Compounds for imaging amyloid-β deposits in an Alzheimer’s brain: a patent review

Bibliography

• Alzheimer’s Association. 2014 Alzheimer’s disease facts and figures. Alzheimers Dement 2014;10(2):e47-92
   PubMed Web of Science ®Google Scholar
• Hardy J, Selkoe DJ. The amyloid hypothesis of Alzheimer’s disease: progress and problems on the road to therapeutics. Science 2002;297(5580):353-6
   PubMed Web of Science ®Google Scholar
• Selkoe DJ. Alzheimer’s disease: genes, proteins, and therapy. Physiol Rev 2001;81(2):741-66
   PubMed Web of Science ®Google Scholar
• Kung HF. The beta-amyloid hypothesis in Alzheimer’s disease: seeing is believing. ACS Med Chem Lett 2012;3(4):265-7
   PubMed Web of Science ®Google Scholar
• Jack CRJr, Knopman DS, Jagust WJ, et al. Tracking pathophysiological processes in Alzheimer’s disease: an updated hypothetical model of dynamic biomarkers. Lancet Neurol 2013;12(2):207-16
   PubMed Web of Science ®Google Scholar
• Syvanen S, Eriksson J. Advances in PET imaging of P-glycoprotein function at the blood-brain barrier. ACS Chem Neurosci 2013;4(2):225-37
   PubMed Web of Science ®Google Scholar
• Cui M. Past and recent progress of molecular imaging probes for beta-amyloid plaques in the brain. Curr Med Chem 2014;21(1):82-112
   PubMed Web of Science ®Google Scholar
• Higuchi M, Iwata N, Matsuba Y, et al. 19F and 1H MRI detection of amyloid beta plaques in vivo. Nat Neurosci 2005;8(4):527-33
   PubMed Web of Science ®Google Scholar
• Poduslo JF, Curran GL, Peterson JA, et al. Design and chemical synthesis of a magnetic resonance contrast agent with enhanced in vitro binding, high blood-brain barrier permeability, and in vivo targeting to Alzheimer’s disease amyloid plaques. Biochemistry 2004;43(20):6064-75
   PubMed Web of Science ®Google Scholar
• Wadghiri YZ, Sigurdsson EM, Sadowski M, et al. Detection of Alzheimer’s amyloid in transgenic mice using magnetic resonance microimaging. Magn Reson Med 2003;50(2):293-302
   PubMed Web of Science ®Google Scholar
• Zhu L, Ploessl K, Kung HF. PET/SPECT imaging agents for neurodegenerative diseases. Chem Soc Rev 2014;43(19):6683-91
   PubMed Web of Science ®Google Scholar
• Stuker F, Ripoll J, Rudin M. Fluorescence molecular tomography: principles and potential for pharmaceutical research. Pharmaceutics 2011;3(2):229-74
   PubMedGoogle Scholar
• Weissleder R. A clearer vision for in vivo imaging. Nat Biotechnol 2001;19(4):316-17
   PubMed Web of Science ®Google Scholar
• Haass C, Selkoe DJ. Soluble protein oligomers in neurodegeneration: lessons from the Alzheimer’s amyloid [beta]-peptide. Nat Rev Mol Cell Biol 2007;8(2):101-12
   PubMed Web of Science ®Google Scholar
• Zlokovic BV. Neurovascular mechanisms of Alzheimer’s neurodegeneration. Trends Neurosci 2005;28(4):202-8
   PubMed Web of Science ®Google Scholar
• Glabe CG. Conformation-dependent antibodies target diseases of protein misfolding. Trends Biochem Sci 2004;29(10):542-7
   PubMed Web of Science ®Google Scholar
• Hillen H, Barghorn S, Labkovsky B, et al. inventors Humanized antibodies which bind to amyloid β (aβ) (1-42) globulomer and uses thereof in the diagnosis and treatment of Alzheimer’s Disease and related conditions. WO150946A1; 2008
   Google Scholar
• Ewert S, Auf Der Maur A, Cattepoel S, Nitsch R. Inventors Humanized antibodies against β-amyloid peptides. WO033309A1; 2009
   Google Scholar
• Christensen S, Helboe L. Inventors Anti-pyroglutamated β-amyloid antibodies for diagnosis and therapy of cognitive and neurodegenerative disease. WO136552A1; 2012
