Comparative docking and ADMET study of some curcumin derivatives and herbal congeners targeting β-amyloid

Network Modeling and Analysis in Health Informatics and Bioinformatics

Volumn 2, Issue 1, 2013, Pages 13-27

  Singh, Dev Bukhsh ^a   Gupta, Manish Kumar ^a   Kesharwani, Rajesh Kumar ^b   Misra, Krishna ^b  

^a CSJM UNIVERSITY   (India)

^b INDIAN INSTITUTE OF INFORMATION TECHNOLOGY   (India)

Author keywords

ADMET; Alzheimer's; Beta amyloid; Cassumunin; Curcumin; Descriptors; Disease

Indexed keywords

BINDING ENERGY; DIAGNOSIS; DISEASES; HYDROPHOBICITY; NEURODEGENERATIVE DISEASES; PROTEINS;

ADMET; ALZHEIMER'S; BETA AMYLOIDS; CASSUMUNIN; CURCUMIN; DESCRIPTORS;

GLYCOPROTEINS;

AMYLOID BETA PROTEIN; CURCUMIN; HERBACEOUS AGENT; HOMOTAURINE; PIPERINE;

ALZHEIMER DISEASE; AMINO ACID ANALYSIS; ARTICLE; COMPUTER MODEL; DRUG ABSORPTION; DRUG BINDING SITE; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG METABOLISM; DRUG STRUCTURE; MOLECULAR DOCKING; NEUROPROTECTION; PREVALENCE; PRIORITY JOURNAL; PROTEIN STRUCTURE; SEQUENCE ANALYSIS; TOXICITY;

EID: 84888284638     PISSN: None     EISSN: 21926670     Source Type: Journal    
DOI: 10.1007/s13721-012-0021-7     Document Type: Article

References (52)

