Quinoline-based, glucose-pendant fluorescent zinc probes |
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Authors: | Yuji Mikata Anna Ugai Keiko Yasuda Saori Itami Satoshi Tamotsu Hideo Konno Satoshi Iwatsuki |
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Institution: | KYOUSEI Science Center, Nara Women's University, Nara 630-8506, Japan, (phone/fax: +81-742-20-3095). mikata@cc.nara-wu.ac.jp. |
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Abstract: | Quinoline-based tetradentate ligands with glucose pendants, N,N'-bis2-(β-d-glucopyranosyloxy)ethyl]-N,N'-bis(6-methoxyquinolin-2-yl)methyl]ethylenediamine (N,N'-6-MeOBQBGEN) and its N,N-counterpart, N,N-6-MeOBQBGEN, have been prepared, and their fluorescence-spectral changes upon Zn binding were investigated. Upon excitation at 336?nm, N,N'-6-MeOBQBGEN showed weak fluorescence (?≈ 0.016) in HEPES buffer (HEPES 50?mM, KCl 100?mM, pH?7.5). In the presence of Zn, N,N'-6-MeOBQBGEN exhibited a significant increase in fluorescence (?=0.096) at 414?nm. The fluorescence enhancement is specific for Zn and Cd (I(Cd) /I(Zn) of 50% at 414?nm). On the other hand, N,N-6-MeOBQBGEN exhibited a smaller fluorescence enhancement upon Zn complexation (?=0.043, λ(ex) =334?nm, λ(em) =407?nm) compared with N,N'-6-MeOBQBGEN. Fluorescence microscopic analysis using PC-12 rat adrenal cells revealed that N,N'-6-MeOBQBGEN exhibits a 1.8-fold higher fluorescence-signal response to Zn ion concentration compared with sugar-depleted compound 2 (N,N'-bis(6-methoxyquinolin-2-yl)methyl]ethylenediamine), due to its enhanced uptake into cells due to the targeting ability of the attached carbohydrates. |
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