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פותח על ידי קלירמאש פתרונות בע"מ -
Three-dimensional quantitative structure-activity studies of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera
Year:
1999
Source of publication :
Bioorganic and Medicinal Chemistry
Authors :
גלעדי, קרינה
;
.
רפאלי, עדה
;
.
Volume :
7
Co-Authors:
Hirashima, A., Div. Biorsrc. Bioenvironmental Sci., Graduate School, Kyushu University, Fukuoka 812-8581, Japan
Rafaeli, A., Department of Stored Products, Pheromone Research Laboratory, Volcani Centre, PO Box 6, Bet Dagan 50250, Israel
Gileadi, C., Department of Stored Products, Pheromone Research Laboratory, Volcani Centre, PO Box 6, Bet Dagan 50250, Israel
Kuwano, E., Div. Biorsrc. Bioenvironmental Sci., Graduate School, Kyushu University, Fukuoka 812-8581, Japan
Facilitators :
From page:
2621
To page:
2628
(
Total pages:
8
)
Abstract:
The quantitative structure-activity relationship (QSAR) of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera, was analyzed using physicochemical parameters, molecular shape analysis (MSA), molecular field analysis (MFA), and receptor surface model (RSM), respectively. The dose-response studies were performed in vitro analyzing the effect of these compounds on intracellular cAMP production in the presence of pheromone biosynthesis activating neuropeptide (PBAN) at 1 pmol/intersegment. Six active derivatives were identified in the order of decreasing pheromonostatic activity: 2-(2,6- dimethylanilino)imidazolide (6) > 2-(2-methyl-4-chloroanilino)oxazolidine (1) > clonidine (5) > 2-(2,6-diethylanilino)thiazolidine (8) > 2-(3,5- dichlorobenzylamino)-2-oxazoline (4) > tolazoline (10) which were all active in the nanomolar range in inhibition of cAMP production by 1 pmol PBAN/intersegment. Four other compounds were less active having K(i) in the micromolar range. An MSA was tried to obtain QSAR equation that incorporates spatial molecular similarity data of those compounds. MFA on the training set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points defined by a rectangular or spherical grid. An RSM was generated using some subset of the most active structures. Three-dimensional energetics descriptors were calculated from RSM/ligand interaction and these three-dimensional descriptors were used in QSAR analysis. These results indicate that these derivatives could provide useful information in the characterization and differentiation of octopaminergic receptor types and subtypes. (C) 1999 Elsevier Science Ltd.
Note:
Related Files :
Animals
Female
Lepidoptera
Male
pheromones
עוד תגיות
תוכן קשור
More details
DOI :
10.1016/S0968-0896(99)00189-3
Article number:
Affiliations:
Database:
סקופוס
Publication Type:
מאמר
;
.
Language:
אנגלית
Editors' remarks:
ID:
26843
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:25
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Three-dimensional quantitative structure-activity studies of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera
7
Hirashima, A., Div. Biorsrc. Bioenvironmental Sci., Graduate School, Kyushu University, Fukuoka 812-8581, Japan
Rafaeli, A., Department of Stored Products, Pheromone Research Laboratory, Volcani Centre, PO Box 6, Bet Dagan 50250, Israel
Gileadi, C., Department of Stored Products, Pheromone Research Laboratory, Volcani Centre, PO Box 6, Bet Dagan 50250, Israel
Kuwano, E., Div. Biorsrc. Bioenvironmental Sci., Graduate School, Kyushu University, Fukuoka 812-8581, Japan
Three-dimensional quantitative structure-activity studies of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera
The quantitative structure-activity relationship (QSAR) of octopaminergic agonists responsible for the inhibition of sex-pheromone production in Hercoverpa armigera, was analyzed using physicochemical parameters, molecular shape analysis (MSA), molecular field analysis (MFA), and receptor surface model (RSM), respectively. The dose-response studies were performed in vitro analyzing the effect of these compounds on intracellular cAMP production in the presence of pheromone biosynthesis activating neuropeptide (PBAN) at 1 pmol/intersegment. Six active derivatives were identified in the order of decreasing pheromonostatic activity: 2-(2,6- dimethylanilino)imidazolide (6) > 2-(2-methyl-4-chloroanilino)oxazolidine (1) > clonidine (5) > 2-(2,6-diethylanilino)thiazolidine (8) > 2-(3,5- dichlorobenzylamino)-2-oxazoline (4) > tolazoline (10) which were all active in the nanomolar range in inhibition of cAMP production by 1 pmol PBAN/intersegment. Four other compounds were less active having K(i) in the micromolar range. An MSA was tried to obtain QSAR equation that incorporates spatial molecular similarity data of those compounds. MFA on the training set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points defined by a rectangular or spherical grid. An RSM was generated using some subset of the most active structures. Three-dimensional energetics descriptors were calculated from RSM/ligand interaction and these three-dimensional descriptors were used in QSAR analysis. These results indicate that these derivatives could provide useful information in the characterization and differentiation of octopaminergic receptor types and subtypes. (C) 1999 Elsevier Science Ltd.
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