Citation: MIN Pan, ZHENG De-Ze, CHE Wan-Meng, XING Yue, WU Jing. Design and Synthesis of A β-Diketonate-Europium(Ⅲ) Complex-based Fluorescent Probe for Nitric Oxide Detection and Its Application in Bioimaging[J]. Chinese Journal of Analytical Chemistry, ;2021, 49(10): 1704-1712. doi: 10.19756/j.issn.0253-3820.211233 shu

Design and Synthesis of A β-Diketonate-Europium(Ⅲ) Complex-based Fluorescent Probe for Nitric Oxide Detection and Its Application in Bioimaging

School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China

Corresponding author: WU Jing, wujing@lnnu.edu.cn
Received Date: 19 March 2021
Revised Date: 3 August 2021

Fund Project: Supported by the Undergraduate Training Programs for Innovation and Entrepreneurship of Liaoning Province (No.201910165118).

By using NO-recognizable o-diaminophenyl-substituted terpyridine derivative ligand 4-(4-[(2,2':6',2″-terpyridin)-4'-yl]phenoxy)benzene-1,2-diamine (TPBD) as the ligand, and β-diketone 6-(1',1″-diphenyl-4'-yl)-1,1,1,2,2,3,3-heptafluoro-4,6-hexanedione (DHH) as the coligand, a new β-diketonate-Eu³⁺ complex-based fluorescent probe,[Eu(DHH)₃(TPBD)], was designed and synthesized for detection of NO, and its structure was characterized by mass spectrum and elemental analysis methods. The spectral results indicated that the probe[Eu(DHH)₃(TPBD)] had only weak fluorescence, and its fluorescence intensity was increased by nearly 10 times after reacting with NO. The probe could be used to quantitatively detect NO at concentrations ranging from 0.017-0.83 μmol/L with a detection limit of 7.4 nmol/L. Meanwhile,[Eu(DHH)₃(TPBD)] showed approximately no response to other common reactive oxygen/nitrogen species, which demonstrated the good NO sensitivity of the probe. The fluorescence imaging experiments proved that the probe[Eu(DHH)₃(TPBD)] had low cytotoxicity and mitochondria targetability, and was successfully applied to the time-gated fluorescence imaging of NO in living cells and zebrafish.
- Europium(Ⅲ) complex,
- Nitric oxide,
- Fluorescent probe,
- Time-gated fluorescence imaging
1. [1]
  SNYDERS H. J. Science, 1992, 257(5069):494-496.
2. [2]
  JASID S, SIMONTACCHI M, BARTOLI C G, PUNTARULO S. Plant Physiol., 2006, 142(3):1246-1255.
3. [3]
  MONCADA S, HIGGS A N. J. N. Engl. J. Med., 1993, 329(27):2002-2012.
4. [4]
  ESCH T, STEFANO G B, FRICCHIONE G L, BENSON H. J. Med. Sci. Monit., 2002, 8(6):103-118.
5. [5]
  MIYASAKA N, HIRATA Y. J. Cell. Mol. Life Sci., 1997, 61(21):2073-2081.
6. [6]
  NUSSLER A K, BILLIAR T R. J. Leukocyte Biol., 1993, 54(2):171-178.
7. [7]
  PACHER P, BECKMAN J S, LIAUDET L. J. Physiol. Rev., 2007, 87(1):315-424.
8. [8]
  YOSHIMURA T, YOKOYAMA H, FUJII S, TAKAYAMA F, OIKAWA K, KAMADA H. J. Nat. Biotechnol., 1996, 14(8):992-994.
9. [9]
  HOFSETH L J, HUSSAIN S P, WOGAN G N, HARRIS C C. J. Free Radic. Biol. Med., 2003, 34(8):955-968.
10. [10]
  CALS-GRIERSON M M, ORMEROD A D. Nitric Oxide-Biol. Chem., 2004, 10(4):179-193.
11. [11]
  MONCADA S, PALMER R M, HIGGS E A. J. Pharmacol. Rev., 1991, 43(2):109-142.
12. [12]
  MOROZ L L, DAHLGREN R L, BOUDKO D, SWEEDLER J V, LOVELL P. J. Inorg. Biochem., 2005, 99(4):929-939.
13. [13]
  LI R F, QI H, MA Y, DENG Y P, LIU S N, JIE Y S, JING J Z, HE J L, ZHANG X, WHEATLY L, HUANG C X, SHENG X, ZHANG M L, YIN L. Nat. Commun., 2020, 11:3027.
14. [14]
  LI H, HAO Y H, FENG W, SONG Q H. J. Mater. Chem. B, 2020, 8(42):9785-9793.
15. [15]
  CHEN Y. Nitric Oxide-Biol. Chem., 2020, 98:1-19.
16. [16]
