Inhibition of acetylcholinesterase by coumarins: The case of coumarin 106

Pharmacological Research

Volumn 58, Issue 3-4, 2008, Pages 215-221

  Fallarero, Adyary ^a   Oinonen, Päivi ^b   Gupta, Shikhar ^c   Blom, Pia ^a   Galkin, Anna ^b   Mohan, C Gopi ^c   Vuorela, Pia M ^a  

^a Faculty of Mathematics and Natural Sciences   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

^c NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Acetylcholinesterase; Coumarin 106; Coumarins; Inhibition

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE; COUMARIN 106; COUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CYTOTOXICITY; DRUG POTENCY; ENZYME ACTIVITY; ENZYME BINDING; ENZYME INHIBITION; ENZYME KINETICS; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL;

ACETYLCHOLINESTERASE; ANTINEOPLASTIC AGENTS; BUTYRYLCHOLINESTERASE; CELL LINE, TUMOR; CHOLINESTERASE INHIBITORS; CHROMATOGRAPHY, THIN LAYER; COUMARINS; DATA INTERPRETATION, STATISTICAL; DRUG EVALUATION, PRECLINICAL; HUMANS; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 54849432574     PISSN: 10436618     EISSN: 10961186     Source Type: Journal    
DOI: 10.1016/j.phrs.2008.08.001     Document Type: Article

References (30)

