Design of new drugs for the treatment of Alzheimer's disease based on tacrine structure

Current Drug Targets

Volumn 14, Issue 3, 2013, Pages 378-397

  de Aquino, Roney A N ^a,b   Modolo, Luzia V ^a   Alves, Rosemeire B ^a   de Fátima, Ângelo ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^b CENTRO FEDERAL DE EDUCAÇÃO TECNOLÓGICA DE MINAS GERAIS   (Brazil)

Author keywords

Alzheimer's disease; Bioisosterism; Dimerization; Hybridization; Molecular simplification; Multi target directed ligands; Tacrine

Indexed keywords

ALICYCLIC COMPOUND; AMYLOID BETA PROTEIN; AMYLOID PRECURSOR PROTEIN; ANTIHISTAMINIC AGENT; BIFEMELANE; CARBAMAZEPINE; CHOLINE ACETYLTRANSFERASE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; DONEPEZIL; FERULIC ACID; FLUVOXAMINE; GALANTAMINE; GLUTAMATE DECARBOXYLASE; HISTAMINE H3 RECEPTOR; HUPERZINE A; INDELOXAZINE; NIMODIPINE; PYRAZOLE; QUINOLINE; RASAGILINE; RIVASTIGMINE; TACRINE; XANOMELINE;

ALGORITHM; ALZHEIMER DISEASE; BIOCHEMISTRY; CHEMICAL STRUCTURE; DIMERIZATION; GASTROINTESTINAL DISEASE; HUMAN; HYBRIDIZATION; LIVER TOXICITY; OXIDATIVE STRESS; PALLIATIVE THERAPY; PARKINSON DISEASE; PHARMACODYNAMICS; PHARMACOPHORE; PHYSICAL CHEMISTRY; PROTEIN PHOSPHORYLATION; RECOMMENDED DRUG DOSE; REVIEW; SINGLE DRUG DOSE; X RAY ANALYSIS;

EID: 84875226386     PISSN: 13894501     EISSN: 18735592     Source Type: Journal    
DOI: 10.2174/138945013804999043     Document Type: Review

References (79)

