高选择性过氧化亚硝酰荧光探针的合成及性能研究

引用本文: 后际挺, 王冰雅, 郑凌云. 高选择性过氧化亚硝酰荧光探针的合成及性能研究[J]. 分析化学, 2020, 48(11): 1502-1510. doi: 10.19756/j.issn.0253-3820.201299 shu

Citation: HOU Ji-Ting, WANG Bing-Ya, ZHENG Ling-Yun. Synthesis and Investigation of Fluorescent Probe for Peroxynitrite Detection with High Selectivity[J]. Chinese Journal of Analytical Chemistry, 2020, 48(11): 1502-1510. doi: 10.19756/j.issn.0253-3820.201299 shu

高选择性过氧化亚硝酰荧光探针的合成及性能研究

后际挺 ^{1,
,} ,
王冰雅 ^1, ,
郑凌云 ^2,

1.
信阳师范学院化学化工学院, 信阳 464000;
2.
信阳师范学院分析测试中心, 信阳 464000

通讯作者: 后际挺,houjiting2206@163.com

基金项目:
本文系国家自然科学基金项目（No.21807029）和信阳师范学院‘南湖学者奖励计划’青年项目资助

摘要: 过氧化亚硝酰（ONOO^-）是生物体系中重要活性氧之一，对其高效检测一直备受关注。本研究以4-二乙基氨基水杨醛和6-甲氧基-1-萘满酮为原料，经一步有机反应，合成了一种带氧鎓正离子的荧光探针PFP，用于检测ONOO^-。通过紫外-可见吸收光谱和荧光发射光谱系统考察了探针PFP对ONOO^-的光学响应。结果表明，此探针具有选择性好、灵敏度高（检出限为15.5 nmol/L）、响应快速（数秒内）、Stokes位移较大（42 nm）、水溶性好等优点。细胞毒性实验表明，探针PFP具有良好的生物相容性，探针浓度为20 μmol/L时，细胞存活率>95%。激光扫描共聚焦显微成像结果表明，此探针可用于活细胞中外源性和内源性ONOO^-的荧光成像研究。

关键词:

English

Synthesis and Investigation of Fluorescent Probe for Peroxynitrite Detection with High Selectivity

1.
College of Chemistry and Chemical Engineering, Xinyang Normal University, Xinyang 464000, China;
2.
Analysis&Testing Center, Xinyang Normal University, Xinyang 464000, China

Corresponding author: HOU Ji-Ting, houjiting2206@163.com

Received Date: 24 May 2020
Revised Date: 23 June 2020
Fund Project:
This work was supported by the National Natural Science Foundation of China (No. 21807029) and the Nanhu Scholars Program for Young Scholars of Xinyang Normal University.

Abstract: Peroxynitrite (ONOO^-) is one of the important reactive oxygen species in biosystems, and its effective detection has been attracting numerous attention. A fluorescent probe for ONOO^- detection was prepared via one-step reaction of 4-(diethylamino)salicylaldehyde and 6-methoxy tetralone. The optical response of the probe toward ONOO^- was investigated through UV and fluorescence spectra. The results showed that the probe was superior with the merits of high selectivity, superb sensitivity (the detection limit is 15.5 nmol/L), rapid response (within seconds), large Stokes shift (42 nm) and good water solubility. The 3-(4,5)-dimethylthiahiazo (-z-y1)-3,5-di-phenytetrazoliumromide (MTT) assay indicated an excellent biocompatibility of the probe (the survival rate of the cells was higher than 95% when the concentration of the probe was 20 μmol/L). Finally, the probe was successfully utilized for the fluorescence imaging of exogenous and endogenous ONOO^- in living cells.

Key words:

