Tacrine-NO donor and tacrine-ferulic acid hybrid molecules as new anti-Alzheimer agents: Hepatotoxicity and influence on the cytochrome P450 system in comparison to tacrine

Arzneimittel-Forschung/Drug Research

Volumn 60, Issue 5, 2010, Pages 229-237

  Lupp, Amelie ^a   Appenroth, Dorothea ^a   Fang, Lei ^a   Decker, Michael ^a   Lehmann, Jochen ^a   Fleck, Christian ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Anti Alzheimer agents; CAS 321 64 2; Cytochrome P450; Ferulic acid; NO donors; Tacrine, hepatotoxicity, hybrid molecules

Indexed keywords

CYTOCHROME P450; CYTOCHROME P450 1A1; CYTOCHROME P450 2B1; CYTOCHROME P450 3A2; FL 16; FL 38; FL 67; GLYCOGEN; HEME OXYGENASE 1; TACRINE; TACRINE DERIVATIVE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL DEATH; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INDUCTION; FEMALE; GLYCOGEN LIVER LEVEL; INFLAMMATION; LIVER CELL; LIVER TOXICITY; NONHUMAN; OXIDATIVE STRESS; PROTEIN EXPRESSION; RAT;

EID: 77953202432     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1296278     Document Type: Article

References (50)