1. Davies P, Maloney AJ. Selective loss of central cholinergic neurons in Alzheimer's disease. Lancet 1976; 2: 1403.
2. Summers WK, Viesselman JO, Marsh GM, Candelora K. Use of THA in treatment of Alzheimer-like dementia: pilot study in twelve patients. Biol Psychiatry 1981; 16: 145-53.
3. Summers WK, Majovski VL, Marsh GM, Tachiki K, Kling A. Oral tetrahydroaminoacridine in long-term treatment of senile dementia, Alzheimer type. New Engl J Med 1986; 315: 1241-5.
4. Fu H, Dou J, Li W, et al. Promising multifunctional anti-Alzheimer's dimer bis(7)-cognitin acting as an activator of protein kinase C regulates activities of β-secretase and BACE-1 concurrently. Eur J Pharmacol 2009; 623: 14-21.
5. Li W, Mak M, Jiang H, et al. Novel anti-Alzheimer's dimer bis(7)-cognitin: cellular and molecular mechanisms of neuroprotection through multiple targets. Neurotherapeutics 2009; 6: 187-201.
6. Palma E, Conti L, Roseti C, Limatola C. Novel approaches to study the involvement of a7-nAChR in human diseases. Curr Drug Targets 2012; 13: 579-86.
7. Hernandez CM, Dineley KT. β7 Nicotinic Acetylcholine Receptors in Alzheimer's Disease: Neuroprotective, Neurotrophic or Both? Curr Drug Targets 2012; 13: 613-22.
8. Levin ED. Alpha7-nicotinic receptors and cognition. Curr Drug Targets 2012; 13: 602-6.
9. Neri M, Bonassi S, Russo P. Genetic variations in CHRNA7 or CHRFAM7 and susceptibility to dementia. Curr Drug Targets 2012; 13: 636-43.
10. Thomsen MS, Mikkelsen JD. The alpha7 nicotinic acetylcholine receptor complex: one, two or multiple drug targets? Curr Drug Targets. 2012; 13: 707-20.
11. Zheng H, Fridkin M, Youdim MBH. Novel Chelators Targeting Cell Cycle Arrest, Acetylcholinesterase, and Monoamine Oxidase for Alzheimer's Therapy. Curr Drug Targets 2012; 13: 1096-113.
12. Cramer PE, Cirrito JR, Wesson DW, et al. ApoE-directed therapeutics rapidly clear ć-amyloid and reverse deficits in AD mouse models. Science 2012; 335: 1503-6.
13. León R, Garcia AG, Marco-Contelles J. Recent advances in the multitarget-directed ligands approach for the treatment of Alzheimer's disease. Med Res Rev 2013; 33(1): 139-89
14. Lahiri DK, Farlow MR, Sambamurti K, et al. A Critical Analysis of New Molecular Targets and Strategies for Drug Developments in Alzheimer's Disease. Curr Drug Targets 2003; 4: 97-112.
15. Darreh-Shori T, Soininen H. Effects of cholinesterase inhibitors on the activities and protein levels of cholinesterases in the cerebrospinal fluid of patients with Alzheimer's disease: a review of recent clinical studies. Curr Alzheimer Res 2010; 7: 67-73.
16. Wang B, Zhou SF. Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem 2009; 16: 4066-218.
17. Patocka J, Jun D, Kuca K. Possible role of hydroxylated metabolites of tacrine in drug toxicity and therapy of Alzheimer's disease. Curr Drug Metab 2008; 9: 332-5.
18. Langmuir I. Isomorphism, isosterism and covalence. J Am Chem Soc 1919; 41: 1543-59.
19. Friedman HL. Influence of isosteric replacements upon biological activity. Washington, USA, National Academy of Science 1951; 206: 295-358.
20. Lima LM, Barreiro EJ. Bioisosterism: a useful strategy for molecular modification and drug design. Curr Med Chem 2005; 12: 23-49.
21. Barreiro EJ, Fraga CAM. Química Medicinal: As Bases Moleculares da Ação dos Fármacos, 2nd ed.; Porto Alegre: Art-Med Ltda 2008.
22. Cannon JG. In: Burgés Medicinal Chemistry and Drug Discovery, 2nd ed.; DJ Abraham, Ed.; New Jersey: Wiley-Interscience 2003; pp. 686-714.
23. Ciapetti P, Giethlen B. In: The Practice of Medicinal Chemistry, 3rd ed.; CG Wermuth, Ed.; Burlington: Academic Press 2008; pp. 290-342.
