Tritium-labeled enantiomers of disparlure. Synthesis and in vitro metabolism

Prestwich, Glenn D.; Graham, Steven M.; Kuo, Jing Wen; Vogt, Richard G.

doi:10.1021/ja00184a035

Cited by 43 publications

(17 citation statements)

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“…H-7 and H-8 13 of cis-disparlure showed a multiplet signal at d 2.90 ppm, whereas in trans-disparlure these two methine protons gave a broad triplet at d 2.38 ppm. 12 However, the signals of H-7 and H-8 of (Z)-and (E)-2-methyl-7-octadecene overlapped at d 5.30 ppm 13 and therefore could not be used to distinguish these two isomers. The Z and E alkene isomers and the cis and trans disparlure isomers also ran at different retention times in gas chromatography with an SPB-5 (Supelco) column.…”

Section: Synthesis and Purification Of Disparlurementioning

confidence: 99%

Partition coefficients of disparlure at hydrophobic/aqueous interfaces: A comparative experimental and theoretical study

et al. 2011

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The gypsy moth, Lymantria dispar, uses pheromones, such as (+)-disparlure, for communication. These pheromones are detected by the sensitive antennae of the male moth and travel through their aqueous environment to the sensory neuron, possibly with assistance from pheromone binding proteins (PBPs). The hydrophobicity of disparlure, which is of primary importance for its interactions with PBPs, can be measured by its partition coefficients. These coefficients for heptane/water and chloroform/water interfaces were obtained in this work experimentally and using molecular dynamics (MD) simulations. The agreement between the experimental and calculated values validates the choice of the force field parameters, which can thus be used in future MD simulations of the PBP-pheromone interactions.Résumé : La lymantride spongieuse, mite gitane, Lymantria dispar, fait appel à des phéromones, tel le (+)-disparlure, pour ses communications. Ces phéromones sont détectées par des antennes sensibles des lymantrides mâles et elles circulent dans leur environnement aqueux vers le neurone sensoriel, peut-être avec l'aide de protéines fixatrices de phéromones (PFP). Le caractère hydrophobe du disparlure qui est d'importance capitale pour ses interactions avec les PFP peut être mesuré par ses coefficients de partition. Dans ce travail, on a mesuré expérimentalement ces coefficients pour les systèmes heptane/eau et chloroforme/eau et on les a aussi calculés par la méthode de la dynamique moléculaire (DM). L'accord entre les valeurs calculées et celles obtenues expérimentalement valide le choix des paramètres de champ de force qui pourront être utilisés dans des simulations ultérieures de DM des interactions PFP/phéromone.Mots-clés : lymantride spongieuse, disparlure, coefficients de partition, caractère hydrophobe, époxyde, paramètres des potentiels optimisés pour des simulations de liquides, simulations de dynamiques moléculaires.[Traduit par la Rédaction]

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Section: Synthesis and Purification Of Disparlurementioning

confidence: 99%

Partition coefficients of disparlure at hydrophobic/aqueous interfaces: A comparative experimental and theoretical study

et al. 2011

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“…Pheromones are cleared by degrading enzymes present in the lymph of the sensilla [39]. In gypsy moth the major mechanism of pheromone degradation involves enantioselective biotransformation.…”

Section: Receptologymentioning

confidence: 99%

Potential insight for drug discovery from high-fidelity receptor-mediated transduction mechanisms in insects

Raffa¹,

Raffa²

2011

Expert Opinion on Drug Discovery

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Introduction There is a pervasive and growing concern about the small number of new pharmaceutical agents. There are many proposed explanations for this trend that do not involve the drug-discovery process per se, but the discovery process itself has also come under scrutiny. If the current paradigms are indeed not working, where are novel ideas to come from? Perhaps it is time to look to novel sources. Areas covered The receptor-signaling and 2nd-messenger transduction processes present in insects are quite similar to those in mammals (involving G proteins, ion channels, etc.). However, a review of these systems reveals an unprecedented degree of high potency and receptor selectivity to an extent greater than that modeled in most current drug-discovery approaches. Expert opinion A better understanding of insect receptor pharmacology could stimulate novel theoretical and practical ideas in mammalian pharmacology (drug discovery) and, conversely, the application of pharmacology and medicinal chemistry principles could stimulate novel advances in entomology (safer and more targeted control of pest species).

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“…All these enzymes convert pheromone components into more polar metabolites in one step. However, in the presence of PBPs, pheromone degradation is significantly slower (half-life of the pheromone 10-30 min), suggesting that the primary degradation event is not responsible for the rapid phase of recovery [38,34]. A kinetic study with the purified esterase of the wild silkmoth suggested that the primary degradation event (ester hydrolysis in that case) is sufficiently rapid to account for the initial burst of repolarization [32].…”

Section: Pheromone Olfactionmentioning

confidence: 99%

Insect Pheromone Olfaction: New Targets for the Design of Species-Selective Pest Control Agents

Plettner¹

2002

cmc

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Insects communicate extensively with chemical signals specific to their species (pheromones). The highly sensitive and selective olfactory system involved in detection of these signals has attracted attention as a target for the design of novel pest control agents. This review summarizes efforts in understanding the structure-activity relationships of pheromone olfaction and in the design of compounds that selectively interfere with transport, recognition and degradation of pheromones in the peripheral olfactory system. Pheromone olfaction inhibitors are potential environmentally benign insect control agents.

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Tritium-labeled enantiomers of disparlure. Synthesis and in vitro metabolism

Cited by 43 publications

References 0 publications

Partition coefficients of disparlure at hydrophobic/aqueous interfaces: A comparative experimental and theoretical study

Partition coefficients of disparlure at hydrophobic/aqueous interfaces: A comparative experimental and theoretical study

Potential insight for drug discovery from high-fidelity receptor-mediated transduction mechanisms in insects

Insect Pheromone Olfaction: New Targets for the Design of Species-Selective Pest Control Agents

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