Citation: LIU Ping, HAN Xiao-Yue, YU Fa-Biao, CHEN Ling-Xin. A Near-Infrared Fluorescent Probe for Detection of Nitroxyl in Living Cells[J]. Chinese Journal of Analytical Chemistry, ;2015, 43(12): 1829-1836. doi: 10.11895/j.issn.0253-3820.150445 shu

A Near-Infrared Fluorescent Probe for Detection of Nitroxyl in Living Cells

LIU Ping ¹ ,
HAN Xiao-Yue ^1,2 ,
YU Fa-Biao ^1,, ,
CHEN Ling-Xin ^1,,

1.
¹ Key Laboratory of Coastal Environmental Processes and Ecological Remediation, The Research Centre for Coastal Environmental Engineering and Technology, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China;

Corresponding author: YU Fa-Biao, CHEN Ling-Xin,
Received Date: 28 May 2015
Available Online: 21 August 2015
Fund Project: 本文系国家自然科学基金资助项目(Nos.21405172,21575159,21275158) (Nos.21405172,21575159,21275158)中国科学院青年创新促进会(Grant2015170) (Grant2015170)

Nitroxyl(HNO), the one-electron reduced and protonated congener of nitric oxide(NO), has been demonstrated with excellent bio-pharmacological effects in cardiovascular disorder treatment, which is distinctive from that of NO. The high reactivity of HNO challenges the accurate detection. To resolve this problem, a near-infrared(NIR) metal-free fluorescent probe, ER-JN, was developed for the detection of intracellular HNO concentration in simulated physiological conditions and living cells. The probe was consisted of two moieties, the A BF2-chelated tetraarylazadipyrromethane fluorophore(aza-BODIPY) and the HNO recognition unit, diphenylphosphinobenzoyl group. The probe was purified by column chromatography on silica eluting with CH₂Cl₂ to give the product as a green solid with a yield of 28%. Our probe exhibited high sensitivity, good selectivity, and low cytotoxic effect, and could be applied to the fluorescent bio-imaging of HNO in simulated physiological conditions. When detected HNO, quantum yield increased from 0.01 to 0.35. The linear range located at 0-50μmol/L. The detection limit was 0.03μmol/L(S/N=3). With confocal laser scanning microscope imaging analysis, the probe could detect HNO concentration changes in living cells. Furthermore, the results of flow cytometry confirmed that our probe could be employed for the qualitative and quantitative detection of intracellular HNO concentration level. In this work, we found that probe ER-JN could not only detect HNO in aqueous and in living cells, but also targets endoplasmic reticulum. We anticipated that ER-JN would provide experimental bases in studying physiological and pathological functions of HNO in cells, in vitro and in vivo.
- Fluorescent probe,
- Nitroxyl,
- Cell analysis,
- Near-infrared bioimaging
1. [1]
  1 Irvine J C, Ritchie R H, Favaloro J L, Andrews K L, Widdop R E, Kemp-Harper B K. Trends Pharmacol. Sci., 2008, 29(12):601-608
2. [2]
  2 Paolocci N, Jackson M I, Lopez B E, Miranda K, Tocchetti C G, Wink D A, Hobbs A J, Fukuto J M. Pharmacol. Ther., 2007, 113(2):442-458
3. [3]
  3 Favaloro J L, Kemp-Harper B K. Cardiovasc. Res., 2007, 73(3):587-596
4. [4]
  4 Paolocci N, Saavedra W F, Miranda K M, Martignani C, Isoda T, Hare J M, Espey M G, Fukuto J M, Feelisch M, Wink D A. Proc. Natl. Acad. Sci. USA., 2001, 98(18):10463-10468
5. [5]
  5 Dutton A S, Fukuto J M, Houk K. J. Am. Chem. Soc., 2004, 126(12):3795-3800
6. [6]
  6 Malinski T, Taha Z. Nature, 1992, 358(6388):676-678
7. [7]
  7 Nagano T, Yoshimura T. Chem. Rev., 2002, 102(4):1235-1270
8. [8]
  8 Li X, Gao X, Shi W, Ma H. Chem. Rev., 2014, 114(1):590-596
9. [9]
  9 Wang R, Yu C, Yu F, Chen L. TrAC. Trends Anal. Chem., 2010, 29:1004-1013
10. [10]
