Use of connectivity index and simple topological parameters for estimating the inhibition potency of acetylcholinesterase

Atanasova, 2015, Galantamine derivatives with indole moiety: docking, design, synthesis and acetylcholinesterase inhibitory activity, Bioorg. Med. Chem., 23, 5382, 10.1016/j.bmc.2015.07.058 Bosak, 2017, Resorcinol-, catechol- and saligenin-based bronchodilating β2-agonists as inhibitors of human cholinesterase activity, J. Enzyme Inhib. Med. Chem., 32, 789, 10.1080/14756366.2017.1326109 Bosak, 2019, Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase, Chem. Biol. Interact., 308, 101, 10.1016/j.cbi.2019.05.024 Bourne, 2010, Conformational remodeling of femtomolar inhibitor−acetylcholinesterase complexes in the crystalline state, J. Am. Chem. Soc., 132, 18292, 10.1021/ja106820e Bourne, 2016, Steric and dynamic parameters influencing in situ cycloadditions to form triazole inhibitors with crystalline acetylcholinesterase, J. Am. Chem. Soc., 138, 1611, 10.1021/jacs.5b11384 Bušić, 2016, Pyridoxal oxime derivative potency to reactivate cholinesterases inhibited by organophosphorus compounds, Toxicol. Lett., 262, 114, 10.1016/j.toxlet.2016.09.015 Cheung, 2012, Structures of human acetylcholinesterase in complex with pharmacologically important ligands, J. Med. Chem., 55, 10282, 10.1021/jm300871x Colletier, 2006, Structural insights into substrate traffic and inhibition in acetylcholinesterase, EMBO J., 25, 2746, 10.1038/sj.emboj.7601175 Ellman, 1961, A new and rapid colorimetric determination of acetylcholinesterase activity, Biochem. Pharmacol., 7, 88, 10.1016/0006-2952(61)90145-9 Eyer, 2003, Molar absorption coefficients for the reduced Ellman reagent: reassessment, Anal. Biochem., 312, 224, 10.1016/S0003-2697(02)00506-7 Fekonja, 2007, Inhibition and protection of cholinesterases by methanol and ethanol, J. Enzyme Inhib. Med. Chem., 22, 407, 10.1080/14756360601143857 Felder, 2002, Structure of a complex of the potent and specific inhibitor BW284C51 with Torpedo californica acetylcholinesterase, Acta Crystallogr. Sect. D Biol. Crystallogr., 58, 1765, 10.1107/S0907444902011642 Gerlits, 2019, A new crystal form of human acetylcholinesterase for exploratory room-temperature crystallography studies, Chem. Biol. Interact., 309, 108698, 10.1016/j.cbi.2019.06.011 Giacobini, 2006, Cholinesterases in human brain: the effect of cholinesterase inhibitors on Alzheimer’s disease and related disorders, 235 Gurung, 2017, Identification of molecular descriptors for design of novel Isoalloxazine derivatives as potential Acetylcholinesterase inhibitors against Alzheimer’s disease, J. Biomol. Struct. Dyn., 35, 1729, 10.1080/07391102.2016.1192485 Herkert, 2011, In vitro kinetic interactions of pyridostigmine, physostigmine and soman with erythrocyte and muscle acetylcholinesterase from different species, Toxicol. Lett., 206, 41, 10.1016/j.toxlet.2011.03.004 Jana, 2018, Multiple 3D-QSAR modeling, e-pharmacophore, molecular docking, and in vitro study to explore novel AChE inhibitors, RSC Adv., 8, 39477, 10.1039/C8RA08198K Mati Karelson, 2000. No TitleMolecular Descriptors in QSAR/QSPR, 1st editio. ed. Wiley-Interscience, New York. <https://doi.org/9>. Katalinić, 2010, Structural aspects of flavonoids as inhibitors of human butyrylcholinesterase, Eur. J. Med. Chem., 45, 186, 10.1016/j.ejmech.2009.09.041 Katalinić, 2016, A comprehensive evaluation of novel