1. Cavalli A, Bolognesi ML, Minarini A, Rosini M, Tumiatti V, Recanatini M, et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem. 2008;51:347-372 (Pubitemid 351252260)
2. Luque FA, Jaffe SL. The molecular and cellular pathogenesis of dementia of the Alzheimer's type. An overview. Int Rev Neurobiol. 2009;84:151-165
3. Mimica N, Presecki P. Side effects of approved antidementives. Psychiatr Danub. 2009;21:108-113
4. Davis KL, Thal LJ, Gamzu ER, Davis CS, Woolson RF, Gracon SI, et al. A double-blind, placebo-controlled multicenter study of tacrine for Alzheimer's disease. N Engl J Med. 1992;327:1253-1259
5. Wagstaff AJ, McTavish D. Tacrine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in Alzheimer's disease. Drugs Aging. 1994;4:510-540
6. Watkins PB, Zimmermann HJ, Knapp MJ, Gracon SI, Lewis KW. Hepatotoxic effects of tacrine administration in patients with Alzheimer's disease. JAMA. 1994;271:992-998 (Pubitemid 24099919)
7. Gracon SI, Knapp MJ, Berghoff WG, Pierce M, DeJong R, Lobbestael SJ, et al. Safety of tacrine: clinical trials, treatment IND, and postmarketing experience. Alzheimer Dis Ass Disord. 1998;12:93-101.
8. Thatcher GR, Bennett BM, Reynolds JN. Nitric oxide mimetic molecules as therapeutic agents in Alzheimer's disease. Curr Alzheimer Res. 2005;2:171-182 (Pubitemid 40862878)
9. Barone E, Calabrese V, Mancuso C. Ferulic acid and its therapeutic potential as a hormetin for age-related diseases. Biogerontology. 2009;10:97-108.
10. Wang H, Peng RX. Sodium ferulate alleviated paracetamol-induced liver toxicity in mice. Acta Pharmacol Sin. 1994;15:81-83 (Pubitemid 24033079)
11. 2 -vinyl 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (V-PYRRO/NO), protects against cadmium-induced hepatotoxicity in mice. J Pharmacol Exp Ther. 2004;310:18-24.
12. Malaguarnera L, Madeddu R, Palio E, Arena N, Malaguarnera M. Heme oxygenase-1 levels and oxidative stress-related parameters in non-alcoholic fatty liver disease patients. J Hepatol. 2005;42:585-591 (Pubitemid 40342940)
13. Correia MA. Rat and human liver cytochrome P450: substrate and inhibitor specificities and functional markers. In: Ortiz de Montellano PR, editor. Cytochrome P450: structure, mechanism and biochemistry. 2nd ed. New York and London: PlenumPress; 1995. p. 607-630
14. Lewis DFV. Guide to cytochromes P450: Structure and function. London, Washington, Bristol: Taylor & Francis; 2001.
15. Yoshida T, Kikuchi G. Reaction of the microsomal heme oxygenase with cobaltic protoporphyrin IX, an extremely poor substrate. J Biol Chem. 1978;253:8479-8482
16. Burke MD, Thompson S, Weaver RJ, Wolf CR, Mayer RT. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem Pharmacol. 1994;48:923-936
17. Smolowitz RM, Hahn ME, Stegeman JJ. Immunohistochemical localization of cytochrome P-450IA1 induced by 3,3′,4,4′ -tetrachlorobiphenyl and by 2,3,7,8-tetrachlorodi-benzofuran in liver and extrahepatic tissues of the teleost Stenotomus chrysops (scup). Drug Metab Dispos. 1991;19:113-123
18. Yagi K. Lipid peroxides and human diseases. Chem Phys Lipids. 1987;45:337-351
19. Ellman GL. Tissue sulfhydryl groups. Arch Biochem Biophys. 1959;82:70-77
20. Hissin PJ, Hilf R. A fluorometric method for determination of oxidized and reduced glutathione in tissues. Anal Biochem. 1976;74:214-226
21. Klinger W, Müller D. The influence of age on the protein concentration in serum, liver and kidney of rats determined by various methods. Z Versuchstierk. 1974;16:146-153
22. Pohl RJ, Fouts JR. A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal Biochem. 1980;107:150-155
23. Aitio A. A simple and sensitive assay of 7-ethoxycoumarin deethylation. Anal Biochem. 1978;85:488-491
24. Klinger W, Müller D. Ethylmorphine N-demethylation by liver homogenate of newborn and adult rats: enzyme kinetics and age course of Vmax and Km. Acta Biol Med Germ. 1977;36:1149-1159
25. Decker M. Recent advances in the development of hybrid molecules/designed multiple compounds with antiamnestic properties. Mini Rev Med Chem. 2007;7:221-229 (Pubitemid 46488246)
26. Rosini M, Andrisano V, Bartolini M, Bolognesi ML, Hrelia P, Minarini A, et al. Rational approach to discover multipotent anti-Alzheimer drugs. J Med Chem. 2005;48:360-363 (Pubitemid 40139781)
27. Elsinghorst PW, Cieslik JS, Mohr K, Tränkle C, Gutschow M. First gallamine-tacrine hybrid: design and characterization at cholinesterases and the M2 muscarinic receptor. J Med Chem. 2007;50:5685-5695 (Pubitemid 350106023)
