Highly selective inhibition of butyrylcholinesterase by a novel melatonin-tacrine heterodimers

Journal of Pineal Research

Volumn 54, Issue 4, 2013, Pages 435-441

  Zawadzka, Anna ^a   Łozińska, Iwona ^a   Molȩda, Zuzanna ^a   Panasiewicz, Mirosława ^b   Czarnocki, Zbigniew ^a  

^a UNIVERSITY OF WARSAW   (Poland)

^b MEDICAL CENTER FOR POSTGRADUATE EDUCATION   (Poland)

Author keywords

Alzheimer's disease; Cholinesterases inhibitors; Hybrid drugs

Indexed keywords

3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [10(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) DECYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [12(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) DODECYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [2(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) ETHYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [3(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) PROPYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [4(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) BUTYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [5(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) PENTYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [6(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) HEXYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [7(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) HEPTYL] CARBAMATE; 3[2 (ACETYLAMINO) ETHYL] 1H INDOL 5 YL [8(1,2,3,4 TETRAHYDROACRIDIN 9 YLAMINO) OCTYL] CARBAMATE; ACETYLCHOLINESTERASE; CARBAMIC ACID; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; HETERODIMER; MELATONIN; TACRINE; TACRINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHOLINESTERASE INHIBITION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50;

ALZHEIMER'S DISEASE; CHOLINESTERASES INHIBITORS; HYBRID DRUGS;

BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; MELATONIN; TACRINE;

EID: 84878076445     PISSN: 07423098     EISSN: 1600079X     Source Type: Journal    
DOI: 10.1111/jpi.12006     Document Type: Article

References (35)

