Radiolabeled bioactive benzoheterocycles for imaging β-amyloid plaques in Alzheimer's disease

European Journal of Medicinal Chemistry

Volumn 87, Issue , 2014, Pages 703-721

  Yang, Yanping ^a   Cui, Mengchao ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

Author keywords

Alzheimer's disease; b amyloid plaque; Benzoheterocycles; Imaging agents; Radiolabeled

Indexed keywords

AMYLOID BETA PROTEIN; BENZENE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; BENZOXAZOLE DERIVATIVE; FLUORINE 18; HETEROCYCLIC COMPOUND; IMIDAZOPYRIDINE DERIVATIVE; INDOLE DERIVATIVE; IODINE 125; QUINOXALINE DERIVATIVE; TECHNETIUM 99M; THIOFLAVINE;

ALZHEIMER DISEASE; COMPUTER ASSISTED EMISSION TOMOGRAPHY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; NEUROTOXICITY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; REVIEW; SENILE PLAQUE;

EID: 84908040362     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.10.012     Document Type: Review

References (122)

1. C.L. Masters R. Cappai K.J. Barnham V.L. Villemagne Molecular mechanisms for Alzheimer's disease: implications for neuroimaging and therapeutics J. Neurochem. 97 2006 1700 1725
2. D.J. Selkoe Alzheimer's disease: genes, proteins, and therapy Physiol. Rev. 81 2001 741 766
3. B.D. James S.E. Leurgans L.E. Hebert P.A. Scherr K. Yaffe D.A. Bennett Contribution of Alzheimer disease to mortality in the United States Neurology 82 2014 1045 1050
4. M. Prince M. Prina M. Guerchet World Alzheimer Report 2013: Journey of Caring-an Analysis of Long-term Care for Dementia Sep 2013
5. J. Hardy D.J. Selkoe The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics Science 297 2002 353 356
6. S.M. Ametamey M. Honer P.A. Schubiger Molecular imaging with PET Chem. Rev. 108 2008 1501 1516
7. M. Cui Past and recent progress of molecular imaging probes for β-amyloid plaques in the brain Curr. Med. Chem. 21 2014 82 112
8. M. Zhou X. Wang Z. Liu L. Yu S. Hu L. Chen W. Zeng Advances of molecular imaging probes for the diagnosis of Alzheimer's disease Curr. Alzheimer Res. 11 2014 221 231
9. T.J. Eckroat A.S. Mayhoub S. Garneau-Tsodikova Amyloid-β probes: review of structure-activity and brain-kinetics relationships Beilstein J. Org. Chem. 9 2013 1012 1044
10. C.A. Mathis N.S. Mason B.J. Lopresti W.E. Klunk Development of positron emission tomography β-amyloid plaque imaging agents Semin. Nucl. Med. 42 2012 423 432
11. F. Zeng M.M. Goodman Fluorine-18 radiolabeled heterocycles as PET tracers for imaging beta-amyloid plaques in Alzheimer's disease Curr. Top. Med. Chem. 13 2013 909 919
12. P.S. Vassar C.F. Culling Fluorescent stains, with special reference to amyloid and connective tissues Arch. Pathol. 68 1959 487 498
13. M. Biancalana S. Koide Molecular mechanism of Thioflavin-T binding to amyloid fibrils Biochim. Biophys. Acta 1804 2010 1405 1412
14. M. Biancalana K. Makabe A. Koide S. Koide Aromatic cross-strand ladders control the structure and stability of beta-rich peptide self-assembly mimics J. Mol. Biol. 383 2008 205 213
15. C. Wu Z. Wang H. Lei Y. Duan M.T. Bowers J.E. Shea The binding of Thioflavin T and its neutral analog BTA-1 to protofibrils of the Alzheimer's disease Abeta (16-22) peptide probed by molecular dynamics simulations J. Mol. Biol. 384 2008 718 729
16. C.A. Mathis Y. Wang D.P. Holt G.-F. Huang M.L. Debnath W.E. Klunk Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents J. Med. Chem. 46 2003 2740 2754
17. G. Henriksen A.I. Hauser A.D. Westwell B.H. Yousefi M. Schwaiger A. Drzezga H.-J. Wester Metabolically stabilized benzothiazoles for imaging of amyloid plaques J. Med. Chem. 50 2007 1087 1089
18. V. Facchinetti R. da R. Reis C.R.B. Gomes T.R.A. Vasconcelos Chemistry and biological activities of 1,3-benzothiazoles Mini Rev. Org. Chem. 9 2012 44 53
