[ ${\beta}-Amyloid$ ] Imaging Probes

베타아밀로이드 영상용 프로브

  • Jeong, Jae-Min (Department of Nuclear Medicine, Seoul National University College of Medicine)
  • 정재민 (서울대학교 의과대학 핵의학교실)
  • Published : 2007.04.30

Abstract

Imaging distribution of ${\beta}-amyloid$ plaques in Alzheimer's disease is very important for early and accurate diagnosis. Early trial of the ${\beta}-amyloid$ plaques includes using radiolabeled peptides which can be only applied for peripheral ${\beta}-amyloid$ plaques due to limited penetration through the blood brain barrier (BBB). Congo red or Chrysamine G derivatives were labeled with Tc-99m for imaging ${\beta}-amyloid$ plaques of Alzheimer patient's brain without success due to problem with BBB penetration. Thioflavin T derivatives gave breakthrough for ${\beta}-amyloid$ imaging in vivo, and a benzothiazole derivative [C-11]6-OH-BTA-1 brought a great success. Many other benzothiazole, benzoxazole, benzofuran, imidazopyridine, and styrylbenzene derivatives have been labeled with F-18 and I-123 to improve the imaging quality. However, [C-11]6-OH-BTA-1 still remains as the best. However, short half-life of C-11 is a limitation of wide distribution of this agent. So, it is still required to develop an Tc-99m, F-18 or I-123 labeled agent for ${\beta}-amyloid$ imaging agent.

