Observation of quantum signature in rivastigmine chemical bond break-up and quantum energetics, spectral studies of anti-Alzheimer inhibitors

References

• Ali, M. R., Sadoqi, M., Møller, S. G., Boutajangout, A., & Mezei, M. (2017). Assessing the binding of cholinesterase inhibitors by docking and molecular dynamics studies. Journal of Molecular Graphics and Modelling, 76, 36–42. doi:10.1016/j.jmgm.2017.06.027
   PubMed Web of Science ®Google Scholar
• Alonso, J. A., & March, N. H. (1983). Equivalence of ionization potential and magnitude of chemical potential in Hartree–Fock theory of atoms. The Journal of Chemical Physics, 78(3), 1382–1383. doi:10.1063/1.444878
   Web of Science ®Google Scholar
• Armakovic, S., Armakovic, S. J., Setrajcic, J. P., & Setrajcic, I. J. (2012). Active components of frequently used beta-blockers from the aspect of computational study. Journal of Molecular Modeling, 18(9), 4491–4501. doi:10.1007/s00894-012-1457-5
   PubMed Web of Science ®Google Scholar
• Bar-On, P., Millard, C. B., Harel, M., Dvir, H., Enz, A., Sussman, J. L., & Silman, I. (2002). Kinetic and structural studies on the interaction of cholinesterases with the anti-Alzheimer drug rivastigmine. Biochemistry, 41(11), 3555–3564. doi:10.1021/bi020016x
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1993). A new mixing of Hartree–Fock and local density‐functional theories. The Journal of Chemical Physics, 98(2), 1372–1377. doi:10.1063/1.464304
   Web of Science ®Google Scholar
• Binkley, J. S., Pople, J. A., & Hehre, W. J. (1980). Self-consistent molecular orbital methods. 21. Small split-valence basis sets for first-row elements. Journal of the American Chemical Society, 102(3), 939–947. doi:10.1021/ja00523a008
   Web of Science ®Google Scholar
• Bryce, R. A. (2013). The application of quantum mechanics in structure-based drug design AU-Mucs. Expert Opinion on Drug Discovery, 8(3), 263–276. doi:10.1517/17460441.2013.752812
   PubMed Web of Science ®Google Scholar
• Burcl, R., Handy, N. C., & Carter, S. (2003). Vibrational spectra of furan, pyrrole, and thiophene from a density functional theory anharmonic force field. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 59(8), 1881–1893. doi:10.1016/S1386-1425(02)00421-3
   PubMed Web of Science ®Google Scholar
• Burkert, U., & Allinger, N. L. (1982). Pitfalls in the use of the torsion angle driving method for the calculation of conformational interconversions. Journal of Computational Chemistry, 3(1), 40–46. doi:10.1002/jcc.540030108
   Web of Science ®Google Scholar
• Chai, J.-D., & Head-Gordon, M. (2008). Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Physical Chemistry Chemical Physics, 10(44), 6615–6620. doi:10.1039/b810189b
   PubMed Web of Science ®Google Scholar
• Cheng, S., Song, W., Yuan, X., & Xu, Y. (2017). Gorge motions of acetylcholinesterase revealed by microsecond molecular dynamics simulations. Scientific Reports, 7(1), 3219. doi:10.1038/s41598-017-03088-y
   PubMedGoogle Scholar
• Cheung, J., Rudolph, M. J., Burshteyn, F., Cassidy, M. S., Gary, E. N., Love, J., … Height, J. J. (2012). Structures of human acetylcholinesterase in complex with pharmacologically important ligands. Journal of Medicinal Chemistry, 55(22), 10282–10286. doi:10.1021/jm300871x
   PubMed Web of Science ®Google Scholar
• Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., & Stewart, J. J. P. (1985). Development and use of quantum mechanical molecular models. 76. AM1: A new general purpose quantum mechanical molecular model. Journal of the American Chemical Society, 107(13), 3902–3909. doi:10.1021/ja00299a024
   Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., …., Fox, D. J. (2016). Gaussian 16 Rev. B.01. Wallingford, CT: Gaussian Inc.