28. Fernandez-Bachiller MI, Perez C, Campillo NE, Paez JA, Gonzalez-Munoz GC, Usan P, et al. Tacrine-melatonin hybrids as multifunctional agents for Alzheimer's disease, with cholinergic, antioxidant, and neuroprotective properties. J Med Chem. 2009;4:828-841
29. Marco-Contelles J, Leon R, de los Rios C, Samadi A, Bartolini M, Andrisano V, 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
30. Perissutti E, Fiorino F, Severino B, Frecentese F, Massarelli P, Nencini C, et al. Synthesis of 6β -D-glucosyl and 6-nitroxy (-)galanthamine derivatives as acetylcholinesterase inhibitors. Pharmazie. 2007:62:403-405
31. Fang L, Appenroth D, Decker M, Kiehntopf M, Lupp A, Peng S, et al. NO-donating tacrine hybrid compounds improve scopolamine-induced cognition impairment and show less hepatotoxicity. J Med Chem. 2008;51:7666-7669
32. O'Brien JT, Eagger S, Levy R. Effects of tetrahydroaminoacridine on liver function in patients with Alzheimer's disease. Age Ageing. 1991;20:129-131
33. Stachlewitz RF, Arteel GE, Raleigh JA, Connor HD, Mason RP, Thurman RG. Development and characterization of a new model of tacrine-induced hepatotoxicity: role of the sympathetic nervous system and hypoxia- reoxygenation. J Pharmacol Exp Ther. 1997;282:1591-1599
34. Dogterom P, Nagelkerke JF, Mulder GJ. Hepatotoxicity of tetrahydroaminoacridine in isolated rat hepatocytes: effect of glutathione and vitamin E. Biochem Pharmacol. 1988;37:2311-2313
35. Berson A, Renault S, Lettéron P, Robin MA, Fromenty B, Fau D, et al. Uncoupling of rat and human mitochondria: a possible explanation for tacrine-induced liver dysfunction. Gastroenterol. 1996;110:1878-1890 (Pubitemid 26169225)
36. Lagadic-Gossmann D, Missel M, Le Bot MA, Guillouzo A. Toxic effects of tacrine on primary hepatocytes and liver epithelial cells in culture. Cell Biol Toxicol. 1998;14:361-373
37. Galisteo M, Rissel M, Sergent O, Chevanne M, Cillard J, Guillouzo A, et al. Hepatotoxicity of tacrine: occurrence of membrane fluidity alterations without involvement of lipid peroxidation. JPET. 2000;294:160-167
38. Green VJ, Pirmohamed M, Kitteringham NR, Knapp MJ, Park BK. Glutathione S-transferase μ genotype (GSTM1*0) in Alzheimer's patients with tacrine transaminitis. Br J Clin Pharmacol. 1995;39:411-415
39. De Sousa M, Pirmohamed M, Kitteringham NR, Woolf T, Park BK. No association between tacrine transaminitis and the glutathione transferase θ genotype in patients with Alzheimer's disease. Pharmacogenetics. 1998;8:353-355
40. Osseni RA, Debbasch C, Christen MO, Rat P, Warnet JM. Tacrine-induced reactive oxygen species in a human liver cell line: the role of anethole dithiolethione as a scavenger. Toxicol in Vitro. 1999;13:683-688
41. Saxena G, Singh SP, Agrawal R, Nath C. Effect of donepezil and tacrine on oxidative stress in intracerebral streptozotocin-induced model of dementia in mice. Eur J Pharmacol. 2008;581:283-289
42. Forsyth DR, Wilcock GK, Morgan RA, Truman CA, Ford JM, Roberts CJC. Pharmacokinetics of tacrine hydrochloride in Alzheimer's disease. Clin Pharmacol Ther. 1989;46:634-641
43. Madden S, Woolf TF, Pool WF, Park BK. An investigation into the formation of stable, protein-reactive and cytotoxic metabolites from tacrine in vitro. Biochem Pharmacol. 1993;46:13-20.
44. Spaldin V, Madden S, Adams DA, Edwards RJ, Davies DS, Park BK. Determination of human hepatic cytochrome P4501A2 activity in vitro: use of tacrine as an isoenzyme-specific probe. Drug Metab Dispos. 1995;23:929-934
45. Fontana RJ, Turgeon DK, Woolf TF, Knapp MJ, Foster NL, Watkins PB. The caffeine breath test does not identify patients susceptible to tacrine hepatotoxicity. Hepatology. 1996;23:1429-1435
46. Benoit GG, Naud CF, Simard MA, Astier AL. Noninterference of cytochrome P4501A2 in the cytotoxicity of tacrine using genetically engineered V79 Chinese hamster cells for stable expression of the human or rat isoform and two human hepatocyte cell lines. Biochem Pharmacol. 1997;53:423-427
47. Sinz MW, Woolf TF. Characterization of the induction of rat microsomal cytochrome P450 by tacrine. Biochem Pharmacol. 1997;54:425-427
48. Danbury TC, Eccles M, Ford J, Roberts CJ. Effect of tacrine hydrochloride on hepatic drug metabolism. Eur J Drug Metab Pharmacokin. 1999;24:91-96
49. Peng JZ, Remmel RP, Sawchuk RJ. Inhibition of murine cytochrome P4501A by tacrine: in vitro studies. Drug Metab Dispos. 2004;32:805-812
50. Remmele W, Stegner HE. Vorschlag zur einheitlichen Definierung eines immunreaktiven Score (IRS) für den immunhistochemischen Östrogenrezeptornachweis (ER-ICA) im Mammakarzinomgewebe. Pathologe. 1987;8:138-140