  10 Wrobel A T, Johnstone T C, Deliz L A, Lippard S J, Rivera-Fuentes P. J. Am. Chem. Soc., 2014, 136(12):4697-4705
11. [11]
  11 McQuade L E, Lippard S J. Curr. Opin. Chem. Biol., 2010, 14(1):43-49
12. [12]
  12 Zhou Y, Liu K, Li J, Fang Y, Zhao T, Yao C. Org. Lett., 2011, 13(6):1290-1293
13. [13]
  13 Wang R, Yu F, Chen L, Chen H, Wang L, Zhang W. Chem. Commun., 2012, 48(96):11757-11759
14. [14]
  14 Wang R,Yu F, Liu, Chen L. Chem. Commun., 2012, 48(43):5310-5312
15. [15]
  15 JING Xiao-Tong, YU Fa-Biao, CHEN Ling-Xin. Process in Chemistry, 2014, 26(5):866-878 景晓彤, 于法标, 陈令新. 化学进展, 2014, 26(5):866-878
16. [16]
  16 GAO Min, YU Fa-Biao, CHEN Ling-Xin. Process in Chemistry, 2014, 26(6):1065-1078 高敏, 于法标, 陈令新. 化学进展, 2015, 87(7):3631-3638
17. [17]
  17 Wang R, Chen L, Liu P, Zhang Q, Wang Y Q. Chem. Eur. J., 2012, 18(36):11343-11349
18. [18]
  18 Gao M, Yu F, Chen H, Chen L. Anal. Chem., 2015, 87(7):3631-3638
19. [19]
  19 Gao M, Wang R, Yu F, You J, Chen L. Analyst, 2015, 140(11):3766-3772
20. [20]
  20 Jing X, Yu F, Chen L. Chem. Commun., 2014, 50(91):14253-14256
21. [21]
  21 Liu P, Jing X, Yu F, Lv C, Chen L. Analyst, 2015, 140(13):4576-4583
1. [1]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
2. [2]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
3. [3]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
4. [4]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
5. [5]
  Yang Wang , Yunpeng Fu , Xiaoji Liu , Guotao Zhang , Guobin Li , Wanqiang Liu , Jinglun Wang . Structural Analysis of Nitrile Solutions Based on Infrared Spectroscopy Probes. University Chemistry, 2025, 40(4): 367-374. doi: 10.12461/PKU.DXHX202406113
6. [6]
  Han ZHANG , Jianfeng SUN , Jinsheng LIANG . Hydrothermal synthesis and luminescent properties of broadband near-infrared Na₃CrF₆ phosphor. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 349-356. doi: 10.11862/CJIC.20240098
7. [7]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
8. [8]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
9. [9]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
10. [10]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
11. [11]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394
12. [12]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
13. [13]
  Jiahui CHEN , Tingting ZHENG , Xiuyun ZHANG , Wei LÜ . Research progress of near-infrared absorption inorganic nanomaterials in photothermal and photodynamic therapy of tumors. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2396-2414. doi: 10.11862/CJIC.20240106
14. [14]
  Mi Wen , Baoshuo Jia , Yongqi Chai , Tong Wang , Jianbo Liu , Hailong Wu . Improvement of Fluorescence Quantitative Analysis Experiment: Simultaneous Determination of Rhodamine 6G and Rhodamine 123 in Food Using Chemometrics-Assisted Three-Dimensional Fluorescence Method. University Chemistry, 2025, 40(4): 390-398. doi: 10.12461/PKU.DXHX202405147
15. [15]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
16. [16]
  Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235
17. [17]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
18. [18]
  Shuyu Liu , Xiaomin Sun , Bohan Song , Gaofeng Zeng , Bingbing Du , Chongshen Guo , Cong Wang , Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113
19. [19]
  Shipeng WANG , Shangyu XIE , Luxian LIANG , Xuehong WANG , Jie WEI , Deqiang WANG . Piezoelectric effect of Mn, Bi co-doped sodium niobate for promoting cell proliferation and bacteriostasis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1919-1931. doi: 10.11862/CJIC.20240094
20. [20]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(310)
HTML views(33)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142