Application of Molecular Docking, Homology Modeling, and Chemometric Approaches to Neonicotinoid Toxicity against Aphis craccivora.
cowpea aphid
molecular modeling
pesticides
pharmacophore
regression approaches
Journal
Molecular informatics
ISSN: 1868-1751
Titre abrégé: Mol Inform
Pays: Germany
ID NLM: 101529315
Informations de publication
Date de publication:
03 2022
03 2022
Historique:
received:
01
04
2021
accepted:
15
10
2021
pubmed:
29
10
2021
medline:
3
5
2022
entrez:
28
10
2021
Statut:
ppublish
Résumé
Neonicotinoids are known as effective pesticides against various insect species. They can harm useful insects including honeybees, with a relatively low threat to nontarget organisms and the environment. This paper presents combined methods to explore the insecticidal activity of neonicotinoids with diverse scaffolds, active against Aphis craccivora. Pharmacophore, molecular docking into the active site of nicotinic acetylcholine receptor homology model, and linear and non-linear regression approaches were used to find new insecticide candidates. The potential toxic effects against honeybees were evaluated using the molecular docking in the active site of the new Aphis mellifera homology model. Four new untested compounds were assigned as insecticide candidates, active against Aphis craccivora with less potential toxic effects for honeybees. This approach may be an effective strategy to design environmentally friendly insecticides against the cowpea aphid.
Identifiants
pubmed: 34710288
doi: 10.1002/minf.202100058
doi:
Substances chimiques
Insecticides
0
Neonicotinoids
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2100058Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
J. J. Villaverde, B. Sevilla-Morán, C. López-Goti, J. L. Alonso-Prados, P. Sandín-España, SAR QSAR Environ. Res. 2020 31, 49-72.
Regulation (EC) No 1107/2009 - plant protection products of the European Parliament and of the Council of 21 October 2009 concerning the placing of plant protection products on the market and repealing Council Directives 79/117/EEC and 91/414/EEC, https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32009R1107&from=EN, accessed 01 February 2021.
J. J. Villaverde, B. Sevilla-Morán, C. López-Goti, J. L. Alonso-Prados, P. Sandín-España, J. Agric. Food Chem. 2017, 65(10), 2017-2018.
J. E. Casida, Annu. Rev. Entomol. 2018, 63, 125-144.
H. A. Craddock, D. Huang, P. C. Turner, L. Quirós-Alcalá, D. C. Payne-Sturges, Environ. Health. 2019, 18, 7.
J. M. Bonmatin, E. A. D. Mitchell, G. Glauser, E. Lumawig-Heitzman, F. Claveria, M. B. van Lexmond, K. Taira, F. Sánchez-Bayo, Sci. Total Environ. 2021, 757, 143822.
B. Buszewski, M. Bukowska, M. Ligor, I. Staneczko-Baranowska, Environ. Sci. Pollut. Res. Int. 2019, 26, 34723-34740.
T. J. Wood, D. Goulson, Environ. Sci. Pollut. Res. Int. 2017, 24, 17285-17325.
A. K. Hassani, M. Dacher, V. Gary, M. Lambin, M. Gauthier, C. Armengaud, Arch. Environ. Contam. Toxicol. 2008, 54, 653-661.
D. Alberoni, R. Favaro, L. Baffoni, S. Angeli, D. Di Gioia, Sci. Total Environ. 2020, 762, 144116.
Z. Huang, H. Li, Y. Wei, J. Xiong, J. You, Sci. Total Environ. 2020, 714, 136878.
N. Simon-Delso, V. Amaral-Rogers, L. P. Belzunces, J. M. Bonmatin, M. Chagnon, C. Downs, L. Furlan, D. W. Gibbons, C. Giorio, V. Girolami, D. Goulson, D. P. Kreutzweiser, C. H. Krupke, M. Liess, E. Long, M. McField, P. Mineau, E. A. D. Mitchell, C. A. Morrissey, D. A. Noome, L. Pisa, J. Settele, J. D. Stark, A. Tapparo, H. Van Dyck, J. Van Praagh, J. P. Van der Sluijs, P. R. Whitehorn, M. Wiemers, Environ. Sci. Pollut. Res. Int. 2015, 22, 5-34.
B. K. Klatt, A. Holzschuh, C. Westphal, Y. Clough, I. Smit, E. Pawelzik, T. Tscharntke, Proc. R. Soc. B. 2014, 281, 2013-2440.
M. P. D. Garratt, T. D. Breeze, N. Jenner, C. Polce, J. C. Biesmeijer, S. G. Potts, Agric. Ecosyst. Environ. 2014, 184, 34-40.