19. R. Leuma Yona S. Mazères P. Faller E. Gras Thioflavin derivatives as markers for amyloid-β fibrils: insights into structural features important for high-affinity binding ChemMedChem 3 2008 63 66
20. J.X. Qiao T.C. Wang C. Hu J. Li R.R. Wexler P.Y.S. Lam Transformation of anionically activated trifluoromethyl groups to heterocycles under mild aqueous conditions Org. Lett. 13 2011 1804 1807
21. S. Ranjit X. Liu Direct arylation of benzothiazoles and benzoxazoles with aryl boronic acids Chem. Eur. J. 17 2011 1105 1108
22. D. Alagille R.M. Baldwin G.D. Tamagnan One-step synthesis of 2-arylbenzothiazole ("BTA") and-benzoxazole precursors for in vivo imaging of β-amyloid plaques Tetrahedron Lett. 46 2005 1349 1351
23. H. Bonin R. Leuma-Yona B. Marchiori P. Demonchaux E. Gras Highly practical boronic acid surrogates for the Suzuki-Miyaura cross-coupling Tetrahedron Lett. 52 2011 1132 1135
24. A.E. Johnson F. Jeppsson J. Sandell D. Wensbo J.A.M. Neelissen A. Juréus P. Ström H. Norman L. Farde S.P.S. Svensson AZD2184: a radioligand for sensitive detection of β-amyloid deposits J. Neurochem. 108 2009 1177 1186
25. W.E. Klunk Y. Wang G.-f. Huang M.L. Debnath D.P. Holt C.A. Mathis Uncharged Thioflavin-T derivatives bind to amyloid-beta protein with high affinity and readily enter the brain Life Sci. 69 2001 1471 1484
26. W.E. Klunk H. Engler A. Nordberg Y. Wang G. Blomqvist D.P. Holt M. Bergström I. Savitcheva G.-F. Huang S. Estrada B. Ausén M.L. Debnath J. Barletta J.C. Price J. Sandell B.J. Lopresti A. Wall P. Koivisto G. Antoni C.A. Mathis B. Långström Imaging brain amyloid in Alzheimer's disease with Pittsburgh compound-B Ann. Neurol. 55 2004 306 319
27. 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 S.T. DeKosky Post-mortem correlates of in vivo PiB-PET amyloid imaging in a typical case of Alzheimer's disease Brain 131 2008 1630 1645
28. A. Kadir A. Marutle D. Gonzalez M. Schöll O. Almkvist M. Mousavi T. Mustafiz T. Darreh-Shori I. Nennesmo A. Nordberg Positron emission tomography imaging and clinical progression in relation to molecular pathology in the first Pittsburgh compound B positron emission tomography patient with Alzheimer's disease Brain 134 2011 301 317
29. K. Serdons T. Verduyckt D. Vanderghinste P. Borghgraef J. Cleynhens F. Van Leuven H. Kung G. Bormans A. Verbruggen 11C-labelled PIB analogues as potential tracer agents for in vivo imaging of amyloid β in Alzheimer's disease Eur. J. Med. Chem. 44 2009 1415 1426
30. S. Nyberg M. Jönhagen Z. Cselényi C. Halldin P. Julin H. Olsson Y. Freund-Levi J. Andersson K. Varnäs S. Svensson L. Farde Detection of amyloid in Alzheimer's disease with positron emission tomography using [11C]AZD2184 Eur. J. Nucl. Med. Mol. Imaging 36 2009 1859 1863
31. J.D. Andersson K. Varnäs Z. Cselényi B. Gulyás D. Wensbo S.J. Finnema B.-M. Swahn S. Svensson S. Nyberg L. Farde C. Halldin Radiosynthesis of the candidate β-amyloid radioligand [11C]AZD2184: positron emission tomography examination and metabolite analysis in cynomolgus monkeys Synapse 64 2010 733 741
32. Z.P. Zhuang M.P. Kung C. Hou D.M. Skovronsky T.L. Gur K. Plössl J.Q. Trojanowski V.M.Y. Lee H.F. Kung Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates J. Med. Chem. 44 2001 1905 1914
33. U. Berndt C. Stanetty T. Wanek C. Kuntner J. Stanek M. Berger M. Bauer G. Henriksen H.-J. Wester H. Kvaternik P. Angelberger C. Noe Synthesis of a [18F]fluorobenzothiazole as potential amyloid imaging agent J. Label. Comp. Radiopharm. 51 2008 137 145
34. M.-Q. Zheng D.-Z. Yin J.-P. Qiao L. Zhang Y.-X. Wang Syntheses and evaluation of fluorinated benzothiazole anilines as potential tracers for β-amyloid plaques in Alzheimer's disease J. Fluor. Chem. 129 2008 210 216
