Decyl-thio-trifluoropropanone, a competitive inhibitor of moth pheromone receptors

Journal of Comparative Physiology - A Sensory, Neural, and Behavioral Physiology

Volumn 186, Issue 3, 2000, Pages 315-323

  Pophof, B ^a   Gebauer, T ^a   Ziegelberger, G ^a  

^a MAX PLANCK INSTITUTE FOR ORNITHOLOGY   (Germany)

Author keywords

Aldehyde oxidase; Esterase; Olfaction; Single sensillum recording; Trifluoromethyl ketone

Indexed keywords

KETONE; PHEROMONE;

ANIMAL; ARTICLE; BINDING COMPETITION; CHEMORECEPTOR; DOSE RESPONSE; NERVE CELL; ODOR; PHYSIOLOGY; PROTEIN BINDING; SILKWORM;

ANIMALS; BINDING, COMPETITIVE; BOMBYX; CHEMORECEPTORS; DOSE-RESPONSE RELATIONSHIP, DRUG; KETONES; NEURONS; PHEROMONES; PROTEIN BINDING; SMELL;

ANIMALIA; ANTHERAEA POLYPHEMUS; BOMBYX MORI; IMBRASIA; IMBRASIA CYTHEREA; LEPIDOPTERA; POLYPHEMUS;

EID: 0034113951     PISSN: 03407594     EISSN: None     Source Type: Journal    
DOI: 10.1007/s003590050432     Document Type: Article

References (36)

