2-Aminotryptanthrin derivative with pyrene as a FRET-based fluorescent chemosensor for Al3+.
1-(2-Tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for Al3+. Excited at 325 nm, corresponding to absorption of the pyrene unit of T2NH-P5P, emission at 600 nm from the 2-aminotryptanthrin unit has been observed, indicating that intramolecular fluorescence resonance energy transfer (FRET) occurs in T2NH-P5P. However, when Al3+ is added to a solution of T2NH-P5P, the fluorescence of 2-aminotryptanthrin is quenched (FRET-off), whereas that of the pyrene group is revived. Such a FRET "on-off" behavior of T2NH-P5P is not observed for other metal cations (Ca2+, Ba2+, and Zn2+).
Kawakami
Jun
J
Graduate School of Science and Technology, Hirosaki University, 3 Bunkyo-cho, Hirosaki, Aomori 036-8561, Japan. jun@cc.hirosaki-u.ac.jp
Kikuchi
Kenta
K
Chiba
Kazunori
K
Matsushima
Noriyuki
N
Yamaya
Asako
A
Ito
Shunji
S
Nagaki
Masahiko
M
Kitahara
Haruo
H
D000535:Aluminum / Q000032:analysis* / Q000737:chemistry; D002623:Chemistry Techniques, Analytical / Q000295:instrumentation*; D031541:Fluorescence Resonance Energy Transfer / Q000379:methods*; D011092:Polyethylene Glycols / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D011799:Quinazolines / Q000737:chemistry*
C547577:1-(2-tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane; D011721:Pyrenes; D011799:Quinazolines; C046243:tryptanthrine; D011092:Polyethylene Glycols; C030984:pyrene; D000535:Aluminum