35. M.-Q. Zheng D.-Z. Yin L. Zhang B. Lei D.-F. Cheng H.-C. Cai Y.-J. Han M.-X. Wu H. Zhang J. Wang Biological characters of [18F]O-FEt-PIB in a rat model of Alzheimer's disease using micro-PET imaging Acta Pharmacol. Sin. 29 2008 548 554
36. B. Neumaier S. Deisenhofer C. Sommer C. Solbach S.N. Reske F. Mottaghy Synthesis and evaluation of 18F-fluoroethylated benzothiazole derivatives for in vivo imaging of amyloid plaques in Alzheimer's disease Appl. Radiat. Isot. 68 2010 1066 1072
37. K. Serdons D. Vanderghinste M. Van Eeckhoudt P. Borghgraef H. Kung F. Van Leuven T. de Groot G. Bormans A. Verbruggen Synthesis and evaluation of two fluorine-18 labelled phenylbenzothiazoles as potential in vivo tracers for amyloid plaque imaging J. Label. Comp. Radiopharm. 52 2009 473 481
38. K.A. Stephenson R. Chandra Z.-P. Zhuang C. Hou S. Oya M.-P. Kung H.F. Kung Fluoro-pegylated (FPEG) imaging agents targeting A β aggregates Bioconjug. Chem. 18 2006 238 246
39. M. Cui X. Wang P. Yu J. Zhang Z. Li X. Zhang Y. Yang M. Ono H. Jia H. Saji B. Liu Synthesis and evaluation of novel 18F labeled 2-pyridinylbenzoxazole and 2-pyridinylbenzothiazole derivatives as ligands for positron emission tomography (PET) imaging of β-amyloid plaques J. Med. Chem. 55 2012 9283 9296
40. C. Mathis B. Lopresti N. Mason J. Price N. Flatt W. Bi S. Ziolko S. DeKosky W. Klunk Comparison of the amyloid imaging agents [F-18]3'-F-PIB and [C-11]PIB in Alzheimer's disease and control subjects J. Nucl. Med. 48 Suppl. 2 2007 56
41. M. Koole D.M. Lewis C. Buckley N. Nelissen M. Vandenbulcke D.J. Brooks R. Vandenberghe K. Van Laere Whole-body biodistribution and radiation dosimetry of 18F-GE067: a radioligand for in vivo brain amyloid imaging J. Nucl. Med. 50 2009 818 822
42. A. Snellman J. Rokka F. Lopez-Picon O. Eskola I. Wilson G. Farrar M. Scheinin O. Solin J. Rinne M. Haaparanta-Solin Pharmacokinetics of [18F]flutemetamol in wild-type rodents and its binding to beta amyloid deposits in a mouse model of Alzheimer's disease Eur. J. Nucl. Med. Mol. Imaging 39 2012 1784 1795
43. S. Hatashita H. Yamasaki Y. Suzuki K. Tanaka D. Wakebe H. Hayakawa [18F]Flutemetamol amyloid-beta PET imaging compared with [11C]PIB across the spectrum of Alzheimer's disease Eur. J. Nucl. Med. Mol. Imaging 41 2014 290 300
44. N. Nelissen K. Van Laere L. Thurfjell R. Owenius M. Vandenbulcke M. Koole G. Bormans D.J. Brooks R. Vandenberghe Phase 1 study of the Pittsburgh compound B derivative 18F-flutemetamol in healthy volunteers and patients with probable Alzheimer disease J. Nucl. Med. 50 2009 1251 1259
45. R. Vandenberghe K. Van Laere A. Ivanoiu E. Salmon C. Bastin E. Triau S. Hasselbalch I. Law A. Andersen A. Korner L. Minthon G. Garraux N. Nelissen G. Bormans C. Buckley R. Owenius L. Thurfjell G. Farrar D.J. Brooks 18F-flutemetamol amyloid imaging in Alzheimer disease and mild cognitive impairment: a phase 2 trial Ann. Neurol. 68 2010 319 329
46. K. Serdons T. Verduyckt D. Vanderghinste J. Cleynhens P. Borghgraef P. Vermaelen C. Terwinghe F.V. Leuven K.V. Laere H. Kung G. Bormans A. Verbruggen Synthesis of 18F-labelled 2-(4'-fluorophenyl)-1,3-benzothiazole and evaluation as amyloid imaging agent in comparison with [11C]PIB Bioorg. Med. Chem. Lett. 19 2009 602 605
47. K. Serdons C. Terwinghe P. Vermaelen K. Van Laere H. Kung L. Mortelmans G. Bormans A. Verbruggen Synthesis and evaluation of 18F-Labeled 2-phenylbenzothiazoles as positron emission tomography imaging agents for amyloid plaques in Alzheimer's disease J. Med. Chem. 52 2009 1428 1437
