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1.
Chem Biodivers ; 1(11): 1652-67, 2004 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-17191806

RESUMO

Several compounds were found to suppress the calling behavior and in vitro pheromone biosynthesis of the Indian meal moth, Plodia interpunctella. The compounds were screened by means of a calling-behavior bioassay with female P. interpunctella. Five derivatives with activities in the nanomolar range were identified, in order of decreasing pheromonostatic activity: 4-hydroxybenzaldehyde semicarbazone (42) > 5-(4-methoxyphenyl)-1,3-oxazole (38) > 5-[4-(tert-butyl)phenyl]-1,3-oxazole (40) > 5-(3-methoxyphenyl)-1,3-oxazole (35) > 5-(4-cyanophenyl)-1,3-oxazole (36). These compounds also showed in vitro inhibitory activity in intracellular de novo pheromone biosynthesis, as determined with isolated pheromone-gland preparations that incorporated [1-(14)C]sodium acetate in the presence of the so-called pheromone-biosynthesis-activating neuropeptide (PBAN). The non-additive effect of the inhibitor with antagonist (yohimbine) for the tyramine (TA) receptor suggests that it could be a tyraminergic antagonist. Three-dimensional (3D) computer models were built from a set of compounds. Among the common-featured models generated by the program Catalyst/HipHop, aromatic-ring (AR) and H-bond-acceptor-lipophilic (HBAl) features were considered to be essential for inhibitory activity in the calling behavior and in vitro pheromone biosynthesis. Active compounds, including yohimbine, mapped well onto all the AR and HBAl features of the hypothesis. Less-active compounds were shown to be unable to achieve an energetically favorable conformation, consistent with our 3D common-feature pharmacophore models. The present hypothesis demonstrates that calling behavior and PBAN-stimulated incorporation of radioactivity are inhibited by tyraminergic antagonists.


Assuntos
Mariposas/metabolismo , Feromônios/antagonistas & inibidores , Feromônios/biossíntese , Tiramina/fisiologia , Comunicação Animal , Animais , Feminino , Masculino , Octopamina/química , Octopamina/metabolismo , Octopamina/farmacologia , Estrutura Terciária de Proteína/fisiologia , Atrativos Sexuais/antagonistas & inibidores , Atrativos Sexuais/biossíntese , Tiramina/química , Tiramina/farmacologia
2.
Bioorg Med Chem ; 11(1): 95-103, 2003 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-12467712

RESUMO

Three-dimensional pharmacophore hypotheses were built from a set of 36 octopamine (OA)/tyramine (TA) agonists responsible for the inhibition of sex-pheromone production in Plodia interpunctella. Among the ten chemical-featured models generated by a program Catalyst/Hypo, hypotheses including hydrogen-bond acceptor (HBA), hydrogen-bond acceptor aliphatic (HBAl), hydrophobic (Hp), hydrophobic aromatic (HpAr) and hydrophobic aliphatic (HpAl) features were considered to be important and predictive in evaluating OA/TA agonists. Active agonists mapped well onto all the features of the hypothesis such as HBA, HBAl, Hp, HpAr and HpAl features. On the other hand, inactive compounds were shown to be poorly capable of achieving an energetically favorable conformation shared by the active molecules in order to fit the 3-D chemical-feature pharmacophore models. Those hypotheses are considered to be used in designing new leads for hopefully more active compounds. Further research on the comparison of models from the agonists may help elucidate the mechanisms of OA/TA receptor-ligand interactions.


Assuntos
Acetatos/metabolismo , Mariposas/metabolismo , Octopamina/agonistas , Tiramina/agonistas , Acetatos/química , Animais , Radioisótopos de Carbono , Desenho de Fármacos , Ligação de Hidrogênio , Interações Hidrofóbicas e Hidrofílicas , Modelos Moleculares , Estrutura Molecular , Octopamina/farmacologia , Relação Quantitativa Estrutura-Atividade , Atrativos Sexuais/antagonistas & inibidores , Atrativos Sexuais/biossíntese , Relação Estrutura-Atividade , Tiramina/farmacologia
3.
J Insect Sci ; 3: 4, 2003.
Artigo em Inglês | MEDLINE | ID: mdl-15841221

