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Journal of Chemistry
Volume 2017, Article ID 4746158, 10 pages
https://doi.org/10.1155/2017/4746158
Research Article

Synthesis of Ibuprofen Conjugated Molecular Transporter Capable of Enhanced Brain Penetration

1India Innovation Research Centre, 465 Patparganj Industrial Area, Delhi 110092, India
2Department of Life Science, Division of Molecular and Life Science and Division of Integrative Biosciences and Biotechnology, Pohang University of Science and Technology, Pohang, Republic of Korea
3Department of Chemical Engineering, Soonchunhyang University, Asan, Republic of Korea
4Department of Pathology, Soonchunhyang University, Asan, Republic of Korea
5Department of Pharmaceutical Engineering, Soonchunhyang University, Asan, Republic of Korea

Correspondence should be addressed to Jungkyun Im; rk.ca.hcs@9725mikj

Received 23 August 2016; Revised 28 November 2016; Accepted 29 November 2016; Published 16 January 2017

Academic Editor: Josefina Pons

Copyright © 2017 Goutam Biswas 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. J. A. Mitchell, P. Akarasereenont, C. Thiemermann, R. J. Flower, and J. R. Vane, “Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase,” Proceedings of the National Academy of Sciences of the United States of America, vol. 90, no. 24, pp. 11693–11697, 1993. View at Publisher · View at Google Scholar · View at Scopus
  2. R. J. Flower, “The development of COX2 inhibitors,” Nature Reviews Drug Discovery, vol. 2, no. 3, pp. 179–191, 2003. View at Publisher · View at Google Scholar · View at Scopus
  3. A. H. Moore, M. J. Bigbee, G. E. Boynton et al., “Non-steroidal anti-inflammatory drugs in Alzheimer's disease and Parkinson's disease: reconsidering the role of neuroinflammation,” Pharmaceuticals, vol. 3, no. 6, pp. 1812–1841, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. J. L. Eriksen, S. A. Sagi, T. E. Smith et al., “NSAIDs and enantiomers of flurbiprofen target γ-secretase and lower Aβ42 in vivo,” The Journal of Clinical Investigation, vol. 112, no. 3, pp. 440–449, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. A. Lleó, O. Berezovska, L. Herl et al., “Nonsteroidal anti-inflammatory drugs lower Aβ42 and change presenilin 1 conformation,” Nature Medicine, vol. 10, no. 10, pp. 1065–1066, 2004. View at Publisher · View at Google Scholar · View at Scopus
  6. M. H. DeLegge and A. Smoke, “Neurodegeneration and inflammation,” Nutrition in Clinical Practice, vol. 23, no. 1, pp. 35–41, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. H. Chen, S. M. Zhang, M. A. Hernán et al., “Nonsteroidal anti-inflammatory drugs and the risk of Parkinson disease,” Archives of Neurology, vol. 60, no. 8, pp. 1059–1064, 2003. View at Publisher · View at Google Scholar · View at Scopus
  8. F. L. Heppner, R. M. Ransohoff, and B. Becher, “Immune attack: the role of inflammation in Alzheimer disease,” Nature Reviews Neuroscience, vol. 16, no. 6, pp. 358–372, 2015. View at Publisher · View at Google Scholar · View at Scopus
  9. T. Wyss-Coray and L. Mucke, “Ibuprofen, inflammation and Alzheimer disease,” Nature Medicine, vol. 6, no. 9, pp. 973–974, 2000. View at Publisher · View at Google Scholar · View at Scopus
  10. E. E. Tuppo and H. R. Arias, “The role of inflammation in Alzheimer's disease,” The International Journal of Biochemistry & Cell Biology, vol. 37, no. 2, pp. 289–305, 2005. View at Publisher · View at Google Scholar · View at Scopus
  11. G. P. Lim, F. Yang, T. Chu et al., “Ibuprofen suppresses plaque pathology and inflammation in a mouse model for Alzheimer's disease,” The Journal of Neuroscience, vol. 20, no. 15, pp. 5709–5714, 2000. View at Google Scholar · View at Scopus
  12. S. C. Vlad, D. R. Miller, N. W. Kowall, and D. T. Felson, “Protective effects of NSAIDs on the development of Alzheimer disease,” Neurology, vol. 70, no. 19, pp. 1672–1677, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. X. Gao, H. Chen, M. A. Schwarzschild, and A. Ascherio, “Use of ibuprofen and risk of Parkinson disease,” Neurology, vol. 76, no. 10, pp. 863–869, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. Z. Xuan, L. Xing, G. Tao, S. Xun, and Z.-R. Zhang, “In vitro and in vivo investigation of dexibuprofen derivatives for CNS delivery,” Acta Pharmacologica Sinica, vol. 33, no. 2, pp. 279–288, 2012. View at Publisher · View at Google Scholar · View at Scopus
