Synthesis and biological evaluation of novel radioiodinated imidazopyridine derivatives for amyloid-β imaging in Alzheimer's disease

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 15, 2014, Pages 4189-4197

  Chen, Chun Jen ^a,b,c   Bando, Kazunori ^a   Ashino, Hiroki ^a   Taguchi, Kazumi ^a   Shiraishi, Hideaki ^a   Fujimoto, Osuke ^a   Kitamura, Chiemi ^a   Matsushima, Satoshi ^a   Fujinaga, Masayuki ^b   Zhang, Ming Rong ^b   Kasahara, Hiroyuki ^a   Minamizawa, Takao ^a   Jiang, Cheng ^d   Ono, Maiko ^b   Higuchi, Makoto ^b   Suhara, Tetsuya ^b   Yamada, Kazutaka ^c   Ji, Bin ^b  

^a Fujifilm RI Pharma Co Ltd   (Japan)

^b NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^c GIFU UNIVERSITY   (Japan)

^d FUDAN UNIVERSITY   (China)

Author keywords

Alzheimer's disease (AD); Amyloid peptide (A ); Autoradiography; Positron emission tomography (PET); Single photon emission computed tomography (SPECT)

Indexed keywords

1 [4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)PHENYL] 1 ETHANOL; 1 [4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)PHENYL] 2 ETHANONE; 2 [4 (1H 3 PYRAZOLYL)PHENYL] 6 (TRIBUTYLSTANNYL)IMIDAZO[1,2 A]PYRIDINE; 2 [4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)PHENYL] 1,3 THIAZOLE; 2 [4 [1 (TERT BUTOXYCARBONYL) 3 PYRAZOYL]PHENYL] 6 (TRIBUTYLSTANNYL) IMIDAZO[1,2 A]PYRIDINE; 3 [4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)] 1,2,4 OXADIAZOLE; 3(DIMETHYLAMINO) 1 [4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)PHENYL] 2 PROPEN 1 ONE; 4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL) 1 BENZENECARBOTHIOAMIDE; 4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)BENZALDEHYDE; 4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)BENZONITRILE; 5 [4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)PHENYL] 1,3 OXAZOLE; 5 [4 (6 IODOIMIDAZO[1,2 A]PYRIDINE 2 YL)PHENYL] 1,3 OXAZOLE I 125; 5 [4 [6 (TRIBUTYLSTANNYL)IMIDAZO[1,2 A]PYRIDIN 2 YL]PHENYL] 1,3 OXAZOLE; 6 IODO 2 [4 (1H 1,2,3,4 TETRAZOL 5 YL)PHENYL]IMIDAZO[1,2 A]PYRIDINE; 6 IODO 2 [4 (1H 3 PYRAZOLYL)PHENYL]IMIDAZO[1,2 A]PYRIDINE; 6 IODO 2 [4 (1H 3 PYRAZOLYL)PHENYL]IMIDAZO[1,2 A]PYRIDINE I 125; AMYLOID BETA PROTEIN[1-40]; DRK 092; DRM 015; DRM 101; DRM 102; DRM 105; DRM 106; HYDROXY 4 (6 IODOIMIDAZO[1,2 A]PYRIDIN 2 YL)BENZAMIDINE; IMIDAZOPYRIDINE DERIVATIVE; IODINATED CONTRAST MEDIUM; IODINE 125; UNCLASSIFIED DRUG; AMYLOID BETA PROTEIN; DRK092; IMIDAZOLE DERIVATIVE; PEPTIDE FRAGMENT; PYRIDINE DERIVATIVE; RADIOACTIVE IODINE; RADIOPHARMACEUTICAL AGENT;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ARTICLE; AUTORADIOGRAPHY; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG SYNTHESIS; HIPPOCAMPUS; HUMAN; HUMAN TISSUE; IMAGE ANALYSIS; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; RAT; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; ANIMAL; BRAIN; CHEMISTRY; DIAGNOSTIC USE; METABOLISM; SCINTISCANNING; SPRAGUE DAWLEY RAT; SYNTHESIS; TISSUE DISTRIBUTION;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; AUTORADIOGRAPHY; BRAIN; HIPPOCAMPUS; HUMANS; IMIDAZOLES; IODINE RADIOISOTOPES; PEPTIDE FRAGMENTS; POSITRON-EMISSION TOMOGRAPHY; PYRIDINES; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 84905079629     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.05.043     Document Type: Article

References (24)