48. K. Serdons K. Van Laere P. Janssen H.F. Kung G. Bormans A. Verbruggen Synthesis and evaluation of three 18F-labeled aminophenylbenzothiazoles as amyloid imaging agents J. Med. Chem. 52 2009 7090 7102
49. B.C. Lee J.S. Kim B.S. Kim J.Y. Son S.K. Hong H.S. Park B.S. Moon J.H. Jung J.M. Jeong S.E. Kim Aromatic radiofluorination and biological evaluation of 2-aryl-6-[18F]fluorobenzothiazoles as a potential positron emission tomography imaging probe for β-amyloid plaques Bioorg. Med. Chem. 19 2011 2980 2990
50. K. Serdons T. Verduyckt J. Cleynhens C. Terwinghe L. Mortelmans G. Bormans A. Verbruggen Synthesis and evaluation of a 99mTc-BAT-phenylbenzothiazole conjugate as a potential in vivo tracer for visualization of amyloid β Bioorg. Med. Chem. Lett. 17 2007 6086 6090
51. X. Chen P. Yu L. Zhang B. Liu Synthesis and biological evaluation of 99mTc, Re-monoamine-monoamide conjugated to 2-(4-aminophenyl)benzothiazole as potential probes for β-amyloid plaques in the brain Bioorg. Med. Chem. Lett. 18 2008 1442 1445
52. K. Serdons T. Verduyckt J. Cleynhens G. Bormans A. Verbruggen Development of 99mTc-Thioflavin-T derivatives for detection of systemic amyloidosis J. Label. Comp. Radiopharm. 51 2008 357 367
53. K. Serdons D. Vanderghinste M. Van Eeckhoudt J. Cleynhens T. de Groot G. Bormans A. Verbruggen Synthesis and evaluation of two uncharged 99mTc-labeled derivatives of Thioflavin-T as potential tracer agents for fibrillar brain amyloid J. Label. Comp. Radiopharm. 52 2009 227 235
54. M. Sagnou S. Tzanopoulou C.P. Raptopoulou V. Psycharis H. Braband R. Alberto I.C. Pirmettis M. Papadopoulos M. Pelecanou A phenylbenzothiazole conjugate with the tricarbonyl fac-[M(I)(CO)3]+ (M Combining double low line Re, 99Tc, 99mTc) core for imaging of β-amyloid plaques Eur. J. Inorg. Chem. 2012 2012 4279 4286
55. C. Wu J. Wei K. Gao Y. Wang Dibenzothiazoles as novel amyloid-imaging agents Bioorg. Med. Chem. 15 2007 2789 2796
56. M.-C. Cui Z.-J. Li R.-K. Tang B.-L. Liu Synthesis and evaluation of novel benzothiazole derivatives based on the bithiophene structure as potential radiotracers for β-amyloid plaques in Alzheimer's disease Bioorg. Med. Chem. 18 2010 2777 2784
57. K. Matsumura M. Ono S. Hayashi H. Kimura Y. Okamoto M. Ihara R. Takahashi H. Mori H. Saji Phenyldiazenyl benzothiazole derivatives as probes for in vivo imaging of neurofibrillary tangles in Alzheimer's disease brains MedChemComm 2 2011 596 600
58. K. Matsumura M. Ono H. Kimura M. Ueda Y. Nakamoto K. Togashi Y. Okamoto M. Ihara R. Takahashi H. Saji 18F-labeled phenyldiazenyl benzothiazole for in vivo imaging of neurofibrillary tangles in Alzheimer's disease brains ACS Med. Chem. Lett. 3 2011 58 62
59. C. Gan L. Zhou Z. Zhao H. Wang Benzothiazole schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer's disease Med. Chem. Res. 22 2013 4069 4074
60. Z.-P. Zhuang M.-P. Kung C. Hou K. Plössl D. Skovronsky T.L. Gur J.Q. Trojanowski V.M.Y. Lee H.F. Kung IBOX(2-(4'-dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain Nucl. Med. Biol. 28 2001 887 894
61. M. Terashima M. Ishii Y. Kanaoka A facile synthesis of 2-substituted benzoxazoles Synthesis 1982 1982 484 485
62. S.H. Hausner D. Alagille A.O. Koren L. Amici J.K. Staley K.P. Cosgrove R.M. Baldwin G.D. Tamagnan Synthesis of 5-and 6-substituted 2-(4-dimethylaminophenyl)-1,3-benzoxazoles and their in vitro and in vivo evaluation as imaging agents for amyloid plaque Bioorg. Med. Chem. Lett. 19 2009 543 545
63. B.-M. Swahn D. Wensbo J. Sandell D. Sohn C. Slivo D. Pyring J. Malmström E. Arzel M. Vallin M. Bergh F. Jeppsson A.E. Johnson A. Juréus J. Neelissen S. Svensson Synthesis and evaluation of 2-pyridylbenzothiazole, 2-pyridylbenzoxazole and 2-pyridylbenzofuran derivatives as 11C-PET imaging agents for β-amyloid plaques Bioorg. Med. Chem. Lett. 20 2010 1976 1980