1. ACD/ChemSketch Freeware, version 8. 0 (2006) Advanced Chemistry Development, Inc., Toronto, ON, Canada.
2. Adhikary R, Barnes CA, Trampel RL, Wallace SJ, Kee TW, Petrich JW (2011) Photoinduced trans-to-cis isomerization of cyclocurcumin. J Phys Chem B 115(36): 10707-10714.
3. Agdeppa ED, Kepe V, Petri A, Satyamurthy N, Liu J, Huang SC, Small GW, Cole GM, Barrio JR (2003) In vitro detection of (S)-naproxen and ibuprofen binding to plaques in the Alzheimer's brain using the positron emission tomography molecular imaging probe 2-(1-[6-[(2-[(18)F]fluoroethyl)(methyl)amino]-2-naphthyl]ethylidene)malononitrile. Neuroscience 117(3): 723-730.
4. Azzimondi G, D'Alessandro R, Pandolfo G, Feruglio FS (1998) Comparative study of the prevalence of dementia in two Sicilian communities with different psychosocial backgrounds. Neuroepidemiology 17(4): 199-209.
5. Boersma F, Eefsting JA, van den Brink W, Koeter M, van Tilburg W (1998) Prevalence of dementia in a rural Netherlands population and the influence of DSM-III-R and CAMDEX criteria for the prevalence of mild and more severe forms. J Clin Epidemiol 51(3): 189-197.
6. Brayne C, Nickson J, McCraken C, Gill C, Johnson AL (1998) Cognitive function and dementia in six areas of England and Wales: distribution of MMSE and prevalence of GMS organicity level in the MRC CFA Study. Psychol Med 28(2): 319-335.
7. Cam JA, Bu G (2006) Modulation of beta-amyloid precursor protein trafficking and processing by the low density lipoprotein receptor family. Mol Neurodegener 1: 8.
8. Cole GM, Morihara T, Lim GP, Yang F, Begum A, Frautschy SA (2004) NSAID and antioxidant prevention of Alzheimer's disease: lessons from in vitro and animal models. Ann N Y Acad Sci 1035: 68-84.
9. Crescenzi O, Tomaselli S, Guerrini R, Salvadori S, D'Ursi AM, Temussi PA, Picone D (2002) Solution structure of the Alzheimer amyloid beta-peptide (1-42) in an apolar microenvironment. Similarity with a virus fusion domain. Eur J Biochem 269(22): 5642-5648.
10. Dundas J, Ouyang Z, Tseng J, Binkowski A, Turpaz Y, Liang J (2006) CASTp: computed atlas of surface topography of proteins with structural and topographical mapping of functionally annotated residues. Nucleic Acids Res 34(Web Server issue): W116-W118.
11. Ertl P, Rohde B, Selzer P (2000) 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 43(20): 3714-3717.
12. Fiala JC (2007) Mechanism of amyloid plaque pathogenesis. Acta Neuropathol 114: 551-571.
13. Fillenbaum GG, Heyman A, Huber MS, Woodbury MA, Leiss J, Schmader KE, Bohannon A, Trapp-Moen B (1998) The prevalence and 3-year incidence of dementia in older black and white community residents. J Clin Epidemiol 51(7): 587-595.
14. Ghanta J, Shen CL, Kiessling LL, Murphy RM (1996) A strategy for designing inhibitors of beta-amyloid toxicity. J Biol Chem 271(47): 29525-29528.
15. Gupta MK, Singh DB, Rath SK, Misra K (2012) Metabolic modeling and simulation analysis of thyroid disorder pathway. J Comput Sci Syst Biol 5(2): 52-61.
16. Herrera E Jr, Caramelli P, Nitrini R (1998) Estudo epidemiológico populacional de demência na cidade de Catanduva-Estado de São Paulo, Brasil. Rev Psiq Clín (São Paulo) 25: 70-73.
17. Jorgensen WL (1998) BOSS-Biochemical and Organic Simulation System. In: Schleyer PvR (ed) The Encyclopedia of Computational Chemistry, vol 5. Wiley, Athens, pp 3281-3285.
18. Kim W, Hecht MH (2006) Generic hydrophobic residues are sufficient to promote aggregation of the Alzheimer's Abeta42 peptide. Proc Natl Acad Sci 103(43): 15824-15829.
19. Kung MP, Skovronsky DM, Hou C, Zhuang ZP, Gur TL, Zhang B, Trojanowski JQ, Lee VM, Kung HF (2003) Detection of amyloid plaques by radioligands for Abeta40 and Abeta42: potential imaging agents in Alzheimer's patients. J Mol Neurosci 20(1): 15-24.
20. Lee VM (2002) Amyloid binding ligands as Alzheimer's disease therapies. Neurobiol Aging 23(6): 1039-1042.
21. Lim GP, Chu T, Yang F, Beech W, Frautschy SA, Cole GM (2001) The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse. J Neurosci 21(21): 8370-8377.
22. Lin RT, Lai CL, Tai CT, Liu CK, Yen YY, Howng SL (1998) Prevalence and subtypes of dementia in southern Taiwan: impact of age, sex, education, and urbanization. J Neurol Sci 160(1): 67-75.
23. Lipinski CA, Lombardo F, Dominy BW, Fenney PJ (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46: 3-26.
24. Lopes MA, Hototian SR, Reis GC, Elkis H, Bottino CMC et al (2007) Systemic review of dementia prevalence-1994 to 2000. Dement Neuropsychol 1(3): 230-240.
25. Lührs T, Ritter C, Adrian M, Riek-Loher D, Bohrmann B, Döbeli H, Schubert D, Riek R (2005) 3D structure of Alzheimer's amyloid-beta (1-42) fibrils. Proc Natl Acad Sci 102(48): 17342-17347.
