Citation: GAO Man, HE Xin, CUI Jingnan, LIU Tao, TIAN Zhenhao, HE Shengui. A Coumarin-Based Fluorescent Probe for Rapid Detection of Endogenous Formaldehyde[J]. Chinese Journal of Applied Chemistry, ;2019, 36(9): 1053-1060. doi: 10.11944/j.issn.1000-0518.2019.09.190023 shu

A Coumarin-Based Fluorescent Probe for Rapid Detection of Endogenous Formaldehyde

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, Liaoning 116024, China

Corresponding author: CUI Jingnan, jncui@dlut.edu.cn
Received Date: 22 January 2019
Revised Date: 11 March 2019
Accepted Date: 23 April 2019

Fund Project: the National Natural Science Foundation of China 21572029Supported by the National Natural Science Foundation of China(No.21572029)

Figures(9)

A coumarin-based formaldehyde(FA) fluorescent probe Coun was designed and synthesized. The mechanism of this fluorescent probes for FA is based on blocking electron transfer between hydrazine and the dye upon FA nucleophilic addition. The results show that the optimal reaction time of Coun and FA is 4 min, which greatly improved the detection efficiency with detection limit of 5×10^-6 μmol/L. In addition, the probe has good cell membrane permeability, and can be used in the biological field to detect endogenous formaldehyde.
- fluorescent probe,
- formaldehyde,
- fast response,
- cell imaging
1. [1]
  HONG Jiamin. Summary of Research Progress on Hazards and Detection Methods of Formaldehyde Pollution[J]. Anhui J Prev Med, 2007,13(1):44-47.
2. [2]
  HUANG Zhongqian, LI Yanan, GAO Lixia. Research Progress on Formaldehyde Analysis Methods in Food[J]. J Food Saf Qual, 2015,6(12):4712-4718.
3. [3]
  LI Xinru. Talking about the Harm and Prevention of Indoor Formaldehyde Pollution[J]. J Jiaozuo Univ, 2017,31(4):83-84.
4. [4]
  SUN Zhaodong. Brief Introduction of the Harm of Formaldehyde and Its Prevention and Treatment Methods[J]. Technol Wind, 2014,14(161):194-200.
5. [5]
  TONG Zhiqian, WAN You, LUO Wenhong. Endogenous Formaldehyde and Its Related Major Human Diseases[J]. Prog Nat Sci, 2008,18(11):1201-1210. doi: 10.3321/j.issn:1002-008X.2008.11.001
6. [6]
  LONG Yunfei, ZHOU Liping, HAN Ming. Determination of Trace Formaldehyde Based on the Formation of Silver Nanoparticles[J]. Chinese J Appl Chem, 2009,26(11):1349-1352. doi: 10.3969/j.issn.1000-0518.2009.11.022
7. [7]
  YANG Lei, LIU Wenjie. Research and Development of Formaldehyde Detection Fluorescent Probe[J]. China Fiber Ins, 2018,20:77-79.
8. [8]
  Tang Y, Kong X, Xu A. Development of a Two-Photon Fluorescent Probe for Imaging of Endogenous Formaldehyde in Living Tissues[J]. Angew Chem, 2016,128:3417-3420. doi: 10.1002/ange.201510373
9. [9]
  Song H, Rajendiran S, Kim N. A Tailor Designed Fluorescent 'Turn-On' Sensor of Formaldehyde Based on the BODIPY Motif[J]. Tetrahedron Lett, 2012,53:4913-4916. doi: 10.1016/j.tetlet.2012.06.117
10. [10]
  Roth A, Li H, Anorma C. A Reaction-Based Fluorescent Probe for Imaging of Formaldehyde in Living Cells[J]. J Am Chem Soc, 2015,137(34):10890-10893. doi: 10.1021/jacs.5b05339
11. [11]
  Brewer T F, Chang C J. An Aza-Cope Reactivity-Based Fluorescent Probe for Imaging Formaldehyde in Living Cells[J]. J Am Chem Soc, 2015,137(34):10886-10889. doi: 10.1021/jacs.5b05340
12. [12]
  Xie Z, Ge J, Zhang H. A Highly Selective Two-Photon Fluorescence Probe for Formaldehyde and Its Bioimaging Application in Cells and Zebrafish[J]. Sens Actuators B:Chem, 2016,241:1050-1056.
13. [13]
  Chen L, Fu Y, Fang W. Screening of a Highly Effective Fluorescent Derivatization Reagent for Carbonyl Compounds and Its Application in HPLC with Fluorescence Detection[J]. Talanta, 2018,186:221-228. doi: 10.1016/j.talanta.2018.04.017
14. [14]
  Macmillan K S, Nguyen T, Hwang I. Total Synthesis and Evaluation of Iso-Duocarmycin SA and Iso-Yatakemycin[J]. J Am Chem Soc, 2009,131(3):1187-1194. doi: 10.1021/ja808108q
15. [15]
  YANG Chunhao, SHAO Jimin, ZHU Weiliang, et al. Substituted Amide Phenols and Their Preparation Methods, Pharmaceutical Compositions and Applications: CN, 105085433.A[P]. 2015-11-25(in Chinese).
16. [16]
  Wang P, Xia Y, Zou L. An Optimized Two-Photon Fluorescent Probe for Biological Sensing and Imaging of Catechol-O-Methyltransferase[J]. Chem Eur J, 2017,23(45):10800-10807. doi: 10.1002/chem.201701384
17. [17]
  Banerjee A, Panosian T D, Mukherjee K. Site-Specific Orthogonal Labeling of the Carboxy Terminus of α-Tubulin[J]. ACS Chem Biol, 2010,5(8):777-785. doi: 10.1021/cb100060v
18. [18]
  Okata H, Hatta W, Iijima K. Detection of Acetaldehyde in the Esophageal Tissue among Healthy Male Subjects after Ethanol Drinking and Subsequent L-Cysteine Intake[J]. Tohoku J Exp Med, 2018,244(4):317-325. doi: 10.1620/tjem.244.317
19. [19]
  Daniele D R, Amanda J S, Nicoletta P. A Review of Recent Studies on Malondialdehyde as Toxic Molecule and Biological Marker of Oxidative Stress[J]. Nutr Metab Cardiovasc Dis, 2005,15(4):316-328. doi: 10.1016/j.numecd.2005.05.003
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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  Di WU , Ruimeng SHI , Zhaoyang WANG , Yuehua SHI , Fan YANG , Leyong ZENG . Construction of pH/photothermal dual-responsive delivery nanosystem for combination therapy of drug-resistant bladder cancer cell. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1679-1688. doi: 10.11862/CJIC.20240135
11. [11]
  Yongmei Liu , Lisen Sun , Zhen Huang , Tao Tu . Curriculum-Based Ideological and Political Design for the Experiment of Methanol Oxidation to Formaldehyde Catalyzed by Electrolytic Silver. University Chemistry, 2024, 39(2): 67-71. doi: 10.3866/PKU.DXHX202308020
12. [12]
  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
13. [13]
  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
14. [14]
  Xiyuan Su , Zhenlin Hu , Ye Fan , Xianyuan Liu , Xianyong Lu . Change as You Want: Multi-Responsive Superhydrophobic Intelligent Actuation Material. University Chemistry, 2024, 39(5): 228-237. doi: 10.3866/PKU.DXHX202311059
15. [15]
  Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
16. [16]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
17. [17]
  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
18. [18]
  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
19. [19]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
20. [20]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(257)
HTML views(34)

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