Nuclear Medicine and Biology
Volume 36, Issue 2 , Pages 107-116 , February 2009

18F-Labeled benzylideneaniline derivatives as new ligands for β-amyloid plaque imaging in Alzheimer's disease

  • Hak Jeong Lee

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
    • Cancer Research Institute, Seoul National University College of Medicine, Seoul National University, Jongno-gu, Seoul 110-744, South Korea
    • Department of Biomedical Sciences, Seoul National University College of Medicine, Jongno-gu, Seoul 110-799, South Korea
  • ,
  • Jae Min Jeong

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
    • Cancer Research Institute, Seoul National University College of Medicine, Seoul National University, Jongno-gu, Seoul 110-744, South Korea
    • Department of Biomedical Sciences, Seoul National University College of Medicine, Jongno-gu, Seoul 110-799, South Korea
    • Corresponding Author InformationCorresponding author. Department of Nuclear Medicine, Seoul National University Hospital, Jongno-gu, Seoul 110-744, South Korea. Tel.: +82 2 2072 3805; fax: +82 2 745 7690.
  • ,
  • Ganesha Rai

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Yun-Sang Lee

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Young Soo Chang

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
    • Cancer Research Institute, Seoul National University College of Medicine, Seoul National University, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Young Ju Kim

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
    • Cancer Research Institute, Seoul National University College of Medicine, Seoul National University, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Hyung Woo Kim

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Dong Soo Lee

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Jung Key Chung

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea
    • Cancer Research Institute, Seoul National University College of Medicine, Seoul National University, Jongno-gu, Seoul 110-744, South Korea
    • Department of Biomedical Sciences, Seoul National University College of Medicine, Jongno-gu, Seoul 110-799, South Korea
  • ,
  • Inhee Mook-Jung

      Affiliations

    • Cancer Research Institute, Seoul National University College of Medicine, Seoul National University, Jongno-gu, Seoul 110-744, South Korea
    • Department of Biomedical Sciences, Seoul National University College of Medicine, Jongno-gu, Seoul 110-799, South Korea
    • Department of Biochemistry, Seoul National University College of Medicine, Jongno-gu, Seoul 110-744, South Korea
  • ,
  • Myung Chul Lee

      Affiliations

    • Department of Nuclear Medicine, Seoul National University College of Medicine and Institute of Radiation Medicine, Jongno-gu, Seoul 110-744, South Korea

Received 24 September 2008 ,Revised 3 November 2008 ,Accepted 4 November 2008.

