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Structure−Activity Relationship of Imidazo[1,2-a]pyridines as Ligands for Detecting β-Amyloid Plaques in the Brain

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Departments of Radiology and Pharmacology, University of Pennsylvania, 3700 Market Street, Room 305, Philadelphia, Pennsylvania 19104, Department of Psychiatry, University of Toronto, PET Centre, Centre for Addiction and Mental Health, 250 College Street, Toronto, Ontario, Canada M5T 1R8, and Departments of Neurology, Molecular Biology and Pharmacology, Washington University, St. Louis, Missouri 63110
Cite this: J. Med. Chem. 2003, 46, 2, 237–243
Publication Date (Web):December 18, 2002
https://doi.org/10.1021/jm020351j
Copyright © 2003 American Chemical Society
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    Abstract

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    A series of novel β-amyloid (Aβ) aggregate-specific ligands, 2-(4‘-dimethylaminophenyl)-6-iodoimidazo[1,2-a]pyridine, 16(IMPY), and its related derivatives were prepared. An in vitro binding study with preformed Aβ aggregates showed that 16(IMPY) and its bromo derivative competed with binding of 2-(4‘-dimethylaminophenyl)-6-iodobenzothiazole, [125I]7(TZDM), a known ligand for Aβ aggregates, with high binding affinities (Ki = 15 and 10 nM, respectively). In vitro autoradiography of brain sections of a transgenic mouse (Tg2576) with [125I]16(IMPY) displayed high selective binding to amyloid-like structures, comparable to that observed by staining with thioflavin-S visualized under fluorescence. In vivo biodistribution after an intravenous injection of [125I]16(IMPY) in normal mice showed a high initial brain uptake and fast washout, indicating a low background activity associated with this iodinated ligand. Taken together, the data suggests that [123I]16(IMPY) may be useful for imaging Aβ aggregates in patients with Alzheimer's disease.

    †

     Department of Radiology, University of Pennsylvania.

    §

     University of Toronto.

    ⊥

     Washington University.

    *

     To whom correspondence should be addressed. Tel.:  (215) 662-3096. Fax:  (215) 349-5035. E-mail:  [email protected].

    ‡

     Department of Pharmacology, University of Pennsylvania.

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