title: Quantitative structure-activity relationship study using refractotopological state atom index on some neonicotinoid insecticides.
abstract: Importance of atom-level topological descriptors like electrotopological state atom (E-state) index in QSAR study is increasing. These descriptors help to relate structure and activity at atomic/fragmental level. In view of the earlier success of E-state index on some azidopyridinyl neonicotinoid insecticides, a relatively new atom-level topological descriptor; refractotopological state atom (R-state) index was used in this work. This was used to identify the important atoms/fragments related to dispersive/van der Waals interactions of neonicotinoids with the nicotinic acetylcholine receptor (nAChR). This study showed the structural requirements for the mammal alpha(4)beta(2) and Drosophila nAChR agonistic activity. It also revealed that substituted imine, nitromethylene at X-position were selective to the insecticidal activity. Azido substitution at pyridine ring of neonicotinoids disfavored the binding with the receptors. This study confirmed the validity of the R-state index as a new tool for quantitative structure-activity relationships. It has the ability to find out the required structural features as well as to predict the activity of the neonicotinoids.
authors.affiliation: Division of Medicinal and Pharmaceutical Chemistry, Department of Pharmaceutical Technology, PO Box No 17020, Jadavpur University, Kolkata 700 032, India.
authors.forename: Bikash
authors.initials: B
authors.lastname: Debnath
authors.forename: Shovanlal
authors.initials: S
authors.lastname: Gayen
authors.forename: Anindya
authors.initials: A
authors.lastname: Basu
authors.forename: Balaram
authors.initials: B
authors.lastname: Ghosh
authors.forename: Kolluru
authors.initials: K
authors.lastname: Srikanth
authors.forename: Tarun
authors.initials: T
authors.lastname: Jha
mesh_terms: D000691:Anabasine / Q000737:chemistry*; D000818:Animals; D004330:Drosophila; D057927:Hydrophobic and Hydrophilic Interactions; D007306:Insecticides / Q000737:chemistry*; D008322:Mammals; D008958:Models, Molecular; D011485:Protein Binding; D021281:Quantitative Structure-Activity Relationship; D011978:Receptors, Nicotinic / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D011978:Receptors, Nicotinic; D000691:Anabasine