Structural features controlling the binding of β-carbolines to the benzodiazepine receptor

Acta Crystallographica Section B: Structural Science

Volumn 60, Issue 4, 2004, Pages 481-489

  Ferretti, Valeria ^a   Gilli, Paola ^a   Borea, Pier Andrea ^b  

^a Dipartimento di Chimica   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; CRYSTAL STRUCTURE; DATA ACQUISITION; HYDROGEN BONDS; MATHEMATICAL MODELS; MOLECULAR STRUCTURE;

CARBOLINES; MOLECULAR-MECHANICS SIMULATION; STEREOCHEMICAL MODELS; X-RAY STRUCTURES;

DRUG DOSAGE;

4 AMINOBUTYRIC ACID A RECEPTOR; 5 BENZYLOXY 4 METHOXYMETHYL BETA CARBOLINE 3 CARBOXYLIC ACID ETHYL ESTER; 6 BENZYLOXY 4 METHOXYMETHYL BETA CARBOLINE 3 CARBOXYLIC ACID ETHYL ESTER; CARBOLINE DERIVATIVE; N METHYL BETA CARBOLINE 3 CARBOXAMIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; IN VITRO STUDY; METABOLISM; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

CARBOLINES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, GABA-A; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 7944236063     PISSN: 01087681     EISSN: None     Source Type: Journal    
DOI: 10.1107/S0108768104013564     Document Type: Article

References (50)

