Table of Contents Author Guidelines Submit a Manuscript
Journal of Analytical Methods in Chemistry
Volume 2018, Article ID 1651989, 5 pages
https://doi.org/10.1155/2018/1651989
Research Article

A Pyridazine-Based Fluorescent Probe Targeting Aβ Plaques in Alzheimer’s Disease

1Research Division for Biotechnology, Advanced Radiation Technology Institute, Korea Atomic Energy Research Institute, Jeongeup 580-185, Republic of Korea
2Technology Innovation Support Team, Korea Research Institute of Chemical Technology (KRICT), Deajeon 305-600, Republic of Korea

Correspondence should be addressed to Yong Dae Park; rk.er.ireak@krapdy

Received 10 October 2017; Accepted 14 December 2017; Published 27 February 2018

Academic Editor: Subhankar Singha

Copyright © 2018 Yong Dae Park 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. G. Edwards III, I. Moreno-Gonzalez, and C. Soto, “Amyloid-beta and tau pathology following repetitive mild traumatic brain injury,” Biochemical and Biophysical Research Communications, vol. 483, no. 4, pp. 1137–1142, 2017. View at Publisher · View at Google Scholar · View at Scopus
  2. E. D. Roberson and L. Mucke, “100 years and counting: prospects for defeating Alzheimer’s disease,” Science, vol. 314, no. 5800, pp. 781–784, 2006. View at Publisher · View at Google Scholar · View at Scopus
  3. J. H. Kim, J. Lee, S. Lee, and E. J. Cho, “Quercetin and quercetin-3-β-d-glucoside improve cognitive and memory function in Alzheimer’s disease mouse,” Applied Biological Chemistry, vol. 59, no. 5, pp. 721–728, 2016. View at Publisher · View at Google Scholar · View at Scopus
  4. C. A. Mathis, Y. Wang, and W. E. Klunk, “Imaging beta-amyloid plaques and neurofibrillary tangles in the aging human brain,” Current Pharmaceutical Design, vol. 10, no. 13, pp. 1469–1492, 2004. View at Publisher · View at Google Scholar · View at Scopus
  5. A. Nordberg, “PET imaging of amyloid in Alzheimer’s disease,” The Lancet Neurology, vol. 3, no. 9, pp. 519–527, 2004. View at Publisher · View at Google Scholar · View at Scopus
  6. D. J. Selkoe, “Imaging Alzheimer’s amyloid,” Nature Biotechnology, vol. 18, no. 8, pp. 823-824, 2000. View at Publisher · View at Google Scholar · View at Scopus
  7. E. D. Agdeppa, V. Kepe, J. Liu et al., “Binding characteristics of radiofluorinated 6-dialkylamino-2-naphthylethylidene derivatives as positron emission tomography imaging probes for beta-amyloid plaques in Alzheimer’s disease,” Journal of Neuroscience, vol. 21, no. 24, p. RC189, 2001. View at Google Scholar
  8. H. F. Kung, S. R. Choi, W. Qu, W. Zhang, and D. Skovronsky, “18F stilbenes and styrylpyridines for PET imaging of Aβ plaques in Alzheimer’s disease: a miniperspective,” Journal of Medicinal Chemistry, vol. 53, no. 3, pp. 933–941, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. C. A. Mathis, Y. Wang, D. P. Holt, G. F. Huang, M. L. Debnath, and W. E. Klunk, “Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents,” Journal of Medicinal Chemistry, vol. 46, no. 13, pp. 2740–2754, 2003. View at Publisher · View at Google Scholar · View at Scopus
  10. N. Okamura, Y. Shiga, S. Furumoto et al., “In vivo detection of prion amyloid plaques using [(11)C]BF-227 PET,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 37, no. 5, pp. 934–941, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. M. Ono, A. Wilson, J. Nobrega et al., “11C-labeled stilbene derivatives as Aβ-aggregate-specific PET imaging agents for Alzheimer’s disease,” Nuclear Medicine and Biology, vol. 30, no. 6, pp. 565–571, 2003. View at Publisher · View at Google Scholar · View at Scopus
  12. C. C. Rowe, U. Ackerman, W. Browne et al., “Imaging of amyloid beta in Alzheimer’s disease with 18F-BAY94-9172, a novel PET tracer: proof of mechanism,” The Lancet Neurology, vol. 7, no. 2, pp. 129–135, 2008. View at Publisher · View at Google Scholar · View at Scopus
