Development of an oxidative dehydrogenation-based fluorescent probe for Cu2+ and its biological imaging in living cells.
Based on a boron dipyrromethene (BODIPY) derivative containing an N, O and S tridentate ligand, a Cu(2+) fluorescent probe BTCu was developed. The detection mechanism was verified as Cu(2+)-promoted oxidative dehydrogenation of an amine moiety, leading to a formation of a fluorescent Cu(+)-Schiff base complex. Free BTCu exhibited a maximum absorption wavelength at 496 nm, and a very weak maximum emission at 511 nm. Upon addition of various metals ions, it showed large fluorescence enhancement toward Cu(2+) (417-fold in MeCN and 103-fold in MeCN/HEPES solution, respectively) with high selectivity. The detection limits are as low as 1.74×10(-8) M and 4.96×10(-8) M in the two different solutions, respectively. And BTCu could work in a wide pH range with an extraordinary low pK(a) of 1.21±0.06. Using fluorescence microscopy, the probe was shown to be capable of penetrating into living cells and imaging intracellular Cu(2+) changes.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, No. 2 Linggong Road, High-tech District, Dalian 116024, China. fanjl@dlut.edu.cn
Jiangli
J
Fan
Xiaojian
X
Liu
Mingming
M
Hu
Hao
H
Zhu
Fengling
F
Song
Xiaojun
X
Peng
D001896:Boron Compounds / Q000737:chemistry*; D002413:Cations, Divalent / Q000032:analysis; D003300:Copper / Q000032:analysis*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D042541:Intracellular Space / Q000737:chemistry*; D057230:Limit of Detection; D008856:Microscopy, Fluorescence / Q000379:methods*; D010084:Oxidation-Reduction; D012545:Schiff Bases / Q000737:chemistry; D013050:Spectrometry, Fluorescence / Q000379:methods
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D002413:Cations, Divalent; D005456:Fluorescent Dyes; D012545:Schiff Bases; D003300:Copper