title: 2-Aminotryptanthrin derivative with pyrene as a FRET-based fluorescent chemosensor for metal ions.
abstract: 1-(2-tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for metal ions. We investigated the metal-ion recognition of T2NH-P5P by separately adding Mg(2+), Ca(2+), Ba(2+), Fe(2+), Fe(3+), Co(2+), Ni(2+), Cu(2+), Ag(+), Zn(2+), Cd(2+), Hg(2+), Al(3+), and Pb(2+) in an acetonitrile solution. When using excitation at 325 nm, which corresponds to the absorption of the pyrene unit of T2NH-P5P, emission at 600 nm, from the 2-aminotryptanthrin unit, was observed, indicating that intramolecular fluorescence resonance energy transfer (FRET) occurs in T2NH-P5P (FRET-on). However, when Fe(2+), Fe(3+), Ni(2+), Cu(2+), Cd(2+), Hg(2+), and Al(3+) were added to an acetonitrile solution of T2NH-P5P, the behavior changed from FRET-on to FRET-off, which means that the fluorescence of 2-aminotryptanthrin was quenched, whereas that of the pyrene group was revived (FRET-off). Especially, this behavior was remarkable for Fe(2+), Fe(3+), Cu(2+), and Hg(2+). T2NH-P5P is suitable for use as a fluorescent chemosensor for Fe(2+), Fe(3+), Cu(2+), and Hg(2+).
authors.affiliation: Graduate School of Science and Technology, Hirosaki University.
authors.forename: Jun
authors.initials: J
authors.lastname: Kawakami
authors.forename: Arisa
authors.initials: A
authors.lastname: Soma
authors.forename: Kenta
authors.initials: K
authors.lastname: Kikuchi
authors.forename: Yoh
authors.initials: Y
authors.lastname: Kikuchi
authors.forename: Shunji
authors.initials: S
authors.lastname: Ito
authors.forename: Haruo
authors.initials: H
authors.lastname: Kitahara
mesh_terms: D002412:Cations / Q000032:analysis; D005453:Fluorescence; D031541:Fluorescence Resonance Energy Transfer / Q000379:methods*; D005456:Fluorescent Dyes / Q000737:chemistry; D008670:Metals / Q000032:analysis*; D011092:Polyethylene Glycols / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: C547577:1-(2-tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane; D002412:Cations; D005456:Fluorescent Dyes; D008670:Metals; D011721:Pyrenes; D011092:Polyethylene Glycols; C030984:pyrene