  13. Z. P. Zhuang, M. P. Kung, A. Wilson et al., “Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting beta-amyloid plaques in the brain,” Journal of Medicinal Chemistry, vol. 46, no. 2, pp. 237–243, 2003. View at Publisher · View at Google Scholar · View at Scopus
  14. R. Weissleder and U. Mahmood, “Molecular imaging,” Radiology, vol. 219, no. 2, pp. 316–333, 2001. View at Publisher · View at Google Scholar
  15. W. M. Chang, M. Dakanali, C. C. Capule, C. J. Sigurdson, J. Yang, and E. A. Theodorakis, “ANCA: a family of fluorescent probes that bind and stain amyloid plaques in human tissue,” ACS Chemical Neuroscience, vol. 2, no. 5, pp. 249–255, 2011. View at Publisher · View at Google Scholar
  16. G. Yu, H. Jung, and H. Mok, “Indocyanine green-incorporated exosomes for improved in vivo imaging of sentinel lymph node,” Applied Biological Chemistry, vol. 59, no. 1, pp. 71–76, 2016. View at Publisher · View at Google Scholar · View at Scopus
  17. M. Hintersteiner, A. Enz, P. Frey et al., “In vivo detection of amyloid-beta deposits by near-infrared imaging using an oxazine-derivative probe,” Nature Biotechnology, vol. 23, no. 5, pp. 577–583, 2005. View at Publisher · View at Google Scholar · View at Scopus
  18. E. E. Nesterov, J. Skoch, B. T. Hyman, W. E. Klunk, B. J. Bacskai, and T. M. Swager, “In vivo optical imaging of amyloid aggregates in brain: design of fluorescent markers,” Angewandte Chemie International Edition, vol. 44, no. 34, pp. 5452–5456, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. S. B. Raymond, J. Skoch, I. D. Hills, E. E. Nesterov, T. M. Swager, and B. J. Bacskai, “Smart optical probes for near-infrared fluorescence imaging of Alzheimer’s disease pathology,” European Journal of Nuclear Medicine and Molecular Imaging, vol. 35, no. S1, pp. S93–S98, 2008. View at Publisher · View at Google Scholar · View at Scopus
  20. Q. Li, J. S. Lee, C. Ha et al., “Solid-phase synthesis of styryl dyes and their application as amyloid sensors,” Angewandte Chemie International Edition, vol. 43, no. 46, pp. 6331–6335, 2004. View at Publisher · View at Google Scholar · View at Scopus
  21. C. Ran, X. Xu, S. B. Raymond et al., “Design, synthesis, and testing of difluoroboron-derivatized curcumins as near-infrared probes for in vivo detection of amyloid-beta deposits,” Journal of the American Chemical Society, vol. 131, no. 42, pp. 15257–15261, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. M. Ono, M. Ishikawa, H. Kimura et al., “Development of dual functional SPECT/fluorescent probes for imaging cerebral beta-amyloid plaques,” Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 13, pp. 3885–3888, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. W. E. Klunk, H. Engler, A. Nordberg et al., “Imaging brain amyloid in Alzheimer’s disease with Pittsburgh Compound-B,” Annals of Neurology, vol. 55, no. 3, pp. 306–319, 2004. View at Publisher · View at Google Scholar · View at Scopus
  24. Y. D. Park, J. H. Park, M. G. Hur et al., “Fluorescent 2-styrylpyridazin-3(2H)-one derivatives as probes targeting amyloid-beta plaques in Alzheimer’s disease,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 12, pp. 4106–4110, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. S. J. Jung, S. H. Park, E. J. Lee et al., “Development of fluorescent probes that bind and stain amyloid plaques in Alzheimer’s disease,” Archives of Pharmacal Research, vol. 38, no. 11, pp. 1992–1998, 2015. View at Publisher · View at Google Scholar · View at Scopus
  26. M. Staderini, M. A. Martin, M. L. Bolognesi, and J. C. Menendez, “Imaging of beta-amyloid plaques by near infrared fluorescent tracers: a new frontier for chemical neuroscience,” Chemical Society Reviews, vol. 44, no. 7, pp. 1807–1819, 2015. View at Publisher · View at Google Scholar · View at Scopus