1. H. Braak, and E. Braak Acta Neuropathol. (Berl) 82 1991 239
2. J. Maeda, B. Ji, T. Irie, T. Tomiyama, M. Maruyama, T. Okauchi, M. Staufenbiel, N. Iwata, M. Ono, T.C. Saido, K. Suzuki, H. Mori, M. Higuchi, and T. Suhara J. Neurosci. 27 2007 10957
3. W.E. Klunk, H. Engler, A. Nordberg, Y. Wang, G. Blomqvist, D.P. Holt, M. Bergstrom, I. Savitcheva, G.F. Huang, S. Estrada, B. Ausen, M.L. Debnath, J. Barletta, J.C. Price, J. Sandell, B.J. Lopresti, A. Wall, P. Koivisto, G. Antoni, C.A. Mathis, and B. Langstrom Ann. Neurol. 55 2004 306
4. V. Camus, P. Payoux, L. Barre, B. Desgranges, T. Voisin, C. Tauber, R. La Joie, M. Tafani, C. Hommet, G. Chetelat, K. Mondon, V. de La Sayette, J.P. Cottier, E. Beaufils, M.J. Ribeiro, V. Gissot, E. Vierron, J. Vercouillie, B. Vellas, F. Eustache, and D. Guilloteau Eur. J. Nucl. Med. Mol. Imaging 39 2012 621
5. Z. Cselenyi, M.E. Jonhagen, A. Forsberg, C. Halldin, P. Julin, M. Schou, P. Johnstrom, K. Varnas, S. Svensson, and L. Farde J. Nucl. Med. 53 2012 415
6. H. Engler, A. Forsberg, O. Almkvist, G. Blomquist, E. Larsson, I. Savitcheva, A. Wall, A. Ringheim, B. Langstrom, and A. Nordberg Brain 129 2006 2856
7. M.D. Ikonomovic, W.E. Klunk, E.E. Abrahamson, C.A. Mathis, J.C. Price, N.D. Tsopelas, B.J. Lopresti, S. Ziolko, W. Bi, W.R. Paljug, M.L. Debnath, C.E. Hope, B.A. Isanski, R.L. Hamilton, and S.T. DeKosky Brain 131 2008 1630
8. V. Leinonen, I. Alafuzoff, S. Aalto, T. Suotunen, S. Savolainen, K. Nagren, T. Tapiola, T. Pirttila, J. Rinne, J.E. Jaaskelainen, H. Soininen, and J.O. Rinne Arch. Neurol. 65 2008 1304
9. A. Okello, J. Koivunen, P. Edison, H.A. Archer, F.E. Turkheimer, K. Nagren, R. Bullock, Z. Walker, A. Kennedy, N.C. Fox, M.N. Rossor, J.O. Rinne, and D.J. Brooks Neurology 73 2009 754
10. W. Zhang, M.P. Kung, S. Oya, C. Hou, and H.F. Kung Nucl. Med. Biol. 34 2007 89
11. S.R. Choi, G. Golding, Z. Zhuang, W. Zhang, N. Lim, F. Hefti, T.E. Benedum, M.R. Kilbourn, D. Skovronsky, and H.F. Kung J. Nucl. Med. 2009 1887 50
12. H. Hampel, G. Wilcock, S. Andrieu, P. Aisen, K. Blennow, K. Broich, M. Carrillo, N.C. Fox, G.B. Frisoni, M. Isaac, S. Lovestone, A. Nordberg, D. Prvulovic, C. Sampaio, P. Scheltens, M. Weiner, B. Winblad, N. Coley, and B. Vellas Prog. Neurobiol. 95 2011 579
13. H. Watanabe, M. Ono, R. Ikeoka, M. Haratake, H. Saji, and M. Nakayama Bioorg. Med. Chem. 17 2009 6402
14. Y. Maya, M. Ono, H. Watanabe, M. Haratake, H. Saji, and M. Nakayama Bioconjugate Chem. 20 2009 95
15. W. Qu, M.P. Kung, C. Hou, S. Oya, and H.F. Kung J. Med. Chem. 50 2007 3380
16. M. Ono, Y. Cheng, H. Kimura, H. Watanabe, K. Matsumura, M. Yoshimura, S. Iikuni, Y. Okamoto, M. Ihara, R. Takahashi, and H. Saji PLoS ONE 8 2013 e74104
17. Z.P. Zhuang, M.P. Kung, A. Wilson, C.W. Lee, K. Plossl, C. Hou, D.M. Holtzman, and H.F. Kung J. Med. Chem. 46 2003 237
18. A.B. Newberg, N.A. Wintering, K. Plossl, J. Hochold, M.G. Stabin, M. Watson, D. Skovronsky, C.M. Clark, M.P. Kung, and H.F. Kung J. Nucl. Med. 47 2006 748
19. M.P. Kung, C. Hou, Z.P. Zhuang, B. Zhang, D. Skovronsky, J.Q. Trojanowski, V.M. Lee, and H.F. Kung Brain Res. 956 2002 202
20. M.P. Kung, C. Hou, Z.P. Zhuang, A.J. Cross, D.L. Maier, and H.F. Kung Eur. J. Nucl. Med. Mol. Imaging 31 2004 1136
21. M.P. Kung, C.C. Weng, K.J. Lin, I.T. Hsiao, T.C. Yen, and S.P. Wey Chang Gung Med. J. 35 2012 211
22. E.H. Kerns, L. Di, S. Petusky, T. Kleintop, D. Huryn, O. McConnell, and G. Carter J. Chromatogr. B 791 2003 381
23. F. Lombardo, M.Y. Shalaeva, K.A. Tupper, and F. Gao J. Med. Chem. 44 2001 2490
24. R.M. Kessler, M.S. Ansari, T. de Paulis, D.E. Schmidt, J.A. Clanton, H.E. Smith, R.G. Manning, D. Gillespie, and M.H. Ebert J. Nucl. Med. 32 1991 1593