572
Views
26
CrossRef citations to date
0
Altmetric
Research Article

Novel coumarin derivatives as potent acetylcholinesterase inhibitors: insight into efficacy, mode and site of inhibition

, , , , &
Pages 1750-1765 | Received 09 Feb 2018, Accepted 10 Apr 2018, Published online: 07 May 2018

References

  • Abraham, M. J. , Murtola, T ., Schulz, R ., Páll, S ., Smith, J. C ., Hess, B ., & Lindahl, E . (2015). GROMACS: High performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX , 1-2 , 19–25. doi:10.1016/j.softx.2015.06.001
  • Ager, R. R. , Davis, J. L. , Agazaryan, A. , Benavente, F. , Poon, W. W. , LaFerla, F. M. , & Blurton-Jones, M. (2015). Human neural stem cells improve cognition and promote synaptic growth in two complementary transgenic models of Alzheimer’s disease and neuronal loss. Hippocampus , 25 , 813–826. doi:10.1002/hipo.22405
  • Alvarez, A. , Bronfman, F. , Pérez, C. A. , Vicente, M. , Garrido, J. , & Inestrosa, N. C. (1995). Acetylcholinesterase, a senile plaque component, affects the fibrillogenesis of amyloid-β-peptides. Neuroscience Letters , 201 (1), 49–52. doi:10.1016/0304-3940(94)12127-C
  • Anand, P. , Singh, B. , & Singh, N. (2012). A review on coumarins as acetylcholinesterase inhibitors for Alzheimer’s disease. Bioorganic and Medicinal Chemistry , 20 , 1175–1180. doi:10.1016/j.bmc.2011.12.042
  • Ariga, G. G. , Naik, P. N. , Nandibewoor, S. T. , & Chimatadar, S. A. (2017). Quenching of fluorescence by meclizine, a probe study for structural and conformational changes in human serum albumin. Journal of Biomolecular Structure and Dynamics , 35 , 3161–3175. doi:10.1080/07391102.2016.1245159
  • Azam, F. , Alabdullah, N. H. , Ehmedat, H. M. , Abulifa, A. R. , Taban, I. , & Upadhyayula, S. (2017). NSAIDs as potential treatment option for preventing amyloid β toxicity in Alzheimer’s disease: An investigation by docking, molecular dynamics, and DFT studies. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2017.1338164
  • Bajda, M. , Więckowska, A. , Hebda, M. , Guzior, N. , Sotriffer, C. A. , & Malawska, B. (2013). Structure-based search for new inhibitors of cholinesterases. International Journal of Molecular Sciences , 14 , 5608–5632. doi:10.3390/ijms14035608
  • Bharti, R. , & Parvin, T. (2015). Molecular diversity from the L-proline-catalyzed, three-component reactions of 4-hydroxycoumarin, aldehyde, and 3-aminopyrazole or 1,3-dimethyl-6-aminouracil. Synthetic Communications , 45 , 1442–1450. doi:10.1080/00397911.2015.1023900
  • Birks, J. (2006). Cholinesterase inhibitors for Alzheimer’s disease. Cochrane Database of Systematic Reviews . Art. No.: CD005593. doi:10.1002/14651858.CD005593
  • Bourne, Y. , Kolb, H. C. , Radić, Z. , Sharpless, K. B. , Taylor, P. , Marchot, P. , & Marchottll, P. (2017). Freeze-frame inhibitor captures acetyicholinesterase in a unique conformation. Proceedings of the National Academy of Sciences , 101 , 1449–1454. doi:10.1073/pnas.0308206100
  • Castro, A. , & Martinez, A. (2001). Peripheral and dual binding site acetylcholinesterase inhibitors: Implications in treatment of Alzheimer’s disease. Mini Reviews in Medicinal Chemistry , 1 , 267–272. doi:10.2174/1389557013406864
  • Cazelli, D. S. P. , Barroso, M. E. S. , Pizi, R. B. , Orlandi, M. , de Souza, T. B. , Carvalho, D. T. , … Endringer, D. C. (2017). The relationship between the antimicrobial activity of eugenol and the LPETG peptide structure and associated analysis for docking purposes. Chemical Papers , 71 , 1877–1886. doi:10.1007/s11696-017-0181-0
