Small molecular floribundiquinone B derived from medicinal plants inhibits acetylcholinesterase activity

Being a neurodegenerative disorder, Alzheimer's disease (AD) is the one of the most terrible diseases. And acetylcholinesterase (AChE) is considered as an important target for treating AD. Acetylcholinesterase inhibitors (AChEI) are considered to be one of the effective drugs for the treatment of AD. The aim of this study is to find a novel potential AChEI as a drug for the treatment of AD. In this study, instead of using the synthetic compounds, we used those extracted from plants to investigate the interaction between floribundiquinone B (FB) and AChE by means of both the experimental approach such as fluorescence spectra, ultraviolet-visible (UV-vis) absorption spectrometry, circular dichroism (CD) and the theoretical approaches such as molecular docking. The findings reported here have provided many useful clues and hints for designing more effective and less toxic drugs against Alzheimer's disease.

[1]  Zoran Radić,et al.  Structural insights into ligand interactions at the acetylcholinesterase peripheral anionic site , 2003, The EMBO journal.

[2]  K. Chou,et al.  Prediction of the tertiary structure of a caspase‐9/inhibitor complex , 2000, FEBS letters.

[3]  J. Hardy,et al.  The Amyloid Hypothesis of Alzheimer ’ s Disease : Progress and Problems on the Road to Therapeutics , 2009 .

[4]  K. Chou,et al.  Insights from investigating the interaction of oseltamivir (Tamiflu) with neuraminidase of the 2009 H1N1 swine flu virus. , 2009, Biochemical and biophysical research communications.

[5]  N. Cutler,et al.  Galantamine hydrobromide: an agent for Alzheimer's disease. , 2003, American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists.

[6]  K. Chou,et al.  The biological functions of low‐frequency vibrations (phonons). VI. A possible dynamic mechanism of allosteric transition in antibody molecules , 1987, Biopolymers.

[7]  M Farlow,et al.  A controlled trial of tacrine in Alzheimer's disease. The Tacrine Study Group. , 1992, JAMA.

[8]  A. Cavalli,et al.  Acetylcholinesterase inhibitors: SAR and kinetic studies on omega-[N-methyl-N-(3-alkylcarbamoyloxyphenyl)methyl]aminoalkoxyaryl derivatives. , 2001, Journal of medicinal chemistry.

[9]  K. Chou,et al.  Prediction of the tertiary structure and substrate binding site of caspase‐8 , 1997, FEBS letters.

[10]  K. Chou,et al.  Prediction of protein structural classes. , 1995, Critical reviews in biochemistry and molecular biology.

[11]  K. Chou,et al.  iRNA-PseColl: Identifying the Occurrence Sites of Different RNA Modifications by Incorporating Collective Effects of Nucleotides into PseKNC , 2017, Molecular therapy. Nucleic acids.

[12]  K. Chou,et al.  Low-frequency collective motion in biomacromolecules and its biological functions. , 1988, Biophysical chemistry.

[13]  K. Goa,et al.  Galantamine , 2000, Drugs.

[14]  Kuo-Chen Chou,et al.  Energetic analysis of the two controversial drug binding sites of the M2 proton channel in influenza A virus. , 2009, Journal of theoretical biology.

[15]  Th. Förster Zwischenmolekulare Energiewanderung und Fluoreszenz , 1948 .

[16]  K. Chou,et al.  iPGK-PseAAC: Identify Lysine Phosphoglycerylation Sites in Proteins by Incorporating Four Different Tiers of Amino Acid Pairwise Coupling Information into the General PseAAC. , 2017, Medicinal chemistry (Shariqah (United Arab Emirates)).

[17]  K. Chou,et al.  iNitro-Tyr: Prediction of Nitrotyrosine Sites in Proteins with General Pseudo Amino Acid Composition , 2014, PloS one.

[18]  Kuo-Chen Chou,et al.  Binding mechanism of coronavirus main proteinase with ligands and its implication to drug design against SARS , 2003, Biochemical and Biophysical Research Communications.