References 

  1. Vickers JC, Dickson TC, Adlard PA, Saunders HL, King CE, McCormack G. The cause of neuronal degeneration in Alzheimer's disease. Prog Neurobiol. 2000;60:139–165
  2. Shastry BS. Molecular genetics of familial Alzheimer disease. Am J Med Sci. 1998;315:266–272
  3. Nussbaum RL, Ellis CE. Alzheimer's disease and Parkinson's disease. N Engl J Med. 2003;348:1356–1364
  4. Hardy J, Selkoe DJ. The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science. 2002;297:353–356
  5. Selkoe DJ, Schenk D. Alzheimer's disease: molecular understanding predicts amyloid-based therapeutics. Annu Rev Pharmacol Toxicol. 2003;43:545–584
  6. Zamrini E, De Santi S, Tolar M. Imaging is superior to cognitive testing for early diagnosis of Alzheimer's disease. Neurobiol Aging. 2004;25:685–691
  7. Selkoe DJ. Amyloid β-protein and the genetics of Alzheimer's disease. J Biol Chem. 1996;271:18295–18298
  8. Yankner BA. Mechanisms of neuronal degeneration in Alzheimer's disease. Neuron. 1996;16:921–932
  9. Benveniste H, Einstein G, Kim KR, Hulette C, Johnson GA. Detection of neuritic plaques in Alzheimer's disease by magnetic resonance microscopy. Proc Natl Acad Sci U S A. 1999;96:14079–14084
  10. Zhang J, Yarowsky P, Gordon MN, Di Carlo G, Munireddy S, van Zijl PC, et al. Detection of amyloid plaques in mouse models of Alzheimer's disease by magnetic resonance imaging. Magn Reson Med. 2004;51:452–457
  11. Higuchi M, Iwata N, Matsuba Y, Sato K, Sasamoto K, Saido TC. 19F and 1H MRI detection of amyloid β plaques in vivo. Nat Neurosci. 2005;8:527–533
  12. Hintersteiner M, Enz A, Frey P, Jaton AL, Kinzy W, Kneuer R, et al. In vivo detection of amyloid-β deposits by near-infrared imaging using an oxazine-derivative probe. Nat Biotechnol. 2005;23:577–583
  13. Bacskai BJ, Kajdasz ST, Christie RH, Carter C, Games D, Seubert P, et al. Imaging of amyloid-β deposits in brains of living mice permits direct observation of clearance of plaques with immunotherapy. Nat Med. 2001;7:369–372
  14. Skoch J, Dunn A, Hyman BT, Bacskai BJ. Development of an optical approach for noninvasive imaging of Alzheimer's disease pathology. J Biomed Opt. 2005;10:11007
  15. Nordberg A. PET imaging of amyloid in Alzheimer's disease. Lancet Neurol. 2004;3:519–527
  16. Friedland RP, Kalaria R, Berridge M, Miraldi F, Hedera P, Reno J, et al. Neuroimaging of vessel amyloid in Alzheimer's disease. Ann N Y Acad Sci. 1997;826:242–247
  17. Kung HF, Lee CW, Zhuang ZP, Kung MP, Hou C, Plossl K. Novel stilbenes as probes for amyloid plaques. J Am Chem Soc. 2001;123:12740–12741
  18. Zhuang ZP, Kung MP, Hou C, Skovronsky DM, Gur TL, Plossl K, et al. Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. J Med Chem. 2001;44:1905–1914
  19. Styren SD, Hamilton RL, Styren GC, Klunk WK. X-34, a fluorescent derivative of Congo red: a novel histochemical stain for Alzheimer's disease pathology. J Histochem Cytochem. 2000;48:1223–1232
  20. Klunk WE, Bacskai BJ, Mathis CA, Kajdasz ST, McLellan ME, Frosch MP, et al. Imaging Aβ plaques in living transgenic mice with multiphoton microscopy and methoxy-X04, a systemically administered Congo red derivative. J Neuropathol Exp Neurol. 2002;61:797–805
  21. Mathis CA, Wang Y, Holt DP, Huang GF, Debnath ML, Klunk WE. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem. 2003;46:2740–2754
  22. Klunk WE, Wang Y, Huang GF, Debnath ML, Holt DP, Mathis CA. Uncharged thioflavin-T derivatives bind to amyloid-beta protein with high affinity and readily enter the brain. Life Sci. 2001;69:1471–1484
  23. Kung MP, Hou C, Zhuang ZP, Zhang B, Skovronsky D, Trojanowski JQ, et al. IMPY: an improved thioflavin-T derivative for in vivo labeling of beta-amyloid plaques. Brain Res. 2002;956:202–210
  24. Chang YS, Jeong JM, Lee YS, Kim HW, Ganesha RB, Kim YJ, et al. Synthesis and evaluation of benzothiophene derivatives as ligands for imaging β-amyloid plaques in Alzheimer's disease. Nucl Med Biol. 2006;33:811–820
  25. Agdeppa ED, Kepe V, Liu J, Flores-Torres S, Satyamurthy N, Petric A, 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. J Neurosci. 2001;21:RC189
  26. Berridge MS, Tewson TJ. Chemistry of fluorine-18 radiopharmaceuticals. Int J Rad Appl Instrum A. 1986;37:685–693
  27. Neuvonen K, Fulop F, Neuvonen H, Koch A, Kleinpeter E, Pihlaja K. Comparison of the electronic structures of imine and hydrazone side-chain functionalities with the aid of 13C and 15N NMR chemical shifts and PM3 calculations. The influence of CN-substitution on the sensitivity to aromatic substitution. J Org Chem. 2003;68:2151–2160
  28. Chang YS, Jeong JM, Lee YS, Kim HW, Rai GB, Lee SJ, et al. Preparation of 18F-human serum albumin: a simple and efficient protein labeling method with 18F using a hydrazone-formation method. Bioconjug Chem. 2005;16:1329–1333
  29. Dayal SK, Ehrenson S, Taft RW. Substituent effects, electronic transmission, and structural dependence of pi delocalization as studied with the p-fluorophenyl tag. J Am Chem Soc. 1972;94:9113–9122
  30. Radhi MA, Palyi G, Marko L. Hydrogenation of N-benzylideneaniline with CO+H2O and transalkylation reactions of benzaldehyde with tertiary aliphatic amines catalyzed by iron pentacarbonyl. J Mol Catalysis. 1983;22:195–203
  31. Radhi MA, Marka L. Hydrogenation of N-benzylideneaniline with molecular hydrogen using iron pentacarbonyl as catalyst precursor. J Organometallic Chem. 1984;262:359–364
  32. French AN, Napolitano E, VanBrocklin HF, Hanson RN, Welch MJ, Katzenellenbogen JA. Synthesis, radiolabeling and tissue distribution of 11 beta-fluoroalkyl- and 11 beta-fluoroalkoxy-substituted estrogens: target tissue uptake selectivity and defluorination of a homologous series of fluorine-18-labeled estrogens. Nucl Med Biol. 1993;20:31–47
  33. Jeong JM. β-Amyloid imaging probes. Nucl Med Mol Imaging. 2007;41:112–117
  34. Bacskai BJ, Klunk WE, Mathis CA, Hyman BT. Imaging amyloid-β deposits in vivo. J Cereb Blood Flow Metab. 2002;22:1035–1041
  35. Rowe CC, Ackerman U, Browne W, Mulligan R, Pike KL, O'Keefe G, et al. Imaging of amyloid β in Alzheimer's disease with 18F-BAY94-9172, novel PET tracer: proof of mechanism. Lancet Neurol. 2008;7:129–135

PII: S0969-8051(08)00242-4

doi: 10.1016/j.nucmedbio.2008.11.004

Nuclear Medicine and Biology
Volume 36, Issue 2 , Pages 107-116 , February 2009