Fluoro-substituted and 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques.
Two styrylbenzene derivatives, (E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (FSB) and (E,E)-1-bromo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene-alpha,alpha'-(13)C(2) ([(13)C]BSB), were synthesized for use as a histochemical stain to detect amyloid plaques of Alzheimer's disease (AD) brain sections. An analysis of fluorescence spectra demonstrated that FSB shows approximately twofold fluorescence intensity relative to the conventional styrylbenzene derivative, (E,E)-1-bromo-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (BSB). Moreover, FSB was found to stain amyloid plaques and neurofibrillary tangles of AD brains with greater fluorescence intensity and a lower level of background signals compared to BSB. These finding indicate that FSB can be an excellent fluorescent compound to label human amyloid lesions with high sensitivity and specificity. Because of the possession of a nuclide with a quantized angular momentum, both FSB and [(13)C]BSB are also potential contrast agents for magnetic resonance imaging to locate AD pathologies in vivo.
Sato
Kumi
K
Dojindo Laboratories, Tabaru 2025-5, Mashiki-machi, Kumamoto 861-2202, Japan.
Higuchi
Makoto
M
Iwata
Nobuhisa
N
Saido
Takaomi C
TC
Sasamoto
Kazumi
K
D000544:Alzheimer Disease / Q000000981:diagnostic imaging*; D001921:Brain / Q000000981:diagnostic imaging*; D003287:Contrast Media / Q000138:chemical synthesis* / Q000737:chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D008279:Magnetic Resonance Imaging; D058225:Plaque, Amyloid / Q000378:metabolism*; D011859:Radiography; D013329:Structure-Activity Relationship; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry
C496441:(E,E)-1-bromo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene-alpha alpha'-(13)C(2); C496440:(E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene; D003287:Contrast Media; D005456:Fluorescent Dyes; D013343:Styrenes