[19]  K. Chou,et al.  Progress in computational approach to drug development against SARS. , 2006, Current medicinal chemistry.

[20]  Kuo-Chen Chou,et al.  Modeling the tertiary structure of human cathepsin-E. , 2005, Biochemical and biophysical research communications.

[21]  Joseph R. Lakowicz,et al.  Principles of Fluorescence Spectroscopy, Third Edition , 2008 .

[22]  M. Gütschow,et al.  Novel heterobivalent tacrine derivatives as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase. , 2006, Journal of medicinal chemistry.

[23]  K. Chou,et al.  A Model for Structure-Dependent Binding of Congo Red to Alzheimer β-Amyloid Fibrils , 1998, Neurobiology of Aging.

[24]  Kuo-Chen Chou,et al.  An Unprecedented Revolution in Medicinal Chemistry Driven by the Progress of Biological Science. , 2017, Current topics in medicinal chemistry.

[25]  Guo-Ping Zhou,et al.  3D structural conformation and functional domains of polysialyltransferase ST8Sia IV required for polysialylation of neural cell adhesion molecules. , 2015, Protein and peptide letters.

[26]  Thomas J. Raub,et al.  Determination of the Affinity of Drugs toward Serum Albumin by Measurement of the Quenching of the Intrinsic Tryptophan Fluorescence of the Protein , 1999, The Journal of pharmacy and pharmacology.

[27]  Liangliang Kong,et al.  Architecture of the Mitochondrial Calcium Uniporter , 2016, Nature.

[28]  R. Cramer,et al.  Topomer CoMFA: a design methodology for rapid lead optimization. , 2003, Journal of medicinal chemistry.

[29]  K. Chou,et al.  Design Novel Dual Agonists for Treating Type-2 Diabetes by Targeting Peroxisome Proliferator-Activated Receptors with Core Hopping Approach , 2012, PloS one.

[30]  X. Tang,et al.  Anticholinesterase effects of huperzine A, E2020, and tacrine in rats. , 1998, Zhongguo yao li xue bao = Acta pharmacologica Sinica.

[31]  K. Chou,et al.  The biological functions of low-frequency vibrations (phonons). 4. Resonance effects and allosteric transition. , 1984, Biophysical chemistry.

[32]  M. Xie,et al.  Interaction between hesperetin and human serum albumin revealed by spectroscopic methods. , 2005, Biochimica et biophysica acta.

[33]  Kuo-Chen Chou,et al.  Theoretical studies of Alzheimer's disease drug candidate 3-[(2,4-dimethoxy)benzylidene]-anabaseine (GTS-21) and its derivatives. , 2005, Biochemical and biophysical research communications.

[34]  Gerhard Wagner,et al.  Solution Structure of the RAIDD CARD and Model for CARD/CARD Interaction in Caspase-2 and Caspase-9 Recruitment , 1998, Cell.

[35]  Kuo-Chen Chou,et al.  Docking and molecular dynamics study on the inhibitory activity of novel inhibitors on epidermal growth factor receptor (EGFR). , 2011, Medicinal chemistry (Shariqah (United Arab Emirates)).

[36]  S. Yoshida,et al.  Antiamnesic and cholinomimetic side-effects of the cholinesterase inhibitors, physostigmine, tacrine and NIK-247 in rats. , 1993, European journal of pharmacology.

[37]  J. Chou,et al.  Unusual architecture of the p7 channel from hepatitis C virus , 2013, Nature.

[38]  K. Chou,et al.  A pharmacophore model specific to active site of CYP1A2 with a novel molecular modeling explorer and CoMFA. , 2012, Medicinal chemistry (Shariqah (United Arab Emirates)).

[39]  K. Chou Impacts of bioinformatics to medicinal chemistry. , 2015, Medicinal chemistry (Shariqah (United Arab Emirates)).

[40]  Kuo-Chen Chou,et al.  Multiple field three dimensional quantitative structure–activity relationship (MF‐3D‐QSAR) , 2008, J. Comput. Chem..