1. HEBERT LE, SCHERR PA, BECKETT LA et al. Age-specific incidence of Alzheimer's disease in a community population. J Am Med Assoc 1995; 273:1354-1359.
2. DUFOUIL C, ALPEROVITCH A. Epidemiology of Alzheimer's disease. Rev Prat 2005; 55:1869-1878.
3. BARTUS RT, DEAN RL, BEER B, LIPPA AS. The cholinergic hypothesis in geriatric memory dysfunction. Science 1982; 217:408-417.
4. GREIG NH, UTSUKI T, YU Q et al. A new therapeutic target in Alzheimer's disease treatment: attention to butyrylcholinesterase. Curr Med Res Opin 2001; 17:159-165.
5. GUILLOZET AL, SMILEY JF, MASH DC, MESULAM MM. Butyrylcholinesterase in the life cycle of amyloid plaques. Ann Neurol 1997; 42:909-918.
6. MUÑOZ-TORRERO D, CAMPS P. Dimeric and hybrid anti-Alzheimer drug candidates. Curr Med Chem 2006; 13:399-422.
7. 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.
8. CARLIER PR, HAN YF, CHOW ES-H et al. Evaluation of shorttether bis-THA AChE inhibitors. A further test of the dual binding site hypothesis. Bioorg Med Chem 1999; 7:351-357.
9. SHAO D, ZOU C, LUO C, TANG X, LI Y. Synthesis and evaluation of tacrine-E2020 hybrids as acetylcholinesterase for the treatment of Alzheimer's disease. Bioorg Med Chem Lett 2004; 14:4639-4642.
10. CAMPS P, MUÑOZ-TORRERO D. Tacrine-huperzine A hybrids (Huprines): a new class of highly potent selective acetylcholinesterase inhibitors of interest for the treatment of Alzheimer's disease. Mini-Rev Med Chem 2001; 1:163-174.
11. STEHLE JH, SAADE A, RAWASHDEH O et al. A survey of the molecular details in the human pineal gland in light of phylogeny, structure, function and chronobiological diseases. J Pineal Res 2011; 51:17-43.
12. DOMINGUEZ-RODRIGUEZ A, ABREU-GONZALEZ P, SANCHEZSANCHEZ JJ, KASKI JC, REITER RJ. Melatonin and circadian biology in human cardiovascular disease. J Pineal Res 2010; 49:14-22.
13. CARDINALI DP, SRINIVASAN V, BRZEZINSKI A, BROWN GM. Melatonin and its analogs in insomnia and depression. J Pineal Res 2012; 52:365-375.
14. HARDELAND R, MADRID JA, TAN DX, REITER RJ. Melatonin, the circadian multioscillator system and health: the need for detailed analyses of peripheral melatonin signaling. J Pineal Res 2012; 52:139-166.
15. TAN DX, CHEN LD, POEGGELER B, MANCHESTER LC, REITER RJ. Melatonin: a potent, endogenous hydroxyl radical scavenger. Endocr J 1993; 1:57-60.
16. OCHOA JJ, DIAZ-CASTRO J, KAJARABILLE N et al. Melatonin supplementation ameliorates oxidative stress and inflammatory signaling induced by strenuous exercise in adult human males. J Pineal Res 2011; 51:373-380.
17. GALANO A, TAN DX, REITER RJ. Melatonin as a natural ally against oxidative stress: a physicochemical examination. J Pineal Res 2011; 51:1-16.
18. BLASK DE, HILL SM, DAUCHY RT et al. Circadian regulation of molecular, dietary, and metabolic signaling mechanisms of human breast cancer growth by nocturnal melatonin signal and the consequences of its disruption by light at night. J Pineal Res 2011; 51:259-269.
19. ROSALES-CORRAL SA, ACUÑA-CASTROVIEJO D, COTO-MONTES A et al. Alzheimer's disease: pathological mechanisms and the beneficial role of melatonin. J Pineal Res 2012; 52:167 -202.
20. OLCESE JM, CAO C, MORI T et al. Protection against cognitive deficits and markers of neurodegeneration by long-term oral administration of melatonin in a transgenic model of Alzheimer disease. J Pineal Res 2009; 47:82-96.
21. TAN DX, REITER RJ, MANCHESTER LC et al. Chemical and physical properties and potential mechanisms: melatonin as a broad spectrum antioxidant and free radical scavenger. Curr Top Med Chem 2002; 2:181-197.
22. KILIC U, YILMAZ B, UGUR M et al. Evidence that membrane-bound G-protein-coupled melatonin receptors MT1 and MT2 are not involved in the neuroprotective effects of melatonin in focal cerebral ischemia. J Pineal Res 2012; 52:228-235.
23. CARILLO-VICO A, GUERRERO JM, LARDONE PJ, REITER RJ. A review of the multiple actions of melatonin on the immune system. Endocrine 2005; 27:189-200.
24. PAPPOLLA MA, BOZNER P, SOTO C et al. Inhibition of Alzheimer β-fibrillogenesis by melatonin. J Biol Chem 1998; 273:7185-7188.
25. RODRÍGUEZ-FRANCO MI, FERNÁNDEZ-BACHILLER MI, PÉREZ C, HERNÁNDEZ-LEDESMA B, BARTOLOMÉB. Novel tacrine-melatonin hybrids as dual-acting drugs for Alzheimer disease, with improved acetylcholinesterase inhibitory and antioxidant properties. J Med Chem 2006; 49:459-462.
26. FERNÁNDEZ-BACHILLER MI, PÉREZ C, CAMPILLO NE et al. Tacrine-melatonin hybrids as multifunctional agents for Alzheimer's disease, with cholinergic, antioxidant, and neuroprotective properties. ChemMedChem 2009; 4:828-841.
27. SIWICKA A, MOLȨDA Z, WOJTASIEWICZ K et al. The oxidation products of melatonin derivatives exhibit acetylcholinesterase and butyrylcholinesterase inhibitory activity. J Pineal Res 2008; 45:40-49.
28. MOLȨDA Z, WOJTASIEWICZ K, PANASIEWICZ M, PACUSZKA T, CZARNOCKI Z. Selective inhibition of butyrylcholinesterase by singlet oxygen generated melatonin derivatives. J Pineal Res 2010; 49:55-59.
29. ZAWADZKA A, CZARNOCKI Z, ŁOZIŃSKA I, MOLȨDA Z, PANASIEWICZ M. New hybrid cholinesterases inhibitors. Pat. Appl. No. P.395113 in the Patent Office of the Republic of Poland.
30. ZAWADZKA A, CZARNOCKI Z, ŁOZIŃSKA I, MOLȨDA Z, PANASIEWICZ M. Hybrid cholinesterases inhibitors. Pat. Appl. No. P.398731 in the Patent Office of the Republic of Poland.
31. HU M-K, WU L-J, HSIAO G, YEN M-H. Homodimeric tacrine congeners as acetylcholinesterase inhibitors. J Med Chem 2002; 45:2277-2282.
32. CARLIER PR, CHOW ES-H, HAN Y, LIU J, YAZAL JE, PANG Y-P. Heterodimeric tacrine-based acetylcholinesterase inhibitors: investigating ligand-peripheral site interactions. J Med Chem 1999; 42:4225-4231.
33. ELLMAN GL, COURTNEY KD, ANDERS V, FEARTHERSTONE RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961; 7:88-95.
34. BRZOSTOWSKA M, HE XS, GREIG NH, BROSSI A. Selective inhibition of acetyl- and butyrylcholinesterases by phenylcarbamates of (-)-eseroline, (-)-(N1)-noreseroline and physovenol. Med Chem Res 1992; 2:238-246.
35. ATACK JR, YU QS, SONCRANT TT, BROSSI A, RAPOPORT SI. Comparative inhibitory effects on various physostigmine analogues against acetyl and butyrylcholinesterases. J Pharmacol Exp Ther 1989; 249:194-202.