水溶性荧光探针的合成及对亚硫酸氢根和pH值的双重检测

引用本文: 戚少龙, 杜建时, 李容杭, 李强, 祝录宝, 时亚男, 王欣宇, 杨清彪, 张桂荣, 李耀先. 水溶性荧光探针的合成及对亚硫酸氢根和pH值的双重检测[J]. 分析化学, 2020, 48(3): 347-354. doi: 10.19756/j.issn.0253-3820.191609 shu

Citation: QI Shao-Long, DU Jian-Shi, LI Rong-Hang, LI Qiang, ZHU Lu-Bao, SHI Ya-Nan, WANG Xin-Yu, YANG Qing-Biao, ZHANG Gui-Rong, LI Yao-Xian. Synthesis of Water-soluble Fluorescent Probe for Dual Detection of HSO₃^- and pH Value[J]. Chinese Journal of Analytical Chemistry, 2020, 48(3): 347-354. doi: 10.19756/j.issn.0253-3820.191609 shu

水溶性荧光探针的合成及对亚硫酸氢根和pH值的双重检测

戚少龙 ^1, ,
杜建时 ^1, ,
李容杭 ^4, ,
李强 ^2, ,
祝录宝 ^2, ,
时亚男 ^3, ,
王欣宇 ^1, ,
杨清彪 ^2, ,
张桂荣 ^3, ,
李耀先 ^2,

1.
吉林大学中日联谊医院, 吉林省淋巴外科重点实验室, 吉林省淋巴外科工程实验室, 长春 130031;
2.
吉林大学化学学院, 长春 130061;
3.
吉林大学生命科学学院, 长春 130061;
4.
吉林大学第二医院, 长春 130041
基金项目:
本文系国家自然科学基金项目（No.21174052）、吉林省科技厅重点项目（No.20180201085GX）和吉林省省级产业创新专项资金项目（No.2018C052-5）资助

摘要: 以吲哚磺酸盐与不同结构的芳香醛为原料，合成了检测HSO₃^-的3种新型荧光探针ISBD、ISPD和ISND，并对筛选出的性能更优的双功能（HSO₃^-/pH）荧光探针ISND进行深入研究。检测可在1 min内快速完成，检出限为8.11×10^-8 mol/L。干扰实验结果表明，包括F^-、Cl^-、Br^-、I^-、NO₃^-、HCO₃^-、S^2-、SCN^-、ClO^-、NO₂^-、C₂O₄^2-、OAc^-、N₃^-、Cys、Hcy、GSH和CN^-在内的17种干扰物质对HSO₃^-的检测基本没有影响。同时，探针ISND具有细胞毒性低、细胞膜通透性好等优点，可实现对细胞内HSO₃^-的检测及成像。同ISBD相比，当芳香醛中引入羟基后，探针ISPD和ISND能够通过两个不同的发射波长完成对HSO₃^-（ISPD为385 nm，ISND为458 nm）以及pH值（ISPD为560 nm，ISND为565 nm）的差异性双重检测，在传感分析、生物信号传导及检测方面具有良好的应用前景。

关键词:

English

Synthesis of Water-soluble Fluorescent Probe for Dual Detection of HSO₃^- and pH Value

1.
China-Japan Union Hospital of Jilin University, Key Laboratory of Lymphatic Surgery Jilin Province, Engineering Laboratory of Lymphatic Surgery Jilin Province, Changchun 130031, China;
2.
College of Chemistry, Jilin University, Changchun 130061, China;
3.
School of Life Sciences, Jilin University, Changchun 130061, China;
4.
The Second Hospital of Jilin University, Changchun 130041, China
Received Date: 16 October 2019
Revised Date: 20 December 2019
Fund Project:
This work was supported by the National Natural Science Foundation of China (No.21174052), the Key Projects of Jilin Province Science and Technology Department, China (No.20180201085GX) and the Provincial Industrial Innovation Special Fund Project of Jilin Province, China (No.2018C052-5).