   Google Scholar
• Fukui, K., Yonezawa, T., & Shingu, H. (1952). A molecular orbital theory of reactivity in aromatic hydrocarbons. The Journal of Chemical Physics, 20(4), 722–725. doi:10.1063/1.1700523
   Web of Science ®Google Scholar
• Grossberg, G. T. (2003). Cholinesterase inhibitors for the treatment of Alzheimer’s disease: Getting on and staying on. Current Therapeutic Research, 64(4), 216–235. doi:10.1016/S0011-393X(03)00059-6
   PubMed Web of Science ®Google Scholar
• Halgren, T. A. (1996). Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. Journal of Computational Chemistry, 17(5–6), 490–519. doi:10.1002/(sici)1096-987x(199604)17:5/6 < 490::aid-jcc1 > 3.0.co;2-p
   Web of Science ®Google Scholar
• Hickey, A. L., & Rowley, C. N. (2014). Benchmarking quantum chemical methods for the calculation of molecular dipole moments and polarizabilities. The Journal of Physical Chemistry A, 118(20), 3678–3687. doi:10.1021/jp502475e
   PubMed Web of Science ®Google Scholar
• Khoirunisa, V., Rusydi, F., Kasai, H., Gandaryus, A. G., & Dipojono, H. K. (2016). A first principle study on the interaction between acetylcholinesterase and acetylcholine, and also rivastigmine in Alzheimer’s disease case. Journal of Physics: Conference Series, 739, 12136. doi:10.1088/1742-6596/739/1/012136
   Google Scholar
• Larkin, P. (2011). Infrared and Raman spectroscopy: Principles and spectral interpretation. (1st ed.). Amsterdam, Netherlands: Elsevier.
   Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Lee, C.-H., Lu, W., Michel, J. C., Goehring, A., Du, J., Song, X., & Gouaux, E. (2014). NMDA receptor structures reveal subunit arrangement and pore architecture. Nature, 511(7508), 191–197. doi:10.1038/nature13548
   PubMed Web of Science ®Google Scholar
• March, N. H. (2015). Is the Hartree-Fock prediction that the chemical potential µ of non-relativistic neutral atoms is equal to minus the ionisation potential I sensitive to electron correlation? AU. Physics and Chemistry of Liquids, 53(6), 696–705. doi:10.1080/00319104.2015.1029478
   Web of Science ®Google Scholar
• Maurel, F. (2015). Simulation with quantum mechanics/molecular mechanics for drug discovery AU-Barbault. Expert Opinion on Drug Discovery, 10(10), 1047–1057. doi:10.1517/17460441.2015.1076389
   PubMed Web of Science ®Google Scholar
• Mayo, S. L., Olafson, B. D., & Goddard, W. A. (1990). DREIDING: A generic force field for molecular simulations. The Journal of Physical Chemistry, 94(26), 8897–8909. doi:10.1021/j100389a010
   Web of Science ®Google Scholar
• Nascimento, É. C. M., Martins, J. B. L., dos Santos, M. L., & Gargano, R. (2008). Theoretical study of classical acetylcholinesterase inhibitors. Chemical Physics Letters, 458(4–6), 285–289. doi:10.1016/j.cplett.2008.05.006
   Web of Science ®Google Scholar
• Pearson, R. G. (1986). Absolute electronegativity and hardness correlated with molecular orbital theory. Proceedings of the National Academy of Sciences, 83(22), 8440–8441. doi:10.1073/pnas.83.22.8440
   PubMed Web of Science ®Google Scholar
• Pearson, R. G. (1995). The principle of maximum physical hardness. International Journal of Quantum Chemistry, 56(4), 211–215. doi:10.1002/qua.560560404
   Web of Science ®Google Scholar
• Pèpe, G., Siri, D., & Reboul, J.-P. (1992). The molecular electrostatic potential and drug design. Journal of Molecular Structure: Theochem, 256, 175–185. doi:10.1016/0166-1280(92)87166-W
