Ginger components as new leads for the design and development of novel multi-targeted anti-Alzheimer’s drugs: a computational investigation

References

• Fan LY Chiu MJ Combotherapy and current concepts as well as future strategies for the treatment of Alzheimer’s disease Neuropsychiatr Dis Treat 2014 10 439 451 24648738
   PubMed Web of Science ®Google Scholar
• Azam F Therapeutic potential of free radical scavengers in neurological disorders Kozyrev D Slutsky V Handbook of Free radicals: Formation, Types and Effects New York Nova Publishers 2010 57 97
   Google Scholar
• Mandel S Youdim MB Catechin polyphenols: neurodegeneration and neuroprotection in neurodegenerative diseases Free Radic Biol Med 2004 37 3 304 317 15223064
   PubMed Web of Science ®Google Scholar
• Chancellor B Duncan A Chatterjee A Art therapy for Alzheimer’s disease and other dementias J Alzheimers Dis 2014 39 1 1 11 24121964
   PubMed Web of Science ®Google Scholar
• Allain H Bentue-Ferrer D Tribut O Gauthier S Michel BF Drieu-La Rochelle C Alzheimer’s disease: the pharmacological pathway Fundam Clin Pharmacol 2003 17 4 419 428 12914543
   PubMed Web of Science ®Google Scholar
• Schneider LS Alzheimer disease pharmacologic treatment and treatment research Continuum (Minneap Minn) 2013 19 2 Dementia 339 357 23558481
   PubMedGoogle Scholar
• Hampel H Current insights into the pathophysiology of Alzheimer’s disease: selecting targets for early therapeutic intervention Int Psychogeriatr 2012 24 Suppl 1 S10 S17 22784422
   PubMed Web of Science ®Google Scholar
• Azam F Madi AM Ali HI Molecular docking and prediction of pharmacokinetic properties of dual mechanism drugs that block MAO-B and adenosine A2A J Young Pharm 2012 4 3 184 192 23112538
   PubMedGoogle Scholar
• Morphy JR Harris CJ Designing Multi-Target Drugs RSC Drug Discovery Series No. 21 Cambridge Royal Society of Chemistry 2012
   Google Scholar
• Silva MI de Melo CTV Vasconcelos LF de Carvalho AMR Sousa FCF Bioactivity and potential therapeutic benefits of some medicinal plants from the Caatinga (semi-arid) vegetation of Northeast Brazil: a review of the literature Brazilian Journal of Pharmacognosy 2012 22 193 207
   Web of Science ®Google Scholar
• Shukla Y Singh M Cancer preventive properties of ginger: a brief review Food Chem Toxicol 2007 45 5 683 690 17175086
   PubMed Web of Science ®Google Scholar
• Surh Y Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances Mutat Res 1999 428 1–2 305 327 10518003
   PubMed Web of Science ®Google Scholar
• Ali BH Blunden G Tanira MO Nemmar A Some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe): a review of recent research Food Chem Toxicol 2008 46 2 409 420 17950516
   PubMed Web of Science ®Google Scholar
• Pan MH Hsieh MC Hsu PC 6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages Mol Nutr Food Res 2008 52 12 1467 1477 18683823
   PubMed Web of Science ®Google Scholar
• Jung HW Yoon CH Park KM Han HS Park YK Hexane fraction of Zingiberis Rhizoma Crudus extract inhibits the production of nitric oxide proinflammatory cytokines in LPS-stimulated BV2 microglial cells via the NF kappaB pathway Food Chem Toxicol 2009 47 6 1190 1197 19233241
   PubMed Web of Science ®Google Scholar
• Tripathi S Maier KG Bruch D Kittur DS Effect of 6-gingerol on proinflammatory cytokine production and costimulatory molecule expression in murine peritoneal macrophages J Surg Res 2007 138 2 209 213 17291534
   PubMed Web of Science ®Google Scholar
• Ha SK Moon E Ju MS 6-Shogaol a ginger product modulates neuroinflammation: a new approach to neuroprotection Neuropharmacology 2012 63 2 211 223 22465818
   PubMed Web of Science ®Google Scholar
• Kim DS Kim DS Oppel MN Shogaols from Zingiber officinale protect human neuroblastoma and normal human umbilical vein endothelial cells from beta-amyloid (25–35) insult Planta Med 2002 68 4 375 376 11988870
