QSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells

Ogura, Takehiko; Nakagawa, Yoshiaki; Minakuchi, Chieka; Miyagawa, Hisashi

doi:10.1584/jpestics.30.1

Cited by 19 publications

(16 citation statements)

References 28 publications

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“…Nakagawa's research [50] indicated hydrophobic, steric, and electrostatic effects were likely favorable to the larvicidal activity, which is consistent with our QSAR results. The accurate quantum chemical descriptors were used in our research, while the semiempirical parameters were used in Nakagawa's research.…”

Section: Qsar Analysis and Model Validationsupporting

confidence: 91%

“…(5)) showed that the electron-donating ability of the carbonyl group significantly affected the activity of the target compounds, where the larger the weighted electrophilic electron density of the oxygen atom marked with asterisk symbol, the higher the activity. Ogura et al [50] also reported the electron effects of the oxygen atom on the carbonyl group were significant.…”

Section: Discussionmentioning

confidence: 97%

“…Ogura [50] thought the hydrophobic interaction and steric repulsion of the substituents on the phenyl ring influenced the biological activity. In the current QSAR study, we added the electronic polarizability () descriptor, which was correlated with the hydrophobicity and steric effect of the target compounds, suggesting the biological activity was also affected by their hydrophobicity and steric property.…”

Section: Discussionmentioning

confidence: 99%

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QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

et al. 2010

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QSAR studies of 27 diacyl-hydrazine derivatives containing furan rings were conducted and compared with the DFT method and AM1-MOPAC method. q 2 values of 0.61 and 0.40 validated the predictability and reliability of eq. (5) from the DFT method were higher than those of eq. (6) from the AM1-MOPAC method. The DFT-optimized conformations and ESP-fitting charges of the target compounds were also used for 3D-QSAR analysis, including CoMFA and CoMSIA. The leave-one-out cross-validation correlation coefficient and the good correlation between the predicted and experimental activities of excluded test compounds revealed that CoMFA and CoMSIA models were robust. The QSAR results were consistent with the 3D-QSAR results, indicating that the electrostatic and hydrophobic properties of the target compounds were significant to the biological activity. These models are useful tools for predicting the larvicidal activities of new compounds and designing new specific insect growth regulators. diacyl-hydrazine, QSAR, 3D-QSAR, DFT, insect growth regulator

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Section: Qsar Analysis and Model Validationsupporting

confidence: 91%

Section: Discussionmentioning

confidence: 97%

Section: Discussionmentioning

confidence: 99%

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QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

et al. 2010

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“…To determine the physicochemical mechanism of these substituents, binding activity was quantitatively analyzed using substituent parameters. We previously demonstrated that the hydrophobicity of substituent is important for the binding of DAHs to the ecdysone receptor of Sf-9 cells [33]. Therefore, activity was quantitatively analyzed using hydrophobicity ΔClogP [ClogP (X) -ClogP (H)] to formulate statistically significant values using Eq.…”

Section: Qsar Analysismentioning

confidence: 99%

Structure–activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells

Yokoi¹,

Minami²,

Nakagawa³

et al. 2015

Pesticide Biochemistry and Physiology

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Diacylhydrazines are the first non-steroidal ecdysone agonists, and five compounds are used as insecticides in agriculture. After the discovery of diacylhydrazine-type compounds, numerous non-steroidal structures were reported as ecdysone agonists. Among various ecdysone agonists, imidazothiadiazoles are reported to be very potent in vitro; however, the experimental detail for the structure identification and bioassays are not stated in the paper (Holmwood and Schindler, Bioorg. Med. Chem. 17, 4064-4070, 2009). In our present study, we synthesized 18 imidazothiadiazole-type compounds and confirmed the chemical structures by spectrometric analyses. The binding activity of the synthesized compounds to the ecdysone receptor was evaluated in terms of the concentration required for 50% inhibition of [(3)H]ponasterone A incorporation [IC50 (M)] into lepidopteran (Sf-9), coleopteran (BCRL-Lepd-SL1), and dipteran (NIAS-AeAl2) cells. 6-(2-Chlorophenyl)-2-(trifluoromethyl)imidazo[2,1-b] [1,3,4]-thiadiazol-5-yl)acrylamide analogs with CONHR (secondary amide) were very potent against Sf-9 cells, but further alkylation (tertiary amide: CONR2) decreased the activity dramatically. Additionally, a primary amide analog (CONH2) was inactive. The activity also decreased 150-fold by the saturation of olefin region of the acrylamide moiety. In addition, various substituents were introduced at the 2-position of the imidazothiadiazole ring to disclose the physicochemical properties of the substituents which are important for receptor binding. The activity increased by 7500-fold with the introduction of the CF2CF2CF3 group compared to the unsubstituted compound against Sf-9 cells. Quantitative structure-activity relationship analysis for these substituents indicated that hydrophobic and electron-withdrawing groups were favorable for binding. Some of the compounds with strong receptor binding activity showed good larvicidal activity against Spodoptera litura. In contrast, the binding affinity of imidazothiadiazole analogs was low or not observed against dipteran and coleopteran cells.

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“…Ogura and co-workers quantitatively analyzed the binding activity of 20 DBHs (X = 2−Cl) with various substituents (Y) at the para -position of B-ring as shown in Eq. 7.9 (Ogura et al 2005 ) . The electronic effect at the B-ring moiety on the larvicidal and molting hormonal activity was not signi fi cant, while an electron-donating group at the B-ring is favored for receptor binding.…”

Section: Substitution Atmentioning

confidence: 99%

Advanced Screening to Identify Novel Pesticides

Nakagawa

Harada

2012

Advanced Technologies for Managing Insect Pests

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QSAR for Binding Affinity of Substituted Dibenzoylhydrazines to Intact Sf-9 Cells

Cited by 19 publications

References 28 publications

QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

QSAR and 3D-QSAR studies of the diacyl-hydrazine derivatives containing furan rings based on the density functional theory

Structure–activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells

Advanced Screening to Identify Novel Pesticides

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