   Google Scholar
• Duan DR, Moll JR, Rudolph A. Inventors Diagnosis and treatment of traumatic brain injury using fluorescence labeled probes for Aβ-protein determination. WO056958A2; 2011
   Google Scholar
• Dealwis C. inventor Pyro-glutamate-amyloid-beta targeting agents, particularly antibodies, for treating and diagnosing Alzheimer disease. WO129276A2; 2010
   Google Scholar
• Barghorn S, Ebert U, Hillen H, et al. Inventors Humanized antibodies to amyloid-beta (aβ) (20-42) globulomer and uses thereof in the diagnosis and treatment of Alzheimer’s Disease and related conditions. WO150949A1; 2008
   Google Scholar
• Poduslo JF, Wengenack TM, Curran GL. Inventors Methods for detecting plaques in vivo. WO074374A1; 2001
   Google Scholar
• Poduslo JF, Curran GL, Wengenack TM. Inventors Methods for detecting parenchymal plaques in vivo. US0022736A1; 2004
   Google Scholar
• Lieberburg I, Callaway J, Grundman M. Inventors Humanized anti-human β-amyloid peptide antibodies for treatment of amyloidogenic diseases. WO017467A1; 2009
   Google Scholar
• Poduslo JF, Curran GL. Inventors Treatment for central nervous system disorders with compositions containing amyloid-β polypeptides. WO020212A2; 2003
   Google Scholar
• Wu C, Scott J, Shea JE. Binding of Congo red to amyloid protofibrils of the Alzheimer Abeta(9-40) peptide probed by molecular dynamics simulations. Biophys J 2012;103(3):550-7
   PubMed Web of Science ®Google Scholar
• Roterman I, KrUl M, Nowak M, et al. Why Congo red binding is specific for amyloid proteins - model studies and a computer analysis approach. Med Sci Monit 2001;7(4):771-84
   PubMedGoogle Scholar
• Klunk WE, Debnath ML, Pettegrew JW. Development of small molecule probes for the beta-amyloid protein of Alzheimer’s disease. Neurobiol Aging 1994;15(6):691-8
   PubMed Web of Science ®Google Scholar
• Klunk WE, Debnath ML, Pettegrew JW. Chrysamine-G binding to Alzheimer and control brain: autopsy study of a new amyloid probe. Neurobiol Aging 1995;16(4):541-8
   PubMed Web of Science ®Google Scholar
• Klunk WE, Bacskai BJ, Mathis CA, et al. 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(9):797-805
   PubMed Web of Science ®Google Scholar
• Klunk WE, Pettegrew JW, Mathis CAJr. Inventors Alkyl, alkenyl and alkynyl chrysamine G derivatives for the antemortem diagnosis of Alzheimer’s disease and in vivo imaging and prevention of amyloid deposition. US6168776B1; 2001
   Google Scholar
• Klunk WE, Pettegrew JW, Mathis CAJr. Inventors Compounds for the antemortem diagnosis of Alzheimer’s disease and in vivo imaging and prevention of amyloid deposition. WO9924394A2; 1999
   Google Scholar
• Klunk WE, Pettegrew JW, Mathis CAJr. Inventors Alkyl, alkenyl and alkynyl Chrysamine G derivatives for the antemortem diagnosis of Alzheimer’s disease and in vivo imaging and prevention of amyloid deposition. WO9847969A1; 1998
   Google Scholar
• Goldstein LE, Smith FX, Sullivan KR, et al. Inventors Ophthalmic formulations of Chrysamine G derivative contrast agents for detecting amyloid-β plaques. WO144065A1; 2008
   Google Scholar
• LeVine Iii H. [18] Quantification of beta-sheet amyloid fibril structures with thioflavin T. In: Ronald W, editor. Methods in enzymology. Academic Press, New York; 1999. p. 274-84
   Google Scholar
• Wolfe LS, Calabrese MF, Nath A, et al. Protein-induced photophysical changes to the amyloid indicator dye thioflavin T. Proc Natl Acad Sci USA 2010;107(39):16863-8
   PubMed Web of Science ®Google Scholar
