Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents

Journal of Medicinal Chemistry

Volumn 46, Issue 13, 2003, Pages 2740-2754

  Mathis, Chester A ^a,b   Wang, Yanming ^a   Holt, Daniel P ^a   Huang, Guo Feng ^a   Debnath, Manik L ^a   Klunk, William E ^a  

^a UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^b PRESBYTERIAN UNIVERSITY HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMYLOID BETA PROTEIN; BENZOTHIAZOLE DERIVATIVE; CARBON 11; CONTRAST MEDIUM; METHYL IODIDE; N METHYL 2 (4' METHYLAMINOPHENYL) 6 HYDROXYBENZOTHIAZOLE C 11; N METHYL 6 HYDROXYNBENZOTHIAZOLE H 3; UNCLASSIFIED DRUG; 2 (4' (METHYLAMINO)PHENYL) 6 HYDROXYBENZOTHIAZOLE; 2-(4'-(METHYLAMINO)PHENYL)-6-HYDROXYBENZOTHIAZOLE; AMYLOID BETA PROTEIN[1-40]; ANILINE DERIVATIVE; CARBON; PEPTIDE FRAGMENT; RADIOPHARMACEUTICAL AGENT; THIAZOLE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DRUG BINDING; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; FRONTAL CORTEX; ISOTOPE LABELING; MOUSE; NONHUMAN; ANIMAL; BRAIN; CHEMISTRY; COMPUTER ASSISTED EMISSION TOMOGRAPHY; IN VITRO STUDY; MALE; METABOLISM; PAPIO; PATHOLOGY; SYNTHESIS;

AMYLOID BETA-PROTEIN; ANILINE COMPOUNDS; ANIMALS; BRAIN; CARBON RADIOISOTOPES; FEMALE; ISOTOPE LABELING; MALE; MICE; PAPIO; PEPTIDE FRAGMENTS; RADIOPHARMACEUTICALS; THIAZOLES; TOMOGRAPHY, EMISSION-COMPUTED;

EID: 0038792263     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030026b     Document Type: Article

References (64)

