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Quinoline‐Based, Glucose‐Pendant Fluorescent Zinc Probes
Author(s) -
Mikata Yuji,
Ugai Anna,
Yasuda Keiko,
Itami Saori,
Tamotsu Satoshi,
Konno Hideo,
Iwatsuki Satoshi
Publication year - 2012
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201100445
Subject(s) - fluorescence , chemistry , ethylenediamine , quinoline , hepes , zinc , nuclear chemistry , inorganic chemistry , organic chemistry , biochemistry , physics , quantum mechanics
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 m M , KCl 100 m M , 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 ( 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 ( ϕ =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.