• Mathis CA, Mason NS, Lopresti BJ, Klunk WE. Development of positron emission tomography beta-amyloid plaque imaging agents. Semin Nucl Med 2012;42(6):423-32
   PubMed Web of Science ®Google Scholar
• Nyberg S, Jonhagen ME, Cselenyi Z, et al. Detection of amyloid in Alzheimer’s disease with positron emission tomography using [11C]AZD2184. Eur J Nucl Med Mol Imaging 2009;36(11):1859-63
   PubMed Web of Science ®Google Scholar
• Johnson AE, Jeppsson F, Sandell J, et al. AZD2184: a radioligand for sensitive detection of beta-amyloid deposits. J Neurochem 2009;108(5):1177-86
   PubMed Web of Science ®Google Scholar
• Kung HF, Kung M-P, Zhuang Z-P. Inventors Stilbene derivatives and their use for binding and imaging amyloid plaques. WO018070A1; 2003
   Google Scholar
• Yang F, Lim GP, Begum AN, et al. Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J Biol Chem 2005;280(7):5892-901
   PubMed Web of Science ®Google Scholar
• Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of curcumin: problems and promises. Mol Pharm 2007;4(6):807-18
   PubMed Web of Science ®Google Scholar
• Cui M, Ono M, Kimura H, et al. Synthesis and structure-affinity relationships of novel dibenzylideneacetone derivatives as probes for beta-amyloid plaques. J Med Chem 2011;54(7):2225-40
   PubMed Web of Science ®Google Scholar
• Ran C, Xu X, Raymond SB, et al. Design, synthesis, and testing of difluoroboron-derivatized curcumins as near-infrared probes for in vivo detection of amyloid-beta deposits. J Am Chem Soc 2009;131(42):15257-61
   PubMed Web of Science ®Google Scholar
• Zhang X, Tian Y, Yuan P, et al. A bifunctional curcumin analogue for two-photon imaging and inhibiting crosslinking of amyloid beta in Alzheimer’s disease. Chem Commun (Camb) 2014;50(78):11550-3
   PubMed Web of Science ®Google Scholar
• Zhang X, Tian Y, Li Z, et al. Design and synthesis of curcumin analogues for in vivo fluorescence imaging and inhibiting copper-induced cross-linking of amyloid beta species in Alzheimer’s disease. J Am Chem Soc 2013;135(44):16397-409
   PubMed Web of Science ®Google Scholar
• Ran C, Moore A. Inventors Methods and system for detecting soluble amyloid-β. WO014648A2; 2011
   Google Scholar
• Chongzhao R, Moore A. Inventors Difluoroboron curcumin derivatives for amyloid-β plaque imaging in Alzheimer’s disease diagnosis. WO017094A2; 2010
   Google Scholar
• Mukherjee J, Head E, Wang C, Patel PC. Inventors Beta-amyloid senile plaques and neurofibrillary tangle imaging agents comprising 11C or 18F label for diagnosing neurodegenerating. Alzheimer’s disease. US0004107A1; 2009
   Google Scholar
• Agdeppa ED, Kepe V, Liu J, et al. 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(24):RC189
   PubMed Web of Science ®Google Scholar
• Shoghi-Jadid K, Small GW, Agdeppa ED, et al. Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease. Am J Geriatr Psychiatry 2002;10(1):24-35
   PubMed Web of Science ®Google Scholar
• Small GW, Kepe V, Ercoli LM, et al. PET of brain amyloid and tau in mild cognitive impairment. N Engl J Med 2006;355(25):2652-63
   PubMed Web of Science ®Google Scholar
• Hotta N, Akanuma Y, Kawamori R, et al. Long-term clinical effects of epalrestat, an aldose reductase inhibitor, on diabetic peripheral neuropathy: the 3-year, multicenter, comparative Aldose Reductase Inhibitor-Diabetes Complications Trial. Diabetes Care 2006;29(7):1538-44
   PubMed Web of Science ®Google Scholar
• Bulic B, Pickhardt M, Khlistunova I, et al. Rhodanine-based tau aggregation inhibitors in cell models of tauopathy. Angew Chem Int Ed Engl 2007;46(48):9215-19
   PubMed Web of Science ®Google Scholar
