A naphthalene-based fluorescent probe with a large Stokes shift for mitochondrial pH imaging

被引：35
|
作者：
Lin, Bo [1 ]
Fan, Li [2 ]
Ge, Jinyin [1 ]
Zhang, Wenjia [1 ]
Zhang, Caihong [1 ]
Dong, Chuan [2 ]
Shuang, Shaomin [1 ]
机构：
[1] Shanxi Univ, Coll Chem & Chem Engn, Taiyuan 030006, Shanxi, Peoples R China
[2] Shanxi Univ, Inst Environm Sci, Taiyuan 030006, Shanxi, Peoples R China
来源：
ANALYST | 2018年 / 143卷 / 20期
基金：
中国国家自然科学基金;
关键词：
LIVING CELLS; RATIOMETRIC DETECTION; CARDIAC MITOCHONDRIA; HYDROGEN-SULFIDE; PROTEIN MUTANT; BETA-CELLS; TISSUES; ACIDIFICATION; TRANSPORT; CALCIUM;
D O I：
10.1039/c8an01371c
中图分类号：
O65 [分析化学];
学科分类号：
070302 ; 081704 ;
摘要：
A mitochondrial-targeted pH fluorescent probe 4-(2-(6-hydroxynaphthalen-2-yl)vinyl)-1-methylpyridin-1-ium was facilely synthesized via the carbon-carbon double bond bridging of 6-hydroxy-2-naphthaldehyde and 1,4-dimethylpyridinium iodide salt. The probe exhibited remarkable pH-dependent behavior in the linear range of 7.60-10.00, with a pK(a) value of 8.85 +/- 0.04 near mitochondrial pH. A significantly large Stokes shift of 196 nm was obtained, which reduces the interference of excitation light. Application of the probe in live HepG2 cells indicated that the probe had excellent mitochondrial targeting ability and was successfully used to visualize mitochondrial pH fluctuations in live cells.
引用
收藏
页码：5054 / 5060
页数：7
相关论文
共 50 条
  • [1] Chiral-aminoquinoline-based fluorescent pH probe with large stokes shift for bioimaging
    Xie, Yong-Sheng
    Zhang, Xin-Ling
    Xie, Kun
    Zhao, Yanmei
    Wu, Huan
    Yang, Jidong
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2017, 179 : 51 - 57
  • [2] A naphthalene-based fluorescent probe for ratiometric imaging of lysosomal hydrogen sulfide in living cells
    Gao, Cai
    Liu, Xianjun
    Chen, Wen
    Wang, Fenglin
    Jiang, Jian-Hui
    METHODS AND APPLICATIONS IN FLUORESCENCE, 2019, 7 (01):
  • [3] A red-emitting fluorescent probe for imaging hydrogen sulphide with a large Stokes shift
    Chen, Song
    Hou, Peng
    Song, Xiangzhi
    SENSORS AND ACTUATORS B-CHEMICAL, 2015, 221 : 951 - 955
  • [4] A novel imidazo[1,5-α]pyridine-based fluorescent probe with a large Stokes shift for imaging hydrogen sulfide
    Chen, Song
    Li, Hongmei
    Hou, Peng
    SENSORS AND ACTUATORS B-CHEMICAL, 2018, 256 : 1086 - 1092
  • [5] A highly sensitive fluorescent probe based on the Michael addition mechanism with a large Stokes shift for cellular thiols imaging
    Chen, Song
    Hou, Peng
    Wang, Jing
    Fu, Shuang
    Liu, Lei
    ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2018, 410 (18) : 4323 - 4330
  • [6] A rapid and selective fluorescent probe with a large Stokes shift for the detection of hydrogen sulfide
    Chen, Song
    Hou, Peng
    Wang, Jing
    Fu, Shuang
    Liu, Lei
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2018, 203 : 258 - 262
  • [7] A colorimetric and ratiometric fluorescent probe with a large stokes shift for detection of hydrogen sulfide
    Xiang, Kaiqiang
    Liu, Yunchang
    Li, Changjiang
    Tian, Baozhu
    Tong, Tianzhong
    Zhang, Jinlong
    DYES AND PIGMENTS, 2015, 123 : 78 - 84
  • [8] A pyrene-based colorimetric and fluorescent pH probe with large stokes shift and its application in bioimaging
    Chao, Jianbin
    Song, Kailun
    Zhang, Yongbin
    Yin, Caixia
    Huo, Fangjun
    Wang, Juanjuan
    Zhang, Ting
    TALANTA, 2018, 189 : 150 - 156
  • [9] A novel fluorescent probe with a large stokes shift for cysteine based on dicyanoisophorone
    Hou, Jiaqi
    Cai, Pengfei
    Wang, Chengyun
    Shen, Yongjia
    TETRAHEDRON LETTERS, 2018, 59 (26) : 2581 - 2585
  • [10] Rational development of an ESIPT-based fluorescent probe with large Stokes shift for imaging of hydrogen sulfide in live cells
    Du, Yuting
    Wang, Hongliang
    Qin, Lu
    Zhao, Miao
    Pan, Caixia
    BIOORGANIC CHEMISTRY, 2022, 129
12345