Three-dimensional structure of a complex of E2020 with acetylcholinesterase from Torpedo californica

Journal of Physiology Paris

Volumn 92, Issue 3-4, 1998, Pages 191-194

  Kryger, G ^a   Silman, I ^a   Sussman, J L ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; ANION; CHOLINESTERASE; DONEPEZIL; PHENYLALANINE; TRYPTOPHAN;

ALZHEIMER DISEASE; BINDING AFFINITY; CONFERENCE PAPER; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; ENANTIOMER; ENZYME ACTIVE SITE; NONHUMAN; TORPEDO CALIFORNICA;

EID: 0032458505     PISSN: 09284257     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0928-4257(98)80008-9     Document Type: Conference Paper

References (23)

1. Axelsen P.H. Harel M. Silman I. Sussman J.L. Structure and dynamics of the active site gorge of acetylcholinesterase: synergistic use of molecular dynamics simulation and X-ray crystallography Prot. Sci. 3 1994 188 197
2. Brünger A.T. Kuriyan J. Karplus M. Crystallographic R factor refinement by molecular dynamics Science 235 1987 458 460
3. Cardozo M.G. Iimura Y. Sugimoto H. Yamanishi Y. Hopfinger A.J. QSAR analyses of the substituted indanone and benzylpiperidine rings of a series of indanone benzylpiperidine inhibitors of acetylcholinesterase J. Med. Chem. 35 1992 584 589
4. Cardozo M.G. Kawai T. Imura Y. Sugimoto H. Yamanishi Y. Hopfinger A.J. Conformational-analyses and molecular-shape comparisons of a series of indanone benzylpiperidine inhibitors of acetylcholinesterase J. Med. Chem. 35 1992 590 601
5. Dogherty D. Cation-p interaction in chemistry and biology: a new view of benzene, Phe, Tyr, and Trp Science 271 1996 163 1684
6. Gauthier S. Gauthier L. E. Giacobini R. Becker Cholinergic Basis for Alzheimer Therapy 1991 Birkhäuser New York 224 230
7. Boston Giacobini E. Becker R. Alzheimer Disease: Therapeutic Strategies Birkhäuser 1994
8. Harel M. Schalk I. Ehret-Sabatier L. Bouet F. Goeldner M. Hirth C. Axelsen P. Silman I. Sussman J.L. The X-ray structure of a transition state analog complex reveals the molecular origins of the catalytic power and substrate specificity of acetylcholinesterase Proc. Natl. Acad. Sci. USA 90 1993 9031 9035
9. Harel M. Quinn D.M. Nair H.K. Silman I. Sussman J.L. Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase J. Am. Chem. Soc. 118 1996 2340 2346
10. Inestrosa N.C. Alvarez A. Perez C.A. Moreno R.D. Vicente M. Linker C. Casanueva O.I. Soto C. Garrido J. Acetylcholinesterase accelerates assembly of amyloid-betapeptides into Alzheimer's fibrils: possible role of the peripheral site of the enzyme Neuron 16 1996 881 891
11. 1H-inden-1-one hydrochloride (E2020) and related inhibitors to free and acetylated acetylcholinesterase and corresponding structure-activity analyses J. Med. Chem. 39 1996 4460 4470
12. Laskowski R.A. SURFNET: a program for visualizing molecular surfaces, cavities and intermolecular interactions J. Mol. Graph. 13 1995 323 330
13. Main A.R. Goldberg A.M. Hanin I Biology of Cholinergic Function 1976 Raven Boston 269 353
14. Matsui K. Oda Y. Obe H. Tanaka S. Asakawa N. Direct determination of 2020 enantiometers in plasma by liquid chromatography-mass spectrometry and column-switching techniques J. Chromatogr. A 694 1995 209 218
15. Quinn D.M. Chem. Rev. 87 1987 955 975
16. Raves M.L. Harel M. Pang Y.-P. Silman I. Kozikowski A.P. Sussman J.L. Structure of acetylcholinesterase complexed with the nootropic alkaloid, (−)-huperzine A Nature Struct. Biol. 4 1996 57 63
17. Reyes A.E. Perez D.R. Alvarez A. Garrido J. Gentry M.K. Doctor B.P. Inestrosa N.C. A monoclonal antibody against acetylcholinesterase inhibits the formation of amyloid fibrils induced by the enzyme Biochem. Biophys. Res. Commun. 232 1997 652 655
18. Sugimoto H. Tsuchiya Y. Sugumi H. Higurashi K. Karibe N. Imura Y. Sasaki A. Araki S. Yamanishi Y. Yamatsu K. Synthesis and antiacetylcholinesterase activity of 1-benzyl-4-((5,6-dimethoxy-1-indanon-2-YI)methyl)piperidine hydrochloride (E2020) and related-compounds J. Med. Chem. 35 1992 4542 4548
19. Sugimoto H. Iimura Y. Yamanishi Y. Yamatsu K. Synthesis and structure-activity-relationships of acetylcholinesterase inhibitors — 1-benzyl-4-(2-phtalimidoethyl)piperidine and related derivatives Bioorg. Med. Chem. Lett. 2 1992 871 876
20. Sussman J.L. Harel M. Frolow F. Oefner C. Goldman A. Toker L. Silman I Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein Science 253 1991 872 879
21. Taylor P. Gilman A.G. Nies A.S. Rall T.W. Taylor P. The Pharmacological Basis of Therapeutics 5th edn. 1990 Macmillan New York 131 150
22. Taylor P. Lappi S. Interaction of fluorescence probes with acetylcholinesterase The site and specificity of propidium binding Biochemistry 14 1975 1989 1997
23. Thomsen T. Kewitz H. Selective inhibition of human acetylcholinesterase by galanthamine in vitro and in vivo Life Sci. 46 1990 1553 1558