• Ono M, Hayashi S, Matsumura K, et al. Rhodanine and thiohydantoin derivatives for detecting tau pathology in Alzheimer’s brains. ACS Chem Neurosci 2011;2(5):269-75
   PubMed Web of Science ®Google Scholar
• Augelli-Szafran CE, Glase SA, Walker LC, Yasunaga T. Inventors Rhodanine derivatives for use in a method of inhibiting amyloid protein aggregation and imaging amyloid deposits. WO076987A1; 2000
   Google Scholar
• Zanda M, Platt B, Greig IR, Calamai E. Inventors Preparation of 18F-labeled barbiturate compounds as positron emission imaging agents. WO038153A1; 2013
   Google Scholar
• Akhtari M. inventor Functionalized magnetic nanoparticles and use in imaging amyloid deposits and neurofibrillary tangles. WO145169A2; 2012
   Google Scholar
• Annapragada A, Eriksen JL, Tanifum EA, et al. Inventors Lipid-based nanoparticles comprising an amyloid-binding ligand for imaging and/or treatment of Alzheimer disease. WO139080A2; 2012
   Google Scholar
• Black KL, Ljubimova JY, Ljubimov AV, Holler E. Inventors Polymalic acid-based nanoconjugates and their preparation for contrast agent targeting and imaging. WO139030A1; 2012
   Google Scholar
• Klein WL, Krafft GA, Finch CE. Targeting small Abeta oligomers: the solution to an Alzheimer’s disease conundrum? Trends Neurosci 2001;24(4):219-24
   PubMed Web of Science ®Google Scholar
• Glabe CG. Common mechanisms of amyloid oligomer pathogenesis in degenerative disease. Neurobiol Aging 2006;27(4):570-5
   PubMed Web of Science ®Google Scholar
• Cole GM, Frautschy SA. Alzheimer’s amyloid story finds its star. Trends Mol Med 2006;12(9):395-6
   PubMed Web of Science ®Google Scholar
• Ferreira ST, Vieira MNN, De Felice FG. Soluble protein oligomers as emerging toxins in Alzheimer’s and other amyloid diseases. IUBMB Life 2007;59(4-5):332-45
   PubMed Web of Science ®Google Scholar
• Maezawa I, Hong HS, Liu R, et al. Congo red and thioflavin-T analogs detect Abeta oligomers. J Neurochem 2008;104(2):457-68
   PubMed Web of Science ®Google Scholar
• Reinke AA, Seh HY, Gestwicki JE. A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta. Bioorg Med Chem Lett 2009;19(17):4952-7
   PubMed Web of Science ®Google Scholar
• Montalto MC, Agdeppa ED, Siclovan TM, Williams AC. Inventors Compositions and methods for non-invasive imaging of soluble beta-amyloid. US0223909A1; 2004
   Google Scholar
• Siclovan TM, Montalto MC, Lam TCH, et al. Inventors Agents for imaging soluble a-beta. US0189967A1; 2007
   Google Scholar
• Arzel E, Swahn B-M, Wensbo D. Inventors Indole derivatives as Aβ-amyloid protein inhibitors and their preparation, pharmaceutical compositions and use in the treatment of Alzheimer’s diseases. WO108729A1; 2008
   Google Scholar
• Jeong JM, Lee DS, Chung J-K, Lee MC. Inventors Heterocyclic indene derivatives and their radioisotope labeled compounds for imaging beta-amyloid deposition. US0299041A1; 2008
   Google Scholar
• Klunk WE, Mathis CAJr, Wang Y. Inventors Preparation of radiolabeled and nonradiolabeled (benzothiazolyl)anilines as imaging agents for amyloid β in the detection of Alzheimer’s disease, Down’s syndrome, or apolipoprotein E4 homozygotes. WO083195A1; 2004
   Google Scholar
• Klunk WE, Mathis CAJr. Inventors Amyloid imaging as a surrogate marker for efficacy of anti-amyloid therapies. WO014381A2; 2006
   Google Scholar
• Cai L, Pike VW, Innis RB. Inventors (Aminophenyl)imidazo[1,2-a]pyridine derivatives useful as beta-amyloid PET imaging agents and their preparation. WO124345A2; 2007
   Google Scholar
• Wang Y, Wu C. Inventors Amyloid-imaging agents. US0123373A1; 2009