I. Denholm, G. J. Devine, M. S. Williamson, Science. 2002, 297, 2222-2223.
R. Nauen, I. Denholm, Arch. Insect Biochem. Physiol. 2005, 58, 200-215.
C. Bass, I. Denholm, M. S. Williamson, R. Nauen, Pestic. Biochem. Physiol. 2015, 121, 78-87.
M. Ji, New Agric. 2017, 2, 33-34.
A. Whittaker, Datasheet-Aphis craccivora. In: Invasive species compendium-CABI, Wallingford, UK. 2018. (accessed 7 September 2020).
China Neonicotinoid Insecticides, Market Report 2016 Edition, https://www.reportbuyer.com/product/3952801/, accessed 14 September 2020.
C. Moffat, S. T. Buckland, A. J. Samson, R. McArthur, V. C. Pino, K. A. Bollan, J. T.-J. Huang, C. N. Connolly, Sci. Rep. 2016, 6, 24764.
T. Iwasa, N. Motoyama, J. T. Ambrose, R. M. Roe, Crop Prot. 2004, 23, 371-378.
J. Kimura-Kuroda, Y. Komuta, Y. Kuroda, M. Hayashi, H. Kawano, PLoS One. 2012, 7, e32432.
L. W. Pisa, V. Amaral-Rogers, L. P. Belzunces, J. M. Bonmatin, C. A. Downs, D. Goulson, D. P. Kreutzweiser, C. Krupke, M. Liess, M. McField, C. A. Morrissey, D. A. Noome, J. Settele, N. Simon-Delso, J. D. Stark, J. P. Van der Sluijs, H. Van Dyck, M. Wiemers, Environ. Sci. Pollut. Res. Int. 2015, 22, 68-102.
A. Bora, S. Avram, S. Funar-Timofei, L. Halip, Rev. Roum. Chim. 2018, 63, 861-867.
A. Bora, T. Suzuki, S. Funar-Timofei, Environ. Sci. Pollut. Res. Int. 2019, 26, 14547-14561.
E. Carnesecchi, A. A. Toropov, A. P. Toropova, N. Kramer, C. Svendsen, J. L. Dorne, E. Benfenati, Sci. Total Environ. 2020, 704, 135302.
F. Como, E. Carnesecchi, S. Volani, J. L. Dorne, J. Richardson, A. Bassan, M. Pavan, E. Benfenati, Chemosphere. 2017, 166, 438-444.
L. Crisan, A. Borota, T. Suzuki, S. Funar-Timofei, Mol. Inf. 2019, 38, 1800119.
S. Funar-Timofei, A. Borota, L. Crisan, Mol. Diversity 2017, 21, 437-454.
Y. Zhao, Y. Li, Ecotoxicol. Environ. Saf. 2018, 164, 467-473.
B. Wang, J. Cheng, Z. Xu, X. Xu, X. Shao, Z. Li, Molecules. 2012,17, 10014-10025.
Z. Ye, L. Shi, X. Shao, X. Xu, Z. Xu, Z. Li, J. Agric. Food Chem. 2013, 61, 312-319.
X. Shao, X. Huang, Q. Shi, Z. Li, L. Tao, G. Song, J. Heterocycl. Chem. 2012, 49, 1136-1142.
S. Lu, X. Shao, Z. Li, Z. Xu, S. Zhao, Y. Wu, X. Xu, J. Agric. Food Chem. 2012, 60, 322-330.
Z. Ye, S. Xia, X. Shao, J. Cheng, X. Xu, Z. Xu, Z. Li, X. Qian, J. Agric. Food Chem. 2011, 59(19), 10615-10623.
R. Xu, M. Luo, R. Xia, X. Meng, X. Xu, Z. Xu, J. Cheng, X. Shao, H. Li, Z. Li, J. Agric. Food Chem. 2014, 62, 11070-11079.
X. Shao, H. Fu, X. Xu, X. Xu, Z. Liu, Z. Li X Qian, J. Agric. Food Chem. 2010, 58, 2696-2702.
P. C. D. Hawkins, A. G. Skillman, G. L. Warren, B. A. Ellingson, M. T. Stahl, J. Chem. Inf. Model. 2010, 50, 572-584.
M. T. Muhammed, E. Aki-Yalcin, Chem. Biol. Drug Des. 2019, 93, 12-20.
R. A. Laskowski, M. W. MacArthur, D. S. Moss, J. M. Thornton, J. Appl. Cryst. 1993, 26, 283-291.
M. McGann, J. Chem. Inf. Model. 2011, 51, 578-596.
M. McGann, J. Comput.-Aided Mol. Des. 2012, 26, 897-906.
B. P. Kelley, S. P. Brown, G. L. Warren, S. W. Muchmore, J. Chem. Inf. Model. 2015, 55, 1771-1780.
G. Wolber, T. Seidel, F. Bendix, T. Langer, Drug Discovery Today 2008, 13, 23-29.
S. L. Dixon, A. M. Smondyrev, E. H. Knoll, S. N. Rao, D. E. Shaw, R. A. Friesner, J. Comput.-Aided Mol. Des. 2006, 20, 647-671.
