Naphthol-based fluorescent sensors for aluminium ion and application to bioimaging.
Three naphthol Schiff base-type fluorescent sensors, 1,3-Bis(2-hydroxy-1-naphthylideneamino)propane (L1), 1,3-Bis(1-naphthylideneamino)-2-hydroxypropane (L2) and 1,3-Bis(2-hydroxy-1-naphthylideneamino)-2-hydroxypropane (L3), have been synthesized. Their recognition abilities for Al(3+) are studied by fluorescence spectra. Coordination with Al(3+) inhibited the CN isomerization of Schiff base which intensely increase the fluorescence of L1-L3. Possessing a suitable space coordination structure, L3 is a best selective probe for Al(3+) over other metal ions in MeOH-HEPES buffer (3/7, V/V, pH=6.6, 25°C, λem=435nm). A turn-on ratio over 140-fold is triggered with the addition of 1.0 equiv. Al(3+) to L3. The binding constant Ka of L3-Al(3+) is found to be 1.01×10(6.5)M(-1) in a 1:1 complex mode. The detection limit for Al(3+) is 0.05μM. Theoretical calculations have also been included in support of the configuration of the L3-Al(3+) complex. Importantly, the probe L3 has been successfully used for fluorescence imaging in colon cancer SW480 cells.
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China. Electronic address: liubin@sxu.edu.cn.
Bin
B
Liu
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China.
Pan-Feng
PF
Wang
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China.
Jie
J
Chai
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China.
Xiang-Quan
XQ
Hu
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China.
Tingting
T
Gao
Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China.
Jian-Bin
JB
Chao
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China.
Ting-Gui
TG
Chen
Institute of Molecular Science, Key Laboratory of Chemical Biology of Molecular Engineering of Education Ministry, Shanxi University, Taiyuan 030006, China. Electronic address: yangbs@sxu.edu.cn.
Bin-Sheng
BS
Yang
D000535:Aluminum / Q000032:analysis*; D002412:Cations / Q000032:analysis; D045744:Cell Line, Tumor; D003110:Colonic Neoplasms / Q000000981:diagnostic imaging; D005456:Fluorescent Dyes / Q000737:chemistry*; D006801:Humans; D007536:Isomerism; D008856:Microscopy, Fluorescence / Q000379:methods; D008958:Models, Molecular; D009284:Naphthols / Q000737:chemistry*; D061848:Optical Imaging / Q000379:methods*; D012545:Schiff Bases / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000379:methods
D002412:Cations; D005456:Fluorescent Dyes; D009284:Naphthols; D012545:Schiff Bases; D000535:Aluminum
Aluminium ion; CN isomerization; Cell imaging; Chemosensor; Fluorescence; Naphthol