   Google Scholar
• Kim SE, Lee BC, Kim JS, Chun YS. Inventors Fluorinated benzothiazole derivatives, their preparation method and use as imaging agents for diagnosing Alzheimer’s disease. WO053218A1; 2010
   Google Scholar
• Kung H, Kung M-P, Zhuang Z-P. Inventors Amyloid plaque aggregation inhibitors and diagnostic imaging agents. WO085903A2; 2002
   Google Scholar
• Goodman MM, Zeng F. Inventors Alzheimer’s disease imaging agents. WO033080A2; 2007
   Google Scholar
• Arzel E, Swahn B-M, Wensbo D. Inventors Benzothiophene and benzofuran derivatives as Aβ-amyloid protein inhibitors and their preparation, pharmaceutical compositions and use in the treatment of Alzheimer’s diseases patent. WO108730A1; 2008
   Google Scholar
• Siclovan TM, Montalto MC, Fish KM, et al. Inventors Methods for imaging soluble A-Beta. US0140960A1; 2007
   Google Scholar
• Cashion DK, Chen G, Kasi D, et al. Inventors Preparation of aromatic and heteroaromatic derivatives as imaging agents for detecting neurological disorders. WO119565A1; 2011
   Google Scholar
• Hassfeld J, Roehn U, Friebe M, et al. Inventors Preparation of benzothiazolylamide derivatives for diagnostic imaging agents for detection of amyloid beta. WO066357A1; 2010
   Google Scholar
• Kolb HC, Walsh JC, Zhang W, et al. Inventors Heterocyclic compounds as imaging agents useful for identifying AD pathology and their preparation. WO011964A2; 2010
   Google Scholar
• Edin M, Malmstroem J, Pyring D, et al. Inventors Novel heteroaryl substituted imidazo[1,2-a]pyridine derivatives as amyloid deposit imaging agents and their preparation and use in the diagnosis and treatment of Alzheimer’s diseases. WO091195A1; 2008
   Google Scholar
• Barta NS, Bigge CF. Inventors Method of inhibiting amyloid protein aggregation and imaging amyloid deposits using aminoindane derivatives. WO083425A1; 2001
   Google Scholar
• Augelli-Szafran CE, Lai Y, Sakkab AT, Walker LC. Inventors Method of inhibiting amyloid protein aggregation, treating Alzheimer’s disease, and imaging amyloid deposits using isoindoline derivatives. WO076969A1; 2000
   Google Scholar
• Mukherjee J, Pan M-L. Inventors Beta-amyloid plaque imaging agents. US0315826A1; 2013
   Google Scholar
• Olbrich C, Krause M, Burkhard A. Inventors Formulations suitable for PET imaging with hydrophobic PET agents. WO076825A1; 2011
   Google Scholar
• Berndt M, Friebe M, Hultsch C, et al. Inventors Method for production of F-18 labeled amyloid beta ligands. WO151273A1; 2011
   Google Scholar
• Berndt M, Brockschnieder D, Heinrich T, Berger M. Inventors Fluoro(styryl)pyridine derivatives as β-amyloid imaging agent and their preparation and use for diagnosing Alzheimer’s disease. WO141515A1; 2011
   Google Scholar
• Smith TAD, Schweiger LF. Inventors Preparation of [11C]methoxy-radiolabeled 2,3’,4,5’-tetramethylstilbene (TMS) and its medical use. WO2009001046A2; 2008
   Google Scholar
• Olbrich C, Krause M, Burkhard A, et al. Inventors Formulations of fluorinated stilbene suitable for pet imaging. WO175641A1; 2012
   Google Scholar
• Jeong JM, Lee DS, Chung J-K, Lee MC. Inventors Benzylideneaniline derivatives and their radioisotope labeled compounds for binding and imaging of beta-amyloid plaques. US0122341A1; 2007
   Google Scholar
• Kung HF, Kung MP. Inventors Acetylene derivatives and their use for binding and imaging amyloid plaques. US0166299A1; 2008
   Google Scholar
• Kung HF, Kung MP. Inventors Acetylene derivatives and their use for binding and imaging amyloid plaques. WO073350A2; 2008
   Google Scholar