Aromatic radiofluorination and biological evaluation of 2-aryl-6-[ 18F]fluorobenzothiazoles as a potential positron emission tomography imaging probe for β-amyloid plaques

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 9, 2011, Pages 2980-2990

  Lee, Byung Chul ^a,b   Kim, Ji Sun ^a   Kim, Bom Sahn ^c   Son, Ji Yeon ^a   Hong, Soo Kyung ^a   Park, Hyun Soo ^a   Moon, Byung Seok ^a,b   Jung, Jae Ho ^a   Jeong, Jae Min ^b   Kim, Sang Eun ^a,b  

^a Seoul National University Bundang Hospital   (South Korea)

^b Seoul National University College of Medicine   (South Korea)

^c Ewha Womans University School of Medicine   (South Korea)

Author keywords

Amyloid; Alzheimer's disease; Diaryliodonium salt; PET

Indexed keywords

2 (4' AMINOPHENYL) 6 BROMOBENZOTHIAZOLE; 2 (4' AMINOPHENYL) 6 FLUOROBENZOTHIAZOLE; 2 (4' AMINOPHENYL) 6 FLUOROBENZOTHIAZOLE F 18; 2 (4' DIMETHYLAMINOPHENYL) 6 BROMOBENZOTHIAZOLE; 2 (4' DIMETHYLAMINOPHENYL) 6 FLUOROBENZOTHIAZOLE; 2 (4' DIMETHYLAMINOPHENYL) 6 IODO(PHENYL)BENZOTHIAZOLE IODONIUM TOSYLATE; 2 (4' DIMETHYLAMINOPHENYL) 6 TRIBUTYLSTANNYLBENZOTHIAZOLE; 2 (4' METHYLAMINOPHENYL) 6 FLUOROBENZOTHIAZOLE; 2 (4' N DIMETHYLAMINOPHENYL) 6 FLUOROBENZOTHIAZOLE F 18; 2 (4' N METHYLAMINOPHENYL) 6 FLUOROBENZOTHIAZOLE F 18; 2 (4' N TERT BUTYLOXYCARBONYL METHYLAMINOPHENYL) 6 BROMOBENZOTHIAZOLE; 2 (4' N TERT BUTYLOXYCARBONYL METHYLAMINOPHENYL) 6 IODO(2' THIOPHENYL)BENZOTHIAZOLE IODONIUM TOSYLATE; 2 (4' N TERT BUTYLOXYCARBONYL METHYLAMINOPHENYL) 6 IODO(3' THIOPHENYL)BENZOTHIAZOLE IODONIUM TOSYLATE; 2 (4' N TERT BUTYLOXYCARBONYL METHYLAMINOPHENYL) 6 IODO(4' METHOXYPHENYL)BENZOTHIAZOLE IODONIUM TOSYLATE; 2 (4' N TERT BUTYLOXYCARBONYL METHYLAMINOPHENYL) 6 IODO(4' METHYLPHENYL)BENZOTHIAZOLE IODONIUM TOSYLATE; 2 (4' N TERT BUTYLOXYCARBONYL METHYLAMINOPHENYL) 6 TRIBUTYLSTANNYLBENZOTHIAZOLE; 2 (4' NITROPHENYL) 6 BROMOBENZOTHIAZOLE; 2 (4' NITROPHENYL) 6 FLUOROBENZOTHIAZOLE; 2 (4' NITROPHENYL) 6 IODO(PHENYL)BENZOTHIAZOLE IODONIUM TOSYLATE; 2 (4' NITROPHENYL) 6 TRIBUTYLSTANNYLBENZOTHIAZOLE; 2 ARYL 6 FLUOROBENZOTHIAZOLE DERIVATIVE F 18; AMYLOID BETA PROTEIN; BENZOTHIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AMYLOID PLAQUE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING SITE; BLOOD BRAIN BARRIER; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; FLUORINATION; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; REACTION TIME; TISSUE DISTRIBUTION;

ANIMALS; BENZOTHIAZOLES; BRAIN; FLUORESCENT DYES; FLUORINE RADIOISOTOPES; KINETICS; MICE; MICE, TRANSGENIC; PLAQUE, AMYLOID; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION;

MUS;

EID: 79955471678     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.029     Document Type: Article

References (36)