oximes in creation of butyrylcholinesterase-based nerve agent bioscavengers, Toxicol. Appl. Pharmacol., 310, 195, 10.1016/j.taap.2016.09.015 Kier, 1976 Kier, 1976, Molecular connectivity vii: specific treatment of heteroatoms, J. Pharm. Sci., 65, 1806, 10.1002/jps.2600651228 Kier, 1986 Kovarik, 2008, In vitro evaluation of aldoxime interactions with human acetylcholinesterase, Croat. Chem. Acta, 81, 47 Kubinyi, H., 1993. QSAR: Hansch Analysis and Related Approaches, Methods and Principles in Medicinal Chemistry. Wiley, Weinheirn. <https://doi.org/10.1002/9783527616824>. Kumar, 2017, DMSO: a mixed-competitive inhibitor of human acetylcholinesterase, ACS Chem. Neurosci., 8, 2618, 10.1021/acschemneuro.7b00344 Kumar, 2020, In silico modeling for dual inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes in Alzheimer’s disease, Comput. Biol. Chem., 88, 107355, 10.1016/j.compbiolchem.2020.107355 Leach, 1996 Lučić, 1999, Multivariate regression outperforms several robust architectures of neural networks in QSAR modeling, J. Chem. Inf. Comput. Sci., 39, 121, 10.1021/ci980090f Maček Hrvat, 2018, The estimation of oxime efficiency is affected by the experimental design of phosphylated acetylcholinesterase reactivation, Toxicol. Lett., 293, 222, 10.1016/j.toxlet.2017.11.022 Maček Hrvat, 2020, Evaluation of high-affinity phenyltetrahydroisoquinoline aldoximes, linked through anti-triazoles, as reactivators of phosphylated cholinesterases, Toxicol. Lett., 321, 83, 10.1016/j.toxlet.2019.12.016 Maraković, 2016, Design and synthesis of N-substituted-2-hydroxyiminoacetamides and interactions with cholinesterases, Chem. Biol. Interact., 259, 122, 10.1016/j.cbi.2016.05.035 Maraković, 2020, Enantioseparation, in vitro testing, and structural characterization of triple-binding reactivators of organophosphate-inhibited cholinesterases, Biochem. J., 477, 2771, 10.1042/BCJ20200192 Mary, 1998, Potent acetylcholinesterase inhibitors: design, synthesis, and structure–activity relationships of bis-interacting ligands in the galanthamine series, Bioorg. Med. Chem., 6, 1835, 10.1016/S0968-0896(98)00133-3 Miličević, 2008, Influence of chelate ring interactions on copper(II) chelate stability studied by connectivity index functions, J. Phys. Chem. A, 112, 7745, 10.1021/jp802018m Miličević, 2021, RETRACTED: Development of a simple QSAR model for reliable evaluation of acetylcholinesterase inhibitor potency, Eur. J. Pharm. Sci., 160, 105757, 10.1016/j.ejps.2021.105757 Mohammad, 2017, Acetylcholinesterase inhibitors for treating dementia symptoms - a safety evaluation, Exp. Opin. Drug Saf., 16, 1009, 10.1080/14740338.2017.1351540 Niu, 2017, 2D-SAR and 3D-QSAR analyses for acetylcholinesterase inhibitors, Mol. Divers., 21, 413, 10.1007/s11030-017-9732-0 Online SMILES Translator and Structure File Generator, 2020. Ordentlich, 1993, Dissection of the human acetylcholinesterase active center determinants of substrate specificity. Identification of residues constituting the anionic site, the hydrophobic site, and the acyl pocket, J. Biol. Chem., 268, 17083, 10.1016/S0021-9258(19)85305-X Rahman, 2006, New natural cholinesterase inhibiting and calcium channel blocking quinoline alkaloids, J. Enzyme Inhib. Med. Chem., 21, 703, 10.1080/14756360600889708 Randić, 2008, On history of the Randić index and emerging hostility toward chemical graph theory, MATCH Commun. Math. Comput. Chem., 59, 5 Raos, 