Novel cholinesterase inhibitors based on O-aromatic N, N-disubstituted carbamates and thiocarbamates

Molecules

Volumn 21, Issue 2, 2016, Pages

  Krátký, Martin ^a   Štěpánková, Šárka ^b   Vorčáková, Katarína ^b   Švarcová, Markéta ^a   Vinšová, Jarmila ^c   Decker, Michael ^d  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b UNIVERSITY OF PARDUBICE   (Czech Republic)

^c J E PURKINJE UNIVERSITY   (Czech Republic)

^d NONE

Author keywords

Acetylcholinesterase; Butyrylcholinesterase; Carbamate; Enzyme inhibition; Salicylanilide; Thiocarbamate

Indexed keywords

ACETYLCHOLINESTERASE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; PROTEIN BINDING; THIOCARBAMIC ACID DERIVATIVE;

CHEMISTRY; ENZYME ACTIVE SITE; HEP-G2 CELL LINE; HUMAN; IC50; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CATALYTIC DOMAIN; CHOLINESTERASE INHIBITORS; HEP G2 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES;

EID: 84963664610     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21020191     Document Type: Article

References (36)

1. Schwarz, S.; Lucas, S.D.; Sommerwerk, S.; Csuk, R. Amino derivatives of glycyrrhetinic acid as potential inhibitors of cholinesterases. Bioorg. Med. Chem. 2014, 22, 3370-3378.
2. Saeed, A.; Mahesar, P.A.; Zaib, S.; Khan, M.S.; Matin, A.; Shahid, M.; Iqbal, J. Synthesis, cytotoxicity and molecular modelling studies of new phenylcinnamide derivatives as potent inhibitors of cholinesterases. Eur. J. Med. Chem. 2014, 78, 43-53.
3. Colovic, M.B.; Krstic, D.Z.; Lazarevic-Pasti, T.D.; Bondzic, A.M.; Vasic, V.M. Acetylcholinesterase Inhibitors: Pharmacology and Toxicology. Curr. Neuropharmacol. 2013, 11, 315-335.
4. Mesulam, M.M.; Guillozet, A.; Shaw, P.; Levey, A.; Duysen, E.G.; Lockridge, O. Acetylcholinesterase knockouts establish central cholinergic pathways and can use butyrylcholinesterase to hydrolyze acetylcholine. Neuroscience 2002, 110, 627-639.
5. Ibach, B.; Haen, E. Acetylcholinesterase inhibition in Alzheimer's disease. Curr. Pharm. Des. 2004, 10, 231-251.
6. Leger, G.C.; Massoud, F. Novel disease-modifying therapeutics for the treatment of Alzheimer's disease. Expert Rev. Clin. Pharmacol. 2013, 6, 423-442.
7. Francis, P.T.; Nordberg, A.; Arnold, S.E. A preclinical view of cholinesterase inhibitors in neuroprotection: Do they provide more than symptomatic benefits in Alzheimer's disease? Trends Pharmacol. Sci. 2005, 26, 104-111.
8. Chaudhaery, S.S.; Roy, K.K.; Shakya, N.; Saxena, G.; Sammi, S.R.; Nazir, A.; Nath, C.; Saxena, A.K. Novel Carbamates as Orally Active Acetylcholinesterase Inhibitors Found to Improve Scopolamine-Induced Cognition Impairment: Pharmacophore-Based Virtual Screening, Synthesis, and Pharmacology. J. Med. Chem. 2010, 53, 6490-6505.
9. Wieckowska, A.; Bajda, M.; Guzior, N.; Malawska, B. Novel alkyl- and arylcarbamate derivatives with N-benzylpiperidine and N-benzylpiperazine moieties as cholinesterases inhibitors. Eur. J. Med. Chem. 2010, 45, 5602-5611.
10. Imramovský, A.; Pejchal, V.; Štěpánková, Š.; Vorcáková, K.; Jampílek, J.; Vančo, J.; Šimůnek, P.; Královec, K.; Brůcková, L.; Mandíková, J.; et al. Synthesis and in vitro evaluation of new derivatives of 2-substituted-6-fluorobenzo[d]thiazoles as cholinesterase inhibitors. Bioorg. Med. Chem. 2013, 21, 1735-1748.
11. Yuan, W.; Shang, Z.; Qiang, X.; Tan, Z.; Deng, Y. Synthesis of pterostilbene and resveratrol carbamate derivatives as potential dual cholinesterase inhibitors and neuroprotective agents. Res. Chem. Intermed. 2014, 40, 787-800.
12. Gocer, H.; Akincioglu, A.; Goksu, S.; Gulcin, I.; Supuran, C.T. Carbonic anhydrase and acetylcholinesterase inhibitory effects of carbamates and sulfamoylcarbamates. J. Enzyme Inhib. Med. Chem. 2015, 3, 316-320.
13. Pohanka, M. Cholinesterases, a target of pharmacology and toxicology. Biomed. Pap. 2011, 155, 219-229.
14. Imramovsky, A.; Stepankova, S.; Vanco, J.; Pauk, K.; Monreal-Ferriz, J.; Vinsova, J.; Jampilek, J. Acetylcholinesterase-Inhibiting Activity of Salicylanilide N-Alkylcarbamates and Their Molecular Docking. Molecules 2012, 17, 10142-10158.
15. Lin, G.; Lai, C.Y.; Liao, W.C. Molecular Recognition by Acetylcholinesterase at the Peripheral Anionic Site: Structure-Activity Relationships for Inhibitions by Aryl Carbamates. Bioorg. Med. Chem. 1999, 7, 2683-2689.
16. Krátký, M.; Vinšová, J. Salicylanilide Ester Prodrugs as Potential Antimicrobial Agents - A Review. Curr. Pharm. Des. 2011, 17, 3494-3505.