[41]  S. Harrison,et al.  Mitochondrial uncoupling protein 2 structure determined by NMR molecular fragment searching , 2011, Nature.

[42]  Kuo-Chen Chou,et al.  Prediction of the Tertiary Structure of the β-Secretase Zymogen☆ , 2002 .

[43]  J. Chou,et al.  Structure and mechanism of the M2 proton channel of influenza A virus , 2008, Nature.

[44]  Kuo-Chen Chou,et al.  Insights from modeling the tertiary structure of human BACE2. , 2004, Journal of proteome research.

[45]  Kuo-Chen Chou,et al.  Insights from Modeling the 3D Structure of New Delhi Metallo-β-Lactamse and Its Binding Interactions with Antibiotic Drugs , 2011, PloS one.

[46]  Kuo-Chen Chou,et al.  Insights into the Mutation-Induced HHH Syndrome from Modeling Human Mitochondrial Ornithine Transporter-1 , 2012, PloS one.

[47]  K. Chou,et al.  iSNO-AAPair: incorporating amino acid pairwise coupling into PseAAC for predicting cysteine S-nitrosylation sites in proteins , 2013, PeerJ.

[48]  Royer,et al.  Fluorescence spectroscopy as a tool to investigate protein interactions. , 1997, Current opinion in biotechnology.

[49]  Junying Yuan,et al.  Solution Structure of BID, an Intracellular Amplifier of Apoptotic Signaling , 1999, Cell.

[50]  Ren Long,et al.  iRSpot-EL: identify recombination spots with an ensemble learning approach , 2017, Bioinform..

[51]  Jian-shuang Jiang,et al.  Anthraquinone-benzisochromanquinone dimers from the roots of Berchemia floribunda. , 2008, Chemical & pharmaceutical bulletin.

[52]  Kuo-Chen Chou,et al.  iRNA-2methyl: Identify RNA 2'-O-methylation Sites by Incorporating Sequence-Coupled Effects into General PseKNC and Ensemble Classifier. , 2017, Medicinal chemistry (Shariqah (United Arab Emirates)).

[53]  Kuo-Chen Chou,et al.  iATC-mISF: a multi-label classifier for predicting the classes of anatomical therapeutic chemicals , 2017, Bioinform..

[54]  K. Chou,et al.  Low-frequency resonance and cooperativity of hemoglobin. , 1989, Trends in biochemical sciences.

[55]  K. Chou Structural bioinformatics and its impact to biomedical science. , 2004, Current medicinal chemistry.

[56]  Guo-Ping Zhou,et al.  Characterization by NMR and molecular modeling of the binding of polyisoprenols and polyisoprenyl recognition sequence peptides: 3D structure of the complexes reveals sites of specific interactions. , 2003, Glycobiology.

[57]  K. Courtney,et al.  A new and rapid colorimetric determination of acetylcholinesterase activity. , 1961, Biochemical pharmacology.

[58]  Kathryn Ziegler-Graham,et al.  Forecasting the global burden of Alzheimer’s disease , 2007, Alzheimer's & Dementia.

[59]  Kuo-Chen Chou,et al.  Designing Inhibitors of M2 Proton Channel against H1N1 Swine Influenza Virus , 2010, PloS one.

[60]  Wei Chen,et al.  iRNA-AI: identifying the adenosine to inosine editing sites in RNA sequences , 2016, Oncotarget.

[61]  K. Chou,et al.  Collective motion in DNA and its role in drug intercalation , 1988, Biopolymers.

[62]  P Dal-Bianco,et al.  Efficacy and safety of rivastigmine in patients with Alzheimer's disease: international randomised controlled trial. , 1999, BMJ.

[63]  A. Romieu,et al.  Synthesis and structure-activity relationship of Huprine derivatives as human acetylcholinesterase inhibitors. , 2009, Bioorganic & medicinal chemistry.

[64]  Guo-Ping Zhou,et al.  NMR studies on how the binding complex of polyisoprenol recognition sequence peptides and polyisoprenols can modulate membrane structure. , 2005, Current protein & peptide science.