64. B.-M. Swahn J. Sandell D. Pyring M. Bergh F. Jeppsson A. Juréus J. Neelissen P. Johnström M. Schou S. Svensson Synthesis and evaluation of pyridylbenzofuran, pyridylbenzothiazole and pyridylbenzoxazole derivatives as 18F-PET imaging agents for β-amyloid plaques Bioorg. Med. Chem. Lett. 22 2012 4332 4337
65. J. Chang K. Zhao S. Pan Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases-a solution-phase strategy for library synthesis Tetrahedron Lett. 43 2002 951 954
66. M. Cui M. Ono H. Kimura M. Ueda Y. Nakamoto K. Togashi Y. Okamoto M. Ihara R. Takahashi B. Liu H. Saji Novel 18F-labeled benzoxazole derivatives as potential positron emission tomography probes for imaging of cerebral β-amyloid plaques in Alzheimer's disease J. Med. Chem. 55 2012 9136 9145
67. N. Okamura T. Suemoto T. Shiomitsu M. Suzuki H. Shimadzu H. Akatsu T. Yamamoto H. Arai H. Sasaki K. Yanai M. Staufenbiel Y. Kudo T. Sawada A novel imaging probe for in vivo detection of neuritic and diffuse amyloid plaques in the brain J. Mol. Neurosci. 24 2004 247 255
68. N. Okamura T. Suemoto H. Shimadzu M. Suzuki T. Shiomitsu H. Akatsu T. Yamamoto M. Staufenbiel K. Yanai H. Arai H. Sasaki Y. Kudo T. Sawada Styrylbenzoxazole derivatives for in vivo imaging of amyloid plaques in the brain J. Neurosci. 24 2004 2535 2541
69. H. Shimadzu T. Suemoto M. Suzuki T. Shiomitsu N. Okamura Y. Kudo T. Sawada Novel probes for imaging amyloid-β: F-18 and C-11 labeling of 2-(4-aminostyryl)benzoxazole derivatives J. Label. Comp. Radiopharm. 47 2004 181 190
70. Y. Kudo N. Okamura S. Furumoto M. Tashiro K. Furukawa M. Maruyama M. Itoh R. Iwata K. Yanai H. Arai 2-(2-[2-Dimethylaminothiazol-5-yl]ethenyl)-6-(2-[fluoro]ethoxy)benzoxazole: a novel PET agent for in vivo detection of dense amyloid plaques in Alzheimer's disease patients J. Nucl. Med. 48 2007 553 561
71. N. Okamura S. Furumoto Y. Funaki T. Suemoto M. Kato Y. Ishikawa S. Ito H. Akatsu T. Yamamoto T. Sawada H. Arai Y. Kudo K. Yanai Binding and safety profile of novel benzoxazole derivative for in vivo imaging of amyloid deposits in Alzheimer's disease Geriatr. Gerontol. Int. 7 2007 393 400
72. S. Furumoto N. Okamura K. Furukawa M. Tashiro Y. Ishikawa K. Sugi N. Tomita M. Waragai R. Harada T. Tago R. Iwata K. Yanai H. Arai Y. Kudo A 18F-Labeled BF-227 derivative as a potential radioligand for imaging dense amyloid plaques by positron emission tomography Mol. Imaging Biol. 15 2013 497 506
73. H. Ito H. Shinotoh H. Shimada M. Miyoshi K. Yanai N. Okamura H. Takano H. Takahashi R. Arakawa F. Kodaka M. Ono Y. Eguchi M. Higuchi T. Fukumura T. Suhara Imaging of amyloid deposition in human brain using positron emission tomography and [18F]FACT: comparison with [11C]PIB Eur. J. Nucl. Med. Mol. Imaging 41 2014 745 754
74. T. Kaneta N. Okamura A. Arai K. Takanami K. Furukawa M. Tashiro S. Furumoto R. Iwata S. Takahashi H. Arai K. Yanai Y. Kudo Analysis of early phase [11C]BF-227 PET, and its application for anatomical standardization of late-phase images for 3D-SSP analysis Jpn. J. Radiol. 32 2014 138 144
75. E.D. Hostetler S. Sanabria-Bohórquez H. Fan Z. Zeng L. Gammage P. Miller S. O'Malley B. Connolly J. Mulhearn S.T. Harrison S.E. Wolkenberg J.C. Barrow D.L. Williams Jr. R.J. Hargreaves C. Sur J.J. Cook [18F]Fluoroazabenzoxazoles as potential amyloid plaque PET tracers: synthesis and in vivo evaluation in rhesus monkey Nucl. Med. Biol. 38 2011 1193 1203
76. S.T. Harrison J. Mulhearn S.E. Wolkenberg P.J. Miller S.S. O'Malley Z. Zeng D.L. Williams E.D. Hostetler S. Sanabria-Bohórquez L. Gammage H. Fan C. Sur J.C. Culberson R.J. Hargreaves J.J. Cook G.D. Hartman J.C. Barrow Synthesis and evaluation of 5-fluoro-2-aryloxazolo[5,4-b]pyridines as β-amyloid PET ligands and identification of MK-3328 ACS Med. Chem. Lett. 2 2011 498 502