   PubMed Web of Science ®Google Scholar
• Lee C Park GH Kim CY Jang JH [6]-Gingerol attenuates β-amyloid-induced oxidative cell death via fortifying cellular antioxidant defense system Food Chem Toxicol 2011 49 6 1261 1269 21396424
   PubMed Web of Science ®Google Scholar
• Zeng GF Zhang ZY Lu L Xiao DQ Zong SH He JM Protective effects of ginger root extract on Alzheimer disease-induced behavioral dysfunction in rats Rejuvenation Res 2013 16 2 124 133 23374025
   PubMed Web of Science ®Google Scholar
• Oboh G Ademiluyi AO Akinyemi AJ Inhibition of acetylcholinesterase activities and some pro-oxidant induced lipid peroxidation in rat brain by two varieties of ginger (Zingiber officinale) Exp Toxicol Pathol 2012 64 4 315 319 20952170
   PubMedGoogle Scholar
• Shushni MA Azam F Lindequist U Oxasetin from Lophiostoma sp. of the Baltic Sea: identification, in silico binding mode prediction and antibacterial evaluation against fish pathogenic bacteria Nat Prod Commun 2013 8 9 1223 1226 24273851
   PubMed Web of Science ®Google Scholar
• Azam F Prasad MV Thangavel N Shrivastava AK Mohan G Structure-based design, synthesis and molecular modeling studies of 1-(substituted aryl)-3-(thiazol-2-yl)urea derivatives as novel anti-Parkinsonian agents Med Chem 2012 8 6 1057 1068 22741780
   PubMed Web of Science ®Google Scholar
• Azam F Prasad MV Thangavel N Structure-based design, synthesis and molecular modeling studies of 1-(benzo[d]thiazol-2-yl)-3-(substituted aryl)urea derivatives as novel anti-Parkinsonian agents Med Chem Res 2012 21 9 2630 2643
   Web of Science ®Google Scholar
• Ahmed MA Azam F Rghigh AM Gbaj A Zetrini AE Structure-based design, synthesis, molecular docking and biological activities of 2-(3 benzoylphenyl) propanoic acid derivatives as dual mechanism drugs J Pharm Bioallied Sci 2011 4 1 43 50 22368397
   PubMedGoogle Scholar
• Peng F Tao Q Wu X Cytotoxic, cytoprotective and antioxidant effects of isolated phenolic compounds from fresh ginger Fitoterapia 2012 83 3 568 585 22248534
   PubMed Web of Science ®Google Scholar
• Morris GM Goodsell DS Halliday RS Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function Journal of Computational Chemistry 1998 19 14 1639 1662
   Web of Science ®Google Scholar
• Lipinski CA Lombardo F Dominy BW Feeney PJ Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv Drug Deliv Rev 2001 46 1–3 3 26 11259830
   PubMed Web of Science ®Google Scholar
• Zhao Y Abraham MH Le J Rate-limited steps of human oral absorption and QSAR studies Pharm Res 2002 19 10 1446 1457 12425461
   PubMed Web of Science ®Google Scholar
• Wang R Lu Y Wang S Comparative evaluation of 11 scoring functions for molecular docking J Med Chem 2003 46 12 2287 2303 12773034
   PubMed Web of Science ®Google Scholar
• Ghayur MN Gilani AH Ahmed T Muscarinic, Ca++ antagonist and specific butyrylcholinesterase inhibitory activity of dried ginger extract might explain its use in dementia J Pharm Pharmacol 2008 60 10 1375 1383 18812031
   PubMed Web of Science ®Google Scholar
• Choi DK Koppula S Suk K Inhibitors of microglial neurotoxicity: focus on natural products Molecules 2011 16 2 1021 1043 21350391
   PubMed Web of Science ®Google Scholar
• Bustamam A Ibrahim S Al-Zubairi AS Met M Syam MM Zerumbone: a natural compound with anti-cholinesterase activity Am J Pharmacol Toxicol 2008 3 3 209 211
   Google Scholar
• Shim S Kwon J Effects of [6]-shogaol on cholinergic signaling in HT22 cells following neuronal damage induced by hydrogen peroxide Food Chem Toxicol 2012 50 5 1454 1459 22381256
   PubMed Web of Science ®Google Scholar
• Shin SG Kim JY Chung HY Jeong JC Zingerone as an antioxidant against peroxynitrite J Agric Food Chem 2005 53 19 7617 7622 16159194
