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.
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