Bis-huperzine B: Highly potent and selective acetylcholinesterase inhibitors

Journal of Medicinal Chemistry

Volumn 48, Issue 3, 2005, Pages 655-657

  Feng, Song ^a   Wang, Zhifei ^a   He, Xuchang ^a   Zheng, Suxin ^a   Xia, Yu ^a   Jiang, Hualiang ^a   Tang, Xican ^a   Bai, Donglu ^a  

^a Shanghai Jiao Tong University Affiliated Sixth People s Hospital   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; BIS(12 HUPERZINE B); BIS(14 HUPERZINE B); BIS(16 HUPERZINE B); BIS(18 HUPERZINE B); BIS(20 HUPERZINE B); BIS(8 HUPERZINE B); BIS(9 HUPERZINE B); CHOLINESTERASE; CHOLINESTERASE INHIBITOR; HUPERZINE B; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; INHIBITION KINETICS;

ACETYLCHOLINESTERASE; ALKALOIDS; ANIMALS; BRIDGED COMPOUNDS; BUTYRYLCHOLINESTERASE; CATALYTIC DOMAIN; CHOLINESTERASE INHIBITORS; LYCOPODIACEAE; MODELS, MOLECULAR; PYRIDONES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 13444273000     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0496178     Document Type: Article

References (19)

1. Hieble, J. P.; Ruffilo, R. R., Jr. In Principles of Pharmacology Basic Concepts and Clinical Application; Munson, P. L., Ed.; Chapman & Hall: New York, 1995; pp 145-159.
2. (a) Pang, Y. P.; Quiram, P.; Jelacic, T.; Hong, F.; Brimijoin, S. Highly Potent, Selective, and Low-cost bis-Tetrahydroaminacrine Inhibitors of Acetylcholinesterase: Steps Toward Novel Drugs for Treating Alzheimer's Disease. J. Biol. Chem. 1996, 271, 23646-23649.
3. (b) Carlier, P. R.; Han, Y. F.; Chow, E. S. H.; Li, C. P. L.; Wang, H.; Lieu, T. X.; Wong, H. S.; Pang, Y. P.; Evaluation of short-tether bis-THA AChE inhibitors. A further test of the dual binding site hypothesis. Bioorg. Med. Chem. 1999, 7, 351-357.
4. Jin, G. Y.; Luo, X. M.; He, X. C.; Jiang, H. L.; Zhang, H. Y.; Bai, D. L. Synthesis and docking studies of alkylene-linked dimers of (-)-huperzine A. Arzneim. Forsch. 2003, 53, 753-757.
5. Carlier, P. R.; Du, D. M.; Han, Y. F.; Liu, J.; Perola, E.; Williams, I. D.; Pang, Y. P. Dimerization of an inactive fragment of huperzine a produces a drug with twice the potency of the natural product. Angew. Chem., Int. Ed. 2000, 39, 1775-1777.
6. Wong, D. M.; Greenblatt, H. M.; Dvir, H.; Carlier, P. R.; Han, Y. F.; Pang, Y. P.; Silman, I.; Sussman, J. L. Acetylcholinesterase Complexed with Bivalent Ligands Related to Huperzine A: Experimental Evidence for Species-Dependent Protein-Ligand Complementarity. J. Am. Chem. Soc. 2003, 125, 363-373.
7. Inestrosa, N. C.; Alvarez, A.; Perez, C. A.; Moreno, R. D.; Vicente, M.; Linker, C.; Casanueva, O. I.; Sato, C,; Garrido, J. Acetylcholinesterase accelerates assembly of amyloid-beta-peptides into Alzheimer's fibrils: possible role of the peripheral site of enzyme. Neuron 1996, 16, 881-891.
8. (a) Xu, H.; Tang, X. C.; Cholinesterase inhibition by huperzine B. Acta Pharmacol. Sin. 1987, 8, 18-22.
9. (b) X. D. Zhu, X. C. Tang, Improvement of impaired memory in mice by huperzine A and huperzine B. Acta Pharmacol. Sin. 1988, 9, 492-497.
10. (c) Liu, J.; Zhang, H. Y.; Wang, L. M.; Tang, X. C.; Inhibitory effect of huperzine B on the cholinesterase activity in mice. Acta Pharmacol. Sin. 1999, 20, 141-145.
11. Bai, D. L.; Tang, X. C.; He, X. C. Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease. Curr. Med. Chem. 2000, 7, 355-374.
12. Yan, X. F.; Lu, W. H.; Lou, W, J.; Tang, X. C. Effects of huperzine A and B on skeletal muscle and electroencephalogram. Acta Pharmacol. Sin. 1987, 8, 117-123.
13. Sugimoto, H.; Yamanishi, Y.; Limura, Y.; Kawakami, Y.; Donepezil hydrochloride (E2020) and other acetylcholinesterase inhibitors. Curr. Med. Chem. 2000, 7, 303-339.
14. (a)Ellman, G. L.; Courtney, K. D.; Valentino Andre, J. R.; Featherstone, R. M. A rapid method for the estimation of acetylcholinesterase, Biochem. Pharmacology. 1961, 7, 88-95.
15. (b) Cheng D. H.; Tang X. C. Comparative studies of huperzine A, E2020, and tacrine on behavior and cholinesterase activities. Pharmacol. Biochem. Behav. 1998, 60, 377-386.
16. Ewing, T. J.; Kuntz, I. D. Critical evaluation of search algorithms used in automated molecular docking. J. Comput. Chem. 1997, 18, 1175-1189.
17. DOCK 4.0, Molecular Design Institute, San Francisco, CA.
18. Dvir, H.; Jiang, H. L.; Wong, D. M.; Harel, M.; Chetrit, M.; He, X. C.; Jin, G. Y.; Yu, G. L.; Tang, X. C.; Silman, I.; Bai, D. L.; Sussman, J. L. X-ray structures of Torpedo californica acetylcholinesterase complexed with (+)-Huperzine A and (-)-Huperzine B: Structural evidence for an active site rearrangement. Biochemistry 2002, 41, 10810-10818.
19. Wallace, A. C.; Laskowski, R. A.; Thornton, J. M.; A program to generate schematic diagrams of protein-ligand interactions. LIGPLOT: Protein Eng. 1995, 8, 127-134.