24. Hernandes MZ, Cavalcanti SM, Moreira DR, et al. Halogen atoms in the modern medicinal chemistry: hints for the drug design. Curr Drug Targets. 2010; 11(3): 303-14.
25. Sheridan RP. The most common chemical replacements in druglike compounds. J Chem Inf Comput Sci 2002; 42: 103-8.
26. Barreiro EJ, Câmara CA, Verli H, et al. Design, synthesis and pharmacological profile of new tacrine isosteres: a new class of potent and selective acetylcholinesterase inhibitors. J Med Chem 2003; 46: 1144-52.
27. Harel M, Schalk I, Ehret-Sabatier L, et al. Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase. Proc Natl Acad Sci USA 1993; 90: 9031-5.
28. Samadi A, Valderas C, de los Ríos C, et al. Cholinergic and neuroprotective drugs for the treatment of Alzheimer and neuronal vascular diseases. II. Synthesis, biological assessment, and molecular modelling of new tacrine analogs from highly substituted 2-aminopyridine-3-carbonitriles. Bioorg Med Chem 2011; 19: 122-133.
29. Silva D, Chioua M, Samadi A, et al. Synthesis and pharmacological assessment of diversely substituted pyrazolo[3,4-b]quinoline, and benzo[b]pyrazolo[4,3-g][1,8]naphthyridine derivatives. Eur J Med Chem 2011; 46: 4676-81.
30. Badran MM, Hakeem MA, Abuel-Maaty SM, El-Malah A, Salam RMA. Design, synthesis, and molecular-modeling study of aminothienopyridine analogs of tacrine for Alzheimer's disease. Arch Pharm Chem Life Sci 2010; 10: 590-601.
31. Camps P, El Achab R, Görbig DM, et al. Synthesis, in vitro pharmacology, and molecular modeling of very potent tacrinehuperzine a hybrids as Acetylcholinesterase inhibitors of potential interest for the treatment of Alzheimer's disease. J Med Chem 1999; 42: 3227-42.
32. Salaheldin AM, Oliveira-Campos AMF, Parpot P, Rodrigues LM, Oliveira MM, Peixoto F. Synthesis of new tacrine analogs from 4-amino-1H-pyrrole-3-carbonitrile. Helv Chim Acta 2010; 93: 242-8.
33. Lee HM, Song YH. Synthesis of new 4-amino-2,3,5,6,7,8-hexahydro-1H-10-thia-9-azapentaleno[1,2-b]naphthalen-5-ol derivatives. Bull Korean Chem Soc 2010; 31: 185-8.
34. Lee T, Lee D, Lee Y, Gong YD. Solid-phase synthesis of thiazolo[4,5-b]pyridine derivatives using Friedländer reaction. J Comb Chem 2010; 12: 95-9.
35. Pisoni DS, Costa JS, Gamba D, et al. Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogs from terpenic cyclanones. Eur J Med Chem 2010; 45: 526-35.
36. Costa JS, Pisoni DS, da Silva CB, Petzhold CL, Russowsky D, Ceschi MA. Lewis acid promoted Friedländer condensation reactions between anthranilonitrile and ketones for the synthesis of tacrine and its analogs. J Braz Chem Soc 2009; 20: 1448-54.
37. Ehrlich, P. Gesammelte Arbeiten zur Immunitätsforschung, A. Hirschwald: Berlin, 1904, pp. 404-442.
38. Bolognesi ML, Simoni E, Rosini M, Minarini A, Tumiatti V, Melchiorre C. Multitarget-directed ligands: innovative chemical probes and therapeutic tools against Alzheimer's disease. Curr Top Med Chem 2011; 11: 2797-806.
39. Viegas-Junior C, Danuello A, da Silva BV, Barreiro EJ, Fraga CAM. Molecular hybridization: a useful tool in the design of new drug prototypes. Curr Med Chem 2007; 14: 1829-52.
40. Scott LE, Orvig C. Medicinal inorganic chemistry approaches to passivation and removal of aberrant metal ions in disease. Chem Rev 2009; 109: 4885-910.
41. Melchiorre C, Bolognesi ML, Minarini A, Rosini M, Tumiatti V. Polyamines in drug discovery: from the universal template approach to the multitarget-directed ligand design strategy. J Med Chem 2010; 53: 5906-14.