  • Chen, Y. , Liu, Z. L. , Fu, T. M. , Li, W. , Xu, X. L. , & Sun, H. P. (2015). Discovery of new acetylcholinesterase inhibitors with small core structures through shape-based virtual screening. Bioorganic and Medicinal Chemistry Letters , 25 , 3442–3446. doi:10.1016/j.bmcl.2015.07.026
  • Colletier, J.-P. , Fournier, D. , Greenblatt, H. M. , Stojan, J. , Sussman, J. L. , Zaccai, G. , & Weik, M. (2006). Structural insights into substrate traffic and inhibition in acetylcholinesterase. The EMBO Journal , 25 , 2746–2756. doi:10.1038/sj.emboj.7601175
  • Colovic, M. B. , Krstic, D. Z. , Lazarevic-Pasti, T. D. , Bondzic, A. M. , & Vasic, V. M. (2013). Acetylcholinesterase Inhibitors: Pharmacology and Toxicology. Current Neuropharmacology , 11 , 315–335. doi:10.2174/1570159X11311030006
  • Copeland, R. A. (2013). Evaluation of enzyme inhibitors in drug discovery. A guide for medicinal chemists and pharmacologists. Methods of Biochemical Analysis . 46 . Hoboken, New Jersey: Wiley-Interscience. ISBN 0-471-68696-4
  • Craig, L. A. , Hong, N. S. , & McDonald, R. J. (2011). Revisiting the cholinergic hypothesis in the development of Alzheimer’s disease. Neuroscience and Biobehavioral Reviews , 35 , 1397–1409. doi:10.1016/j.neubiorev.2011.03.001
  • De Souza, L. G. , Rennó, M. N. , & Figueroa-Villar, J. D. (2016). Coumarins as cholinesterase inhibitors: A review. Chemico-Biological Interactions , 254 , 11–23. doi:10.1016/j.cbi.2016.05.001
  • Di Pietro, O. , Viayna, E. , Vicente-García, E. , Bartolini, M. , Ramón, R. , Juárez-Jiménez, J. , & Muñoz-Torrero, D. (2014). 1,2,3,4-Tetrahydrobenzo[h][1,6]naphthyridines as a new family of potent peripheral-to-midgorge-site inhibitors of acetylcholinesterase: Synthesis, pharmacological evaluation and mechanistic studies. European Journal of Medicinal Chemistry , 73 , 141–152. doi:10.1016/j.ejmech.2013.12.008
  • Dvir, H. , Silman, I. , Harel, M. , Rosenberry, T. L. , & Sussman, J. L. (2010). Acetycholinesterase: From 3D structure to function. Chemico-Biological Interactions , 187 , 10–22. doi:10.1016/j.cbi.2010.01.042
  • Ellman, G. L. , Courtney, K. D. , Andres, V. , & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology , 7 , 88–95. doi:10.1016/0006-2952(61)90145-9
  • Ezra, A. , Rabinovich-Nikitin, I. , Rabinovich-Toidman, P. , & Solomon, B. (2015). Multifunctional effect of human serum albumin reduces Alzheimer’s disease related pathologies in the 3xTg mouse model. Journal of Alzheimer’s Disease , 50 (1), 175–188. doi:10.3233/JAD-150694
  • Fallarero, A. , Oinonen, P. , Gupta, S. , Blom, P. , Galkin, A. , Mohan, C. G. , & Vuorela, P. M. (2008). Inhibition of acetylcholinesterase by coumarins: The case of coumarin 106. Pharmacological Research , 58 , 215–221. doi:10.1016/j.phrs.2008.08.001
  • Ferreira Neto, D. C. , Alencar Lima, J. , Diz, Sobreiro Francisco , de Almeida, J. , Costa França, T. C. , Jorge do Nascimento, C. , & Figueroa Villar, J. D. (2017). New semicarbazones as gorge-spanning ligands of acetylcholinesterase and potential new drugs against Alzheimer’s disease: Synthesis, molecular modeling, NMR, and biological evaluation. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2017.1407676
  • Francis, P. T. , Palmer, A. M. , Snape, M. , & Wilcock, G. K. (1999). The cholinergic hypothesis of Alzheimer’s disease: A review of progress. Journal of Neurology, Neurosurgery & Psychiatry , 66 , 137–147. PMID: 10071091.10.1136/jnnp.66.2.137
  • Frisch, M. J. , Trucks, G. W ., Schlegel, H. B ., Scuseria, G. E ., Robb, M. A ., Cheeseman, J. R , … Fox, D. J . (2009). Gaussian 09. 2009 . Wallingford, CT: Gaussian, Inc.
