1H NMR Relaxation Investigation of Inhibitors Interacting with Torpedo californica Acetylcholinesterase

Journal of Magnetic Resonance

Volumn 144, Issue 1, 2000, Pages 129-133

  Delfini, Maurizio ^a   Gianferri, Raffaella ^a   Dubbini, Veronica ^a   Manetti, Cesare ^a   Gaggelli, Elena ^b   Valensin, Gianni ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE INHIBITOR; NAPHTHYRIDINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TORPEDO;

ANIMALS; CHOLINESTERASE INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHYRIDINES; TORPEDO;

EID: 0034183042     PISSN: 10907807     EISSN: None     Source Type: Journal    
DOI: 10.1006/jmre.2000.2031     Document Type: Article

References (26)

1. J. L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman, Atomic structure of acetylcholinesterase from Torpedo californica: A prototypic acetylcholine-binding protein, Science 253, 872-879 (1991).
2. Y. Bourne, P. Taylor, P. E. Bougis, and P. Marchot, Crystal structure of mouse acetylcholinesterase, J. Biol. Chem. 274, 2963-2970 (1999).
3. G. Pacheco, R. Palacios-Esquivel, and D. E. Moss, Cholinesterase inhibitors proposed for treating dementia in Alzheimer's disease: Selectivity towards human brain acetylcholinesterase compared with butyrylcholinesterase, J. Pharmacol. Exp. Ther. 274, 767-770 (1995).
4. S. C. Samuels and K. L. Davis, A risk-benefit assessment of tacrine in the treatment of Alzheimer's disease, Drug Saf. 16, 66-77 (1997).
5. G. Kryger, I. Silman, and J. L. Sussman, Structure of acetylcholinesterase complexed with E2020 (Aricept): Implication for the design of new anti-Alzheimer drugs, Structure 7, 297-307 (1999).
6. G. R. Swanwick and B. A. Lawlor, Initiating and monitoring cholinesterase inhibitor treatment for Alzheimer's disease, Int. J. Geriatr. Psychiatry 14, 244-248 (1999).
7. K. L. Davis and P. Powchik, Tacrine. Lancet 345, 625-630 (1995).
8. S. L. Nightingale, Donezipil approved for treatment of Alzheimer's disease, J. Am. Med. Assoc. 277, 10 (1997).
9. M. Harel, I. Schalk, L. Ehret-Sabattier, F. Bouet, M. Goeldner, C. Hirth, P. Axersen, I. Silman, and J. Sussman, Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase, Proc. Natl. Acad. Sci. USA 90, 9031-9035 (1993).
10. Y. Bourne, P. Taylor, and P. Marchot, Acetylcholinesterase inhibition by fasciculin: Crystal structure of the complex, Cell 83, 503-512 (1995).
11. M. L. Raves, M. Harel, Y. P. Pang, I. Silman, A. P. Kozikowski, and J. L. Sussman, Structure of acetylcholinesterase complexes with the nootropic alkaloid (-)-huperzine A, Nat. Struct. Biol. 4, 57-63 (1997).
12. I. Silman, C. B. Millard, A. Ordentlich, H. M. Greenblatt, M. Harel, D. Barak, A. Shafferman, and J. L. Sussman, A preliminary comparison of structural models for catalytic intermediates of acetylcholinesterase, Chem. Biol. Interact. 119-120, 43-52 (1999).
13. C. B. Millard, G. Kryger, A. Ordentlich, M. Harel, M. L. Raves, Y. Segall, D. Barak, A. Shafferman, I. Silman, and J. L. Sussman, Crystal structures of aged phosphonylated acetylcholinesterase: Nerve agent reaction products at the atomic level, Biochemistry 38, 7032-7039 (1999).
14. H. Sugimoto, Y. Imura, Y. Yamanishi, and K. Yamatsu, Synthesis and structure-activity relationships of acetylcholinesterase inhibitors - 1-benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine and related compounds, J. Med. Chem. 38, 4841-4829 (1995).
15. D. H. Cheng, H. Ren, and X. C. Tang, Huperzine A, a novel promising acetyl-cholinesterase inhibitor, Neuroreport 8, 97-101 (1996).
16. M. R. Del Giudice, A. Borioni, C. Mustazza, F. Gatta, A. Meneguz, and M. T. Volpe, Synthesis and cholinesterase inhibitory activity of 6-, 7-methoxy-(and hydroxy-) tacrine derivatives, Farmaco 51, 693-698 (1996).
17. G. A. Morris and R. Freeman, Selective excitation in Fourier transform nuclear magnetic resonance, J. Magn. Reson. 29, 433-462 (1978).
18. H. Geen, X.-L. Wu, P. Xu, J. Friedrich, and R. Freeman, Selective excitation at two arbitrary frequencies. The double-DANTE sequence, J. Magn. Reson. 81, 646-652 (1989).
19. R. Freeman, H. D. W. Hill, B. L. Tomlinson, and L. D. Hall, Dipolar contribution to NMR spin-lattice relaxation of protons, J. Chem. Phys. 61, 4466-4473 (1974).
20. H. Sigel and N. A. Corfù, The assisted self-association of ATP4- by a poly(amino acid) [poly(Lys)] and its significance for cell organelles that contain high concentrations of nucleotides, Eur. J. Biochem. 240, 508-517, (1996).
21. L. D. Hall and H. D. W. Hill, Spin-lattice relaxation of protons. A general, quantitative evaluation of contributions from the intramolecular dipole-dipole mechanism, J. Am. Chem. Soc. 98, 1269-1270 (1976).
22. G. Valensin, T. Kushnir, and G. Navon, Selective and nonselective proton spin-lattice relaxation studies of enzyme-substrate interactions, J. Magn. Reson. 46, 23-29 (1982).
23. 1, Magn. Reson. Chem. 30, 461-465 (1992).
24. 1H NMR relaxation investigation of the interaction of vinblastine with tubulin, J. Magn. Reson. B 104, 89-94 (1994).
25. 1H NMR studies on the interaction of β-carboline derivatives with human serum albumin, J. Magn. Reson. 130, 281-286 (1998).
26. G. Valensin, E. Gaggelli, and P. E. Valensin, Proton relaxation investigations of drugs bound to macromolecular receptors, in "NMR Spectroscopy in Drug Research" (J. W. Jaroszewski, K. Schaumburg, and H. Kofod, Eds.), pp. 409-422, Munksgaard, Copenaghen (1988).