Synthesis and evaluation of18F-labeled 2-phenylbenzothiazoles as positron emission tomography imaging agents for amyloid plaques in alzheimer's disease

Journal of Medicinal Chemistry

Volumn 52, Issue 5, 2009, Pages 1428-1437

  Serdons, Kim ^a,d   Terwinghe, Christelle ^b   Vermaelen, Peter ^b   Van Laere, Koen ^b   Kung, Hank ^c   Mortelmans, Luc ^b   Bormans, Guy ^a   Verbruggen, Alfons ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b UNIVERSITY HOSPITALS LEUVEN   (Belgium)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

^d NONE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

6 HYDROXY 2 (4' FLUOROPHENYL) 1,3 BENZOTHIAZOLE F 18; 6 METHOXY 2 (4' FLUOROPHENYL) 1,3 BENZOTHIAZOLE F 18; 6 METHYL 2 (4' FLUOROPHENYL) 1,3 BENZOTHIAZOLE F 18; BENZOTHIAZOLE DERIVATIVE; TRACER; UNCLASSIFIED DRUG; 6 METHYL 2 (4' FLUOROPHENYL) 1,3 BENZOTHIAZOLE; 6-METHYL-2-(4'-FLUOROPHENYL)-1,3-BENZOTHIAZOLE; DIAGNOSTIC AGENT; FLUORINE; RADIOPHARMACEUTICAL AGENT; THIAZOLE DERIVATIVE;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD BRAIN BARRIER; DRUG DISTRIBUTION; DRUG SCREENING; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; ANIMAL; BRAIN; CHEMISTRY; HUMAN; METABOLISM; RAT; SCINTISCANNING; SENILE PLAQUE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TISSUE DISTRIBUTION; WISTAR RAT;

ALZHEIMER DISEASE; ANIMALS; BENZOTHIAZOLES; BLOOD-BRAIN BARRIER; BRAIN; FLUORINE RADIOISOTOPES; HUMANS; MALE; MICE; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RATS, WISTAR; SENILE PLAQUES; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; TISSUE DISTRIBUTION;

EID: 64349115270     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8013376     Document Type: Article

References (36)