1. Giacobini E. Cholinesterase inhibitors: new roles and therapeutic alternatives. Pharmacol Res 50 4 (2004) 433-440
2. Inestrosa N.C., Alvarez A., Pérez C.A., Moreno R.D., Vicente M., Linker C., et al. Acetylcholinesterase accelerates assembly of amyloid-beta-peptides into Alzheimer's fibrils: possible role of the peripheral site of the enzyme. Neuron 16 4 (1996) 881-891
3. Decker M., Kraus B., and Heilmann J. Design, synthesis and pharmacological evaluation of hybrid molecules out of quinazolinimines and lipoic acid lead to highly potent and selective butyrylcholinesterase inhibitors with antioxidant properties. Bioorg Med Chem 16 8 (2008) 4252-4261
4. Kamal M.A., Klein P., Luo W., Li Y., Holloway H.W., Tweedie D., et al. Kinetics of human serum butyrylcholinesterase inhibition by a novel experimental Alzheimer therapeutic, dihydrobenzodioxepine cymserine. Neurochem Res 33 5 (2008) 745-753
5. Newman D.J., and Cragg G.M. Natural products as sources of new drugs over the last 25 years. J Nat Prod 70 3 (2007) 461-477
6. Onor M.L., Trevisiol M., and Aguglia E. Rivastigmine in the treatment of Alzheimer's disease: an update. Clin Interv Aging 2 1 (2007) 17-32
7. Hoult J.R., and Payá M. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen Pharmacol 27 4 (1996) 713-722
8. Brühlmann C., Ooms F., Carrupt P.A., Testa B., Catto M., Leonetti F., et al. Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase. J Med Chem 44 19 (2001) 3195-3198
9. Kang S.Y., Lee K.Y., Sung S.H., Park M.J., and Kim Y.C. Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships. J Nat Prod 64 5 (2001) 683-685
10. Shen Q., Peng Q., Shao J., Liu X., Huang Z., Pu X., et al. Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors. Eur J Med Chem 40 12 (2005) 1307-1315
11. Di Giovanni, Borloz A., Urbain A., Marston A., Hostettmann K., Carrupt P.A., et al. In vitro screening assays to identify natural or synthetic acetylcholinesterase inhibitors: thin layer chromatography versus microplate methods. Eur J Pharm Sci 33 2 (2008) 109-119
12. Piazzi L., Cavalli A., Colizzi F., Belluti F., Bartolini M., Mancini F., et al. Multi-target-directed coumarin derivatives: hAChE and BACE1 inhibitors as potential anti-Alzheimer compounds. Bioorg Med Chem Lett 18 1 (2008) 423-426
13. Houghton P.J., and Howes M.J. Natural products and derivatives affecting neurotransmission relevant to Alzheimer's and Parkinson's disease. Neurosignals 14 1-2 (2005) 6-22
14. Wilson R.M., and Danishefsky S.J. Small molecule natural products in the discovery of therapeutic agents: the synthesis connection. J Org Chem 71 22 (2006) 8329-8351
15. Ellman G.L., Courtney K.D., Andres Jr. V., and Feather-Stone R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 7 (1961) 88-95
16. Ingkaninan K., de Best C.M., van der Heijden R., Hofte A.J., Karabatak B., Irth H., et al. High-performance liquid chromatography with on-line coupled UV, mass spectrometric and biochemical detection for identification of acetylcholinesterase inhibitors from natural products. J Chromatogr A 872 1-2 (2000) 61-73
17. Zhang J.H., Chung T.D.Y., and Oldenburg K.R. A simple statistical parameter for use in evaluation and validation of high throughput screening assays. J Biomol Screen 4 2 (1999) 67-73
18. Marston A., Kissling J., and Hostettmann K. A rapid TLC bioautographic method for the detection of acetylcholinesterase and butyrylcholinesterase inhibitors in plants. Phytochem Anal 13 1 (2002) 51-54
19. Pohjala L., Tammela P., Samanta S.K., Yli-Kauhaluoma J., and Vuorela P. Assessing the data quality in predictive toxicology using a panel of cell lines and cytotoxicity assays. Anal Biochem 362 2 (2007) 221-228
20. Bollini S., Herbst J.J., Gaughan G.T., Verdoorn T.A., Ditta J., Dubowchik G.M., et al. High throughput fluorescence polarization method for identification of FKBP12 ligands. J Biomol Screen 7 6 (2001) 526-530
21. Rollinger J.M., Hornick A., Langer T., Stuppner H., and Prast H. Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. J Med Chem 47 25 (2004) 6248-6254
22. Miyazawa M., Tsukamoto T., Anzai J., and Ishikawa Y. Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster. J Agric Food Chem 52 14 (2004) 4401-4405
23. Krupka R.M., and Laidler K.J. Molecular mechanisms for hydrolytic enzyme action. Nature 190 (1961) 916-918
24. Rampa A., Bisi A., Belluti F., Gobbi S., Valenti P., Andrisano V., et al. Acetylcholinesterase inhibitors for potential use in Alzheimer's disease: molecular modeling, synthesis and kinetic evaluation of 11H-indeno-[1,2-b]-quinolin-10-ylamine derivatives. Bioorg Med Chem 8 3 (2000) 497-506
25. Raina P., Santaguida P., Ismaila A., Patterson C., Cowan D., Levine M., et al. Effectiveness of cholinesterase inhibitors and memantine for treating dementia: evidence review for a clinical practice guideline. Ann Intern Med 148 5 (2008) 379-397
26. Carlton B.D., Aubrun J.C., and Simon G.S. Effects of coumarin following perinatal and chronic exposure in Sprague-Dawley rats and CD-1 mice. Fundam Appl Toxicol 30 1 (1996) 145-151
27. Felter S.P., Vassallo J.D., Carlton B.D., and Daston G.P. A safety assessment of coumarin taking into account species-specificity of toxicokinetics. Food Chem Toxicol 44 4 (2006) 462-475
28. Lewis D.F., Ito Y., and Lake B.G. Metabolism of coumarin by human P450s: a molecular modelling study. Toxicol In Vitro 20 (2006) 256-264
29. Wunberg T., Hendrix M., Hillisch A., Lobell M., Meier H., Schmeck C., et al. Improving the hit-to-lead process: data-driven assessment of drug-like and lead-like screening hits. Drug Discov Today 11 3-4 (2006) 175-180
30. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Del Rev 23 (1997) 1-25