109/9781420045154
147. F. Gottschalk, R.W. Scholz, and B. Nowack, Probabilistic material flow modeling for assessing the environmental exposure to compounds: Methodology and an application to engineered nano-TiO2 particles, Environ. Model. Soft. 25 (2010), pp. 320–332.10.1016/j.envsoft.2009.08.011
148. X. Liu, K. Tang, S. Harper, B. Harper, J.A. Steevens, and R. Xu, Predictive modeling of nanomaterial exposure effects in biological systems, Int. J. Nanomed. 8 (2013), pp. 31–43.10.2147/IJN
149. A. Zollanvari, M.J. Cunningham, U. Braga-Neto, and E.R. Dougherty, Analysis and modeling of time-course gene-expression profiles from nanomaterial-exposed primary human epidermal keratinocytes, BMC Bioinf. 10 (2009), sup. 11, S10.10.1186/1471-2105-10-S11-S10
150. T.K. Barik, R. Kamaraju, and A. Gowswami, Silica nanoparticle: A potential new insecticide for mosquito vector control, Parasitol. Res. 111 (2012), pp. 1075–1083.10.1007/s00436-012-2934-6
151. A. Sooresh, H. Kwon, R. Taylor, P. Pietrantonio, M. Pine, and C.M. Sayes, Surface functionalization of silver nanoparticles: Novel applications for insect vector control, Appl. Mater. Interf. 3 (2011), pp. 3779–3787.10.1021/am201167v
152. N. Soni and S. Prakash, Efficacy of fungus mediated silver and gold nanoparticles against Aedes aegypti larvae, Parasitol. Res. 110 (2012), pp. 175–184.10.1007/s00436-011-2467-4
153. M. Kah and T. Hofmann, Nanopesticide research: Current trends and future priorities, Environ. Intern. 63 (2014), pp. 224–235.10.1016/j.envint.2013.11.015
154. C.J.M. Koenraadt, M. Kormaksson, and L.C. Harrington, Effects of inbreeding and genetic modification on Aedes aegypti larval competition and adult energy reserves, Parasit. Vect. 3 (2010), p. 92.10.1186/1756-3305-3-92
155. D.O. Carvalho, D. Nimmo, N. Naish, A.R. McKemey, P. Gray, A.B.B. Wilke, M.T. Marrelli, J.F. Virginio, L. Alphey, and M.L. Capurro, Mass production of genetically modified Aedes aegypti for field releases in Brazil, J. Vis. Exp. 83 (2014), p. e3579.
156. L.E. Yauch and S. Shresta, Dengue virus vaccine development, Adv. Virus Res. 88 (2014), pp. 315–372.10.1016/B978-0-12-800098-4.00007-6
157. I. Rodriguez-Barraquer, L. Mier-y-Teran-Romero, I.B. Schwartz, D.S. Burke, and D.A.T. Cummings, Potential opportunities and perils of imperfect dengue vaccines, Vaccine 32 (2014), pp. 514–520.10.1016/j.vaccine.2013.11.020