Ab initio molecular structure study of alkyl substitute analogues of Alzheimer drug phenserine: Structure-activity relationships for acetyl- and butyrylcholinesterase inhibitory action

Journal of Molecular Structure: THEOCHEM

Volumn 714, Issue 2-3, 2005, Pages 133-136

  Tezer, Nurten ^a  

^a CUMHURIYET UNIVERSITY   (Turkey)

Author keywords

Ab initio; Acetylcholinesterase inhibitors; Geometry optimization

Indexed keywords

ACETYLCHOLINESTERASE; CARBAMIC ACID; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; PHENSERINE;

AB INITIO CALCULATION; ALZHEIMER DISEASE; ARTICLE; DRUG MECHANISM; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 15944386029     PISSN: 01661280     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.theochem.2004.08.062     Document Type: Article

References (25)

1. E.K. Perry, B.E. Tomlinson, G. Blessed, K. Bergman, P.H. Gibson, and R.H. Perry Correlation of cholinergic abnormalities with senile plaques and mental test scores in senile dementia Br. Med. J. 2 1978 1457 1459
2. P.J. Whitehouse, D.L. Price, R.G. Struble, A.W. Clark, J.T. Coyle, and M.R. Delon Alzheimer's disease and senile dementia: loss of neurons in the basal forebrain Science 215 1982 1237 1239
3. R.T. Bartus, R.L. Dean, B. Beer, and A.S. Lippa The cholinergic hypothesis of geriatric memory dysfunction Science 217 1982 408 417
4. E. Giacobini Cholinesterase inhibitors do more than inhibit cholinesterase R. Becker E. Giacobini Alzheimer's Disease: Molecular Biology to Therapy 1997 Birkhauser Boston 188 204
5. E. Giacobini Cholinesterase inhibitors: from the Calabar bean to Alzheimer therapy E. Giacobini Cholinesterases and Cholinesterase Inhibitors 2000 Martin Dunitz London 181 226
6. E. Giacobini Pharmacokinetic and pharmacologic considerations S. Gauthier Pharmacotherapy of Alzheimer's Disease 1998 Martin Dunitz Ltd London
7. I.B. Wilson, and F. Bergmann J. Biol. Chem. 185 1950 479
8. D. Nachmansohn, and I.B. Wilson Adv. Enzymol. 12 1951 259 320
9. L. Terrone Rosenberry Adv. Enzymol. 43 1975 103 218
10. D.M. Quinn Chem. Rev. 87 1987 955 979
11. J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman Science 253 1991 872 879
12. M. Harel, I. Schalk, L. Ehret-Sabatier, F. Bouet, M. Goeldner, C. Hirt, P.H. Axelsen, I. Silman, and J.L. Sussman Proc. Natl Acad. Sci. USA 90 1993 9031 9035
13. F.B. Hasan, S.G. Cohen, and J.B. Cohen J. Biol. Chem. 255 1980 3898 3904
14. N.H. Greig, X.F. Pei, T. Soncrant, D.K. Ingram, and A. Brossi Phenserine and Ring C hetero-analogues: drug candidates for treatment of Alzheimer's disease Med. Res. Rev. 15 1995 3 31
15. A. Brossi, X.F. Pei, and N.H. Greig Invited review. Phenserine, a novel anticholinesterase related to physostigmine: total synthesis and biological properties Aust. J. Chem. 49 1996 171 181
16. N.H. Greig, D. Ingram, W.C. Wallace, T. Utsuki, Q.S. Yu, H.W. Holloway, X.F. Pei, V. Haroutunian, D. Lahiri, A. Brossi, and T.T. Soncrant Phenserine: a selective, long-acting and brain-directed acetylcholinesterase inhibitor affecting cognition and β-APP processing B. Becker E. Giacobini P. Robert Alzheimer's Disease: Molecular Biology to Therapy 1996 Birkhauser Boston 231 237
17. Q.-S. Yu, H.W. Holloway, J.L. Flippen-Anderson, B. Hoffman, A. Brossi, and N.H. Greig Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action J. Med. Chem. 44 2001 4062 4071
18. M.A. Kamal, N.H. Greig, A.S. Alhomida, and A.A. Al-Jafari Human acetylcholinesterase inhibition kinetics of the experimental Alzheimer therapeutic, tolserine Biochem. Pharmacol. 60 2000 561 570
19. A.A. Al-Jafari, M.A. Kamal, N.H. Greig, A.S. Alhomida, and E.R. Perry Kinetics of human erythrocyte acetylcholinesterase inhibition by a novel derivative of physostigmine: phenserine Biochem. Biophys. Res. Commun. 248 1998 180 185
20. N.H. Greig, X.F. Pei, T. Soncrant, D.K. Ingram, and A. Brossi Phenserine and ring C hetero-analogues: drug candidates for treatment of Alzheimer's disease Med. Res. Rev. 15 1995 3 31
21. M. Brzostowska, X.S. He, N.H. Greig, and A. Brossi Selective inhibition of acetyl- and butyrylcholinesterases by phenylcarbamates of (-)-eseroline, (-)-(N1)-noreseroline and physovenol Med. Chem. Res. 2 1992 238 246
22. H. Soreg, and H. Zakut Human Cholinesterases and Anticholinesterases 1993 Academic Press New York
23. H. Soreg, and H. Zakut Amplification of butyrylcholinesterase and acetylcholinesterase genes in normal and tumor tissues: putative relationship to organophosphorous poisoning Pharm. Res. 7 1990 1 7
24. P. Taylor The cholinesterases J. Biol. Chem. 266 1991 4025 4028
25. P. Taylor, and Z. Radic The cholinesterases: from genes to proteins Annu. Rev. Pharmacol. Toxicol. 34 1994 281 320