  • Frisch, M. J. , Trucks, G. W ., Schlegel, H. B ., Scuseria, G. E ., Robb, M. A ., Cheeseman, J. R , … Fox, D. J . (2016). Gaussian 16. 2016 . Wallingford, CT: Gaussian, Inc.
  • Gard, P. R. , & Rusted, J. M. (2004). Angiotensin and Alzheimer´s disease: Therapeutic prospects. Expert Review of Neurotherapeutics , 4 , 87–96. doi:10.1586/14737175.4.1.87
  • Gupta, S. , & Mohan, C. G. (2014). Dual binding site and selective acetylcholinesterase inhibitors derived from integrated pharmacophore models and sequential virtual screening. BioMed Research International , 2014 , 1–21. doi:10.1155/2014/291214
  • Gurung, A. B. , Aguan, K. , Mitra, S. , & Bhattacharjee, A. (2017). Identification of molecular descriptors for design of novel Isoalloxazine derivatives as potential Acetylcholinesterase inhibitors against Alzheimer’s disease. Journal of Biomolecular Structure and Dynamics , 35 , 1729–1742. doi:10.1080/07391102.2016.1192485
  • Hilgert, M. , Nöldner, M. , Chatterjee, S. S. , & Klein, J. (1999). KA-672 inhibits rat brain acetylcholinesterase in vitro but not in vivo . Neuroscience Letters , 263 , 193–196. doi:10.1016/S0304-3940(99)00149-4
  • Hoerr, R. , & Noeldner, M. (2002). Ensaculin (KA-672 HCl): A multitransmitter approach to dementia treatment. CNS Drug Reviews , 8 (2), 143–158 . PMID: 12177685.
  • Hojati, S. , Ghahghaei, A. , & Lagzian, M. (2017). The potential inhibitory effect of β-casein on the aggregation and deposition of Aβ 1-42 fibrils in Alzheimer’s disease: Insight from in - vitro and in - silico studies. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2017.1345326
  • Iqbal, S. , Anantha Krishnan, D. , & Gunasekaran, K. (2017). Identification of potential PKC inhibitors through pharmacophore designing, 3D-QSAR and molecular dynamics simulations targeting Alzheimer’s disease. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2017.1406824
  • Islam, M. M. , Gurung, A. B. , Bhattacharjee, A. , Aguan, K. , & Mitra, S. (2016). Human serum albumin reduces the potency of acetylcholinesterase inhibitor based drugs for Alzheimer’s disease. Chemico-Biological Interactions , 249 , 1–9. doi:10.1016/j.cbi.2016.02.012
  • Islam, M. M. , & Mitra, S. (2016). Cholinergic inhibitors replace thioflavin-T from acetylcholinesterase binding pocket: A potential fluorescence based molecular switch. Chemical Physics Letters , 664 , 63–69. doi:10.1016/j.cplett.2016.09.079
  • Islam, M. A. , & Pillay, T. S. (2018). β-secretase inhibitors for Alzheimer’s disease: Identification using pharmacoinformatics. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2018.1430619
  • Islam, M. M. , Sonu, V. K. , Gashnga, P. M. , Moyon, N. S. , & Mitra, S. (2016). Caffeine and sulfadiazine interact differently with human serum albumin: A combined fluorescence and molecular docking study. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy , 152 , 23–33. doi:10.1016/j.saa.2015.07.051
  • Jafari, F. , Samadi, S. , Nowroozi, A. , Sadrjavadi, K. , Moradi, S. , Ashrafi-Kooshk, M. R. , & Shahlaei, M. (2018). Experimental and computational studies on the binding of diazinon to human serum albumin. Journal of Biomolecular Structure and Dynamics , 36 , 1490–1510. doi:10.1080/07391102.2017.1329096
