Quinoline‐Based, Glucose‐Pendant Fluorescent Zinc Probes

Quinoline‐based tetradentate ligands with glucose pendants, N,N′‐bis[2‐(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 (ϕ≈ 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 (ϕ=0.096) at 414 nm. The fluorescence enhancement is specific for Zn and Cd (ICd/IZn of 50% at 414 nm). On the other hand, N,N‐6‐MeOBQBGEN exhibited a smaller fluorescence enhancement upon Zn complexation (ϕ=0.043, λex=334 nm, λem=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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