title: Quinoline-based, glucose-pendant fluorescent zinc probes.
abstract: 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 (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.
authors.affiliation: KYOUSEI Science Center, Nara Women's University, Nara 630-8506, Japan. mikata@cc.nara-wu.ac.jp
authors.forename: Yuji
authors.initials: Y
authors.lastname: Mikata
authors.forename: Anna
authors.initials: A
authors.lastname: Ugai
authors.forename: Keiko
authors.initials: K
authors.lastname: Yasuda
authors.forename: Saori
authors.initials: S
authors.lastname: Itami
authors.forename: Satoshi
authors.initials: S
authors.lastname: Tamotsu
authors.forename: Hideo
authors.initials: H
authors.lastname: Konno
authors.forename: Satoshi
authors.initials: S
authors.lastname: Iwatsuki
mesh_terms: D000818:Animals; D001692:Biological Transport / Q000187:drug effects; D002460:Cell Line; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000493:pharmacokinetics / Q000494:pharmacology; D005947:Glucose / Q000737:chemistry* / Q000493:pharmacokinetics; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry* / Q000493:pharmacokinetics; D051381:Rats; D015032:Zinc / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D011804:Quinolines; C037219:quinoline; D005947:Glucose; D015032:Zinc