   Google Scholar
• Petersson, G. A., & Al‐Laham, M. A. (1991). A complete basis set model chemistry. II. Open‐shell systems and the total energies of the first‐row atoms. The Journal of Chemical Physics, 94(9), 6081–6090. doi:10.1063/1.460447
   Web of Science ®Google Scholar
• Petersson, G. A., Bennett, A., Tensfeldt, T. G., Al‐Laham, M. A., Shirley, W. A., & Mantzaris, J. (1988). A complete basis set model chemistry. I. The total energies of closed‐shell atoms and hydrides of the first‐row elements. The Journal of Chemical Physics, 89(4), 2193–2218. doi:10.1063/1.455064
   Web of Science ®Google Scholar
• Pietro, W. J., Francl, M. M., Hehre, W. J., DeFrees, D. J., Pople, J. A., & Binkley, J. S. (1982). Self-consistent molecular orbital methods. 24. Supplemented small split-valence basis sets for second-row elements. Journal of the American Chemical Society, 104(19), 5039–5048. doi:10.1021/ja00383a007
   Web of Science ®Google Scholar
• Pongor, G., Pulay, P., Fogarasi, G., & Boggs, J. E. (1984). Theoretical prediction of vibrational spectra. 1. The in-plane force field and vibrational spectra of pyridine. Journal of the American Chemical Society, 106(10), 2765–2769. doi:10.1021/ja00322a006
   Web of Science ®Google Scholar
• Prasad, O., Sinkha, L., Misra, N., Narayan, V., Kumar, N., & Kumar, A. (2010). Analysis of vibrational, structural, and electronic properties of rivastigmine by density functional theory. Zhurnal Prikladnoj Spektroskopii, 77(4), 507–516.
   Google Scholar
• Rahman, A., Ali, M. T., Shawan, M. M. A. K., Sarwar, M. G., Khan, M. A. K., & Halim, M. A. (2016). Halogen-directed drug design for Alzheimer’s disease: A combined density functional and molecular docking study. SpringerPlus, 5(1), 1346. doi:10.1186/s40064-016-2996-5
   PubMedGoogle Scholar
• Rasulev, B., Turabekova, M., Gorska, M., Kulig, K., Bielejewska, A., Lipkowski, J., & Leszczynski, J. (2012). Use of quantitative structure-enantioselective retention relationship for the liquid chromatography chiral separation prediction of the series of pyrrolidin-2-one compounds. Chirality, 24(1), 72–77. doi:10.1002/chir.21028
   PubMed Web of Science ®Google Scholar
• Socrates, G. (2004). Infrared and Raman characteristic group frequencies: Tables and charts. (3rd ed.). Chichester: Wiley.
   Google Scholar
• Song, X., Jensen, M. Ø., Jogini, V., Stein, R. A., Lee, C.-H., Mchaourab, H. S., … Gouaux, E. (2018). Mechanism of NMDA receptor channel block by MK-801 and memantine. Nature, 556(7702), 515–519. doi:10.1038/s41586-018-0039-9
   PubMed Web of Science ®Google Scholar
• Spencer, C. M., & Noble, S. (1998). Rivastigmine. A review of its use in Alzheimer's disease. Drugs & Aging, 13(5), 391–411. doi:10.2165/00002512-199813050-00005
   PubMed Web of Science ®Google Scholar
• Stewart, J. J. P. (1989a). Optimization of parameters for semiempirical methods I. Method. Journal of Computational Chemistry, 10(2), 209–220. doi:10.1002/jcc.540100208
   Web of Science ®Google Scholar
• Stewart, J. J. P. (1989b). Optimization of parameters for semiempirical methods II. Applications. Journal of Computational Chemistry, 10(2), 221–264. doi:10.1002/jcc.540100209
   Web of Science ®Google Scholar
• Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461. doi:10.1002/jcc.21334
   PubMed Web of Science ®Google Scholar