1. Albans KR, Baker R, Jones OT, Jutsum AR, Turnbull MD (1984) Inhibition of response of Heliothis virescens to its natural pheromone by antipheromones. Crop Prot 3: 501-506
2. Bau J, Martínez D, Renou M, Guerrero A (1999) Pheromone-triggered orientation flight of male moths can be disrupted by trifluoromethyl ketones. Chem Senses 24: 473-480
3. Butenandt A, Beckmann R, Stamm D (1961) Über den Sexuallockstoff des Seidenspinners. II. Konstitution und Konfiguration des bombykol. Z Physiol Chem 324: 84-87
4. Durán I, Parrilla A, Feixas J, Guerrero A (1993) Inhibition of antennal esterases of the Egyptian armyworm Spodoptera littoralis by trifluoromethyl ketones. Bioorg Med Chem 3: 2593-2598
5. Gnatzy W, Mohren W, Steinbrecht RA (1984) Pheromone receptors in Bombyx mori and Antheraea pernyi II. Morphometric analysis. Cell Tissue Res 235: 35-42
6. Heinbockel T, Kaissling K-E (1996) Variability of olfactory receptor neuron responses of femle silkmoths (Bombyx mori L.) to benzoic acid and (±)-linalool. J Insect Physiol 42: 565-578
7. Henderson HE, Warren FL, Augustyn OPH, Burger PV, Schneider DF, Boshoff PR, Spies HSC, Geertsema H (1973) Isolation and structure of the sex pheromone of the moth, Nudaurelia cytherea cytherea. J Insect Physiol 19: 1257-1264
8. Kaissling K-E (1986) Temporal characteristics of pheromone receptor cell responses in relation to orientation behaviour of moths. In: Payne TL, Birch MC, Kennedy CEJ (eds) Mechanisms of insect olfaction. Oxford University Press, Oxford, pp 193-200
9. Kaissling K-E (1995) Single unit and electroantennogram recordings in insect olfactory organs. In: Spielman AI, Brand JG (eds) Experimental cell biology of taste and olfaction. Current techniques and protocols. CRC Press, Boca Raton, pp 361-377
10. Kaissling K-E (1998) Pheromone deactivation catalyzed by receptor molecules: a quantitative kinetic model. Chem Senses 23: 385-395
11. Kanaujia S, Kaissling K-E (1985) Interactions of pheromone with moth antennae: adsorption, desorption and transport. J Insect Physiol 31: 71-81
12. Kasang G (1971) Bombykol reception and metabolism on the antennae of the silkmoth Bombyx mori. In: Ohloff G, Thomas AF (eds) Gustation and olfaction. Academic Press, London, pp 245-250
13. Kasang G, Kaissling K-E, Vostrowsky O, Bestmann H-J (1978) Bombykal, a second pheromone component of the silkworm moth Bombyx mori L. Angew Chem Int Ed Engl 17: 60
14. Kasang G, Proff L von, Nicholls M (1988) Enzymatic conversion and degradation of sex pheromones in antennae of the male silkworm Antheraea polyphemus. Z Naturforsch 43c: 275-284
15. Kasang G, Nicholls M, Keil T, Kanaujia S (1989) Enzymatic conversion of sex pheromones in olfactory hairs of the male silkworm moth Antheraea polyphemus. Z Naturforsch 44c: 920-926
16. Keil TA (1984) Reconstruction and morphometry of silkmoth olfactory hairs: a comparative study of sensilla trichodea on the antennae of male Antheraea polyphemus and Antheraea pernyi (Insecta, Lepidoptera). Zoomorphology 104: 147-156
17. Klein U (1987) Sensillum-lymph proteins from antennal olfactory hairs of the moth Antheraea polyphemus (Saturniidae). Insect Biochem 17: 1193-1204
18. Klein U, Keil TA (1984) Dendritic membrane from insect olfactory hairs: isolation method and electron microscopic observations. Cell Mol Neurobiol 4: 385-396
19. Klun JA, Schwarz M, Uebel EC (1991) European corn borer: pheromonal catabolism and behavioral response to sex pheromone. J Chem Ecol 17: 317-334
20. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature (Lond) 227: 680-685
21. Parrilla A, Guerrero A (1994) Trifluoromethyl ketones as inhibitors of the processionary moth sex pheromone. Chem Senses 19: 1-10
22. Parrilla A, Villuendas I, Guerrero A (1994) Synthesis of trifluoromethyl ketones as inhibitors of antennal esterases of insects. Bioorg Med Chem 2: 243-252
23. Pophof B (1998) Inhibitors of sensillar esterase reversibly block the responses of moth pheromone receptor cells. J Comp Physiol A 183: 153-164
24. Priesner E (1979) Progress in the analysis of pheromone receptor systems. Ann Zool Ecol Anim 11: 533-546
25. Prestwich GD, Streinz L (1988) Haloacetate analogs of pheromones: effects on catabolism and electrophysiology in Plutella xylostella. J Chem Ecol 14: 1003-1021
26. Renou M, Lucas P, Malo E, Quero C, Guerrero A (1997) Effects of trifluoromethyl ketones and related compounds on the EAG and behavioural responses to pheromones in male moths. Chem Senses 22: 407-416
27. Renou M, Berthier A, Desbarats L, Van der Pers J, Guerrero A (1999) Actographic analysis of the effects of an esterase inhibitor on male moth responses to sex pheromone. Chem Senses 24: 423-428
28. Rybczynski R, Reagan J, Lerner MR (1989) A pheromone degrading aldehyde oxidase in the antennae of the moth Manduca sexta. J Neurosci 9: 1341-1353
29. Rybczynski R, Vogt RG, Lerner MR (1990) Antennal-specific pheromone-degrading aldehyde oxidases from the moths Antheraea polyphemus and Bombyx mori. J Biol Chem 265: 19712-19715
30. Schwarz M, Klun JA, Uebel EC (1990) European corn borer sex pheromone inhibition and elicitation of behavioral response by analogs. J Chem Ecol 16: 1591-1604
31. Shaw CR, Prasad R (1970) Starch gel electrophoresis of enzymes a compilation of recipes. Biochem Genet 4: 297-320
32. Stange G, Kaissling K-E (1995) The site of action of general anaesthetics in insect olfactory receptor neurons. Chem Senses 20: 421-432
33. Van den Berg MJ, Ziegelberger G (1991) On the function of the pheromone binding protein in the olfactory hairs of Antheraea polyphemus. J Insect Physiol 37: 79-85
34. Vogt RG, Riddiford LM (1981) Pheromone binding and inactivation by moth antennae. Nature (Lond) 293: 161-163
35. Vogt RG, Riddiford LM, Prestwich GD (1985) Kinetic properties of a sex pheromone-degrading enzyme: the sensillar esterase of Antheraea polyphemus. Proc Natl Acad Sci USA 82: 8827-8831
36. Ziegelberger G (1995) Insects: isolation of olfactory sensilla and collection of sensillum lymph. In: Spielman AI, Brand JG (eds) Experimental cell biology of taste and olfaction. Current techniques and protocols. CRC Press, Boca Raton, pp 33-38