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Evidence-Based Complementary and Alternative Medicine
Volume 2013, Article ID 937370, 11 pages
http://dx.doi.org/10.1155/2013/937370
Research Article

Acetylshikonin, a Novel AChE Inhibitor, Inhibits Apoptosis via Upregulation of Heme Oxygenase-1 Expression in SH-SY5Y Cells

School of Biomedical Sciences, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong

Received 14 June 2013; Revised 10 September 2013; Accepted 11 September 2013

Academic Editor: Karl Wah-Keung Tsim

Copyright © 2013 Yan Wang et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. F. Mangialasche, A. Solomon, B. Winblad, P. Mecocci, and M. Kivipelto, “Alzheimer's disease: clinical trials and drug development,” The Lancet Neurology, vol. 9, no. 7, pp. 702–716, 2010. View at Publisher · View at Google Scholar · View at Scopus
  2. L. M. Ittner and J. Götz, “Amyloid-β and tau—a toxic pas de deux in Alzheimer's disease,” Nature Reviews Neuroscience, vol. 12, no. 2, pp. 67–72, 2011. View at Publisher · View at Google Scholar · View at Scopus
  3. H.C. Huang and Z.F. Jiang, “Accumulated amyloid-β peptide and hyperphosphorylated tau protein: relationship and links in Alzheimer's disease,” Journal of Alzheimer's Disease, vol. 16, no. 1, pp. 15–27, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. E. Giacobini, “Invited review. Cholinesterase inhibitors for Alzheimer's disease therapy: from tacrine to future applications,” Neurochemistry International, vol. 32, no. 5-6, pp. 413–419, 1998. View at Publisher · View at Google Scholar · View at Scopus
  5. N. Akula, L. Lecanu, J. Greeson, and V. Papadopoulos, “3D QSAR studies of AChE inhibitors based on molecular docking scores and CoMFA,” Bioorganic and Medicinal Chemistry Letters, vol. 16, no. 24, pp. 6277–6280, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. M. Y. Mizutani and A. Itai, “Efficient method for high-throughput virtual screening based on flexible docking: discovery of novel acetylcholinesterase inhibitors,” Journal of Medicinal Chemistry, vol. 47, no. 20, pp. 4818–4828, 2004. View at Publisher · View at Google Scholar · View at Scopus
  7. P. Kapková, N. Stiefl, U. Sürig, B. Engels, K. Baumann, and U. Holzgrabe, “Synthesis, biological activity, and docking studies of new acetylcholinesterase inhibitors of the bispyridinium type,” Archiv der Pharmazie, vol. 336, no. 11, pp. 523–540, 2003. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Klugman, “Antioxidant enzymatic activities in Alzheimer's disease: the relationship to acetylcholinesterase inhibitors,” Journal of Alzheimer's Disease, vol. 30, pp. 467–474, 2012. View at Publisher · View at Google Scholar
  9. R. Wang, J. Zhou, and X. C. Tang, “Tacrine attenuates hydrogen peroxide-induced apoptosis by regulating expression of apoptosis-related genes in rat PC12 cells,” Molecular Brain Research, vol. 107, no. 1, pp. 1–8, 2002. View at Publisher · View at Google Scholar · View at Scopus
  10. R. Wang, Q. X. Xiao, and C. T. Xi, “Huperzine a attenuates hydrogen peroxide-induced apoptosis by regulating expression of apoptosis-related genes in rat PC 12 cells,” NeuroReport, vol. 12, no. 12, pp. 2629–2634, 2001. View at Google Scholar · View at Scopus
  11. C. McInnes, “Virtual screening strategies in drug discovery,” Current Opinion in Chemical Biology, vol. 11, no. 5, pp. 494–502, 2007. View at Publisher · View at Google Scholar · View at Scopus
  12. J. Q. Araújo, J. A. Lima, A. D. C. Pinto, R. B. De Alencastro, and M. G. Albuquerque, “Docking of the alkaloid geissospermine into acetylcholinesterase: a natural scaffold targeting the treatment of Alzheimer's disease,” Journal of Molecular Modeling, vol. 17, no. 6, pp. 1401–1412, 2011. View at Publisher · View at Google Scholar · View at Scopus
