Theoretical analysis of the electronic properties of the sex pheromone and its analogue derivatives in the female processionary moth Thaumetopoea pytiocampa

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8535-8545

  Chamorro, Ester R ^b   Sequeira, Alfredo F ^b   Zalazar, M Fernanda ^a,b   Peruchena, Nélida M ^a,b  

^a UNIVERSIDAD NACIONAL DEL NORDESTE   (Argentina)

^b UNIVERSIDAD TECNOLÓGICA NACIONAL   (Argentina)

Author keywords

Charge density; Laplacian; Molecular electrostatic potential; Sex pheromone

Indexed keywords

13 HEXADECEN 11 YNYL ACETATE; BINDING PROTEIN; SEX PHEROMONE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; DENSITY FUNCTIONAL THEORY; FEMALE; HORMONE DETERMINATION; HORMONE PROTEIN COMPLEX; MOLECULAR INTERACTION; MOTH; NONHUMAN; THAUMETOPOEA PYTIOCAMPA;

LEPIDOPTERA; THAUMETOPOEA;

EID: 51849096263     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.008     Document Type: Article

References (47)

1. Anderson P., Hansson B.S., Nilsson U., Ha Q., Sjöholm M., Skals N., and Anton S. Chem. Senses 32 (2007) 483-491
2. Tregoni M., Campanacci V., and Cambellau C. Trends Biochem. Sci. 29 (2004) 257-264 and references therein
3. Baker T.C., Ochieng' S.A., Cossé A.A., Lee S.G., Todd J.L., Quero C., and Vickers N. J. Comput. Physiol. A 190 (2004) 155-165
4. Rosell A., and Guerrero G. Curr. Med. Chem. 12-14 (2005) 461-469
5. In: Ridgway R.L., Silverstein R.M., and Inscoe M.N. (Eds). Behaviour-Modifying Chemical for Insect Management (1990), Marcel Dekker, Inc., New York
6. Renou M., and Guerrero A. Annu. Rev. Entomol. 45 (2000) 605-630
7. Pelosi P. J. Neurobiol. 30 (1996) 3-19
8. In: Chu C.K., and Baker D.C. (Eds). Nucleosides and Nucleotides as Antitumor and Antiviral Agents (1993), Plenum Press, New York
9. Camps F., Coll J., Guerrero A., and Riba M. J. Chem. Ecol. 9 (1983) 869-875
10. Camps F., Fabrias G., Gasol V., Guerrero A., Hernandez R., and Montoya R. J. Chem. Ecol. 14 (1988) 1331-1346 and references therein
11. Guerrero A., Murgó R., and Martorell X. Physiol. Entomol. 11 (1986) 73-77
12. Quero C., Camps F., and Guerrero A. J. Chem. Ecol. 21 (1995) 1957-1969
13. Parrilla A., and Guerrero A. Chem. Senses 19 (1994) 1-10
14. Camps F., Gasol V., and Guerrero A. J. Chem. Ecol. 16 (1990) 1155-1172
15. Renou M., Berthier A., and Guerrero A. Pest Manag. Sci. 58 (2002) 839-844
16. Feixas J., Prestwich G.D., and Guerrero A. Eur. J. Biochem. 234 (1995) 521-526
17. Bau J., Martinez D., Renou D., and Guerrero A. Chem. Senses 24 (1999) 473-480
18. Parrilla A., Villuendas I., and Guerrero A. Bioorg. Med. Chem. 8 (1994) 845
19. Ashour M.-B.A., and Hammock B.D. Biochem. Pharmacol. 36 (1987) 1869-1879
20. Prestwich G.D., and Streinz L. J. Chem. Ecol. 14 (1988) 1003-1021
21. Politzer P., and Truhlar D.G. Chemical Applications of Atomic and Molecular Electrostatic Potentials (1991), Plenum Publishing, New York
22. Ruiz J., Perez C., and Pouplana R. Bioorg. Med. Chem. 11 (2003) 4207-4216
23. Boer D.R., Kooijman H., Van der Louw J., Groen M., Kelder J., and Kroon J. Bioorg. Med. Chem. 9 (2001) 2653-2659
24. Okulik N., and Jubert A. J. Mol. Struct. (THEOCHEM) 769 (2006) 135-141
25. Greeling P., Langenaeker W., De Proft F., and Baeten A. Molecular Electrostatic Potentials: Concepts and Applications. Theoretical and Computational Chemistry vol. 3 (1996), Elsevier Science B.V., Amsterdam 587-617
26. Leach A.R. Molecular Modelling: Principles and Applications. 2nd ed. (2001), Pearson Education, EMA
27. Lobayan R.M., Sosa G.L., Jubert A.H., and Peruchena N.M. J. Phys. Chem. A 109 (2005) 181
28. Matta C.F., and Boyd R.J. Quantum Theory of Atoms in Molecules: From Solid State to DNA and Drug Design (2007), Wiley-VCH, Weinheim, Germany
29. Koritsanszky T., Flaig R., Zobel D., Krane H.G., Morgenroth W., and Luger P. Science 279 (1998) 356
30. Bader R.F.W. Atoms in Molecules. A Quantum Theory (1990), Oxford Science Publications, Clarendon Press, London
31. Popelier P.L.A. Atoms in Molecules. An Introduction (2000), Pearson Education, Harlow, UK
32. Becke A.D. J. Chem. Phys. 98 (1993) 5648
33. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Jr., T.V.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.
35. Schlegel H.B. J. Comput. Chem. 3 (1982) 214
36. MOLEKEL 4.3, Flúkiger, P.; Lúthi, H.P.; Portmann, S.; Weber, J. Swiss Center for Scientific Computing, Manno (Switzerland), 2000.
37. AIMPAC: a suite of programs for the theory of atoms in molecules; Bader, R. F. W., co-workers, Eds.; McMaster University: Hamilton, Ontario, Canada.
38. Blieger-König, F.; Schönbohn, J. AIM2000 Program Package, Version. 2.0 Copyright 2002. Chemical adviser by Bader, R.F.W.; McMaster University. Hamilton, Canadá.
39. Blieger-König F., Bader R.F.W., and Tang T.H. J. Comput. Chem. 3 (1982) 317
40. Popelier P.L.A., and Smith P.J. Eur. J. Med. Chem. 41 (2006) 862-873
41. Cremer D., and Kraka E. Croat. Chem. Acta 57 (1984) 1259
42. Carroll M.T., Chang C., and Bader R.F.W. Mol. Phys. 63 (1988) 387-405
43. Castillo N., and Boyd R.J. Chem. Phys. Lett. 403 (2005) 47
44. Popelier P.L.A., and Smith P.J. Phys. Chem. Chem. Phys. 3 (2001) 4208-4212
45. Checinska L., and Grabowski S.J. Chem. Phys. 327 (2006) 202-208
46. Carroll M.T., Cheeseman J.R., Osman R., and Weinstein H. J. Phys. Chem. 93 (1989) 5120-5123
47. Murgich J., Franco H.J., and San-Blas G. J. Phys. Chem. A 110 (2006) 10106-10115