Benzothiazole Schiff-bases as potential imaging agents for β-amyloid plaques in Alzheimer's disease

Medicinal Chemistry Research

Volumn 22, Issue 9, 2013, Pages 4069-4074

  Gan, Changsheng ^a   Zhou, Lin ^a   Zhao, Zhenzhen ^a   Wang, Haoshu ^a  

^a HEFEI UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Alzheimer's disease; Amyloid plaques; Benzothiazole; Binding affinity; Schiff bases

Indexed keywords

6 IODO 2 (4' DIMETHYL AMINO) PHENYL IMIDAZO[1,2 ALPHA]PYRIDINE I 125; AMYLOID BETA PROTEIN; BENZOTHIAZOLE DERIVATIVE; FLUORESCENT DYE; RADIOPHARMACEUTICAL AGENT; SCHIFF BASE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ARTICLE; BINDING AFFINITY; BRAIN; BRAIN HOMOGENATE; DRUG PROTEIN BINDING; HUMAN; HUMAN TISSUE; IN VITRO STUDY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84881143533     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0416-0     Document Type: Article

References (34)

1. Barrio JR, Kepe V, Satyamurthy N, Huang SC, Small G (2008) Amyloid and tau imaging, neuronal losses and function in mild cognitive impairment. J Nutr Health Aging 12:61S-65S
2. Cai L, Innis RB, Pike VW (2007) Radioligand development for PET imaging of beta-amyloid (Abeta) - current status. Curr Med Chem 14:19-52
3. Carter DB, Chou KC (1998) A model for structure-dependent binding of Congo red to Alzheimer beta-amyloid fibrils. Neurobiol Aging 19:37-40
4. Chandra R, Kung MP, Kung HF (2006) Design, synthesis, and structure-activity relationship of novel thiophene derivatives for beta-amyloid plaque imaging. Bioorg Med Chem Lett 16:1350-1352
5. Duan XH, Liu BL (2008) Aβ-binding molecules: possible application as imaging probes and as anti-aggregation agents. Sci China B 51:801-807
6. Guillozet AL, Weintraub S, Mash DC, Mesulam MM (2003) Neurofibrillary tangles, amyloid, and memory in aging and mild cognitive impairment. Arch Neurol 60:729-736
7. Klunk WE, Jacob RF, Mason RP (1999) Quantifying amyloid β-peptide (Aβ) aggregation using the Congo red-Aβ (CR-Aβ) spectrophotometric assay. Anal Biochem 266:66-76
8. Klunk WE, Engler H, Nordberg A, Wang Y, Blomqvist G, Holt DP, Bergstrom M, Savitcheva I, Huang GF, Estrada S, Ausen B, Debnath ML, Barletta J, Price JC, Sandell J, Lopresti BJ, Wall A, Koivisto P, Antoni G, Mathis CA, Langstrom B (2004) Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. Ann Neurol 55:306-319
9. Kudo Y, Okamura N, Furumoto S, Tashiro M, Furukawa K, Maruyama M, Itoh M, Iwata R, Yanai K, Arai H (2007) 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 48:553-561
10. Kung HF, Lee CW, Zhuang ZP, Kung MP, Hou C, Plössl K (2001) Novel stilbenes as probes for amyloid plaques. J Am Chem Soc 123:12740-12741
11. Lee CW, Zhuang ZP, Kung MP, Plössl K, Skovronsky D, Gur T, Hou C, Trojanowski JQ, Lee VM, Kung HF (2001) Isomerization of (Z, Z) to (E, E)1-bromo-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)- styrylbenzene in strong base: probes for amyloid plaques in the brain. J Med Chem 44:2270-2275
12. 18F]AV-45, a novel amyloid imaging agent - a pilot study. Nucl Med Biol 37:497-508
13. 11C]PiB and its multi-modal validation in an APP/PS1 mouse model of Alzheimer's disease. PLoS ONE 7(3):e31310. doi: 10.1371/journal.pone.0031310
14. 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem 46:2740-2754
15. Mathis CA, Wang Y, Klunk WE (2004) Imaging beta-amyloid plaques and neurofibrillary tangles in the aging human brain. Curr Pharm Des 10:1469-1492
16. 18F-flutemetamol in healthy volunteers and patients with probable Alzheimer disease. J Nucl Med 50:1251-1259
17. Nesterov EE, Skoch J, Hyman BT, Klunk WE, Bacskai BJ, Swager TM (2005) In vivo optical imaging of amyloid aggregates in brain: design of fluorescent markers. Angew Chem Int Ed Engl 44:5452-5456
18. Nestor PJ, Scheltens P, Hodges JR (2004) Advances in the early detection of Alzheimer's disease. Nat Med 10:S34-S41
19. 18F-fluoroethylated benzothiazole derivatives for in vivo imaging of amyloid plaques in Alzheimer's disease. Appl Radiat Isot 68(6):1066-1072
20. 123I-IMPY: a novel amyloid plaque-imaging agent for the diagnosis of Alzheimer's disease. J Nucl Med 47:748-754
21. Nordberg A (2004) PET imaging of amyloid in Alzheimer's disease. Lancet Neurol 3:519-527
22. Nordberg A (2009) The future: new methods of imaging exploration in Alzheimer's disease. Front Neurol Neurosci 24:47-53
23. 11C-labeled stilbene derivatives as Abeta-aggregate-specific PET imaging agents for Alzheimer's disease. Nucl Med Biol 30:565-571
24. Petersen RC, Parisi JE, Dickson DW, Johnson KA, Knopman DS, Boeve BF, Jicha GA, Ivnik RJ, Smith GE, Tangalos EG, Braak H, Kokmen E (2006) Neuropathologic features of amnestic mild cognitive impairment. Arch Neurol 63:665-672
25. Querfurth HW, LaFerla FM (2010) Mechanisms of disease: Alzheimer's disease. N Engl J Med 362:329-344
26. 18F-BAY94-9172, a novel PET tracer: proof of mechanism. Lancet Neurol 7:129-135
27. Selkoe DJ (2004) Alzheimer disease: mechanistic understanding predicts novel therapies. Ann Intern Med 140:627-638
28. Shin J, Lee SY, Kim SH, Kim YB, Cho SJ (2008) Multitracer PET imaging of amyloid plaques and neurofibrillary tangles in Alzheimer's disease. Neuroimage 43:236-244
29. Shoghi-Jadid K, Small GW, Agdeppa ED, Kepe V, Ercoli LM, Siddarth P, Read S, Satyamurthy N, Petric A, Huang SC, Barrio JR (2002) Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease. Am J Geriatr Psychiatry 10:24-35
30. Small GW, Kepe V, Ercoli LM, Siddarth P, Bookheimer SY, Miller KJ, Lavretsky H, Burggren AC, Cole GM, Vinters HV, Thompson PM, Huang SC, Satyamurthy N, Phelps ME, Barrio JR (2006) PET of brain amyloid and tau in mild cognitive impairment. N Engl J Med 355:2652-2663
31. 11C]SB-13 PET. Am J Geriatr Psychiatry 12:584-595
32. 18F-AV-45 (florbetapir F 18). J Nucl Med 51:913-920
33. 18F-labeled imidazo[2,1-b]benzothiazole (IBT) for high-contrast PET imaging of β-amyloid plaques. ACS Med Chem Lett 2(9):673-677
34. Zhuang ZP, Kung MP, Wilson A, Lee CW, Plössl K, Hou C, Holtzman DM, Kung HF (2003) Structure-activity relationship of imidazo[1,2-a]pyridines as ligands for detecting beta-amyloid plaques in the brain. J Med Chem 46:237-243