1. Selkoe, D. J. Alzheimer's disease: genes, proteins, and therapy. Phys. Rev. 2001, 81, 741-766.
2. Alzheimer, A. Uber eine eigenartige erkrankung der hirnrinde. Allg. Z. Psychiatr. 1907, 64, 146-148.
3. Hardy, J.; Selkoe, D. J. The amyloid hypothesis of Alzheimer's disease: progress and problems on road to therapeutics. Science 2002, 297. 353-356.
4. Vallet, P. G.; Guntern, R.; Hof, P. R.; Golaz, J.; Delacourte, A.; Robakis, N. K.; Bouras, C. A comparative study of histological and immunohistochemical methods for neurofibrillary tangles and senile plaques in Alzheimer's disease. Acta Neuropathol. 1992, 83, 170-178.
5. 11C-labeled stilbene derivatives as Aβ-aggregate-specific PET imaging agents for Alzheimer's disease. Nucl. Med. Biol. 2003, 30, 565-571.
6. 11C]SB-13 PET. Am. J. Geriatr. Psychiatr. 2004, 12, 584-595.
7. Agdeppa, E.; Kepe, V.; Liu, J.; Flores-Torres, M.; Satyamurthy, N.; Petric, A.; Cole, G.; Small, G.; Huang, S. C.; Barrio, J. Binding characteristics of radiofluorinated 6-dialkylamino-2-naphthylethylidene derivatives as positron emission tomography imaging probes for β-amyloid plaques in Alzheimer's disease. J. Neurosci. 2001, 21, 1-5.
8. Small, G.; Kepe, V.; Ercoli, L.; Siddarth, P.; Bookheimer, S.; Miller, K.; Lavretsky, H.; Burggren, A.; Cole, G.; Vinters, H.; Thompson, P.; Huang, S. C.; Satyamurthy, N.; Phelps, M.; Barrio, J. PET of brain amyloid and tau in mild cognitive impairment. N. Engl. J. Med. 2006, 355, 2652-2663.
9. Zhuang, Z. P.; Klunk, W. E.; Wang, J.; Huang, G. F.; Debnath, M. L.; Holt, D. P.; Mathis, C. A. Radioiodinated styrylbenzenes and thioflavins as probes for amyloid aggregates. J. Med. Chem. 2001, 44, 1905-1914.
10. Klunk, W. E.; Wang, Y.; Huang, G.; Debnath, M. L.; Holt, D. P.; Mathis, C. A. Uncharged thioflavin-T derivatives bind to amyloid-beta protein with high affinity and readily enter the brain. Life Sci. 2001, 69, 1471-1484.
11. Klunk, W. E.; Engler, H.; Nordberg, A.; Wang, Y.; Blomqvist, G.; Holt, D.; Bergström, M.; Savitcheva, I.; Huang, G.; Estrada, S.; Ausen, B.; Debnath, M.; Barletta, J.; Price, J. C.; Sandell, J.; Lopresti, B.; Wall, A.; Koivisto, P.; Antoni, G.; Mathis, C.; Langstrom, B. Imaging brain amyloid in Alzheimer's disease with Pittsbugh compound-B. Ann. Neurol. 2004, 55, 306-319.
12. 11C-PIB positron emission tomography study. Ann. Neurol. 2006, 60, 145-147.
13. Zhuang, Z. P.; Kung, M. P.; Hou, C.; Plossel, K.; Skovronsky, D.; Gur, T. L.; Trojanowski, J. Q.; Lee, V.; Kung, H. F. IBOX(2-(4′- dimethylaminophenyl)-6-iodobenzonxazole): a ligand for imaging amyloid plaques in the brain. Nucl. Med. Biol. 2001, 28, 887-894.
14. Zhuang, Z. P.; Kung, M. P.; Wilson, A.; Lee, C. W.; Plossl, K.; Hou, C.; Holtzman, D.; Kung, H. F. Structure-activity relationship of imidazo[1,2-α]pyridines as ligands for detecting β-amyloid plaques in the brain. J. Med. Chem. 2003, 46, 237-243.
15. Suemoto, T.; Okamura, N.; Shiomitsu, T.; Suzuki, M.; Shimadzu, H.; Akatsu, H.; Yamamoto, T.; Kudo, Y.; Sawada, T. In vivo labeling of amyloid with BF-108. Neurosci. Res. 2004, 48, 65-74.
16. Zhang, W.; Oya, S.; Kung, M. P.; Hou, C.; Maier, D.; Kung, H. F. F-18 polyethyleneglycol stilbenes as PET imaging agents targeting Aβ aggregates in the brain. Nucl. Med. Biol. 2005, 32, 799-809.
17. Chang, Y.; Jeong, J.; Lee, Y. S.; Kim, H.; Rai, G.; Kim, Y.; Lee, D.; Chung, J. K.; Lee, M. Synthesis and evaluation of benzothiophene derivatives as ligands for imaging β-amyloid plaques in Alzheimer's disease. Nucl. Med. Biol. 2006, 33, 811-820.
18. Zhuang, Z. P.; Kung, M. P.; Kung, H. F. Synthesis of biphenyltrienes as probes for β-amyloid plaques. J. Med. Chem. 2006, 49, 2841-2844.
19. 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques. Eur. J. Med. Chem. 2004, 39, 573-578.
20. 18F-labeled styrylpyridines as PET agents for amyloid plaque imaging. Nucl. Med. Biol. 2007, 34, 89-97.
21. Ryu, E.; Choe, Y.; Lee, K. H.; Choi, Y.; Kim, B. T. Curcumin and dehydrozingerone derivatives: synthesis, radiolabelling, and evaluation for β-amyloid plaque imaging. J. Med. Chem. 2006, 49, 6111-6119.
22. Shi, D.; Bradshaw, T.; Wrigley, S; McCall, C.; Lelieveld, P.; Fichtner, I; Stevens, M. Antitumor benzothiazoles. 3. Synthesis of 2-(4- aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J. Med. Chem. 1996, 39, 3375-3384.
23. Kashiyama, E.; Hutchinson, I.; Chua, M.-S.; Stinson, S.; Phillips, L.; Kaur, G.; Sausville, E.; Bradshaw, T.; Westwell, A.; Stevens, M. Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl)-benzothiazoles. J. Med. Chem. 1999, 42, 4172-4184.
24. Hutchinson, I.; Chua, M-S; Browne, H.; Trapani, V.; Bradshaw, T.; Westwell, A; Stevens, M. Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl) benzothiazoles. J. Med. Chem. 2001, 44, 1446-1455.
25. Cava, M.; Levinson, M. Thionation reactions of Lawesson's reagents. Tetrahedron 1985, 41, 5061-5087.
26. von Manfred, S.; Siegfried, J; Manfred, H. Synthese und reaktions-verhalten 2′-substituierter isoflavone. Helv. Chim. Acta 1992, 75, 457-470.
27. Lin, A.; Kasina, S. Synthesis of 3-substituted 7-(3,3-dimethyl-1- triazeno)-10-methylphenothazines as potential antitumor agents. J. Heterocycl. Chem. 1981, 18, 759-761.
28. Mashraqui, S.; Kumar, S.; Trân Huu Dâu, E. Synthesis, molecular structure and optical spectral studies of syn-dithia benzothiazolophane and anti-bis-lactone benzothiazolophane. J. Mol. itruct. 2004, 697, 221-230.
29. Lang, R.; Williams, C.; Garson, M. An improved preparation of 4-amino-3-mercaptobenzoic acid. Org. Prep. Proced. Int. 2003, 35, 520-524.
30. Dishino, D.; Welch, M.; Kilbourn, M.; Raichle, M. Relationship between lipophilicity and brain extraction of C-11-labeled radiophar-maceuticals. J. Nucl. Med. 1983, 24, 1030-1038.
31. Chitneni, S. K.; Serdons, K.; Evens, N.; Fonge, H.; Celen, S.; Deroose, C. M.; Debyser, Z.; Mortelmans, L.; Verbruggen, A. M.; Bormans, G. M. Efficient purification and metabolite analysis of radiotracers using high-performance liquid chromatography and on-line solid-phase extraction. J. Chromatogr., A 2008, 1189, 323-331.
32. 11C]PIB. Neurobiol. Aging 2004, 25 (S2), 277.
33. 11C]methyl triflate for β-amyloid imaging in Alzheimer's disease with PET. Appl. Radiat. Isot. 2005, 62, 591-595.
34. Kung, M. P.; Hou, C.; Zhuang, Z. P.; Skovronsky, D.; Kung, H. F. Binding of two potential imaging agents targeting amyloid plaques in postmortem brain tissues of patients with Alzheimer's disease. Brain Res. 2004, 1025, 89-105.
35. Munson, P. J.; Rodbard, D. Ligand: a versatile computerized approach for characterisation of ligand-binding systems. Anal. Biochem. 1980, 107, 220-239.
36. Yamauchi, H.; Takahashi, J.; Seri, S.; Kawashima, H.; Koike, H.; Kato-Azuma, M. In Technetium and Rhenium in Chemistry and Nuclear Medicine; Nicolini, M., Bandoli, G., Mazzi, U., Eds.; Cortina International: Verona, Italy, 1989; pp 475-502; Vol. 3.