   PubMed Web of Science ®Google Scholar
• Kabuto H Nishizawa M Tada M Higashio C Shishibori T Koho M Zingerone [4-(4-hydroxy-3-methoxyphenyl)-2-butanone] prevents 6-hydroxydopamine-induced dopamine depression in mouse striatum and increases superoxide scavenging activity in serum Neurochem Res 2005 30 3 325 332 16018576
   PubMed Web of Science ®Google Scholar
• Kiuchi F Iwakami S Shibuya M Hanaoka F Sankawa U Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids Chem Pharm Bull 1992 40 2 387 391 1606634
   PubMed Web of Science ®Google Scholar
• Wattanathorn J Jittiwat J Tongun T Muchimapura S Ingkaninan K Zingiber officinale mitigates brain damage and improves memory impairment in focal cerebral ischemic rat Evid Based Complement Alternat Med 2011 2011 429 505
   Web of Science ®Google Scholar
• Belle NA Dalmolin GD Fonini G Rubim MA Rocha JB Polyamines reduces lipid peroxidation induced by different prooxidants agents Brain Res 2004 1008 2 245 251 15145762
   PubMed Web of Science ®Google Scholar
• Kim SO Kundu JK Shin YK [6]-Gingerol inhibits COX-2 expression by blocking the activation of p38 MAP kinase and NF-kappaB in phorbol ester-stimulated mouse skin Oncogene 2005 24 15 2558 2567 15735738
   PubMed Web of Science ®Google Scholar
• Ollis DL Cheah E Cygler M The alpha/beta hydrolase fold Protein Eng 1992 5 3 197 211 1409539
   PubMedGoogle Scholar
• Cygler M Schrag JD Sussman JL Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases, and related proteins Protein Sci 1993 2 3 366 382 8453375
   PubMed Web of Science ®Google Scholar
• Alvarez A Alarcon R Opazo C Stable complexes involving acetylcholinesterase and amyloid-beta peptide change the biochemical properties of the enzyme and increase the neurotoxicity of Alzheimer’s fibrils J Neurosci 1998 18 9 3213 3223 9547230
   PubMed Web of Science ®Google Scholar
• Silman I Sussman JL Acetylcholinesterase: “classical” and “non-classical” functions and pharmacology Curr Opin Pharmacol 2005 5 3 293 302 15907917
   PubMed Web of Science ®Google Scholar
• Musial A Bajda M Malawska B Recent developments in cholinesterases inhibitors for Alzheimer’s disease treatment Curr Med Chem 2007 14 25 2654 2679 17979717
   PubMed Web of Science ®Google Scholar
• Darvesh S Cash MK Reid GA Martin E Mitnitski A Geula C Butyrylcholinesterase is associated with β-amyloid plaques in the transgenic APPSWE/PSEN1dE9 mouse model of Alzheimer disease J Neuropathol Exp Neurol 2012 71 1 2 14 22157615
   PubMed Web of Science ®Google Scholar
• Moroy G Martiny VY Vayer P Villoutreix BO Miteva MA Toward in silico structure-based ADMET prediction in drug discovery Drug Discov Today 2012 17 1–2 44 55 22056716
   PubMed Web of Science ®Google Scholar
• Veber DF Johnson SR Cheng HY Smith BR Ward KW Kopple KD Molecular properties that influence the oral bioavailability of drug candidates J Med Chem 2002 45 12 2615 2623 12036371
   PubMed Web of Science ®Google Scholar
• Ertl P Rohde B Selzer P Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties J Med Chem 2000 43 20 3714 3717 11020286
   PubMed Web of Science ®Google Scholar
• Cheung J Rudolph MJ Burshteyn F Structures of human acetylcholinesterase in complex with pharmacologically important ligands J Med Chem 2012 55 22 10282 10286 23035744
   PubMed Web of Science ®Google Scholar
• McKinney M Miller JH Yamada F Tuckmantel W Kozikowski AP Potencies and stereoselectivities of enantiomers of huperzine A for inhibition of rat cortical acetylcholinesterase Eur J Pharmacol 1991 203 2 303 305 1800123
   PubMed Web of Science ®Google Scholar
• Wandhammer M de Koning M van Grol M A step toward the reactivation of aged cholinesterases – crystal structure of ligands binding to aged human butyrylcholinesterase Chem Biol Interact 2013 203 1 19 23 22922115