[65]  J. Sussman,et al.  Acetylcholinesterase: from 3D structure to function. , 2010, Chemico-biological interactions.

[66]  L. Friedhoff,et al.  Pharmacokinetic and pharmacodynamic profile of donepezil HCl following single oral doses. , 1998, British journal of clinical pharmacology.

[67]  Kuo-Chen Chou,et al.  iRNAm5C-PseDNC: identifying RNA 5-methylcytosine sites by incorporating physical-chemical properties into pseudo dinucleotide composition , 2017, Oncotarget.

[68]  K. Chou,et al.  REVIEW : Recent advances in developing web-servers for predicting protein attributes , 2009 .

[69]  Wei Chen,et al.  iOri-Human: identify human origin of replication by incorporating dinucleotide physicochemical properties into pseudo nucleotide composition , 2016, Oncotarget.

[70]  H. Agarwal,et al.  A pharmacophore model specific to active site of CYP1A2 with a novel molecular modeling explorer and CoMFA. , 2012 .

[71]  A. Castro,et al.  Peripheral and dual binding site acetylcholinesterase inhibitors: implications in treatment of Alzheimer's disease. , 2001, Mini reviews in medicinal chemistry.

[72]  Kuo-Chen Chou,et al.  Prediction of the tertiary structure of the beta-secretase zymogen. , 2002, Biochemical and biophysical research communications.

[73]  Qin Chen,et al.  Comparison between loureirin A and cochinchinenin C on the interaction with human serum albumin. , 2015, European journal of medicinal chemistry.

[74]  Kuo-Chen Chou,et al.  An in-depth analysis of the biological functional studies based on the NMR M2 channel structure of influenza A virus. , 2008, Biochemical and biophysical research communications.

[75]  Kuo-Chen Chou,et al.  Insights from investigating the interactions of adamantane-based drugs with the M2 proton channel from the H1N1 swine virus. , 2009, Biochemical and biophysical research communications.

[76]  Kuo-Chen Chou,et al.  Investigation into adamantane-based M2 inhibitors with FB-QSAR. , 2009, Medicinal chemistry (Shariqah (United Arab Emirates)).

[77]  D. Butterfield,et al.  Direct evidence of oxidative injury produced by the Alzheimer's β-Amyloid peptide (1–40) in cultured hippocampal neurons , 1995, Experimental Neurology.

[78]  K D Watenpaugh,et al.  A model of the complex between cyclin-dependent kinase 5 and the activation domain of neuronal Cdk5 activator. , 1999, Biochemical and biophysical research communications.

[79]  Kuo-Chen Chou,et al.  pSuc-Lys: Predict lysine succinylation sites in proteins with PseAAC and ensemble random forest approach. , 2016, Journal of theoretical biology.

[80]  Kuo-Chen Chou,et al.  iATC-mHyb: a hybrid multi-label classifier for predicting the classification of anatomical therapeutic chemicals , 2017, Oncotarget.

[81]  H. Tajmir-Riahi,et al.  Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin. , 2011, Biochimie.

[82]  Kuo-Chen Chou,et al.  2L-piRNA: A Two-Layer Ensemble Classifier for Identifying Piwi-Interacting RNAs and Their Function , 2017, Molecular therapy. Nucleic acids.

[83]  K. Chou,et al.  Novel Inhibitor Design for Hemagglutinin against H1N1 Influenza Virus by Core Hopping Method , 2011, PloS one.

[84]  D. Jameson,et al.  Fluorescence spectroscopy in biochemistry: teaching basic principles with visual demonstrations , 2001 .

[85]  V. Andrisano,et al.  Cholinesterase inhibitors: SAR and enzyme inhibitory activity of 3-[omega-(benzylmethylamino)alkoxy]xanthen-9-ones. , 2007, Bioorganic & medicinal chemistry.

[86]  Kuo-Chen Chou,et al.  pLoc-mPlant: predict subcellular localization of multi-location plant proteins by incorporating the optimal GO information into general PseAAC. , 2017, Molecular bioSystems.