Abstract: Three new fluorescent probes (ISBD, ISPD and ISND) were designed and synthesized. The UV-visible absorption spectrum, fluorescence spectrum, and response to pH values of the probe were studied, and the HSO₃^-/pH dual detection fluorescent probe ISND with stronger fluorescence intensity (higher fluorescence quantum yield), longer emission wavelength and less interference was selected for the further study. The probe ISND could be used for the sensitive and specific detection of HSO₃^-, with a detection limit of 8.11×10^-8 mol/L (λ_em=458 nm, response time <1 min). In addition, with different emission wavelength (λ_em=565 nm), the probe could accurately detect pH value. Furthermore, the probe ISND had many advantages such as low toxicity and good membrane permeability. It could achieve fluorescence imaging of HSO₃^- in living cell, and exhibited good application prospects in sensing, biological signal transduction and detection.

Key words:

1. [1]
  Ranguelova K, Rice A B, Lardinois O M, Triquigneaux M, Steinckwich N, Eterding L J D, Garantziotis S, Mason R P. Free Radic. Biol. Med.,2013,60:98-106
2. [2]
  Jiang X M, Xu J C, Zhang Y L, Wang H Y, Zeng L T, Zhang Y. Anal. Methods,2016,8(7):1572-1576
3. [3]
  Luo L M, Chen S, Jin H F, Tang C S, Du J B. Biochem. Biophys. Res. Commun.,2011,415(1):61-67
4. [4]
  BAI Jian-Ying. Journal of Environmental and Occupational Medicine,2007,(4):431-434 白剑英.环境与职业医学, 2007,(4):431-434
5. [5]
  Segundo M A, Rangel A O S S, Cladera A. Cerdà V. Analyst,2000,125(8):1501-1505
6. [6]
  Geetha K, Balasubramanian N. Microchem. J.,2000,65(1):45-49
7. [7]
  Cardwell T J, Christophersen M J. Anal. Chim. Acta,2000,416(1):105-110
8. [8]
  Miura Y, Hatakeyama M, Hosino T, Haddad P R. J. Chromatogr.,2002,956(1-2):77-84
9. [9]
  Zhu H, Fan J, Xu Q, Li H, Wang J, Gao P, Peng X. Chem. Commun., 2012,48:11766-11758
10. [10]
  Fan L, Fu Y J, Liu Q L, Lu D T, Dong C, Shuang S M. Chem. Commun., 2012,48(91):11202-11204
11. [11]
  Sun Y, Fan S W, Zhang S, Zhao D, Duan L, Li R F. Sens. Actuators B,2014,193:173-177
12. [12]
  Zhang Q, Zhang Y, Ding S S, Zhang H Y, Feng G Q. Sens. Actuators B,2015,211:377-384
13. [13]
  WANG Jin-Jin, QI Shao-Long, DU Jian-Shi, YANG Qing-Biao, SONG Yan, LI Yao-Xian. Chem. J. Chinese Universities,2019,40(7):1397-1404 王金金, 戚少龙, 杜建时, 杨清彪, 宋岩, 李耀先.高等学校化学学报, 2019,40(7):1397-1404
14. [14]
  Zhu L B, Nie J J, Li Q, Du J S, Fan X W, Bai F Q, Yang Q B, Shan Y M, Li Y X. J. Lumin.,2019,215(7):116620
15. [15]
  Liu X D, Xu Y, Sun R, Xu Y J, Lu J M, Ge J F. Analyst, 2013,138(21):6542-6550
16. [16]
  Tang B, Yu F, Li P, Tong L L, Duan X, Xie T, Wang X. J. Am. Chem. Soc.,2009,131(8):3016-3023
17. [17]
  Deniz E, Isbasar G C, Bozdemir Ö A, Yildirim L T, Siemiarczuk A E, Akkaya U. Org. Lett.,2008,10(16):3401-3403
18. [18]
  Miao J T, Fan C, Shi X Y, Sun R, Xu Y J, Ge J F. Analyst,2014,139(23):6290-6297

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沈阳化工大学材料科学与工程学院沈阳 110142

水溶性荧光探针的合成及对亚硫酸氢根和pH值的双重检测

English

Synthesis of Water-soluble Fluorescent Probe for Dual Detection of HSO₃^- and pH Value

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中国化学会秘书处

水溶性荧光探针的合成及对亚硫酸氢根和pH值的双重检测

English

Synthesis of Water-soluble Fluorescent Probe for Dual Detection of HSO3- and pH Value

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CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

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