J. Verma, V. M. Khedkar, E. C. Coutinho, Curr. Top. Med. Chem. 2010, 10, 95-115.
S. Wold, W. J. Dunn III, J. Chem. Inf. Comput. Sci. 1983, 23, 6-13.
P. Gramatica, N. Chirico, E. Papa, S. Cassani, S. Kovarich, J. Comput. Chem. 2013, 34, 2121-2132.
P. Gramatica, I. J. Q. S. P. R. 2020, 5, 1-36.
U. Depczynski, V. J. Frost, K. Molt, Anal. Chim. Acta. 2000, 420, 217-227.
R. Todeschini, V. Consonni, A. Mauri, M. Pavan, Anal. Chim. Acta. 2004, 515, 199-208.
D. M. Hawkins, S. C. Basak, D. Mills, J. Chem. Inf. Comput. Sci. 2003, 43, 579-586.
H. R. Keller, D. L. Massart, J. P. Brans, Chemom. Intell. Lab. Syst. 1991, 11, 175-189.
S. Chatterjee, B. Price, Regression analysis by example, second ed. John Wiley & Sons, New York. 1991.
I. E. Frank, R. Todeschini, The data analysis handbook. first ed. Elsevier, Amsterdam. 1994.
J. Zupan, J. Gasteiger, Neural Networks for Chemistry and Drug Design. second ed. Wiley-VCH, Weinheim. 1999.
D. J. Livingstone, M. G. Ford, Artificial networks as an alternative to statistics, in: Bioactive Compound Design: Possibilities for Industrial Use. (Eds.: M. G. Ford, et al.), Bios Scientific Publishers, Oxford, p. 99. 1996.
T. Suzuki, M. Ishida, Fire Mater. 1995, 19, 179-189.
T. I. Netzeva, A. P. Worth, T. Aldenberg, R. Benigni, M. T. D. Cronin, P. Gramatica, J. S. Jaworska, S. Kahn, G. Klopman, C. A. Marchant, G. Myatt, N. Nikolova-Jeliazkova, G. Y. Patlewicz, R. Perkins, D. Roberts, T. Schultz, D. W. Stanton, J. J. van de Sandt, W. Tong, G. Veith, C. Yang, Altern. Lab. Anim. 2005, 33, 155-173.
P. Gramatica, Methods Mol. Biol. 2013, 930, 499-526.
P. Gramatica, S. Cassani, P. P. Roy, S. Kovarich, C. W. Yap, E. Papa, Mol. Inf. 2012, 31, 817-835.
M. Pavan, A. Worth, T. Netzeva, EUR 21749 EN. 2005. JRC31399.
P. Gramatica, QSAR Comb. Sci. 2007, 26, 694-701.
K. Roy, S. Kar, P. Ambure, Chemom. Intell. Lab. Syst. 2015, 145, 22-29.
M. P. Jacobson, D. L. Pincus, C. S. Rapp, T. J. F. Day, B. Honig, D. E. Shaw, R. A. Friesner, Proteins. 2004, 55, 351-367.
N. Guex, M. C. Peitsch, Electrophoresis 1997, 18, 2714-2723.
G. W. Bemis, M. A. Murcko, J. Med. Chem. 1996, 39, 2887-2893.
P. Jeschke, Pest Manage. Sci. 2017, 73, 1053-1066.
D. L. J. Alexander, A. Tropsha, D. A. Winkler, J. Chem. Inf. Model. 2015, 55, 1316-1322.
R. Todeschini, V. Consonni, Molecular descriptors for chemoinformatics, in: Methods and Principles in Medicinal Chemistry, (Eds.: R. Mannhold, H. Kubinyi, G. Folkers), Wiley - VCH, Weinheim, 2009.
P. Jeschke, R. Nauen, Neonicotinoid insecticides. in: Comprehensive Molecular Insect Science, Vol. 5, (Eds.: I. Gilbert, L. Iatrou, S. S. Gill), Elsevier, Oxford, 2005, pp. 53-105.
P. Jeschke, R. Nauen, M. Schindler, A. Elbert, J. Agric. Food Chem. 2011, 59, 2897-2908.