Neonicotinoid insecticide design: molecular docking, multiple chemometric approaches, and toxicity relationship with Cowpea aphids.


Journal

Environmental science and pollution research international
ISSN: 1614-7499
Titre abrégé: Environ Sci Pollut Res Int
Pays: Germany
ID NLM: 9441769

Informations de publication

Date de publication:
May 2019
Historique:
received: 12 09 2018
accepted: 19 02 2019
pubmed: 17 3 2019
medline: 20 6 2019
entrez: 17 3 2019
Statut: ppublish

Résumé

Neonicotinoids are the fastest-growing class of insecticides successfully applied in plant protection, human and animal health care. The significant resistance increases led to the urgent need for alternative new neonicotinoids, with improved insecticidal activity. We performed molecular docking to describe a common binding mode of neonicotinoids into the nicotinic acetylcholine receptor, and to select the appropriate conformations to derive models. These were further used in a QSAR study employing both linear and nonlinear approaches to model the inhibitory activity against the Cowpea aphids. Linear modeling was performed by multiple linear regression and partial least squares and nonlinear modeling by artificial neural networks and support vector machine methods. The OECD principles were considered for QSAR models validation. Robust models with predictive power were found for neonicotinoid diverse structures. Based on our QSAR and docking outcomes, five new insecticides were predicted, according to the model applicability domain, the ligand efficiencies, and the binding mode. Therefore, the developed models can be confidently used for the prediction of the insecticidal activity of new chemicals, saving a substantial amount of time and money and, also, contributing to the chemical risk assessment.

Identifiants

pubmed: 30877540
doi: 10.1007/s11356-019-04662-9
pii: 10.1007/s11356-019-04662-9
doi:

Substances chimiques

Insecticides 0
Ligands 0
Neonicotinoids 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

14547-14561

Références

J Chem Inf Comput Sci. 2001 Jan-Feb;41(1):186-95
pubmed: 11206373
Environ Health Perspect. 2003 Aug;111(10):1376-90
pubmed: 12896861
J Chem Inf Comput Sci. 2004 Jul-Aug;44(4):1257-66
pubmed: 15272833
Altern Lab Anim. 2005 Apr;33(2):155-73
pubmed: 16180989
J Agric Food Chem. 2007 Mar 21;55(6):2288-92
pubmed: 17311404
Invert Neurosci. 2008 Jun;8(2):71-81
pubmed: 18338186
Pest Manag Sci. 2008 Nov;64(11):1084-98
pubmed: 18712805
Pest Manag Sci. 2008 Nov;64(11):1082-3
pubmed: 18798167
Bioorg Med Chem Lett. 2008 Dec 15;18(24):6513-6
pubmed: 18951786
J Chem Inf Model. 2008 Nov;48(11):2140-5
pubmed: 18954136
J Agric Food Chem. 2009 Feb 11;57(3):951-7
pubmed: 19138119
Mol Pharmacol. 2009 Jul;76(1):1-10
pubmed: 19321668
Molecules. 2009 Apr 29;14(5):1660-701
pubmed: 19471190
J Chem Inf Model. 2009 Jul;49(7):1669-78
pubmed: 19527034
J Agric Food Chem. 2010 Mar 10;58(5):2741-5
pubmed: 20000775
J Agric Food Chem. 2010 Mar 24;58(6):3415-21
pubmed: 20180506
J Chem Inf Model. 2010 Apr 26;50(4):572-84
pubmed: 20235588
J Agric Food Chem. 2011 Apr 13;59(7):2897-908
pubmed: 20565065
J Chem Inf Model. 2011 Mar 28;51(3):578-96
pubmed: 21323318
J Agric Food Chem. 2011 May 11;59(9):4828-35
pubmed: 21469732
Bioorg Med Chem Lett. 2011 Jun 15;21(12):3583-6
pubmed: 21576019
J Hazard Mater. 2011 Sep 15;192(3):1886-9
pubmed: 21775059
J Chem Inf Model. 2011 Sep 26;51(9):2320-35
pubmed: 21800825
Mini Rev Med Chem. 2012 Jun;12(6):491-504
pubmed: 22587764
J Comput Aided Mol Des. 2012 Aug;26(8):897-906
pubmed: 22669221
J Chem Inf Model. 2012 Nov 26;52(11):2919-36
pubmed: 23082786
Methods Mol Biol. 2013;930:499-526
pubmed: 23086855
Annu Rev Entomol. 2013;58:99-117
pubmed: 23317040
J Agric Food Chem. 2013 Nov 20;61(46):10858-63
pubmed: 24180522
Environ Toxicol Chem. 2014 Apr;33(4):719-31
pubmed: 24692231
J Agric Food Chem. 2014 Jun 18;62(24):5429-42
pubmed: 24834971
Pest Manag Sci. 2015 May;71(5):712-21
pubmed: 24863411
Environ Sci Pollut Res Int. 2015 Jan;22(1):5-34
pubmed: 25233913
J Agric Food Chem. 2014 Nov 19;62(46):11070-9
pubmed: 25347284
Pestic Biochem Physiol. 2015 Jun;121:78-87
pubmed: 26047114
J Chem Inf Model. 2015 Jul 27;55(7):1316-22
pubmed: 26099013
J Chem Inf Model. 2015 Aug 24;55(8):1771-80
pubmed: 26151876
Nucleic Acids Res. 2016 Jan 4;44(D1):D1202-13
pubmed: 26400175
J Hazard Mater. 2016 Feb 13;303:28-40
pubmed: 26513561
Mol Inform. 2012 Dec;31(11-12):817-35
pubmed: 27476736
Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954
pubmed: 27899562
Pest Manag Sci. 2017 Jun;73(6):1053-1066
pubmed: 28145087
Environ Sci Pollut Res Int. 2017 Jun;24(16):14430-14444
pubmed: 28435990
Environ Sci Pollut Res Int. 2017 Nov;24(32):25114-25125
pubmed: 28921381
Environ Sci Pollut Res Int. 2018 Jan;25(1):896-907
pubmed: 29067614
Annu Rev Entomol. 2018 Jan 7;63:125-144
pubmed: 29324040

Auteurs

Alina Bora (A)

Institute of Chemistry Timisoara of the Romanian Academy, 24 Mihai Viteazul Av., 300223, Timisoara, Romania.

Takahiro Suzuki (T)

Natural Science Laboratory, Toyo University, 5-28-20 Hakusan, Bunkyo-ku, Tokyo, 112-8606, Japan.

Simona Funar-Timofei (S)

Institute of Chemistry Timisoara of the Romanian Academy, 24 Mihai Viteazul Av., 300223, Timisoara, Romania. timofei@acad-icht.tm.edu.ro.

Articles similaires

[Redispensing of expensive oral anticancer medicines: a practical application].

Lisanne N van Merendonk, Kübra Akgöl, Bastiaan Nuijen
1.00
Humans Antineoplastic Agents Administration, Oral Drug Costs Counterfeit Drugs

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female
Humans United States Aged Cross-Sectional Studies Medicare Part C
1.00
Humans Yoga Low Back Pain Female Male

Classifications MeSH