1. Allen, F. H. (2002). Acta Cryst. B58, 380-388.
2. Altomare, A., Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A., Moliterni, A. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-121.
3. Bernstein, J. (2002). Polymorphism in Molecular Crystals. Oxford: Clarendon Press.
4. Bertolasi, V., Ferretti, V., Gilli, G. & Borea, P. A. (1984). Acta Cryst. C40, 1981-1983.
5. Bertolasi, V., Ferretti, V., Gilli, G. & Borea, P. A. (1990). J. Chem. Soc. Perkin Trans 2, pp. 283-289.
6. Bock, M., Depke, G., Egner, U., Mueller-Fahrnow, A. & Winter, G. (1994). Tetrahedron, 50, 13125-13134.
7. Borea, P. A. & Ferretti, V. (1986). Biochem. Pharmacol. 35, 2836-2839.
8. Borea, P. A., Gilli, G., Bertolasi, V. & Ferretti, V. (1987). Mol. Pharmacol. 31, 334-344.
9. Braestrup, C., Nielsen, M., Honorè, T., Jensen, L. H. & Petersen, E. M. (1983). Neuropharmacology, 22, 1451-1457.
10. Buhr, A., Schaerer, M. T., Baur, R. & Sigel, E. (1997). Mol. Pharmacol. 52, 676-682.
11. Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.
12. Codding, P. W. (1983). Can. J. Chem. 61, 529-532.
13. Codding, P. W. &. Muir, A. K. S (1985). Mol. Pharmacol. 28, 178-184.
14. Codding, P. W., Roszak, A. W., Szkaradzinska, M. B., Cook, J. M., Hagen, T. J. & Allen, M. S. (1995). Can. J. Chem. 73, 499-512.
15. Codding, P. W., Szkaradzinska, M. B., Roszak, A. W. & Aha, L. J. (1988). Can. J. Chem. 66, 2981-2988.
16. Cox, E. D., Diaz-Arauzo, H., Huang, Q., Reddy, M. S., Ma, C., Harris, B., McKernan, R., Skolnick, P. & Cook, J. M. (1998). J. Med. Chem. 41, 2537-2552.
17. Davies, M., Bateson, A. N. & Dunn, S. M. J. (1998). J. Neurochem. 70, 2188-2194.
18. Dorey, G., Poissonnet, G., Potier, M. C., Prado de Carvalho, L., Verrault, P., Chapouthier, G., Rossier, J., Potier, P. & Dodd, R. H. (1989). J. Med. Chem. 32, 1799-1804.
19. Dunn, S. M. J., Davies, M., Muntoni, A. L. & Lambert, J. J. (1999). Mol. Pharmacol. 56, 768-774.
20. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
21. Flack, H. D. (1983). Acta Cryst. A39, 876-881.
22. Free, S. M. & Wilson, J. W. (1964). J. Med. Chem. 7, 395-399.
23. Gessi, S., Dalpiaz, A., Varani, K. & Borea, P. A. (1999). Life Sci. 64, 185-192.
24. Gilli, G. (2001). A Fortran Computer Program for Free-Wilson Analysis. Department of Chemistry, University of Ferrara, Italy.
25. Gilli, G., Bertolasi, V., Sacerdoti, M. & Borea, P. A. (1978). Acta Cryst. B34, 2826-2829.
26. Gilli, P., Bertolasi, V., Ferretti, V. & Gilli, G. (2000). J. Am. Chem. Soc. 122, 10405-10417.
27. Harris, D. L. & Loew, G. (2000). Bioorg. Med. Chem. 8, 2527-2538.
28. Hollinshead, S. P., Trudell, M. L., Skolnick, P. & Cook, J. M. (1990). J. Med. Chem. 33, 1062-1069.
29. Jeffrey, G. A & Saenger, W. (1991). Hydrogen Bonding in Biological Structures. Berlin: Springer-Verlag.
30. Kubicki, M. & Codding, P. W. (2001). Acta Cryst. C57, 728-731.
31. Loew, G. H., Nienow, J. & Poulsen, M.(1984). Mol. Pharmacol. 26, 19-34.
32. Marder, M., Estiù, G., Blanch, L. B., Viola, H., Wasowski, C., Medina, J. H. & Paladini, A. C. (2001). Bioorg. Med. Chem. 9, 323-335.
33. McKernan, R. M. & Whiting, P. J. (1996). TINS, 19, 139-143.
34. Molecular Operating Environment (2003). Release 2003.02. MOE, Chemical Computing Group Inc., Montreal, Canada.
35. Muir, A. K. S. & Codding, P. W. (1984). Can. J. Chem. 62, 1803-1806.
36. Muir, A. K. S. & Codding, P. W. (1985). Can. J. Chem. 63, 2752-2755.
37. Nardelli, M. (1995). J. Appl. Chem. 28, 659.
38. Nayeem, N., Green, T. P., Martin, I. L. & Barnard, E. A. (1994). J. Neurochem. 62, 815-818.
39. Newell, J. G., Davies, M., Bateson, A. N. & Dunn, S. M. J. (2000). J. Biol. Chem. 275, 14198-14204.
40. Nonius (1997). Kappa-CCD Server Software. Nonius BV, Delft, The Netherlands.
41. Otwinowski, Z. & Minor, W. (1997). Methods Enzymol. 276, 307-326.
42. Purcell, W. P., Bass, G. E. & Clayton, J. M. (1973).Strategy of Drug Design, Appendix IV. New York: John Wiley and Sons.
43. Renard, S., Olivier, A., Granger, P., Avenet, P., Graham, D., Sevrin, M., George, P. & Besnard, F. (1999). J. Biol. Chem, 274, 13370-13374.
44. Schaerer, M. T., Buhr, A., Baur, R. & Sigel, E. (1998). Eur. J. Pharmacol. 354, 283-287.
45. Sheldrick, G. M. (1997). SHELX97. University of Göttingen, Germany.
46. Sigel, E., Schaerer, M. T., Buhr, A. & Baur, R. (1998). Mol. Pharmacol. 54, 1097-1105.
47. Spek, A. L (2001). PLATON. Utrecht University, The Netherlands.
48. Strakhova, M. I., Harvey, S. C., Cook, C. M., Cook, J. M. & Skolnick, P. (2000). Mol. Pharmacol. 58, 1434-1440.
49. Tripos Inc. (1997). Alchemy32, Version 2.0. Tripos Inc., St. Louis, Missouri, USA.
50. Zhang, W., Koehler, K. F., Zhang, P. & Cook, J. M. (1995). Drug Des. Discov. 12, 193-248.