   PubMed Web of Science ®Google Scholar
• Cumming JN Smith EM Wang L Structure based design of iminohydantoin BACE1 inhibitors: identification of an orally available, centrally active BACE1 inhibitor Bioorg Med Chem Lett 2012 22 7 2444 2449 22390835
   PubMed Web of Science ®Google Scholar
• Bhat R Xue Y Berg S Structural insights and biological effects of glycogen synthase kinase 3 specific inhibitor AR-A014418 J Biol Chem 2003 278 46 45937 45945 12928438
   PubMed Web of Science ®Google Scholar
• Hicks JW Wilson AA Rubie EA Woodgett JR Houle S Vasdev N Towards the preparation of radiolabeled 1-aryl-3-benzyl ureas: radiosynthesis of [(11)C-carbonyl] AR-A014418 by [(11)C]CO(2) fixation Bioorg Med Chem Lett 2012 22 5 2099 2101 22321216
   PubMed Web of Science ®Google Scholar
• Niu X Umland S Ingram R IK682, a tight binding inhibitor of TACE Arch Biochem Biophys 2006 451 1 43 50 16762314
   PubMed Web of Science ®Google Scholar
• Duan JJ Chen L Wasserman ZR Discovery of gamma-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor alpha converting enzyme: design, synthesis, and structure-activity relationships J Med Chem 2002 45 23 4954 4957 12408705
   PubMed Web of Science ®Google Scholar
• Cao J Gao H Bemis G Structure-based design and parallel synthesis of n-benzyl isatin oximes as jnk3 map kinase inhibitors Bioorg Med Chem Lett 2009 19 10 2891 2895 19361991
   PubMed Web of Science ®Google Scholar
• Fedorov R Hartmann E Ghosh DK Schlichting I Structural basis for the specificity of the nitric-oxide synthase inhibitors w1400 and nomega-propyl-l-arg for the inducible and neuronal isoforms J Biol Chem 2003 278 46 45818 45825 12954642
   PubMed Web of Science ®Google Scholar
• Congreve M Chessari G Tisi D Woodhead AJ Recent developments in fragment-based drug discovery J Med Chem 2008 51 13 3661 3680 18457385
   PubMed Web of Science ®Google Scholar
• Bencharit S Morton CL Hyatt JL Crystal structure of human carboxylesterase 1 complexed with the Alzheimer’s drug tacrine: from binding promiscuity to selective inhibition Chem Biol 2003 10 4 341 349 12725862
   PubMedGoogle Scholar
• Furukawa H Gouaux E Mechanisms of activation, inhibition and specificity: crystal structures of the NMDA receptor nr1 ligand-binding core EMBO J 2003 22 12 2873 2885 12805203
   PubMed Web of Science ®Google Scholar
• Selinsky BS Gupta K Sharkey CT Loll PJ Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations Biochemistry 2001 40 17 5172 5180 11318639
   PubMed Web of Science ®Google Scholar
• Viegas A Manso J Corvo MC Marques MM Cabrita EJ Binding of ibuprofen, ketorolac, and diclofenac to COX-1 and COX-2 studied by saturation transfer difference NMR J Med Chem 2011 54 24 8555 8562 22091869
   PubMed Web of Science ®Google Scholar
• Vecchio AJ Malkowski MG The structure of ns-398 bound to cyclooxygenase-2 J Struct Biol 2011 176 2 254 258 21843643
   PubMed Web of Science ®Google Scholar
• Cryer B Feldman M Cyclooxygenase-1 and cyclooxygenase-2 selectivity of widely used nonsteroidal anti-inflammatory drugs Am J Med 1998 104 5 413 421 9626023
   PubMed Web of Science ®Google Scholar
• Sung BJ Hwang KY Jeon YH Structure of the catalytic domain of human phosphodiesterase 5 with bound drug molecules Nature 2003 425 6953 98 102 12955149
   PubMed Web of Science ®Google Scholar
• Jiang W Guan J Macielag MJ Pyrroloquinolone PDE5 inhibitors with improved pharmaceutical profiles for clinical studies on erectile dysfunction J Med Chem 2005 48 6 2126 2133 15771456
   PubMed Web of Science ®Google Scholar
• Watermeyer JM Kroger WL O’Neill HG Sewell BT Sturrock ED Probing the basis of domain-dependent inhibition using novel ketone inhibitors of Angiotensin-converting enzyme Biochemistry 2008 47 22 5942 5950 18457420
   PubMed Web of Science ®Google Scholar