  13. T. Frembgen-Kesner and A. H. Elcock, “Computational sampling of a cryptic drug binding site in a protein receptor: explicit solvent molecular dynamics and inhibitor docking to p38 MAP Kinase,” Journal of Molecular Biology, vol. 359, no. 1, pp. 202–214, 2006. View at Publisher · View at Google Scholar · View at Scopus
  14. P. Jia, R. Sheng, J. Zhang et al., “Design, synthesis and evaluation of galanthamine derivatives as acetylcholinesterase inhibitors,” European Journal of Medicinal Chemistry, vol. 44, no. 2, pp. 772–784, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. D. H. Shi, W. Huang, C. Li, L. T. Wang, and S. F. Wang, “Synthesis, biological evaluation and molecular modeling of aloe-emodin derivatives as new acetylcholinesterase inhibitors,” Bioorganic & Medicinal Chemistry, vol. 21, no. 5, pp. 1064–1073, 2013. View at Publisher · View at Google Scholar
  16. S. A. Wildman, X. Zheng, D. Sept, J. T. Auletta, T. L. Rosenberry, and G. R. Marshall, “Drug-like leads for steric discrimination between substrate and inhibitors of human acetylcholinesterase,” Chemical Biology and Drug Design, vol. 78, no. 4, pp. 495–504, 2011. View at Publisher · View at Google Scholar · View at Scopus
  17. K. K. Wong, J. C. K. Ngo, S. Liu et al., “Interaction study of two diterpenes, cryptotanshinone and dihydrotanshinone, to human acetylcholinesterase and butyrylcholinesterase by molecular docking and kinetic analysis,” Chemico-Biological Interactions, vol. 187, no. 1–3, pp. 335–339, 2010. View at Publisher · View at Google Scholar · View at Scopus
  18. Z.U. Zaheer-ul-Haq, S. A. Halim, R. Uddin, and J. D. Madura, “Benchmarking docking and scoring protocol for the identification of potential acetylcholinesterase inhibitors,” Journal of Molecular Graphics and Modelling, vol. 28, no. 8, pp. 870–882, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. J. Egea, M. D. Martín-De-Saavedra, E. Parada et al., “Galantamine elicits neuroprotection by inhibiting iNOS, NADPH oxidase and ROS in hippocampal slices stressed with anoxia/reoxygenation,” Neuropharmacology, vol. 62, no. 2, pp. 1082–1090, 2012. View at Publisher · View at Google Scholar · View at Scopus
  20. S. Li, D. T. M. Ip, H. Q. Lin et al., “High-level expression of functional recombinant human butyrylcholinesterase in silkworm larvae by Bac-to-Bac system,” Chemico-Biological Interactions, vol. 187, no. 1–3, pp. 101–105, 2010. View at Publisher · View at Google Scholar · View at Scopus
  21. A. Ordentlich, D. Barak, C. Kronman et al., “Contribution of aromatic moieties of tyrosine 133 and of the anionic subsite tryptophan 86 to catalytic efficiency and allosteric modulation of acetylcholinesterase,” Journal of Biological Chemistry, vol. 270, no. 5, pp. 2082–2091, 1995. View at Publisher · View at Google Scholar · View at Scopus
  22. K. Zhao, G. Luo, S. Giannelli, and H. H. Szeto, “Mitochondria-targeted peptide prevents mitochondrial depolarization and apoptosis induced by tert-butyl hydroperoxide in neuronal cell lines,” Biochemical Pharmacology, vol. 70, no. 12, pp. 1796–1806, 2005. View at Publisher · View at Google Scholar · View at Scopus
  23. R. Motterlini, R. Foresti, R. Bassi, and C. J. Green, “Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress,” Free Radical Biology and Medicine, vol. 28, no. 8, pp. 1303–1312, 2000. View at Publisher · View at Google Scholar · View at Scopus
  24. M. Kimura, S. Akasofu, H. Ogura, and K. Sawada, “Protective effect of donepezil against Aβ(1-40) neurotoxicity in rat septal neurons,” Brain Research, vol. 1047, no. 1, pp. 72–84, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. H. Y. Zhang and X. C. Tang, “Huperzine B, a novel acetylcholinesterase inhibitor, attenuates hydrogen peroxide induced injury in PC12 cells,” Neuroscience Letters, vol. 292, no. 1, pp. 41–44, 2000. View at Publisher · View at Google Scholar · View at Scopus