1. [1]
  Szabo C, Ischiropoulos H, Radi R. Nat. Rev. Drug Discov., 2007,6(8):662-680
2. [2]
  Radi R. J. Biol. Chem., 2013,288(37):26464-26472
3. [3]
  Liaudet L, Vassall G, Pacher P. Front. Biosci., 2009,14:4809-4814
4. [4]
  Kaur H, Halliwell B. FEBS Lett., 1994,350(1):9-12
5. [5]
  Dean R T, Fu S, Stocker R, Davies M J. Biochem. J., 1997,324(1):1-18
6. [6]
  Kawasaki H, Ikeda K, Shigenaga A, Baba T, Takamori K, Ogawa H, Yamakura F. Free Radical Biol. Med., 2011,50(3):419-427
7. [7]
  Levrand S, Vannay-Bouchiche C, Pesse B, Pacher P, Feihl F, Waeber B, Liaudet L. Free Radical Biol. Med., 2006,41(6):886-895
8. [8]
  Wiseman H, Halliwell B. Biochem. J., 1996,313(1):17-29
9. [9]
  Kossenjans W, Eis A, Sahay R, Brockman D, Myatt L. Am. J. Physiol-Heart Circ. Physiol., 2000,278(4):H1311-H1319
10. [10]
  Shuhendler A J, Pu K, Cui L, Uetrecht J P, Rao J. Nat. Biotechnol., 2014,32(4):373-380
11. [11]
  Hou J T, Yu K K, Sunwoo K, Kim W Y, Koo S, Wang J, Ren W X, Wang S, Yu X Q, Kim J S. Chem, 2020,6(4):832-866
12. [12]
  WANG Xiao-Li, YAO Meng, LI Yin, WEI Chao, WANG Mei. Chinese J. Anal. Chem., 2019,47(12):1915-1921 王肖莉, 姚猛, 李引, 魏超, 王美.分析化学, 2019,47(12):1915-1921
13. [13]
  Xiao H, Zhang W, Li P, Zhang W, Wang X, Tang B. Angew. Chem. Int. Ed., 2020,59(11):4216-4230
14. [14]
  Wu X, Shi W, Li X, Ma H. Acc. Chem. Res., 2019,52(7), 1892-1904
15. [15]
  Yang J, Chi Z, Zhu W, Tang B Z, Li Z. Sci. China Chem., 2019,62(9):1090-1098
16. [16]
  Prolo C, Rios N, Piacenza L, Alvarez M N, Radi R. Free Radical Biol. Med., 2018,128:59-68
17. [17]
  Wang S, Chen L, Jangili P, Sharma A, Li W, Hou J T, Qin C, Yoon J, Kim J S. Coord. Chem. Rev., 2018,374:36-54
18. [18]
  Bai X, Ng K K H, Hu J J, Ye S, Yang D. Annu. Rev. Biochem., 2019,88:605-633
19. [19]
  Yang D, Wang H L, Sun Z N, Chung N W, Shen J G. J. Am. Chem. Soc., 2006,128(18):6004-6005
20. [20]
  Yu F, Li P, Wang B, Han K. J. Am. Chem. Soc., 2013,135(20):7674-7680
21. [21]
  Yudhistira T, Mulay T S V, Lee K J, Kim Y, Park H S, Churchill D G. Chem. Asian J., 2017,12(15):1927-1934
22. [22]
  Song Z, Mao D, Sung S H P, Kwok R T K, Lam J W Y, Kong D, Ding D, Tang B Z. Adv. Mater., 2016,28(33):7249-7256
23. [23]
  Hu J S, Shao C, Wang X, Di X, Xue X, Su Z, Zhao J, Zhu H L, Liu H K, Qian Y. Adv. Sci., 2019,6(15):1900341
24. [24]
  Li H, Li X, Wu X, Shi W, Ma H. Anal. Chem., 2017,89(10):5519-5525
25. [25]
  Zhu B, Zhang M, Wu L, Zhao Z, Liu C, Wang Z, Duan Q, Wang Y, Jia P. Sens. Actuators B, 2018,257:436-441
26. [26]
  Jia X T, Chen Q Q, Yang Y F, Tang Y, Wang R, Xu Y F, Zhu W P, Qian X H. J. Am. Chem. Soc., 2016,138(34):10778-10781
27. [27]
  Zhang W, Liu J, Li P, Wang X, Bi S, Zhang J, Zhang W, Wang H, Tang B. Biomaterials, 2019,225:119499
28. [28]
  Peng T, Chen X M, Gao L, Zhang T, Wang W, Shen J G, Yang D. Chem. Sci., 2016,7(8):5407-5413
29. [29]
  Cheng J, Li D, Sun M, Wang Y, Xu Q Q, Liang X G, Lu Y B, Hu Y, Han F, Li X. Chem. Sci., 2020,11(1):281-289
30. [30]
  Cheng D, Peng J, Lv Y, Su D, Liu D, Chen M, Yuan L, Zhang X. J. Am. Chem. Soc., 2019,141(15):6352-6361
31. [31]
  Xie X L, Liu G Z, Su X X, Li Y, Liu Y W, Jiao X Y, Wang X, Tang B. Anal. Chem., 2019,91(10):6872-6879
32. [32]
  JiangW L, Li Y, Wang W X, Zhao Y T, Fei J, Li C Y. Chem. Commun., 2019,55(95):14307-14310
33. [33]
  Zhou X, Kwon Y, Kim G, Ryu J H, Yoon J. Biosens. Bioelectron., 2015,64:285-291
34. [34]
  Xu W, Teoh C L, Peng J, Su D, Yuan L, Chang Y T. Biomaterials, 2015,56:1-9
35. [35]
  Hou J T, Yang J, Li K, Liao Y X, Yu K K, Xie Y M, Yu X Q. Chem. Commun., 2014,50(69):9947-9950
36. [36]
  HOU Ji-Ting, LI Kun, QIN Cai-Qin, YU Xiao-Qi. Sci. Sin. Chim., 2019,49(2):346-352 后际挺, 李坤, 覃彩芹, 余孝其.中国科学:化学, 2019,49(2):346-352
37. [37]
  Hou J T, Wang B, Zhang Y, Cui B, Cao X, Zhang M, Ye Y, Wang S. Chem. Commun., 2020,56(18):2759-2762
38. [38]
  Shang H M, Chen H, Tang Y, Ma Y, Lin W. Sens. Actuators B, 2017,95:81-86
39. [39]
  Ferrer-Sueta G, Radi R. ACS Chem. Biol., 2009,4(3):161-177
40. [40]
  Li C Q, Trudel L J, Wogan G N. Chem. Res. Toxicol., 2002,15:527-535

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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

高选择性过氧化亚硝酰荧光探针的合成及性能研究

通讯作者: 后际挺,houjiting2206@163.com

English

Synthesis and Investigation of Fluorescent Probe for Peroxynitrite Detection with High Selectivity

Corresponding author: HOU Ji-Ting, houjiting2206@163.com

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

高选择性过氧化亚硝酰荧光探针的合成及性能研究

通讯作者: 后际挺,houjiting2206@163.com

English

Synthesis and Investigation of Fluorescent Probe for Peroxynitrite Detection with High Selectivity

Corresponding author: HOU Ji-Ting, houjiting2206@163.com

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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