  • Jain, P. K. , & Joshi, H. (2012). Coumarin: Chemical and pharmacological profile. Journal of Applied Pharmaceutical Science , 2 (6), 236–240. doi:10.7324/JAPS.2012.2643
  • Kalaria, R. N. , Maestre, G. E. , Arizaga, R. , Friedland, R. P. , Galasko, D. , Hall, K. , … Antuono, P (2008). Alzheimer’s disease and vascular dementia in developing countries: Prevalence, management, and risk factors. The Lancet Neurology , 7 (9), 812–826. doi:10.1016/S1474-4422(08)70169-8
  • Karthikeyan, S. , Bharanidharan, G. , Mani, K. A. , Srinivasan, N. , Kesherwani, M. , Velmurugan, D. , & Ganesan, S. (2017). Determination on the binding of thiadiazole derivative to human serum albumin: A spectroscopy and computational approach. Journal of Biomolecular Structure and Dynamics , 35 (4), 817–828. doi:10.1080/07391102.2016.1162751
  • Khan, A. Y. , & Suresh Kumar, G. (2017). Exploring the binding interaction of potent anticancer drug topotecan with human serum albumin: Spectroscopic, calorimetric and fibrillation study. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2017.1359671
  • Laskowski, R. A. , & Swindells, M. B. (2011). LigPlot+: multiple ligand–protein interaction diagrams for drug discovery. Journal of Chemical Information and Modeling , 51 (10), 2778–2786. doi:10.1021/ci200227u
  • Lexa, K. W. , Dolghih, E. , & Jacobson, M. P. (2014). A structure-based model for predicting serum albumin binding. PLoS One , 9 (4), e93323. doi:10.1371/journal.pone.0093323
  • Llewellyn, D. J. , Langa, K. M. , Friedland, R. P. , & Lang, I. (2010). Serum albumin concentration and cognitive impairment. Current Alzheimer Research , 7 , 91–96. doi:10.2174/156720510790274392
  • Malik, R. , Choudhary, B. S. , Srivastava, S. , Mehta, P. , & Sharma, M. (2017). Identification of novel acetylcholinesterase inhibitors through e-pharmacophore-based virtual screening and molecular dynamics simulations. Journal of Biomolecular Structure and Dynamics , 35 , 3268–3284. doi:10.1080/07391102.2016.1253503
  • Martis, E. A. F. , Chandarana, R. C. , Shaikh, M. S. , Ambre, P. K. , D’Souza, J. S. , Iyer, K. R. , … Pissurlenkar, R. R. S. (2015). Quantifying ligand–receptor interactions for gorge-spanning acetylcholinesterase inhibitors for the treatment of Alzheimer’s disease. Journal of Biomolecular Structure and Dynamics , 33 (5), 1107–1125. doi:10.1080/07391102.2014.931824
  • McGleenon, B. M. , Dynan, K. B. , & Passmore, A. P. (1999). Acetylcholinesterase inhibitors in Alzheimer’s disease. British Journal of Clinical Pharmacology , 48 , 471–480. doi:10.1046/j.1365-2125.1999.00026.x
  • Mehta, M. , Adem, A. , & Sabbagh, M. (2012). New acetylcholinesterase inhibitors for alzheimer’s disease. International Journal of Alzheimer’s Disease , 2012 , 1–8. doi:10.1155/2012/728983
  • Morris, G. M. , Goodsell, D. S. , Halliday, R. S. , Huey, R. , Hart, W. E. , Belew, R. K. , & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry , 19 , 1639–1662. doi:10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
  • Nelson, D. L. , & Cox, M. M. (2004). Lehninger Principles of Biochemistry (4th ed.). New York, NY: W.H. Freeman.