  26. R. Wang, J. Zhou, and X. C. Tang, “Tacrine attenuates hydrogen peroxide-induced apoptosis by regulating expression of apoptosis-related genes in rat PC12 cells,” Molecular Brain Research, vol. 107, no. 1, pp. 1–8, 2002. View at Publisher · View at Google Scholar · View at Scopus
  27. J. Liu, W. Zhou, S.-S. Li et al., “Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues,” Cancer Research, vol. 68, no. 21, pp. 8871–8880, 2008. View at Publisher · View at Google Scholar · View at Scopus
  28. T. Aysun, A. Fatih, A. Hülya, S. Halis, Ö. Ufuk, and E. Havva, “The effects of acetyl shikonin isolated from onosma armeniacum on oxidative stress in ethanol-induced ulcer model of rats,” Turkish Journal of Medical Sciences, vol. 43, pp. 315–320, 2013. View at Publisher · View at Google Scholar
  29. S. Y. Gwon, J. Y. Ahn, C. H. Chung, B. Moon, and T. Y. Ha, “Lithospermum erythrorhizon suppresses high-fat diet-induced obesity, and acetylshikonin, a main compound of Lithospermum erythrorhizon, inhibits adipocyte differentiation,” Journal of Agricultural and Food Chemistry, vol. 60, no. 36, pp. 9089–9096, 2012. View at Publisher · View at Google Scholar
  30. E. Esmaeilzadeh, M. Gardaneh, E. Gharib, and F. Sabouni, “Shikonin protects dopaminergic cell line PC12 against 6-Hydroxydopamine-Mediated neurotoxicity Via both Glutathione-Dependent and independent pathways and by inhibiting apoptosis,” Neurochem Research, vol. 38, no. 8, pp. 1590–1604, 2013. View at Publisher · View at Google Scholar
  31. B. Liu, Z. Jian, Q. Li et al., “Baicalein protects human melanocytes from H2O2-induced apoptosis via inhibiting mitochondria-dependent caspase activation and the p38 MAPK pathway,” Free Radical Biology and Medicine, vol. 53, no. 2, pp. 183–193, 2012. View at Publisher · View at Google Scholar
  32. A. Das, N. L. Banik, and S. K. Ray, “Mechanism of apoptosis with the involvement of calpain and caspase cascades in human malignant neuroblastoma SH-SY5Y cells exposed to flavonoids,” International Journal of Cancer, vol. 119, no. 11, pp. 2575–2585, 2006. View at Publisher · View at Google Scholar · View at Scopus
  33. L. L. Pan, X. H. Liu, Y. L. Jia et al., “A novel compound derived from danshensu inhibits apoptosis via upregulation of heme oxygenase-1 expression in SH-SY5Y cells,” Biochimica et Biophysica Acta, vol. 1830, no. 4, pp. 2861–2871, 2013. View at Publisher · View at Google Scholar
  34. Y. Kitamura, T. Ota, Y. Matsuoka et al., “Hydrogen peroxide-induced apoptosis mediated by p53 protein in glial cells,” Glia, vol. 25, no. 2, pp. 154–164, 1999. View at Publisher · View at Google Scholar
  35. K. Datta, P. Babbar, T. Srivastava, S. Sinha, and P. Chattopadhyay, “p53 dependent apoptosis in glioma cell lines in response to hydrogen peroxide induced oxidative stress,” International Journal of Biochemistry and Cell Biology, vol. 34, no. 2, pp. 148–157, 2002. View at Publisher · View at Google Scholar · View at Scopus
  36. F. Zhang, S. Wang, M. Zhang et al., “Pharmacological induction of heme oxygenase-1 by a triterpenoid protects neurons against ischemic injury,” Stroke, vol. 43, no. 5, pp. 1390–1397, 2012. View at Publisher · View at Google Scholar · View at Scopus
  37. K. N. Nam, M. S. Son, J. H. Park, and E. H. Lee, “Shikonins attenuate microglial inflammatory responses by inhibition of ERK, Akt, and NF-κB: neuroprotective implications,” Neuropharmacology, vol. 55, no. 5, pp. 819–825, 2008. View at Publisher · View at Google Scholar · View at Scopus