Keywords

References

  1. McKhann G., Drachman D, Folstein M, Katzman R, Price D, Stadlan EM. Clinical diagnosis of Alzheimer's disease: a report of the NINCDS-ADRDA Work Group, Department of Health and Human Services Task Force on Alzheimer's Disease. Neurology 1984;34:939-44 https://doi.org/10.1212/WNL.34.7.939
  2. Weiner MF. Alzheimer's disease: diagnosis and treatment. Harvard Rev. Psychiatry 1997;4:306-16 https://doi.org/10.3109/10673229709030558
  3. Selkoe DJ. Amyloid $\beta$-protein and the genetics of Alzheimer's disease. J Biol Chem 1996;271:18295-8 https://doi.org/10.1074/jbc.271.31.18295
  4. Yankner BA. Mechanism of neuronaldegeneration in Alzheimer's disease. Neuron 1996;16:921-32 https://doi.org/10.1016/S0896-6273(00)80115-4
  5. Marshall JR, Stimson ER, Ghilardi JR, Vinters HV, Mantyh PW, Maggio JE. Noninvasive imaging of peripherally injected Alzheimer's disease type synthetic ATEX>$\beta$ amyloid in vivo. Bioconjugate Chem 2002;13:276-84 https://doi.org/10.1021/bc010066z
  6. Schaadt BK, Hendel HW, Gimsing P, Jonsson V, Pedersen H, Hesse $^{99m}Tc$-Aprotinin scintigraphy in amylodosis. J Nucl Med 2003;44:177-83
  7. Bornebroek M, Verzijlbergen JF, Haan J, Van Scheyen EJ, Verhoeff NPLG, Pauwels EKJ, et al. Potential for imaging cerebral amyloid deposits using $ ^{123}I$-labelled serum amyloid P component and SPET. Nucl Med Commun 1996;17:929-33 https://doi.org/10.1097/00006231-199611000-00002
  8. Saito Y, Buciak J, Yang J, Pardridge WM. Vector-mediated delivery of $^{125}I$-labeled $\beta$-amyloid peptide $A{\beta}_{1-40}$ through the blood-brain barrier and binding to Alzheimer disease amyloid of the $A{\beta}_{1-40}$/vector complex. Proc Natl Acad Sci USA 1995;92:10227-31
  9. Klunk WE, Debnath ML, Pettegrew JW. Development of small molecule probes for the beta-amyloid protein of Alzheimer's disease. Neurobiol Aging 1994;15:691-8 https://doi.org/10.1016/0197-4580(94)90050-7
  10. Klunk WE, Debnath ML, Pettegrew JW. Chrysamine-G binding to Alzheimer and control brain: Autopsy study of a new amyloid probe. Neurobiol Aging 1995;16:541-8 https://doi.org/10.1016/0197-4580(95)00058-M
  11. Ashburn TT, Han H, McGuinness BF, Lansbury PT. Amyloid probes based on Congo Red distinguish between fibrils comprising different peptides. Chem Biol 1996;3:351-8 https://doi.org/10.1016/S1074-5521(96)90118-0
  12. Han H, Cho C-G, Lansbury PT Jr. Technetium complexes for the quantitation of brain amyloid. J Am Chem Soc 1996;118:4506-7 https://doi.org/10.1021/ja960207l
  13. Oya S, Plössl K, Kung M-P, Stevenson DA, Kung HF. Small and neutral TcVO BAT, bisaminoethanthiol ($N_2S_2$) complexes for developing new brain imaging agents. Nucl Med Biol 1998;25: 135-40 https://doi.org/10.1016/S0969-8051(97)00153-4
  14. Kung HF, Molnar M, Billings J, Blau M. Synthesis and biodistribution of neutral lipid-soluble Tc-99m complexes that cross the blood-brain barrier. J Nucl Med 1984;25:326-32
  15. Jeong JM, Kim YJ, Lee YS, Ko JI, Son M, Lee DS, et al. Lipiodol solution of a lipophilic agent, $^{188]Re$-TDD, for the treatment of liver cancer. Nucl Med Biol 2001;28:197-204 https://doi.org/10.1016/S0969-8051(00)00208-0
  16. Dezutter NA, Dom RJ, de Groot TJ, Bromans GM, Verbruggen AM. $^{99m}Tc$-MAMA-chrysamine G, a probe for beta-amyloid protein of Alzheimer's disease. Eur J Nucl Med 1999;26:1392-9 https://doi.org/10.1007/s002590050470
  17. Dezutter NA, de Groot TJ, Busson RH, Janssen GA, Verbruggen AM. Preparation of Tc-99m-$N2_S_2$ conjugates of chrysamine G, potential probes for the beta-amyloid protein of Alzheimer's disease. J Label Cmpd Radiopharm 1999;42:309-24 https://doi.org/10.1002/(SICI)1099-1344(199904)42:4<309::AID-JLCR192>3.0.CO;2-O
  18. Zhen W, Han H, Anguiano M, Lemere CA, Cho C-G, Lansbury PT Jr. Synthesis and amyloid binding properties of rhenium complexes: preliminary progress toward a reagent for SPECT imaging of Alzheimer's disease brain. J Med Chem 1999;42:2805-15 https://doi.org/10.1021/jm990103w
  19. Klunk WE, Mathis CA, Wang Y. Thioflavin derivatives for use in antemortem diagnosis of Alzheimer's disease and vivo imaging and prevention of amyloid deposition. US Patent 2002/0133019 A1
  20. Wischik CM, Harrington CR, Rickard JE, Horsley D. Neurofibrillary labels. 2002 PCT WO 02/075318 A2
  21. Mathis CA, Holt DP, Wang Y, Huang GF, Debmath ML, Klunk WE. Lipophilic 11C-labelled thioflavin-T analogues for imaging amyloid plaques in Alzheimer's disease. J Label Compd Radiopharm 2001;44:S26-S8 https://doi.org/10.1002/jlcr.2580440110
  22. Mathis CA, Bacskai BJ, Kajdasz ST, McLellan ME, Frosch MP, Hyman BT, et al. A lipophilic thioflavin-T derivative for positron emission tomography (PET) imaging of amyloid in brain. Bioorg Med Chem Lett 2002;12:295-8 https://doi.org/10.1016/S0960-894X(01)00734-X
  23. 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;46:2740-54 https://doi.org/10.1021/jm030026b
  24. Zhuang Z-P, Kung M-P, Hou C, Skovronsky D, Gur TL, Trojanowski JQ, et al. Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. J Med Chem 2001;44:1905-14 https://doi.org/10.1021/jm010045q
  25. Zhuang Z-P, Kung M-P, Hou C, Plössl K, Skovronsky D, Gur TL, et al. IBOX (2-(4'-dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain. Nucl Med Biol 2001;28:887-94 https://doi.org/10.1016/S0969-8051(01)00264-5
  26. Ono M, Kung M-P, Hou C, Kung HF. Benzofuran derivatives as A $\beta$-aggregate-specific imaging agents for Alzheimer's disease. Nucl Med Biol 2002;29:633-42 https://doi.org/10.1016/S0969-8051(02)00326-8
  27. Zhuang Z-P, Kung M-P, Wilson A, Lee C-W, Plössl K, Hou C, et al. Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting $\beta$-amyloid plaques in the brain. J Med Chem 2003;46:237-43 https://doi.org/10.1021/jm020351j
  28. Chang YS, Jeong JM, Lee Y-S, Kim HW, Rai BG, Kim YJ, et al. Synthesis and evaluation of benzothiophene derivatives as ligands for imaging $\beta$-amyloid plaques in Alzheimer's disease. Nucl Med Biol 2006;33:811-820 https://doi.org/10.1016/j.nucmedbio.2006.06.006