26. Masuda T, Matsumura H, Oyama Y, Takeda Y, Jitoe A, Kida A, Hidaka K (1998) Synthesis of (±)-cassumunins A and B, new curcuminoid antioxidants having protective activity of the living cell against oxidative damage. J Nat Prod 61(5): 609-613.
27. McLaurin J, Kierstead ME, Brown ME, Hawkes CA, Lambermon MH, Phinney AL, Darabie AA, Cousins JE, French JE, Lan MF, Chen F, Wong SS, Mount HT, Fraser PE, Westaway D, St. George-Hyslop P (2006) Cyclohexanehexol inhibitors of Abeta aggregation prevent and reverse Alzheimer phenotype in a mouse model. Nat Med 12(7): 801-808.
28. Mihalek I, Res I, Lichtarge O (2006) Evolutionary trace report_maker: a new type of service for comparative analysis of proteins. Bioinformatics 22(13): 1656-1657.
29. Mills N (2006) ChemDraw Ultra 10. 0. J Am Chem Soc 128(41): 13649-13650.
30. Mishra S, Palanivelu K (2008) The effect of curcumin (turmeric) on Alzheimer's disease: an overview. Ann Indian Acad Neurol 11(1): 13-19.
31. 2. Jpn J Pharmacol 75(4): 363-370.
32. Nakamura S, Iwami J, Matsuda H, Wakayama H, Pongpiriyadacha Y, Yoshikawa M (2009) Structures of new phenylbutanoids and nitric oxide production inhibitors from the rhizomes of Zingiber cassumunar. Chem Pharm Bull (Tokyo) 57(11): 1267-1272.
33. Narlawar R, Baumann K, Schubenel R, Schmidt B (2007) Curcumin derivatives inhibit or modulate beta-amyloid precursor protein metabolism. Neurodegener Dis 4(2-3): 88-93.
34. Ono K, Hasegawa K, Naiki H, Yamada M (2004) Curcumin has potent anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils in vitro. J Neurosci Res 75(6): 742-750.
35. Pajeva IK, Globisch C, Wiese M (2009) Combined pharmacophore modeling, docking, and 3D QSAR studies of ABCB1 and ABCC1 transporter inhibitors. ChemMedChem 4(11): 1883-1896.
36. Punta M, Coggill PC, Eberhardt RY, Mistry J, Tate J, Boursnell C, Pang N, Forslund K, Ceric G, Clements J, Heger A, Holm L, Sonnhammer EL, Eddy SR, Bateman A, Finn RD (2012) The Pfam protein families database. Nucleic Acids Res 40(Database issue): D290-D301.
37. QikProp, version 3. 3 (2010) Schrodinger, LLC, New York.
38. Ringman JM, Frautschy SA, Cole GM, Masterman DL, Cummings JL (2005) A potential role of the curry spice curcumin in Alzheimer's disease. Curr Alzheimer Res 2(2): 131-136.
39. Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R (1995) Anti-tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94(1): 79-83.
40. Santa-Maria I, Hernández F, Del Rio J, Moreno FJ, Avila J (2007) Tramiprosate, a drug of potential interest for the treatment of Alzheimer's disease, promotes an abnormal aggregation of tau. Mol Neurodegener 2: 17.
41. Shaji S, Promodu K, Abraham T, Roy KJ, Verghese A (1996) An epidemiological study of dementia in a rural community in Kerala, Índia. Br J Psychiatry 168(6): 745-749.
42. Singh TR, Chandra S (2012) Linear B cell epitope prediction for epitope vaccine design against meningococcal disease and their computational validations through physicochemical properties. Netw Model Anal Health Inform Bioinform 1: 153-159.
43. Srimal RC, Dhawan BN (1973) Pharmacology of diferuloylmethane (curcumin), a non-steroidal anti-inflammatory agent. J Pharm Pharmacol 25(6): 447-452.
44. Tang W, Su D (2012) Locomotion analysis and its applications in neurological disorders detection: state-of-art review. Netw Model Anal Health Inform Bioinform. doi: 10. 1007/s13721-012-0020-8.
45. Tang W, Yarowsky P, Tasch U (2012) Detecting ALS and Parkinson's disease in rats through locomotion analysis. Netw Model Anal Health Inform Bioinform 1: 63-68.
46. Thomsen R, Christensen MH (2006) MolDock: a new technique for high-accuracy molecular docking. J Med Chem 49(11): 3315-3321.
47. Wang J (2009) Comprehensive assessment of ADMET risks in drug discovery. Curr Pharm 15(19): 2195-2219.
48. Woo JI, Lee JH, Yoo KY, Kim CY, Kim YI, Shin YS (1998) Prevalence estimation of dementia in a rural area of Korea. J Am Geriatr Soc 46(8): 983-987.
49. Yamada M, Sasaki H, Mimori Y, Kasagi F, Sudoh S, Ikeda J, Hosoda Y, Nakamura S, Kodama K (1999) Prevalence and risks of dementia in the Japanese population: RERF'S adult health study Hiroshima subjects. J Am Geriatr Soc 47(2): 189-195.
50. Yang J, Chen C (2004) GEMDOCK: a generic evolutionary method for molecular docking. Proteins 55: 288-304.
51. Yang F, Lim GP, Begum AN, Ubeda OJ, Simmons MR, Ambegaokar SS, Chen PP, Kayed R, Glabe CG, Frautschy SA, Cole GM (2005) Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J Biol Chem 280(7): 5892-5901.
52. Zheng J, Jang H, Ma B, Nussinov R (2008) Annular structures as intermediates in fibril formation of Alzheimer Abeta17-42. J Phys Chem B 112(22): 6856-6865.