  • Pandolfi, F. , De Vita, D. , Bortolami, M. , Coluccia, A. , Di Santo, R. , Costi, R. , … Scipione, L. (2017). New pyridine derivatives as inhibitors of acetylcholinesterase and amyloid aggregation. European Journal of Medicinal Chemistry , 141 , 197–210. doi:10.1016/j.ejmech.2017.09.022
  • Patel, C. N. , Georrge, J. J. , Modi, K. M. , Narechania, M. B. , Patel, D. P. , Gonzalez, F. J. , & Pandya, H. A. (2017). Pharmacophore-based virtual screening of catechol-o-methyltransferase (COMT) inhibitors to combat Alzheimer’s disease. Journal of Biomolecular Structure and Dynamics . doi:10.1080/07391102.2017.1404931
  • Peters, J. , Trovaslet, M. , Trapp, M. , Nachon, F. , Hill, F. , Royer, E. , … Tehei, M. (2012). Activity and molecular dynamics relationship within the family of human cholinesterases. Physical Chemistry Chemical Physics , 14 , 6764–6770. doi:10.1039/C2CP23817A
  • Pettersen, E. F. , Goddard, T. D. , Huang, C. C. , Couch, G. S. , Greenblatt, D. M. , Meng, E. C. , & Ferrin, T. E. (2004). UCSF Chimera–a visualization system for exploratory research and analysis. Journal of Computational Chemistry , 25 , 1605–1612. doi:10.1002/jcc.20084
  • Pheifer, J. H. , & Briggs, D. E. (1995). The estimation of thiols and disulphides in barley. Journal of the Institute of Brewing , 101 , 5–10. doi:10.1002/j.2050-0416.1995.tb00843.x
  • Razavi, S. F. , Khoobi, M. , Nadri, H. , Sakhteman, A. , Moradi, A. , Emami, S. , & Shafiee, A. (2013). Synthesis and evaluation of 4-substituted coumarins as novel acetylcholinesterase inhibitors. European Journal of Medicinal Chemistry , 64 , 252–259. doi:10.1016/j.ejmech.2013.03.021
  • Seeliger, D. , & de Groot, B. L. (2010). Ligand docking and binding site analysis with PyMOL and Autodock/Vina. Journal of Computer-Aided Molecular Design , 24 (5), 417–422. doi:10.1007/s10822-010-9352-6
  • Shen, Q. , Peng, Q. , Shao, J. , Liu, X. , Huang, Z. , Pu, X. , & Ma, L. (2005). Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors. European Journal of Medicinal Chemistry , 40 , 1307–1315. doi:10.1016/j.ejmech.2005.07.014
  • Gonçalves, A. S. , França, T. C. C. , & de Oliveira, O. V. (2016). Computational studies of acetylcholinesterase complexed with fullerene derivatives: A new insight for Alzheimer disease treatment. Journal of Biomolecular Structure and Dynamics , 34 , 1307–1316. doi:10.1080/07391102.2015.1077345
  • Sousa da Silva, A. W. , & Vranken, W. F. (2012). ACPYPE – AnteChamber PYthon Parser interfacE. BMC Research Notes , 5 , 367–374. doi:10.1186/1756-0500-5-367
  • Stanyon, H. F. , & Viles, J. H. (2012). Human serum albumin can regulate amyloid-β peptide fiber growth in the brain interstitium: Implications for Alzheimer disease. Journal of Biological Chemistry , 287 (33), 28163–28168. doi:10.1074/jbc.C112.360800
  • Taverna, M. , Marie, A.-L. , Mira, J.-P. , & Guidet, B. (2013). Specific antioxidant properties of human serum albumin. Annals of Intensive Care , 3 , 4. doi:10.1186/2110-5820-3-4
  • Tayeb, H. O. , Yang, H. D. , Price, B. H. , & Tarazi, F. I. (2012). Pharmacotherapies for Alzheimer’s disease: Beyond cholinesterase inhibitors. Pharmacology and Therapeutics , 134 , 8–25. doi:10.1016/j.pharmthera.2011.12.002