1. Braak, H.; Braak, E. Neuropathological stageing of Alzheimer-related changes. Acta Neuropathol. (Berl.) 1991, 82, 239-259.
2. Mirra, S. S.; Heyman, A.; McKeel, D.; Sumi, S. M.; Crain, B. J.; Brownlee, L. M.; Vogel, F. S.; Hughes, J. P.; van Bell, G.; Berg, L. The consortium to establish a registry for Alzheimer's disease (CERAD). Part II. Standardization of the neuropathologic assessment of Alzheimer's disease. Neurology 1991, 41, 479-486.
3. Klunk, W. E.; Abraham, D. J. Filamentous proteins in Alzheimer's disease: new insights through molecular biology. Psych. Dev. 1988, 6, 121-152.
4. Schenk, D. B.; Rydel, R. E.; May, P.; Little, S.; Panetta, J.; Lieberburg, I.; Sinha, S. Therapeutic approaches related to amyloid-beta peptide and Alzheimer's disease. J. Med. Chem. 1995, 38, 4141-4154.
5. Schenk, D. B.; Seubert, P.; Lieberburg, I.; Wallace, J. Beta-peptide immunization: a possible new treatment for Alzheimer disease. Arch. Neurol. 2000, 57, 934-936.
6. Holtzman, D. M.; Bales, K. R.; Paul, S. M.; DeMattos, R. B. Abeta immunization and anti-Abeta antibodies: potential therapies for the prevention and treatment of Alzheimer's disease. Adv. Drug Deliv. Rev. 2002, 54, 1603-1613.
7. Olson, R. E.; Copeland, R. A.; Seiffert, D. Progress towards testing the amyloid hypothesis: inhibitors of APP processing. Curr. Opin. Drug Discov. Dev. 2001, 4, 390-401.
8. Matsuoka, Y.; Saito, M.; LaFrancois, J.; Saito, M.; Gaynor, K.; Olm, V.; Wang, L.; Casey, E.; Lu, Y.; Shiratori, C.; Lemere, C.; Duff, K. Novel therapeutic approach for the treatment of Alzheimer's disease by peripheral administration of agents with an affinity for β-amyloid. J. Neurosci. 2003, 23, 29-33.
9. Klunk W. E.; Debnath M. L.; Pettegrew J. W. Chrysamine-G binding to Alzheimer and control brain: autopsy study of a new amyloid probe. Neurobiol. Aging 1995, 16, 541-548.
10. Mathis C. A.; Mahmood K.; Debnath M. L.; Klunk W. E. Synthesis of a lipophilic radioiodinated ligand with high affinity to amyloid protein in Alzheimer's disease brain tissue. J. Labelled Compd. Radiopharm. 1997, 40, 94-95.
11. 99mTc-MAMA-Chrysamine G, a Probe for beta-Amyloid Protein of Alzheimer's Disease. Eur. J. Nucl. Med. 1999, 26, 1392-1399.
12. Styren S. D.; Hamilton R. L.; Styren G. C.; Klunk W. E. X-34, a fluorescent derivative of Congo red: a novel histochemical stain for Alzheimer's disease pathology. J. Histochem. Cytochem. 2000, 48, 1223-1232.
13. Klunk W. E.; Bacskai B. J.; Mathis C. A.; Kajdasz S. T.; McLellan M. E.; Frosch M. P.; Debnath M. L.; Holt D. P.; Wang Y.; Hyman B. T. Imaging Abeta plaques in living transgenic mice with multiphoton microscopy and methoxy-X04, a systemically administered Congo red derivative. J. Neuropathol. Exp. Neurol. 2002, 61, 797-805.
14. Wang, Y.; Mathis, C. A.; Huang, G.-F.; Holt, D. P.; Debnath, M. L.; Klunk, W. E. Synthesis and C-11-Labeling of (E, E)-1-(3′, 4′Dihydroxystyryl)-4-(3′-Methoxy-4′-Hydroxystyryl) Benzene for PET Imaging of Amyloid Deposits. J. Labelled Compd. Radiopharm. 2002, 45, 647-664.
15. Klunk, W. E.; Wang, Y.; Huang, G.-F.; 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.
16. Mathis, C. A.; Bacskai, B. J.; Kajdasz, S. T.; McLellan, M. E.; Frosch, M. P.; Hyman, B. T.; Holt, D. P.; Wang, Y.; Huang, G.-F.; Debnath, M. L.; Klunk, W. E. A lipophilic thioflavin-T derivative for positron emission tomography (PET) imaging of amyloid in brain. Bioorg. Med. Chem. Lett. 2002, 12, 295-298.
17. Zhuang Z. P.; Kung M. P.; Hou C.; Plossl K.; Skovronsky D.; Gur T. L.; Trojanowski J. Q.; Lee V. M.; Kung H. F. IBOX (2-(4′-dimethylaminophenyl)-6-iodobenzoxazole): a ligand for imaging amyloid plaques in the brain. Nucl. Med. Biol. 2001, 28, 887-894.
18. Zhuang Z. P.; Kung M. P.; Wilson A.; Lee C. W.; Plossl K.; Hou C.; Holtzman D. M.; Kung H. F. Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting beta-amyloid plaques in the brain. J. Med. Chem. 2003, 46, 237-243.
19. Agdeppa E. D.; Kepe V.; Liu J.; Flores-Torres S.; Satyamurthy N.; Petric A.; Cole G. M.; Small G. W.; Huang S. C.; Barrio J. R. Binding characteristics of radiofluorinated 6-dialkylamino-2-naphthylethylidene derivatives as positron emission tomography imaging probes for beta-amyloid plaques in Alzheimer's disease. J. Neurosci. 2001, 21, RC189-.