  15. Y. Deguchi, H. Hayashi, S. Fujii et al., “Improved brain delivery of a nonsteroidal anti-inflammatory drug with a synthetic glyceride ester: a preliminary attempt at a CNS drug delivery system for the therapy of Alzheimer's disease,” Journal of Drug Targeting, vol. 8, no. 6, pp. 371–381, 2000. View at Publisher · View at Google Scholar · View at Scopus
  16. B. P. Imbimbo, “Why did tarenflurbil fail in Alzheimer's disease?” Journal of Alzheimer's Disease, vol. 17, no. 4, pp. 757–760, 2009. View at Publisher · View at Google Scholar · View at Scopus
  17. D. Zheng, X. Shuai, Y. Li et al., “Novel flurbiprofen derivatives with improved brain delivery: synthesis, in vitro and in vivo evaluations,” Drug Delivery, vol. 23, no. 7, pp. 2183–2192, 2014. View at Publisher · View at Google Scholar
  18. J. M. R. Parepally, H. Mandula, and Q. R. Smith, “Brain uptake of nonsteroidal anti-inflammatory drugs: ibuprofen, flurbiprofen, and indomethacin,” Pharmaceutical Research, vol. 23, no. 5, pp. 873–881, 2006. View at Publisher · View at Google Scholar · View at Scopus
  19. S. Lehrer, “Nasal NSAIDs for Alzheimer's disease,” American Journal of Alzheimer's Disease & Other Dementias, vol. 29, no. 5, pp. 401–403, 2014. View at Publisher · View at Google Scholar · View at Scopus
  20. S. C. Ghosh, B. Kim, J. Im et al., “Mitochondrial affinity of guanidine-rich molecular transporters built on mγo- and scγllo-inositol scaffolds: stereochemistry dependency,” Bulletin of the Korean Chemical Society, vol. 31, no. 12, pp. 3623–3631, 2010. View at Publisher · View at Google Scholar · View at Scopus
  21. J. Im, S. Kim, Y.-H. Jeong et al., “Preparation and evaluation of BBB-permeable trehalose derivatives as potential therapeutic agents for Huntington's disease,” Medicinal Chemistry Communications, vol. 4, no. 2, pp. 310–316, 2013. View at Publisher · View at Google Scholar · View at Scopus
  22. K. K. Maiti, W. S. Lee, T. Takeuchi et al., “Guanidine-containing molecular transporters: sorbitol-based transporters show high intracellular selectivity toward mitochondria,” Angewandte Chemie—International Edition, vol. 46, no. 31, pp. 5880–5884, 2007. View at Publisher · View at Google Scholar · View at Scopus
  23. J. Im, K. K. Maiti, W. Kim, K.-T. Kim, and S.-K. Chung, “Cellular uptake properties of the complex derived from quantum dots and G8 molecular transporter,” Bulletin of the Korean Chemical Society, vol. 32, no. 4, pp. 1282–1292, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. J. Im, W. Kim, K.-T. Kim, and S.-K. Chung, “Preparation of a 3′-azido-3′-deoxythymidine (AZT) derivative, which is blood–brain barrier permeable,” Chemical Communications, no. 31, pp. 4669–4671, 2009. View at Publisher · View at Google Scholar · View at Scopus
  25. J. Im, G. Biswas, W. Kim, K.-T. Kim, and S.-K. Chung, “A blood-brain barrier permeable derivative of 5-fluorouracil: preparation, intracellular localization, and mouse tissue distribution,” Bulletin of the Korean Chemical Society, vol. 32, no. 3, pp. 873–879, 2011. View at Publisher · View at Google Scholar · View at Scopus
  26. S. Bhuniya, Y. J. Seo, and B. H. Kim, “(S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery,” Tetrahedron Letters, vol. 47, no. 40, pp. 7153–7156, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. A. K. Pathak, V. Pathak, L. E. Seitz, K. N. Tiwari, M. S. Akhtar, and R. C. Reynolds, “A facile method for deprotection of trityl ethers using column chromatography,” Tetrahedron Letters, vol. 42, no. 44, pp. 7755–7757, 2001. View at Publisher · View at Google Scholar · View at Scopus
  28. P. A. Wender, W. C. Galliher, E. A. Goun, L. R. Jones, and T. H. Pillow, “The design of guanidinium-rich transporters and their internalization mechanisms,” Advanced Drug Delivery Reviews, vol. 60, no. 4-5, pp. 452–472, 2008. View at Publisher · View at Google Scholar · View at Scopus
  29. J. B. Rothbard, T. C. Jessop, and P. A. Wender, “Adaptive translocation: the role of hydrogen bonding and membrane potential in the uptake of guanidinium-rich transporters into cells,” Advanced Drug Delivery Reviews, vol. 57, no. 4, pp. 495–504, 2005. View at Publisher · View at Google Scholar · View at Scopus
  30. E. Wexselblatt, J. D. Esko, and Y. Tor, “On guanidinium and cellular uptake,” The Journal of Organic Chemistry, vol. 79, no. 15, pp. 6766–6774, 2014. View at Publisher · View at Google Scholar · View at Scopus