Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Chemometric Studies on Brain-uptake of PET Agents via VolSurf Analysis

  • Lee, Hyo-Seon (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Kim, Mi-Kyoung (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Lee, Chae-Woon (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Kim, Jin-Young (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Choo, Il-Han (Department of Neuropsychiatry, Seoul National University College of Medicine) ;
  • Woo, Jong-Inn (Department of Neuropsychiatry, Seoul National University College of Medicine) ;
  • Chong, You-Hoon (Department of Bioscience and Biotechnology, Konkuk University)
  • Published : 2008.01.20
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Abstract

High initial (2 minutes after iv injection) brain-uptake of PET agents is required to deliver the agent to binding sites in brain tissue but, for quantification of the specific binding, relatively rapid washout of free and non-specifically bound PET agents from the brain (30 minutes after injection) also is required. In order to compare the physicochemical properties of the PET agents which are responsible for early brain-uptake and rapid washout, respectively, chemometric analysis on brain-uptake of PET agents was performed via a classical VolSurf approach. According to the PCA and PLS results, high 2-30 min brain-uptake ratio seems to be related to the large hydrophobic regions in the PET agents which are not confined to a particular surface.

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References

  1. Hardy, J.; Selkoe, D. J. Science 2002, 297, 353 https://doi.org/10.1126/science.1072994
  2. Lim, H.-J.; Jung, M. H.; Lee, I. Y. C.; Park, W. K. Bull. Korean Chem. Soc. 2006, 27, 1371 https://doi.org/10.5012/bkcs.2006.27.9.1371
  3. Kim, J.; Myung, E.-K.; Lee, I.-H.; Paik, W. K. Bull. Korean Chem. Soc. 2007, 28, 2283 https://doi.org/10.5012/bkcs.2007.28.12.2283
  4. Nordberg, A. Lancet Neurol. 2004, 3, 519 https://doi.org/10.1016/S1474-4422(04)00853-1
  5. Klunk, W. E.; Engler, H.; Nordberg, A.; Wang, Y.; Blomqvist, G.; Holt, D. P.; Bergstrom, M.; Savitcheva, I.; Huang, G. F.; Estrada, S.; Ausen, B.; Debnath, M. L.; Barletta, J.; Price, J. C.; Sandell, J.; Lopresti, B. J.; Wall, A.; Koivisto, P.; Antoni, G.; Mathis, C. A.; Langstrom, B. Ann. Neurol. 2004, 55, 306 https://doi.org/10.1002/ana.20009
  6. Price, J. C.; Klunk, W. E.; Lopresti, B. J.; Lu, X.; Hoge, J. A.; Ziolko, S. K.; Holt, D. P.; Meltzer, C. C.; Dekosky, S. T.; Mathis, C. A. J. Cereb. Blood Flow Metab. 2005, 25, 1528 https://doi.org/10.1038/sj.jcbfm.9600146
  7. Dishino, D. D.; Welch, M. J.; Kilbourn, M. R.; Raichle, M. E. J. Nucl. Med. 1983, 24, 1030
  8. Levin, V. A. J. Med. Chem. 1980, 23, 682 https://doi.org/10.1021/jm00180a022
  9. Feher, M.; Sourial, E.; Schmidt, J. M. Int. J. Pharm. 2000, 201, 239 https://doi.org/10.1016/S0378-5173(00)00422-1
  10. Cai, L.; Chin, F. T.; Pike, V. W.; Toyama, H.; Liow, J.-S.; Zoghbi, S. S.; Modell, K.; Briard, E.; Shetty, H. U.; Sinclair, K.; Donohue, S.; Tipre, D.; Kung, M.-P.; Dagostin, C.; Widdowson, D. A.; Green, M.; Gao, W.; Herman, M. M.; Ichise, M.; Innis, R. B. J. Med. Chem. 2004, 47, 2208 https://doi.org/10.1021/jm030477w
  11. Ono, M.; Kawashima, H.; Nonaka, A.; Kawai, T.; Haratake, M.; Mori, H.; Kung, M.-P.; Kung, H. F.; Saji, H.; Nakayama, M. J. Med. Chem. 2006, 49,2725 https://doi.org/10.1021/jm051176k
  12. Zhuang, Z.-P.; Kung, M.-P.; Wilson, A.; Lee, C.-W.; Plössl, K.; Hou, C.; Holtzman, D. M.; Kung, H. F. J. Med. Chem. 2003, 46, 237 https://doi.org/10.1021/jm020351j
  13. Zhuang, Z.-P.; Kung, M.-P.; Hou, C.; Plössl, K.; Skovronsky, D.; Gur, T. L.; Trojanowski, J. Q.; Lee, V. M.-Y.; Kung, H. F. Nucl. Med. Biol. 2001, 28, 887 https://doi.org/10.1016/S0969-8051(01)00264-5
  14. Ono, M.; Kung, M.-P.; Hou, C.; Kung, H. F. Nucl. Med. Biol. 2002, 29, 633 https://doi.org/10.1016/S0969-8051(02)00326-8
  15. Ono, M.; Wilson, A.; Nobrega, J.; Westaway, D.; Verhoeff, P.; Zhuang, Z.-P.; Kung, M.-P.; Kung, H. F. Nucl. Med. Biol. 2003, 30, 565 https://doi.org/10.1016/S0969-8051(03)00049-0
  16. Henriksen, G.; Hauser, A.; Westwell, A. D.; Yousefi, B. H.; Schwaiger, M.; Drzezga, A.; Wester, H.-J. J. Med. Chem. 2007, 50, 1087 https://doi.org/10.1021/jm061466g
  17. Chang, Y. S.; Jeong, J. M.; Lee, Y.-S.; Kim, H. W.; Rai, B. G.; Kim, Y. J.; Lee, D. S.; Chung, J.-K.; Lee, M. C. Nucl. Med. Biol. 2006, 33, 811 https://doi.org/10.1016/j.nucmedbio.2006.06.006
  18. Zhuang, Z.-P.; Kung, M.-P.; Hou, C.; Skovronsky, D. M.; Gur, T. L.; Plössl, K.; Trojanowski, J. Q.; Lee, V. M.-Y.; Kung, H. F. J. Med. Chem. 2001, 44, 1905 https://doi.org/10.1021/jm010045q
  19. Ryu, E. K.; Choe, Y. S.; Lee, K.-H.; Choi, Y.; Kim, B.-T. J. Med. Chem. 2006, 49, 6111 https://doi.org/10.1021/jm0607193
  20. Chandra, R.; Kung, M.-P.; Kung, H. F. Bioorg. Med. Chem. Lett. 2006, 16, 1350 https://doi.org/10.1016/j.bmcl.2005.11.055
  21. Mathis, C. A.; Wang, Y.; Holt, D. P.; Huang, G.-F.; Debnath, M. L.; Klunk, W. E. J. Med. Chem. 2003, 46, 2740 https://doi.org/10.1021/jm030026b
  22. Halgren, T. A.; Nachbar, R. B. J. Comput. Chem. 1996, 17, 587
  23. Halgren, T. A. J. Comput. Chem. 1999, 20, 730 https://doi.org/10.1002/(SICI)1096-987X(199905)20:7<730::AID-JCC8>3.0.CO;2-T
  24. Cruciani, G.; Crivori, P.; Carrupt, P.-A.; Testa, B. J. Mol. Struct. (THEOCHEM) 2000, 503, 17 https://doi.org/10.1016/S0166-1280(99)00360-7
  25. Crivori, P.; Cruciani, G.; Carrupt, P.-A.; Testa, B. J. Med. Chem. 2000, 43, 2204 https://doi.org/10.1021/jm990968+

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