  • Tong, F. , Islam, R. M. , Carlier, P. R. , Ma, M. , Ekström, F. , & Bloomquist, J. R. (2013). Effects of anticholinesterases on catalysis and induced conformational change of the peripheral anionic site of murine acetylcholinesterase. Pesticide Biochemistry and Physiology , 106 , 79–84. doi:10.1016/j.pestbp.2013.04.001
  • Trott, O. , & Olson, A. J. (2010). AutoDockVina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computional Chemistry , 31 , 455–461. doi:10.1002/jcc.21334
  • Truhlar, D. G. (2009). Valence Bond Theory for Chemical Dynamics. Journal of Computational Chemistry , 28 , 73–86. doi:10.1002/jcc.20529
  • Volpe, D. A. , Hamed, S. S. , & Zhang, L. K. (2014). Use of different parameters and equations for calculation of IC50 values in efflux assays: Potential sources of variability in IC50 determination . The AAPS Journal , 16 , 172–180. doi:10.1208/s12248-013-9554-7
  • Wan, A. , Miao, Y. , Peng, L. , Cai, Y. , Chen, Y. , He, Y. , … Li, H. (2017). Binding and biologic characterization of recombinant human serum albumin-eTGFBR2 fusion protein expressed in CHO cells. Bioengineered , 8 , 600–612. doi:10.1080/21655979.2017.1292186
  • Wimo, A. , Guerchet, M. , Ali, G. C. , Wu, Y. T. , Prina, A. M. , Winblad, B. , & Prince, M. (2017). The worldwide costs of dementia 2015 and comparisons with 2010. Alzheimer’s and Dementia , 13 , 1–7. doi:10.1016/j.jalz.2016.07.150
  • Wimo, A. , Jönsson, L. , Bond, J. , Prince, M. , & Winblad, B. (2013). The worldwide economic impact of dementia 2010. Alzheimer’s and Dementia , 9 , 1–11. doi:10.1016/j.jalz.2012.11.006
  • Yang, F. , Zhang, Y. , & Liang, H. (2014). Interactive association of drugs binding to human serum albumin. International Journal of Molecular Sciences , 15 , 3580–3595. doi:10.3390/ijms15033580
  • Yesylevskyy, S. O. (2012). Pteros: Fast and easy to use open-source C++ library for molecular analysis. Journal of Computational Chemistry , 33 , 1632–1636. doi:10.1002/jcc.22989
  • Yesylevskyy, S. O. (2015). Pteros 2.0: Evolution of the fast parallel molecular analysis library for C++ and python. Journal of Computational Chemistry , 36 (19), 1480–1488. doi:10.1002/jcc.23943
  • Zemek, F. , Drtinova, L. , Nepovimova, E. , Sepsova, V. , Korabecny, J. , Klimes, J. , & Kuca, K. (2014). Outcomes of Alzheimer’s disease therapy with acetylcholinesterase inhibitors and memantine. Expert Opinion on Drug Safety , 13 , 759–774. doi:10.1517/14740338.2014.914168
  • Zergani, F. , Roohizadeh, R. , Dayer, M.-R. , Namdari, M. , Farokhnia, A. , Sobhany, Y. , & Ghayour, O. (2012). In silico study of global structure of human serum albumin. International Journal of Green Nanotechnology , 4 , 511–515. doi:10.1080/19430892.2012.739454
  • Zunszain, P. A. , Ghuman, J. , McDonagh, A. F. , & Curry, S. (2008). Crystallographic analysis of human serum albumin complexed with 4Z,15E-Bilirubin-IXα. Journal of Molecular Biology , 381 , 394–406. doi:10.1016/j.jmb.2008.06.016

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.