[87]  Kuo-Chen Chou,et al.  Coupling interaction between thromboxane A2 receptor and alpha-13 subunit of guanine nucleotide-binding protein. , 2005, Journal of proteome research.

[88]  A. Saboury,et al.  Interaction of Curcumin and Diacetylcurcumin with the Lipocalin Member β-Lactoglobulin , 2009, The protein journal.

[89]  F. J. Luque,et al.  Novel donepezil-based inhibitors of acetyl- and butyrylcholinesterase and acetylcholinesterase-induced beta-amyloid aggregation. , 2008, Journal of medicinal chemistry.

[90]  O. Ijare,et al.  Study of the interaction of an anticancer drug with human and bovine serum albumin: spectroscopic approach. , 2006, Journal of pharmaceutical and biomedical analysis.

[91]  Hanqi Zhang,et al.  Molecular spectroscopic study on the interaction of tetracyclines with serum albumins. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[92]  Vincenza Andrisano,et al.  Rational approach to discover multipotent anti-Alzheimer drugs. , 2005, Journal of medicinal chemistry.

[93]  Juan Manuel Maler,et al.  Tau protein phosphorylated at threonine 181 in CSF as a neurochemical biomarker in Alzheimer’s disease , 2007, Journal of Molecular Neuroscience.

[94]  Kuo-Chen Chou,et al.  iPreny-PseAAC: Identify C-terminal Cysteine Prenylation Sites in Proteins by Incorporating Two Tiers of Sequence Couplings into PseAAC. , 2017, Medicinal chemistry (Shariqah (United Arab Emirates)).

[95]  Ny Chen,et al.  THE BIOLOGICAL FUNCTIONS OF LOW-FREQUENCY PHONONS .2. COOPERATIVE EFFECTS , 1981 .

[96]  L. Sklar,et al.  Human serum albumin. Spectroscopic studies of binding and proximity relationships for fatty acids and bilirubin. , 1979, The Journal of biological chemistry.

[97]  Rogers Sl,et al.  Pharmacokinetic and pharmacodynamic profile of donepezil HCl following multiple oral doses , 1998 .

[98]  I. Mook‐Jung,et al.  BACE1 (beta-secretase) inhibitory chromone glycosides from Aloe vera and Aloe nobilis. , 2008, Planta Medica.

[99]  E. Cabrita,et al.  A new lupene triterpenetriol and anticholinesterase activity of Salvia sclareoides. , 2007, Fitoterapia.

[100]  Kuo-Chen Chou,et al.  Identification of proteins interacting with human SP110 during the process of viral infections. , 2011, Medicinal chemistry (Shariqah (United Arab Emirates)).

[101]  Wei Chen,et al.  iRNA-PseU: Identifying RNA pseudouridine sites , 2016, Molecular therapy. Nucleic acids.

[102]  K. Chou,et al.  iSNO-PseAAC: Predict Cysteine S-Nitrosylation Sites in Proteins by Incorporating Position Specific Amino Acid Propensity into Pseudo Amino Acid Composition , 2013, PloS one.

[103]  A. Cavalli,et al.  SAR of 9-amino-1,2,3,4-tetrahydroacridine-based acetylcholinesterase inhibitors: synthesis, enzyme inhibitory activity, QSAR, and structure-based CoMFA of tacrine analogues. , 2000, Journal of medicinal chemistry.

[104]  S. Ryu,et al.  In vitro BACE-1 Inhibitory Phenolic Components from the Seeds of Psoralea corylifolia , 2008, Planta medica.

[105]  R. Bartus,et al.  The cholinergic hypothesis of geriatric memory dysfunction. , 1982, Science.

[106]  K. Chou,et al.  THE BIOLOGICAL FUNCTIONS OF LOW-FREQUENCY PHONONS , 1977 .

[107]  Michael S. Seaman,et al.  Structural basis for membrane anchoring of HIV-1 envelope spike , 2016, Science.