77. X. Wang M. Cui P. Yu Z. Li Y. Yang H. Jia B. Liu Synthesis and biological evaluation of novel technetium-99m labeled phenylbenzoxazole derivatives as potential imaging probes for β-amyloid plaques in brain Bioorg. Med. Chem. Lett. 22 2012 4327 4331
78. M. Ono M.-P. Kung C. Hou H.F. Kung Benzofuran derivatives as A β-aggregate-specific imaging agents for Alzheimer's disease Nucl. Med. Biol. 29 2002 633 642
79. A. Hercouet M. Le Corre Une nouvelle voie d'accès aux benzofurannes Tetrahedron Lett. 20 1979 2145 2148
80. M. Ono Y. Cheng H. Kimura H. Watanabe K. Matsumura M. Yoshimura S. Iikuni Y. Okamoto M. Ihara R. Takahashi H. Saji Development of novel 123I-labeled pyridyl benzofuran derivatives for SPECT imaging of β-amyloid plaques in Alzheimer's disease PLoS One 8 2013 e74104
81. M. Ono H. Kawashima A. Nonaka T. Kawai M. Haratake H. Mori M.-P. Kung H.F. Kung H. Saji M. Nakayama Novel benzofuran derivatives for PET imaging of β-amyloid plaques in Alzheimer's disease brains J. Med. Chem. 49 2006 2725 2730
82. Y. Cheng M. Ono H. Kimura S. Kagawa R. Nishii H. Kawashima H. Saji Fluorinated benzofuran derivatives for PET imaging of β-amyloid plaques in Alzheimer's disease brains ACS Med. Chem. Lett. 1 2010 321 325
83. Y. Cheng M. Ono H. Kimura S. Kagawa R. Nishii H. Saji A novel 18F-labeled pyridyl benzofuran derivative for imaging of β-amyloid plaques in Alzheimer's brains Bioorg. Med. Chem. Lett. 20 2010 6141 6144
84. M. Ono Y. Cheng H. Kimura M. Cui S. Kagawa R. Nishii H. Saji Novel 18F-labeled benzofuran derivatives with improved properties for positron emission tomography (PET) imaging of β-amyloid plaques in Alzheimer's brains J. Med. Chem. 54 2011 2971 2979
85. A. Juréus B.-M. Swahn J. Sandell F. Jeppsson A.E. Johnson P. Johnström J.A.M. Neelissen D. Sunnemark L. Farde S.P.S. Svensson Characterization of AZD4694, a novel fluorinated A β plaque neuroimaging PET radioligand J. Neurochem. 114 2010 784 794
86. Z. Cselényi M.E. Jönhagen A. Forsberg C. Halldin P. Julin M. Schou P. Johnström K. Varnäs S. Svensson L. Farde Clinical validation of 18F-AZD4694, an amyloid-β-specific PET radioligand J. Nucl. Med. 53 2012 415 424
87. C.C. Rowe S. Pejoska R.S. Mulligan G. Jones J.G. Chan S. Svensson Z. Cselényi C.L. Masters V.L. Villemagne Head-to-head comparison of 11C-PiB and 18F-AZD4694 (NAV4694) for β-amyloid imaging in aging and dementia J. Nucl. Med. 54 2013 880 886
88. M. Schou K. Varnäs J. Sandell P. Johnström Z. Cselenyi S. Svensson R. Nakao N. Amini L. Bergman A. Sumic B. Gulyas E. Lindström-Böö C. Halldin L. Farde Synthesis, radiolabeling, and in vivo pharmacokinetic evaluation of the amyloid beta radioligand [11C]AZD4694 in nonhuman primates Mol. Imaging Biol. 16 2014 173 179
89. M. Ono Y. Fuchi T. Fuchigami N. Kobashi H. Kimura M. Haratake H. Saji M. Nakayama Novel benzofurans with 99mTc complexes as probes for imaging cerebral β-amyloid plaques ACS Med. Chem. Lett. 1 2010 443 447
90. Y. Cheng M. Ono H. Kimura M. Ueda H. Saji Technetium-99m labeled pyridyl benzofuran derivatives as single photon emission computed tomography imaging probes for β-amyloid plaques in Alzheimer's brains J. Med. Chem. 55 2012 2279 2286
91. Y.S. Chang J.M. Jeong Y.-S. Lee H.W. Kim R.B. Ganesha Y.J. Kim D.S. Lee J.-K. Chung M.C. Lee Synthesis and evaluation of benzothiophene derivatives as ligands for imaging β-amyloid plaques in Alzheimer's disease Nucl. Med. Biol. 33 2006 811 820
92. H. Watanabe M. Ono M. Haratake N. Kobashi H. Saji M. Nakayama Synthesis and characterization of novel phenylindoles as potential probes for imaging of β-amyloid plaques in the brain Bioorg. Med. Chem. 18 2010 4740 4746