RESUMO

Some octopamine agonists were found to suppress the calling behavior of the stored product Indian meal moth, Plodia interpunctella. Compounds were screened using a calling behavior bioassay using female P. interpunctella. Four active derivatives, with inhibitory activity at the nanomolar range, were identified in order of decreasing activity: 2-(1-phenylethylamino)-2-oxazoline > 2-(2-ethyl,6-methylanilino)oxazolidine > 2-(2-methyl benzylamino)-2-thiazoline > 2-(2,6-diethylanilino)thiazolidine. Three-dimensional pharmacophore hypotheses were built from a set of 15 compounds. Among the ten common-featured models generated by the program Catalyst/HipHop, a hypothesis including a hydrogen-bond acceptor lipid, a hydrophobic aromatic and two hydrophobic aliphatic features was considered to be essential for inhibitory activity in the calling behavior. Active compounds mapped well onto all the hydrogen-bond acceptor lipid, hydrophobic aromatic and hydrophobic aliphatic features of the hypothesis. On the other hand, less active compounds were shown not to achieve the energetically favorable conformation that is found in the active molecules in order to fit the 3D common-feature pharmacophore models. The present studies demonstrate that inhibition of calling behavior is via an octopamine receptor.


Assuntos
Agonistas alfa-Adrenérgicos/farmacologia , Antagonistas Adrenérgicos alfa/farmacologia , Comunicação Animal , Mariposas/efeitos dos fármacos , Mariposas/fisiologia , Agonistas alfa-Adrenérgicos/química , Antagonistas Adrenérgicos alfa/química , Animais , Biologia Computacional , Feminino , Modelos Moleculares , Estrutura Molecular , Octopamina/agonistas , Octopamina/antagonistas & inibidores , Receptores Adrenérgicos alfa , Atrativos Sexuais/metabolismo
4.
Pest Manag Sci ; 58(11): 1118-25, 2002 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-12449530

RESUMO

Some octopamine (OA) agonists were found to suppress the calling behaviour and pheromone biosynthesis in vitro of the Indian meal moth, Plodia interpunctella (Hübner), a stored-product pest. Compounds were screened using a calling behaviour bioassay of female P interpunctella. Three active derivatives, with activity at the nanomolar level, were identified. In order of decreasing pheromonostatic activity these were: 2-(2-ethyl-6-methylanilino)oxazolidine > 2-(2,6-diethylanilino)thiazolidine > 2-(2,6-diethylanilino)oxazolidine. These compounds showed also in vitro inhibitory activities in de novo pheromone biosynthesis. Three-dimensional pharmacophore hypotheses were built from a set of 19 compounds. Among the ten common-featured models generated by the program Catalyst/HipHop, a hypothesis including a ring aromatic group (RA), a positive ionizable group (PI) and two hydrophobic aliphatic (HpA1) features was considered to be essential for inhibitory activity in the calling behaviour and pheromone biosynthesis in vitro. Active compounds mapped well onto all the RA, PI and HpA1 features of the hypothesis. Less-active compounds were shown not to achieve the energetically favourable conformation which was found in the active molecules in order to fit the 3-D common-feature pharmacophore models. The present studies demonstrate that inhibition of calling behaviour and PBAN-stimulated incorporation of radioactivity is by OA-agonistic activity.


Assuntos
Acetatos/metabolismo , Comportamento Animal/fisiologia , Lepidópteros/fisiologia , Feromônios/biossíntese , Compostos de Anilina/química , Compostos de Anilina/farmacologia , Animais , Comportamento Animal/efeitos dos fármacos , Radioisótopos de Carbono , Feminino , Larva/efeitos dos fármacos , Larva/fisiologia , Lepidópteros/efeitos dos fármacos , Masculino , Modelos Moleculares , Estrutura Molecular , Octopamina/agonistas , Oxazóis/antagonistas & inibidores , Oxazóis/química , Oxazóis/farmacologia , Feromônios/antagonistas & inibidores , Pupa/efeitos dos fármacos , Tiazóis/química , Tiazóis/farmacologia , Tiazolidinas
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