42. Pereira JD, Caricati-Neto A, Miranda-Ferreira R, et al. Effects of novel tacripyrines ITH12117 and ITH12118 on rat vas deferens contractions, calcium transients and cholinesterase activity. Eur J Pharmacol 2011; 660: 411-19.
43. Marco-Contelles J, León R, de los Ríos C, et al. Tacripyrines, the First Tacrine-Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease. J Med Chem 2009; 52: 2724-2732.
44. Maalej E, Chabchoub F, Samadi A, et al. Synthesis, biological assessment and molecular modeling of 14-aryl-10,11,12,14-tetrahydro-9H-benzo[5,6]chromeno[2,3-b]quinolin-13-amines. Bioorg Med Chem Lett 2011; 21: 2384-88.
45. Hayour H, Bouraiou A, Bouacida S, et al. Synthesis and x-ray structures of new cycloalka[e]pyrano[2,3-b]pyridine derivatives: novel tacrine analogs. Tetrahedron Lett 2011; 52: 4868-71.
46. Inestrosa NC, Alvarez A, Dinamarca MC, Pérez-Acle T, Colombres M. Acetylcholinesterase-amyloid-beta-peptide interaction: effect of congo red and the role of the Wnt pathway. Curr Alzheimer Res 2005; 2: 301-6.
47. Inestrosa NC, Dinamarca MC, Alvarez A. Amyloid-cholinesterase interactions. FEBS J 2008; 275: 625-632.
48. Barnham KJ, Bush AI. Metals in Alzheimer's and Parkinson's diseases. Curr Opin Chem Biol 2008; 12: 222-8.
49. Zheng H, Fridkin M, Youdim MBH. Site-activated chelators derived from anti-Parkinson drug rasagiline as a potential safer and more effective approach to the treatment of Alzheimer's disease. Neurochem Res 2010; 35: 2117-23.
50. Ronco C, Sorin G, Nachon F, et al. Synthesis and structure-activity relationship of huprine derivatives as human acetylcholinesterase inhibitors. Bioorg Med Chem 2009; 17: 4523-36.
51. Camps P, El Achab R, Görbig DM, et al. New Tacrine-Huperzine A Hybrids (Huprines): Highly Potent Tight-Binding Acetylcholinesterase Inhibitors of Interest for the Treatment of Alzheimer's Disease. J Med Chem 2000; 43: 4657-66.
52. Zhou J, Hu X, Zhang H, et al. Synthesis and biological evaluation of 5,6-dihydro-benzo[c] acridin-7-ol derivatives as anti-Alzheimer's disease drugs. Lett Drug Des Discov 2009; 6: 623-8.
53. Tumiatti V, Minarini A, Bolognesi ML. Milelli A, Rosini M, Melchiorre C. Tacrine derivatives and Alzheimer's disease. Curr Med Chem 2010; 17: 1825-38.
54. Li XY, Zhang J, Dai JD, Liu XM, Li ZW. Actions of bis(7)-tacrine and tacrine on transient potassium current in rat DRG neurons and potassium current mediated by KV4.2 expressed in Xenopus oocyte. Brain Res 2010; 1318: 23-32.
55. Xie Q, Wang H, Xia A, et al. bis-(-)-nor-Meptazinols as novel nanomolar cholinesterase inhibitors with high inhibitory potency on amyloid-beta aggregation. J Med Chem 2008; 51: 2027-36.
56. Mary A, Renko DZ, Guillou C, Thal C. Potent acetylcholinesterase inhibitors: design, synthesis, and structure-activity relationships of bis-interacting ligands in the galanthamine series. Bioorg Med Chem 1998; 6: 1835-50.
57. Carlier PR, Du DM, Han YF, et al. Dimerization of an inactive fragment of huperzine A produce a drug with twice the potency of the natural product. Angew Chem Int Ed 2000; 39: 1775-7.
58. Feng S, Wang Z, He X, et al. bis-Huperzine B: highly potent and selective acetylcholinesterase inhibitors. J Med Chem 2005; 48: 655-7.
59. Bolognesi ML, Bartolini M, Mancini F, et al. Bis(7)-Tacrine derivatives as multitarget-directed ligands: Focus on anticholinesterase and antiamyloid activities. ChemMedChem 2010; 5: 1215-20.
60. Pang YP, 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: 23646-9.
61. Korabecny J, Holas O, Musilek K, et al. Synthesis and in vitro evaluation of new tacrine derivates-bis-alkylene linked 7-MEOTA. Lett Org Chem 2010; 7: 327-31.