20. Shoghi-Jadid, K.; Small, G. W.; Agdeppa, E. D.; Kepe, V.; Ercoli, L. M.; Siddarth, P.; Read, S.; Satyamurthy, N.; Petric, A.; Huang, S. C.; Barrio, J. R. Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease. Am. J. Geriatr. Psych. 2002, 10, 24-35.
21. Shi, D. F.; Bradshaw, T. D.; Wrigley, S.; McCall, C. J.; Lelieveld, P.; Fichtner, I.; Stevens, M. F. G. 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.
22. Kawaoka, Y.; Takashita, K. Preparation of 2-aminothiophenols. Japanese Patent 07278100, 1995.
23. Tsuruoka, A.; Kaku Y.; Kakinuma H.; Tsukada I.; Yanagisawa M., Nara K., Naito T. Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. optically active ER-30346 and its derivatives. Chem. Pharm. Bull. 1998, 46, 623-630.
24. Hasebe, N. Use of polyphosphoric acid in the synthesis of 2-arylbenzothiazoles. Yamagata Daigaku Kiyo, Shizen Kagaku 1972, 8, 63-67.
25. Dishino, D. D.; Welch, M. J.; Kilbourn, M. R.; Raichle, M. E. Relationship between lipophilicity and brain extraction of C-11-labeled radiopharmaceuticals. J. Nucl. Med. 1983, 24, 1030-1038.
26. Vera, D. R.; Eckelman, W. C. Receptor 1980 and Receptor 2000: twenty years of progress in receptor-binding radiotracers. Nucl. Med. Biol. 2001, 28, 475-476.
27. Hansch, C.; Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley and Sons: New York, 1979.
28. Lemaire, C.; Cantineau, R.; Guillaume, M.; Plenevaux, A.; Christiaens, L. Fluorine-18-altanserin: a radioligand for the study of serotonin receptors with PET: radiolabeling and in vivo biologic behavior in rats. J. Nucl. Med. 1991, 32, 2266-2272.
29. 3H]WIN 35,428. J. Pharmacol. Exp. Ther. 1991, 257, 954-958.
30. Hume, S. P.; Myers, R.; Bloomfield, P. M.; Opacka-Juffry, J.; Cremer, J. E.; Ahier, R. G.; Luthra, S. K.; Brooks, D. J.; Lammertsma, A. A. Quantitation of carbon-11-labeled raclopride in rat striatum using positron emission tomography. Synapse 1992, 12, 47-54.
31. Suehiro, M.; Scheffel, U.; Dannals, R. F.; Ravert, H. T.; Ricaurte, G. A.; Wagner, H. N. Jr. A PET radiotracer for studying serotonin uptake sites: carbon-11-McN-5652Z. J. Nucl. Med. 1993, 34, 120-127.
32. 11C]WAY 100635: a radioligand for imaging 5-HT1A receptors with positron emission tomography. Life Sci. 1994, 55, PL403-407.
33. 11C]WAY-100635. Eur. J. Pharmacol. 1996, 301, R5-7.
34. Drevets, W. C.; Frank, E.; Price, J. C.; Kupfer, D. J.; Holt, D.; Greer, P. J.; Huang, Y.; Gautier, C.; Mathis, C. PET imaging of serotonin 1A receptor binding in depression. Biol. Psych. 1999, 46, 1375-1387.
35. 11C-raclopride. Psychopharmacology (Berl.) 1987, 92, 278-284.
36. 11C-raclopride in living human brain-a search for extrastriatal central D2-dopamine receptors by PET. Psychopharmacology (Berlin) 1988, 94, 471-478.
37. Smith, G. S.; Price, J. C.; Lopresti, B. J.; Huang, Y.; Holt, D.; Mason, N. S.; Simpson, N. R.; Sweet, R.; Meltzer, C. C.; Sashin, D.; Mathis, C. A. Test-retest variability of serotonin 5-HT2A receptor binding measured with positron emission tomography (PET) and [F-18]altanserin in the human brain. Synapse 1998, 30, 380-392.
38. 18F]altanserin bolus injection PET data II: consideration of radiolabeled metabolites in humans. Synapse 2001, 41, 11-21.
39. Lopresti, B. J.; Mathis, C. A.; Price, J. C.; Villemagne, V. L.; Meltzer, C. C.; Holt, D. P.; Smith, G. S.; Moore, R. Y. Serotonin transporter binding in vivo: further examination of [11C]-McN5652, In Molecular and Pharmacological Brain Imaging with Positron Emission Tomography; Gjedde A., Ed.; Academic Press: San Diego, 2001; pp 265-271.
40. 11C]AFM. J. Cereb. Blood Flow Metab. 2002, 22, 1377-1398.
41. Eckelman, W. C. Sensitivity of New Radiopharmaceuticals. Nucl. Med. Biol. 1998, 25, 169-173.
42. Naslund, J.; Haroutunian, V.; Mohs, R.; Davis, K. L.; Davies, P.; Greengard, P.; Buxbaum, J. D. Correlation between elevated levels of amyloid beta-peptide in the brain and cognitive decline. J. Am. Med. Assoc. 2000, 283, 1571-1577.
43. Klunk, W. E.; Wang, Y.; Huang, G.-F.; Debnath, M. L.; Holt, D. P.; Shao, L.; Hamilton, R. L.; Ikonomovic, M.; DeKosky, S. T.; Mathis, C. A. The binding of 2-(4′-methylaminophenyl)-benzothiazole to postmortem brain homogenates is dominated by the amyloid component. J. Neurosci. 2003, 23, 2086-2092.