93. N. Suzuki S. Yasaki A. Yasuhara T. Sakamoto Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF) Chem. Pharm. Bull. 51 2003 1170 1173
94. H. Sano T. Noguchi A. Tanatani Y. Hashimoto H. Miyachi Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide Bioorg. Med. Chem. 13 2005 3079 3091
95. H. Fu L. Yu M. Cui J. Zhang X. Zhang Z. Li X. Wang J. Jia Y. Yang P. Yu H. Jia B. Liu Synthesis and biological evaluation of 18F-labled 2-phenylindole derivatives as PET imaging probes for β-amyloid plaques Bioorg. Med. Chem. 21 2013 3708 3714
96. B. Robinson The Fischer indole synthesis Chem. Rev. 63 1963 373 401
97. W. Qu S.-R. Choi C. Hou Z. Zhuang S. Oya W. Zhang M.-P. Kung R. Manchandra D.M. Skovronsky H.F. Kung Synthesis and evaluation of indolinyl-and indolylphenylacetylenes as PET imaging agents for β-amyloid plaques Bioorg. Med. Chem. Lett. 18 2008 4823 4827
98. Y. Yang H.-M. Jia B.-L. Liu (E)-5-styryl-1H-indole and (E)-6-styrylquinoline derivatives serve as probes for β-amyloid plaques Molecules 17 2012 4252 4265
99. M.-P. Kung C. Hou Z.-P. Zhuang B. Zhang D. Skovronsky J.Q. Trojanowski V.M.Y. Lee H.F. Kung IMPY: an improved Thioflavin-T derivative for in vivo labeling of β-amyloid plaques Brain Res. 956 2002 202 210
100. Z.-P. Zhuang M.-P. Kung A. Wilson C.-W. Lee K. Plössl C. Hou D.M. Holtzman H.F. Kung Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting β-amyloid plaques in the brain J. Med. Chem. 46 2002 237 243
101. M.-P. Kung C. Hou Z.-P. Zhuang D. Skovronsky H.F. Kung Binding of two potential imaging agents targeting amyloid plaques in postmortem brain tissues of patients with Alzheimer's disease Brain Res. 1025 2004 98 105
102. K. Mei-Ping H. Catherine Z. Zhi-Ping J.C. Alan L.M. Donna F.K. Hank Characterization of IMPY as a potential imaging agent for β-amyloid plaques in double transgenic PSAPP mice Eur. J. Nucl. Med. Mol. Imaging 31 2004 1136 1145
103. P.-J. Song S. Bernard P. Sarradin J. Vergote C. Barc S. Chalon M.-P. Kung H.F. Kung D. Guilloteau IMPY, a potential β-amyloid imaging probe for detection of prion deposits in scrapie-infected mice Nucl. Med. Biol. 35 2008 197 201
104. A.B. Newberg N.A. Wintering K. Plössl J. Hochold M.G. Stabin M. Watson D. Skovronsky C.M. Clark M.-P. Kung H.F. Kung Safety, biodistribution, and dosimetry of 123I-IMPY: a novel amyloid plaque-imaging agent for the diagnosis of alzheimer's disease J. Nucl. Med. 47 2006 748 754
105. B.H. Yousefi A. Manook B. von Reutern M. Schwaiger A. Drzezga H.-J. Wester G. Henriksen Development of an improved radioiodinated 2-phenylimidazo[1,2-a]pyridine for non-invasive imaging of amyloid plaques MedChemComm 3 2012 775 779
106. C.-J. Chen K. Bando H. Ashino K. Taguchi H. Shiraishi O. Fujimoto C. Kitamura S. Matsushima M. Fujinaga M.-R. Zhang H. Kasahara T. Minamizawa C. Jiang M. Ono M. Higuchi T. Suhara K. Yamada B. Ji Synthesis and biological evaluation of novel radioiodinated imidazopyridine derivatives for amyloid-β imaging in Alzheimer's disease Bioorg. Med. Chem. 22 2014 4189 4197
107. L. Cai F.T. Chin V.W. Pike H. Toyama J.-S. Liow S.S. Zoghbi K. Modell E. Briard H.U. Shetty K. Sinclair S. Donohue D. Tipre M.-P. Kung C. Dagostin D.A. Widdowson M. Green W. Gao M.M. Herman M. Ichise R.B. Innis Synthesis and evaluation of two 18F-labeled 6-iodo-2-(4'-N,N-dimethylamino)phenylimidazo[1,2-a]pyridine derivatives as prospective radioligands for β-amyloid in Alzheimer's disease J. Med. Chem. 47 2004 2208 2218
108. F. Zeng J.A. Southerland R.J. Voll J.R. Votaw L. Williams B.J. Ciliax A.I. Levey M.M. Goodman Synthesis and evaluation of two 18F-labeled imidazo[1,2-a]pyridine analogues as potential agents for imaging β-amyloid in Alzheimer's disease Bioorg. Med. Chem. Lett. 16 2006 3015 3018