17. Krátký, M.; Vinšová, J.; Novotná, E.; Wsól, V.; Ulmann, V.; Stolaříková, J.; Fernandes, S.; Bhat, S.; Liu, J.O. Salicylanilide derivatives block Mycobacterium tuberculosis through inhibition of isocitrate lyase and methionine aminopeptidase. Tuberculosis (Edinb.) 2012, 92, 434-439.
18. Krátký, M.; Vinšová, J.; Novotná, E.; Mandíková, J.; Trejtnar, F.; Stolaříková, J. Antibacterial Activity of Salicylanilide 4-(Trifluoromethyl)benzoates. Molecules 2013, 18, 3674-3688.
19. Krátký, M.; Volková, M.; Novotná, E.; Trejtnar, F.; Stolaříková, J.; Vinšová, J. Synthesis and Biological Activity of New Salicylanilide N, N-Disubstituted Carbamates and Thiocarbamates. Bioorg. Med. Chem. 2014, 22, 4073-4082.
20. Krátký, M.; Vinšová, J.; Novotná, E.; Stolafíková, J. Salicylanilide pyrazinoates inhibit in vitro multidrug-resistant Mycobacterium tuberculosis strains, atypical mycobacteria and isocitrate lyase. Eur. J. Pharm. Sci. 2014, 53, 1-9.
21. Krátký, M.; Novotná, E.; Saxena, S.; Yogeeswari, P.; Sriram, D.; Švarcová, M.; Vinšová, J. Salicylanilide Diethyl Phosphates as Potential Inhibitors of Some Mycobacterial Enzymes. Sci. World J. 2014, 2014, doi:10.1155/2014/703053.
22. Chen, C.L.; Liu, F.L.; Lee, C.C.; Chen, T.C.; Ali, A.A.A.; Sytwu, H.K.; Chang, D.M.; Huang, H.S. Modified Salicylanilide and 3-Phenyl-2H-benzo[e][1,3]oxazine-2,4(3H)-dione Derivatives as Novel Inhibitors of Osteoclast Differentiation and Bone Resorption. J. Med. Chem. 2014, 57, 8072-8085.
23. Vinšová, J.; Krátký, M.; Komlóová, M.; Dadapeer, E.; Štěpánková, Š.; Vorcáková, K.; Stolafíková, J. Diethyl 2-(Phenylcarbamoyl)phenyl Phosphorothioates: Synthesis, Antimycobacterial Activity and Cholinesterase Inhibition. Molecules 2014, 19, 7152-7168.
24. Vinšová, J.; Kozic, J.; Krátký, M.; Stolafíková, J.; Mandíková, J.; Trejtnar, F.; Buchta, V. Salicylanilide diethyl phosphates: Synthesis, antimicrobial activity and cytotoxicity. Bioorg. Med. Chem. 2014, 22, 728-737.
25. Ou, S.Y.; Kwok, K.C.; Wang, Y.; Bao, H.Y. An improved method to determine SH and -S-S- group content in soymilk protein. Food Chem. 2004, 88, 317-320.
26. Sinko, G.; Calic, M.; Bosak, A.; Kovarik, Z. Limitation of the Ellman method: Cholinesterase activity measurement in the presence of oximes. Anal. Biochem. 2007, 370, 223-227.
27. Zdrazilova, P.; Stepankova, S.; Komers, K.; Ventura, K.; Cegan, A. Half-inhibition concentrations of new cholinesterase inhibitors. Z. Naturforsch. C 2004, 59, 293-296.
28. Pettersen, E.F.; Goddard, T.D.; Huang, C.C.; Couch, G.S.; Greenblatt, D.M.; Meng, E.C.; Ferrin, T.E. UCSF Chimera - A visualization system for exploratory research and analysis. J. Comput. Chem. 2004, 25, 1605-1612.
29. Trott, O.; Olson, A.J. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 2010, 31, 455-461.
30. Morris, G.M.; Huey, R.; Lindstrom, W.; Sanner, M.F.; Belew, R.K.; Goodsell, D.S.; Olson, A.J. Autodock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J. Comput. Chem. 2009, 30, 2785-2791.
31. Sussman, J.L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Atomic structure of acetylcholinesterase from Torpedo californica: A prototypic acetylcholine-binding protein. Science 1991, 253, 872-879.
32. Harel, M.; Schalk, I.; Ehret-Sabatier, L.; Bouet, F.; Goeldner, M.; Hirth, C.; Axelsen, P.; Silman, I.; Sussman, J.L. Quaternary ligand binding to aromatic residues in the active-site gorge of acetylcholinesterase. Proc. Natl. Acad. Sci. USA 1993, 90, 9031-9035.
33. Axelsen, P.H.; Harel, M.; Silman, I.; Sussman, J.L. Structure and dynamics of the active site gorge of acetylcholinesterase: Synergistic use of molecular dynamics simulation and X-ray crystallography. Protein Sci. 1994, 3, 188-197.
34. Johnson, G.; Moore, S.W. The peripheral anionic site of acetylcholinesterase: Structure, functions and potential role in rational drug design. Curr. Pharm. Des. 2006, 12, 217-225.
35. Nicolet, Y.; Lockridge, O.; Masson, P.; Fontecilla-Camps, J.C.; Nachon, F. Crystal structure of human butyrylcholinesterase and of its complexes with substrate and products. J. Biol. Chem. 2003, 278, 41141-41147.
36. Saxena, A.; Redman, A.M.; Jiang, X.; Lockridge, O.; Doctor, B.P. Differences in active-site gorge dimensions of cholinesterases revealed by binding of inhibitors to human butyrylcholinesterase. Chem. Biol. Interact. 1999, 119, 61-69.