  KUMAR P, KALITA A, MONDAL B. J. Dalton Trans., 2011, 40(34):8656-8663.
17. [17]
  FRANZ K J, SINGH N, SPINGLER B, LIPPARD S J. J. Inorg. Chem. Front., 2000, 39(18):4081-4092.
18. [18]
  YAO H W, GUO X F, WANG H. Anal. Chem., 2020, 92(17):11904-11911.
19. [19]
  SETSUKINAI K, URANO Y, KAKINUMA K, MAJIMA H J, NAGANO T. J. Biol. Chem., 2003, 278(5):3170-3175.
20. [20]
  SHIUE T W, CHEN Y H, WU C M, SINGH G, CHEN H Y, HUNG C H, LIAW W F, WANG Y M. J. Inorg. Chem., 2012, 51(9):5400-5408.
21. [21]
  WANG S X, CHU W H, WANG Y C, LIU S Y, ZHANG J C, LI S H, WEI H Y, ZHOU G Q, QIN X Y. J. Appl. Organomet. Chem., 2013, 27(7):373-379.
22. [22]
  KUMAR P, KALITA A, MONDAL B. J. Dalton Trans., 2011, 40(34):8656-8663.
23. [23]
  MCQUADE L E, LIPPARD S J. J. Inorg. Chem., 2010, 49(16):7464-7471.
24. [24]
  YUAN J L, WANG G L. J. TrAC-Trends Anal. Chem., 2006, 25(5):490-500.
25. [25]
  ELISEEVA S V, BUNZLI J C G. J. Chem. Soc. Rev., 2010, 39(1):189-227.
26. [26]
  BUNZLI J C G. J. Chem. Rev., 2010, 110(5):2729-2755.
27. [27]
  LAW G L, PAL R, PALSSON L O, PARKER D, WONG K L. Chem. Commun., 2009, (47):7321-7323.
28. [28]
  MURRAY N S, JARVIS S P, GUNNLAUGSSON T. Chem. Commun., 2009, (33):4959-4961.
29. [29]
  KWON N, KIM D, SWAMY K M K, YOON J. Coord. Chem. Rev., 2021, 427:213581.
30. [30]
  CHEN Y G, GUO W H, YE Z Q, WANG G L, YUAN J L. Chem. Commun., 2011, 47(22):6266-6268.
31. [31]
  JIN D Y, PIPER J A. Anal. Chem., 2011, 83(6):2294-2300.
32. [32]
  WANG G L, YUAN J L, MATAUMOTO K, HU Z D. Anal. Biochem., 2001, 299(2):169-172.
33. [33]
  ZHANG R, YE Z Q, WANG G L, ZHANG W Z, YUAN J. Chem.-Eur. J., 2010, 16(23):6884-6891.
34. [34]
  LIU M J, YE Z Q, WANG G L, YUAN J L. Talanta, 2012, 99:951-958.
35. [35]
  KOJIMA H, HIROTANI M, NAKATSUBO N, KIKUCHI K, URANO Y, HIGUCHI T, HIRATA Y, NAGANO T. Anal. Chem., 2001, 73(9):1967-1973.
36. [36]
  IZUMI S, URANO Y, HANAOKA K, TERAI T, NAGANO T. J. Am. Chem. Soc., 2009, 131(29):10189-10200.
37. [37]
  GOULD K S, LAMOTTE O, KLINGUERl A, PUGIN A, WENDEHENNE D. J. Cell Environ., 2003, 26(11):1851-1862.
1. [1]
  Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
2. [2]
  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
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]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
5. [5]
  Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
6. [6]
  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
7. [7]
  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
8. [8]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
9. [9]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
10. [10]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
11. [11]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
12. [12]
  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
13. [13]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
14. [14]
  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
15. [15]
  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
16. [16]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
17. [17]
  Qin Hou , Jiayi Hou , Aiju Shi , Xingliang Xu , Yuanhong Zhang , Yijing Li , Juying Hou , Yanfang Wang . Preparation of Cuprous Iodide Coordination Polymer and Fluorescent Detection of Nitrite: A Comprehensive Chemical Design Experiment. University Chemistry, 2024, 39(8): 221-229. doi: 10.3866/PKU.DXHX202312056
18. [18]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(732)
HTML views(109)

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