1. C. Berr, J. Wancata, and K. Ritchie Eur. Neuropsychopharmacol. 15 2005 463
2. D.J. Selkoe Physiol. Rev. 81 2001 741
3. D.J. Selkoe Ann. Intern. Med. 130 2004 627
4. J. Hardy, and D.J. Selkoe Science 297 2002 353
5. C.A. Mathis, Y. Wang, D.P. Holt, G.F. Huang, M.L. Debnath, and W.E. Klunk J. Med. Chem. 46 2003 2740
6. 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
7. H. Archer, P. Edison, D. Brooks, J. Barnes, C. Frost, T. Yeatman, N. Fox, and M. Rossor Ann. Neurol. 60 2006 145
8. W.E. Klunk, and C.A. Mathis Curr. Opin. Neurol. 21 2008 683
9. C.A. Mathis, M.D. Ikonomovicb, M.L. Debnath, R.L. Hamilton, S.T. DeKosky, and W.E. Klunk Neuroimage 41 2008 T113
10. K. Serdons, C. Terwinghe, P. Vermaelen, K.L. Laere, H. Kung, L. Mortelmans, G. Bormans, and A. Verbruggen J. Med. Chem. 52 2009 1428
11. E. Agdeppa, V. Kepe, J. Liu, M. Flores-Torres, N. Satyamurthy, A. Petric, G. Cole, G. Small, S.C. Huang, and J. Barrio J. Neurosci. 21 2001 1
12. C.C. Rowe, U. Ackerman, W. Browne, R. Mulligan, K.L. Pike, O. O'Keefe, H. Tochon-Danguy, G. Chan, S.U. Berlangieri, G. Jones, K.L. Dichnson-Rowe, H.F. Kung, W. Zhang, M.P. Kung, D. Skovronsky, T. Dyrks, G. Holl, S. Krause, M. Friebe, L. Lehman, S. Lindemann, L.M. Dinkelborg, C.L. Masters, and V.L. Villemagne Lancet Neurol. 7 2008 129
13. 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. 50 2009 1887
14. G. Henriksen, A.I. Hquser, A.D. Westwell, B.H. Yousefi, M. Schwaiger, A. Drzega, and H.-J. Wester J. Med. Chem. 50 2007 1087
15. C.A. Mathis, D.P. Holt, Y. Wang, W.F. Huang, M.L. Debnath, L. Shao, and W.E. Klunk J. Nucl. Med. 45 2004 114P (abstract)
16. M.Q. Zheng, D.Z. Yin, L. Zhang, D.F. Cheng, Y.X. Wang, and H.C. Cai J. Labelled Compd. Radiopharm. 50 2007 S86
17. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
18. A. Bondi J. Phys. Chem. 68 1964 441
19. B.C. Lee, K.C. Lee, H. Lee, R.H. Mach, and J.A. Katzenellenbogen Bioconjugate Chem. 18 2007 514
20. B.C. Lee, C.S. Dence, H. Zhou, E.E. Parent, M.J. Welch, and J.A. Katzenellenbogen Nucl. Med. Biol. 36 2009 147
21. S. Telu, J. Chun, F.G. Simeon, S. Lu, and V.W. Pike J. Labelled Compd. Radiopharm. 52 2009 S4
22. B.S. Rathore, and M. Kumar Bioorg. Med. Chem. 14 2006 5678
23. R.L. Mital, and S.K. Jain J. Chem. Soc. 1969 2148
24. E.A. Merritt, V.M.T. Carneiro, L.F. Silva Jr., and B. Olofsson J. Org. Chem. 75 2010 7416
25. T. Nabana, and H. Togo J. Org. Chem. 67 2002 4362
26. Z.P. Zhuang, M.P. Kung, C. Hou, D.M. Skovronsky, T.L. Gur, K. Plossl, V. Trojanowski, M.-Y. Lee, and H.F. Kung J. Med. Chem. 44 2001 1905
27. S.Y. Chang, J.M. Jeong, Y.-S. Lee, H.W. Kim, R.B. Ganesha, Y.J. Kim, D.S. Lee, J.-K. Chung, and M.C. Lee Nucl. Med. Biol. 33 2006 811
28. A.K. Vehmas, D.R. Borchelt, D.L. Price, D. Mccarthy, M. Wills-Karp, M.J. Peper, G. Rudow, J. Luyinbazi, L.T. Siew, and J.C. Troncoso DNA Cell Biol. 20 2001 713
29. T. Ludwig, J. Ermert, and H.H. Coenen Nucl. Med. Biol. 29 2002 255
30. M.S. Haka, M.R. Kilbourn, G.L. Watkins, and S.A. Toorongian J. Labelled Compd. Radiopharm. 27 1989 823
31. G.F. Koser, R.H. Wettach, and C.S. Smith J. Org. Chem. 45 1980 1542
32. M. van der Puy J. Fluorine Chem. 21 1982 385
33. A.J. Lin, and S. Kasina J. Heterocycl. Chem. 18 1981 759
34. J.J. Lubinowski, J.W. Knapczyk, J.L. Calderon, L.R. Petit, and W.E. McEwen J. Org. Chem. 40 1975 3010
35. M.A. Carroll, J. Nairne, G. Smith, and D.A. Widdowson J. Fluorine Chem. 128 2007 127
36. C. Wu, J. Wei, K. Gao, and Y. Wang Bioorg. Med. Chem. 15 2007 2789