109. N. Seneca L. Cai J.-S. Liow S.S. Zoghbi R.L. Gladding J. Hong V.W. Pike R.B. Innis Brain and whole-body imaging in nonhuman primates with [11C]MeS-IMPY, a candidate radioligand for β-amyloid plaques Nucl. Med. Biol. 34 2007 681 689
110. F. Zeng D. Alagille G.D. Tamagnan B.J. Ciliax A.I. Levey M.M. Goodman Synthesis and in vitro evaluation of imidazo[1,2-b]pyridazines as ligands for β-Amyloid plaques ACS Med. Chem. Lett. 1 2010 80 84
111. D. Alagille H. DaCosta R.M. Baldwin G.D. Tamagnan 2-Arylimidazo[2,1-b]benzothiazoles: a new family of amyloid binding agents with potential for PET and SPECT imaging of Alzheimer's brain Bioorg. Med. Chem. Lett. 21 2011 2966 2968
112. B.H. Yousefi A. Manook A. Drzezga B.von. Reutern M. Schwaiger H.J. Wester G. Henriksen Synthesis and evaluation of 11C-labeled imidazo[2,1-b]benzothiazoles (IBTs) as PET tracers for imaging β-amyloid plaques in Alzheimer's disease J. Med. Chem. 54 2011 949 956
113. B.H. Yousefi A. Drzezga B.von. Reutern A. Manook M. Schwaiger H.J. Wester G. Henriksen A novel 18F-labeled imidazo[2,1-b]benzothiazole (IBT) for high-contrast PET imaging of β-amyloid plaques ACS Med. Chem. Lett. 2 2011 673 677
114. M. Cui M. Ono H. Kimura H. Kawashima B.L. Liu H. Saji Radioiodinated benzimidazole derivatives as single photon emission computed tomography probes for imaging of β-amyloid plaques in Alzheimer's disease Nucl. Med. Biol. 38 2011 313 320
115. N. Vasdev P. Cao E.M. van Oosten A.A. Wilson S. Houle G. Hao X. Sun N. Slavine M. Alhasan P.P. Antich F.J. Bonte P. Kulkarni Synthesis and PET imaging studies of [18F]2-fluoroquinolin-8-ol ([18F]CABS13) in transgenic mouse models of Alzheimer's disease MedChemComm 3 2012 1228 1230
116. N. Okamura T. Suemoto S. Furumoto M. Suzuki H. Shimadzu H. Akatsu T. Yamamoto H. Fujiwara M. Nemoto M. Maruyama H. Arai K. Yanai T. Sawada Y. Kudo Quinoline and benzimidazole derivatives: candidate probes for in vivo imaging of tau pathology in Alzheimer's disease J. Neurosci. 25 2005 10857 10862
117. T. Tago S. Furumoto N. Okamura R. Harada Y. Ishikawa H. Arai K. Yanai R. Iwata Y. Kudo Synthesis and preliminary evaluation of 2-arylhydroxyquinoline derivatives for tau imaging J. Label. Comp. Radiopharm. 57 2014 18 24
118. M.T. Fodero-Tavoletti N. Okamura S. Furumoto R.S. Mulligan A.R. Connor C.A. McLean D. Cao A. Rigopoulos G.A. Cartwright G. O'Keefe S. Gong P.A. Adlard K.J. Barnham C.C. Rowe C.L. Masters Y. Kudo R. Cappai K. Yanai V.L. Villemagne 18F-THK523: a novel in vivo tau imaging ligand for Alzheimer's disease Brain 134 2011 1089 1100
119. N. Okamura S. Furumoto R. Harada T. Tago T. Yoshikawa M. Fodero-Tavoletti R.S. Mulligan V.L. Villemagne H. Akatsu T. Yamamoto H. Arai R. Iwata K. Yanai Y. Kudo Novel 18F-labeled arylquinoline derivatives for noninvasive imaging of tau pathology in Alzheimer disease J. Nucl. Med. 54 2013 1420 1427
120. M. Cui M. Ono H. Kimura B. Liu H. Saji Novel quinoxaline derivatives for in vivo imaging of β-amyloid plaques in the brain Bioorg. Med. Chem. Lett. 21 2011 4193 4196
121. P. Yu M. Cui X. Wang X. Zhang Z. Li Y. Yang J. Jia J. Zhang M. Ono H. Saji H. Jia B. Liu 18F-Labeled 2-phenylquinoxaline derivatives as potential positron emission tomography probes for in vivo imaging of β-amyloid plaques Eur. J. Med. Chem. 57 2012 51 58
122. M. Yoshimura M. Ono K. Matsumura H. Watanabe H. Kimura M. Cui Y. Nakamoto K. Togashi Y. Okamoto M. Ihara R. Takahashi H. Saji Structure-activity relationships and in vivo evaluation of quinoxaline derivatives for PET Imaging of β-amyloid plaques ACS Med. Chem. Lett. 4 2013 596 600