Citation: Hou Jing-Ru, Jin Di, Chen Bo, Si Lei-Lei, Jin Yue-Hua, Chen Li-Gong, Yan Xi-Long, Wang Bo-Wei, Li Yang. Two near-infrared highly sensitive cyanine fluorescent probes for pH monitoring[J]. Chinese Chemical Letters, ;2017, 28(8): 1681-1687. doi: 10.1016/j.cclet.2017.03.037 shu

Two near-infrared highly sensitive cyanine fluorescent probes for pH monitoring

Hou Jing-Ru ^a,b ,
Jin Di ^a,b ,
Chen Bo ^a,b ,
Si Lei-Lei ^a,b ,
Jin Yue-Hua ^c ,
Chen Li-Gong ^a,b,d ,
Yan Xi-Long ^a,b,d ,
Wang Bo-Wei ^a,b,*,, ,
Li Yang ^a,b,d,*,,

a.
School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China
b.
Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300350, China
c.
Tianjin Bohai Fine Chemical Co., Ltd., Tianjin 300300, China
d.
Tianjin Engineering Research Center of Functional Fine Chemicals, Tianjin 300350, China

Corresponding author: Wang Bo-Wei, bwwang@tju.edu.cn Li Yang, liyang777@tju.edu.cn

Received Date: 6 January 2017
Revised Date: 20 February 2017
Accepted Date: 26 March 2017
Available Online: 30 August 2017

Figures(9)

Two near-infrared (NIR) pH-activated heptamethine indocyanine probes with quaternary ammonium unit were designed and synthesized. The absorption and emission titrations indicate that cationic structure improves the cyanine dye's aqueous solubility and these two probes exhibit highly sensitive response to pH in acid condition. Their fluorescence intensities both gradually increase about 25-fold from pH 7.60 to 3.00 with pKa values of 4.72 and 4.45 respectively, which are suitable for studying acidic organelles in living cells. Moreover, their fluorescence intensities are linearly proportional to pH values in the range of 5.50-4.00. These results are probably attributed to the protonation of the indole nitrogen atoms, which are verified by 1H NMR spectra. Furthermore, these two probes can achieve real-time imaging of cellular pH and detection of pH in situ in living HeLa cells due to their excellent properties, including good reversibility, desirable photostability, high selectivity, low cytotoxicity and remarkable membrane permeability.
- pH fluorescent probe,
- Near-infrared,
- Indocyanine,
- Quaternary ammonium,
- Biological imaging
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