44. Wolf, D. S.; Gearing, M.; Snowdon, D. A.; Mori, H.; Markesbery, W. R.; Mirra, S. S. Progression of regional neuropathology in Alzheimer disease and normal elderly: findings from the nun study. Alzh. Disease Assoc. Disorders 1999, 13, 226-231.
45. Roth, B. L.; Ernsberger, P.; Steinberg, S. A.; Rao, S.; Rauser, L.; Savage, J.; Hufeisen, S.; Berridge, M. S.; Muzic, R. F. Jr. The in vitro pharmacology of the beta-adrenergic receptor PET ligand (S)-fluorocarazolol reveals high affinity for cloned beta-adrenergic receptors and moderate affinity for the human 5-HT1A receptor. Psychopharmacology (Berlin) 2001, 157, 111-114.
46. 2B receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications. Circulation 2000, 102, 2836-2841.
47. Allsop, D.; Landon, M.; Kidd, M.; Lowe, J. S.; Reynolds, G. P.; Gardner, A. Monoclonal antibodies raised against a sub-sequence of senile plaque core protein react with plaque cores, plaque periphery and cerebrovascular amyloid in Alzheimer's disease. Neurosci. Lett. 1986, 68, 252-256.
48. Glenner, G. G.; Wong, C. W. Alzheimer's disease: initial report of the purification and characterization of a novel cerebrovascular amyloid protein. Biochem. Biophys. Res. Commun. 1984, 120, 885-890.
49. Ikeda, S.; Wong, C. W.; Allsop, D.; Landon, M.; Kidd, M.; Glenner, G. G. Immunogold labeling of cerebrovascular and neuritic plaque amyloid fibrils in Alzheimer's disease with an anti-beta protein monoclonal antibody. Lab. Investig. 1987, 57, 446-449.
50. Okamoto, K.; Yamaguchi, H.; Hirai, S.; Shoji, M.; Inoue, K.; Takatama, M. Immunogold electron microscopic study of cerebrovascular and senile plaque amyloid using anti-beta protein antibody. Prog. Clin. Biol. Res. 1989, 317, 953-963.
51. Wong, C. W.; Quaranta, V.; Glenner, G. G. Neuritic plaques and cerebrovascular amyloid in Alzheimer disease are antigenically related. Proc. Natl. Acad. Sci. U. S. A. 1985, 82, 8729-8732.
52. Yamaguchi, H.; Hirai, S.; Morimatsu, M.; Shoji, M.; Nakazato, Y. Diffuse type of senile plaques in the cerebellum of Alzheimer-type dementia demonstrated by beta protein immunostain. Acta Neuropathol. 1989, 77, 314-319.
53. Eckelman, W. C. The use of in vitro models to predict the distribution of receptor binding radiotracers in vivo. Nucl. Med. Biol. 1989, 16, 233-245.
54. Eckelman, W. C.; Gibson, R. E. The design of site directed radiopharmaceuticals for use in drug discovery. In Nuclear Imaging in Drug Discovery, Development and Approval; Burns, H. D., Gibson, R. E., Dannals, R. F., Siegl P. K. S., Eds.; Birkhauser: Boston, Mass., 1992; pp 113-134.
55. Engler, H.; Blomqvist, G.; Bergstrom, M.; Langstrom, B.; Klunk, W.; Debnath, M.; Holt, D.; Wang, Y.; Huang, G.-F.; Mathis, C. First human study with a benzothiazole amyloid-imaging agent in Alzheimer's disease and control subjects. Neurobiol. Aging 2002, 23 (Suppl.), S1568.
56. Hyman, B. T.; Bacskai, B. J.; Kajdasz, S. T.; Mclellan, M. E.; Frosch, M. P.; Debnath, M. L.; Holt, D. P.; Wang, Y.; Mathis, C. A.; Klunk, W. E. Visualizing amyloid plaques. Neurobiol. Aging 2002, 23 (1S), S149.
57. Bacskai, B. J.; Klunk, W. E.; Mathis, C. A.; Hyman, B. T. Imaging amyloid-beta deposits in vivo. J. Cereb. Blood Flow Metab. 2002, 22, 1035-1041.
58. 11C]methyl)spiperone. Int. J. Radiat. Appl. Isot. 1986, 37, 433-434.
59. Salminen, T.; Pulli, A.; Taskinen, J. Relationship between immobilised artificial membrane chromatographic retention and the brain penetration of structurally diverse drugs. J. Pharm. Biomed. Anal. 1997, 15, 469-477.
60. Drevets, W. C.; Price, J. C.; Kupfer, D. J.; Kinahan, P. E.; Lopresti, B.; Holt, D.; Mathis, C. PET measures of amphetamine-induced dopamine release in ventral versus dorsal striatum. Neuropsychopharmacology 1999, 21, 694-709.
61. 18F]altanserin bolus injection PET data. I: consideration of radiolabeled metabolites in baboons. Synapse 2001, 41, 1-10.
62. Woods, R. P.; Mazziotta, J. C.; Cherry, S. R. MRI-PET registration with an automated algorithm. J. Comput. Assist. Tomogr. 1993, 17, 536-546.
63. Greer, P. J.; Villemagne, V. L.; Ruszkiewicz, J.; Graves, A. K.; Meltzer, C. C.; Mathis, C. A.; Price, J. C. MR atlas of the baboon brain for functional neuroimaging. Brain Res. Bull. 2002, 58, 429-438.
64. 15O PET studies in baboons: before and after amphetamine. J. Nucl. Med. 2002, 43, 1090-1100.