62. Korabecny J, Musilek K, Zemek F, et al. Synthesis and in vitro evaluation of 7-methoxy-N-(pent-4-enyl)-1,2,3,4-tetrahydroacridin-9-amine-new tacrine derivate with cholinergic properties. Bioorg Med Chem Lett 2011; 21: 6563-6.
63. Ouberai M, Brannstrom K, Vestling M, et al. Clicked tacrine conjugates as acetylcholinesterase and aa-amyloid directed compounds. Org Biomol Chem 2011; 9: 1140-7.
64. Barnham KJ, Masters CL, Bush AI. Neurodegenerative diseases and oxidative stress. Nat Rev Drug Discov 2004; 3: 205-14.
65. Chen G, Bower KA, Ma C, Fang S, Thiele CJ, Luo J. Glycogen synthase kinase 3beta (GSK3beta) mediates 6-hydroxydopamineinduced neuronal death. FASEB J 2004; 18: 1162-4.
66. Kulich SM, Chu CT. Sustained extracellular signal-regulated kinase activation by 6-hydroxydopamine: implications for Parkinson's disease. J Neurochem 2001; 77: 1058-66.
67. Zhang H, Mak S, Cui W, Li W, et al. Tacrine(2)-ferulic acid, a novel multifunctional dimer, attenuates 6-hydroxydopamineinduced apoptosis in PC12 cells by activating Akt pathway. Neurochem Int 2011; 59: 981-8.
68. Fang L, Kraus B, Lehmann J, et al. Design and synthesis of tacrine-ferulic acid hybridsas multi-potent anti-Alzheimer drug candidates. Bioorg Med Chem Lett 2008; 18: 2905-9
69. Szymanski P, Karpićski A, Mikiciuk-Olasik E. Synthesis, biological activity and HPLC validation of 1,2,3,4-tetrahydroacridine derivatives as acetylcholinesterase inhibitors. Eur J Med Chem 2011; 46: 3250-7.
70. Fang L, Jumpertz S, Zhang Y, et al. Hybrid molecules from xanomeline and tacrine: enhanced tacrine actions on cholinesterases and muscarinic M1 receptors. J Med Chem 2010; 53: 2094-103.
71. Incerti M, Flammini L, Saccani F, et al. Dual-acting drugs: an in vitro study of nonimidazole histamine H3 receptor antagonists combining anticholinesterase activity. ChemMedChem 2010; 5: 1143-9.
72. de Groot A, Köfalvi A, Wade MR, et al. CB1 receptor antagonism increases hippocampal acetylcholine release: site and mechanism of action. Mol Pharmacol 2006; 70: 1236-45.
73. Lange JHM, Coolen HKAC, van der Neut MAW, et al. Design, synthesis, biological properties, and molecular modeling investigations of novel tacrine derivatives with a combination of acetylcholinesterase inhibition and cannabinoid CB1 receptor antagonism. J Med Chem 2010; 53: 1338-46.
74. Barak D, Kronman C, Ordentlich A, et al. Acetylcholinesterase peripheral anionic site degeneracy conferred by amino acid arrays sharing a common core. J Biol Chem 1994; 269: 6296-305.
75. Camps P, Formosa X, Galdeano C, et al. Pyrano[3,2-c]quinoline-6-chlorotacrine hybrids as a novel family of acetylcholinesteraseand β-amyloid-directed anti-Alzheimer compounds. J Med Chem 2009; 52: 5365-79.
76. Luo W, Li YP, He Y, et al. Synthesis and evaluation of heterobivalent tacrine derivatives as potential multi-functional anti-Alzheimer agents. Eur J Med Chem 2011; 46: 2609-16.
77. Samadi A, Marco-Contelles J, Soriano E, et al. Multipotent drugs with cholinergic and neuroprotective properties for the treatment of Alzheimer and neuronal vascular diseases. I. Synthesis, biological assessment, and molecular modeling of simple and readily available 2-aminopyridine-, and 2-chloropyridine-3,5-dicarbonitriles. Bioorg Med Chem 2010; 18: 5861-72.
78. Hu H, Song L, Fang Q, et al. Tin (IV) chloride-promoted one-pot synthesis of novel tacrine analogs. Molecules 2011; 16: 1878-87.
79. Perspicace E, Thomae D, Hamm G, Hesse S, Kirsch G, Seek P. Synthesis of substituted selenolo[3,2-d][1,2,3]triazines and [1,3]selenazolo[4,5-d][1,2,3]triazines. Synthesis 2009; 20: 3472-6.