2016, How reliable are models based on topological index 3χv for the prediction of stability constants?, Croat. Chem. Acta, 89, 1, 10.5562/cca2723 Raos, 2008, The use of graph-theoretical models to evaluate two electroanalytical methods for determination of stability constants, Croat. Chem. Acta, 81, 511 Rappaport, 1959, An improved method for the estimation of cholinesterase activity in serum, Clin. Chim. Acta, 4, 227, 10.1016/0009-8981(59)90134-2 Reiner, 2000, Comparison of protocols for measuring activities of human blood cholinesterases by the Ellman method, Arh. Hig. Rada Toksikol., 51, 13 Rydberg, 2006, Complexes of alkylene-linked tacrine dimers with torpedo c alifornica acetylcholinesterase: binding of Bis(5)-tacrine produces a dramatic rearrangement in the active-site gorge, J. Med. Chem., 49, 5491, 10.1021/jm060164b Sanad, 2021, Novel nicotinonitrile-coumarin hybrids as potential acetylcholinesterase inhibitors: design, synthesis, in vitro and in silico studies, J. Iran. Chem. Soc., 18, 213, 10.1007/s13738-020-02018-6 Saxena, 1999, Differences in active-site gorge dimensions of cholinesterases revealed by binding of inhibitors to human butyrylcholinesterase, Chem. Biol. Interact., 119–120, 61, 10.1016/S0009-2797(99)00014-9 Selassie, C., Verma, R.P., 2010. History of quantitative structure-activity relationships. In: Burger’s Medicinal Chemistry and Drug Discovery. John Wiley & Sons, Inc., Hoboken, NJ, USA. <https://doi.org/10.1002/0471266949.bmc001.pub2>. Sharma, 1997, Eccentric connectivity index: a novel highly discriminating topological descriptor for structure−property and structure−activity studies, J. Chem. Inf. Comput. Sci., 37, 273, 10.1021/ci960049h Shityakov, 2014, Three-dimensional quantitative structure-activity relationship and docking studies in a series of anthocyanin derivatives as cytochrome P450 3A4 inhibitors, Adv. Appl. Bioinforma. Chem., 11 Simeon-Rudolf, 2001, Inhibition of human blood acetylcholinesterase and butyrylcholinesterase by ethopropazine, Croat. Chem. Acta, 74, 173 Šinko, 2019, Assessment of scoring functions and in silico parameters for AChE-ligand interactions as a tool for predicting inhibition potency, Chem. Biol. Interact., 308, 216, 10.1016/j.cbi.2019.05.047 Šinko, 2006, para - and ortho -Pyridinium aldoximes in reaction with acetylthiocholine, FEBS Lett., 580, 3167, 10.1016/j.febslet.2006.04.070 Šinko, 2007, Limitation of the Ellman method: Cholinesterase activity measurement in the presence of oximes, Anal. Biochem., 370, 223, 10.1016/j.ab.2007.07.023 Šinko, 2010, Interactions of pyridinium oximes with acetylcholinesterase, Chem. Biol. Interact., 187, 172, 10.1016/j.cbi.2010.04.017 Sussman, 1991, Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein, Science (80-)., 253, 872, 10.1126/science.1678899 Tetko, 2005, Virtual computational chemistry laboratory – design and description, J. Comput. Aided. Mol. Des., 19, 453, 10.1007/s10822-005-8694-y Wong, 2014, QSAR analysis on tacrine-related acetylcholinesterase inhibitors, J. Biomed. Sci., 21, 84, 10.1186/s12929-014-0084-0 Xie, 2020, Progress in target drug molecules for Alzheimer’s disease, Curr. Top. Med. Chem., 20, 4, 10.2174/1568026619666191203113745 Zandona, 2020, Targeting organophosphorus compounds poisoning by novel quinuclidine-3 oximes: development of butyrylcholinesterase-based bioscavengers, Arch. Toxicol., 94, 3157, 10.1007/s00204-020-02811-5