Citation: Wang Peipei, Liang Tao, Zuo Miaomiao, Li Zhen, Liu Zhihong. A Ratiometric Upconversion Nanoprobe for Detection of HNO Based on Luminescence Resonance Energy Transfer[J]. Acta Chimica Sinica, ;2020, 78(8): 797-804. doi: 10.6023/A20050146 shu

A Ratiometric Upconversion Nanoprobe for Detection of HNO Based on Luminescence Resonance Energy Transfer

Wang Peipei ^a ,
Liang Tao ^a ,
Zuo Miaomiao ^b ,
Li Zhen ^b,, ,
Liu Zhihong ^a,,

a.
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
b.
College of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062

Corresponding author: Li Zhen, zhenli@hubu.edu.cn Liu Zhihong, zhhliu@whu.edu.cn
Received Date: 6 May 2020
Available Online: 3 June 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21625503, 21807028)the National Natural Science Foundation of China 21625503the National Natural Science Foundation of China 21807028

Figures(7)

Nitroxyl (HNO), produced by nitric oxide (NO) with one-electron reduction and protonation, has recently received substantial interest due to its important roles in various biological functions and pharmacological activities. Research indicates that HNO also has many potential pharmacological applications for different diseases. Therefore, the development of a reliable method for HNO assay in biosystems is highly desired. Ratiometric fluorescent probes show significant advantages over traditional "turn-on" ones, because simultaneous measurement of two emission signals can provide a built-in correction and thus minimize the inaccurate fluorescence signal readouts. As far as we know, there is no ratiometric fluorescent probe for HNO detection based on upconversion nanoparticles (UCNPs). Herein, a ratiometric nanoprobe for HNO assay was constructed based on the luminescence resonance energy transfer (LRET) principle by using UCNPs with a core-shell structure (NaYbF₄:30%Gd@NaYF₄:2%Yb:1%Tm) as the energy donor and an organic dye Fl-TP as the potential energy acceptor. The oleate-coated UCNPs (OA-UCNPs) and Fl-TP were assembled through hydrophobic interaction to construct the upconversion nanoprobe (termed as Fl-TP-UCNPs). Because of the ring-closed form, Fl-TP displayed weak absorption and was non-fluorescent, which blocked the LRET process. After reaction with HNO, the triphenylphosphine moiety left and released Fl-HNO with the fluorescent ring-open form. Fl-HNO showed strong absorption in the range of 400~500 nm, which completely overlapped with the blue luminescence of UCNPs and triggered the LRET process between UCNPs and Fl-HNO. Thus, the luminescence from UCNPs around 480 nm decreased and the emission from Fl-HNO around 525 nm increased with a [HNO]-dependent manner. The ratiometric luminescence intensity F_{525 nm}/F_{480 nm} showed a good linear relationship (R²＝0.9914) to the logarithm of AS (Angeli's salt, a generally used HNO donor) concentration in the range of 3~100 μmol·L^－1 and the limit of detection was 23.4 nmol·L^－1. The excellent sensitivity, stability, selectivity and low cytotoxicity endow Fl-TP-UCNPs with the superior capability for HNO assay in vitro and in vivo. We found that Fl-TP-UCNPs probe is appropriate for monitoring HNO in living cells as well as imaging HNO in liver tissues. This probe may be a powerful tool for HNO assay in various physiological processes.
- upconversion nanoparticles,
- luminescence resonance energy transfer,
- ratiometric signal,
- nitroxyl,
- fluorescence bioimaging
1. [1]
  Chen, X.; Tian, X.; Shin, I.; Yoon, J. Chem. Soc. Rev. 2011, 40, 4783. doi: 10.1039/c1cs15037e
2. [2]
  Chen, X.; Wang, F.; Hyun, J. Y.; Wei, T.; Qiang, J.; Ren, X.; Shin, I.; Yoon, J. Chem. Soc. Rev. 2016, 45, 2976. doi: 10.1039/C6CS00192K
3. [3]
  Fukuto, J. M; Switzer, C. H.; Miranda, K. M.; Wink, D. A. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 335. doi: 10.1146/annurev.pharmtox.45.120403.095959
4. [4]
  Fukuto, J. M; Carrington, S. J. Antioxid. Redox. Signaling 2011, 14, 1649. doi: 10.1089/ars.2010.3855
5. [5]
  Wong, P. S.-Y.; Hyun, J.; Fukuto, J. M.; Shirota, F. N.; Demaster, E. G.; Shoeman, D. W.; Nagasawa, H. T. Biochemistry 1998, 37, 5362. doi: 10.1021/bi973153g
6. [6]
  Jackson, M. I.; Fields, H. F.; Lujan, T. S.; Cantrell, M. M.; Lin, J.; Fukuto, J. M. Arch. Biochem. Biophys. 2013, 538, 120. doi: 10.1016/j.abb.2013.08.008
7. [7]
  Johnson, G. M.; Chozinski, T. J.; Gallagher, E. S.; Aspinwall, C. A.; Miranda, K. M. Free Radical Biol. Med. 2014, 76, 299. doi: 10.1016/j.freeradbiomed.2014.07.022
8. [8]
  Nakagawa, H. Nitric Oxide. 2011, 25, 195. doi: 10.1016/j.niox.2010.12.004
9. [9]
  Fukuto, J. M.; Cisneros, C. J.; Kinkade, R. L. Inorg. Biochem. 2013, 118, 201. doi: 10.1016/j.jinorgbio.2012.08.027
10. [10]
  Switzer, C. H.; Flores-Santana, W.; Mancardi, D.; Donzelli, S.; Basudhar, D.; Ridnour, L. A.; Miranda, K. M.; Fukuto, J. M.; Paolocci, N.; Wink, D. A. Biochim. Biophys. Acta Bioenerg. 2009, 1787, 835. doi: 10.1016/j.bbabio.2009.04.015
11. [11]
  Shafirovich, V.; Lymar, S. V. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 7340. doi: 10.1073/pnas.112202099
12. [12]
  Li, X.; Gao, X.; Shi, W.; Ma, H. Chem. Rev. 2014, 114, 590. doi: 10.1021/cr300508p
13. [13]
  Yuan, L.; Lin, W.; Zheng, K.; Zhu, S. Acc. Chem. Res. 2013, 46, 1462. doi: 10.1021/ar300273v
14. [14]
  Zhang, H.; Liu, R.; Tan, Y.; Xie, W. H.; Lei, H.; Cheung, H. Y.; Sun, H. ACS Appl. Mater. Interfaces 2015, 7, 5438. doi: 10.1021/am508987v
15. [15]
  Rosenthal, J.; Lippard, S. J. J. Am. Chem. Soc. 2010, 132, 5536. doi: 10.1021/ja909148v
16. [16]
  Wrobel, A. T.; Johnstone, T. C.; Liang, A. D.; Lippard, S. J.; Rivera-Fuentes, P. J. Am. Chem. Soc. 2014, 136, 4697. doi: 10.1021/ja500315x
17. [17]
  Li, H.; Yao, Q.; Xu, F.; Xu, N.; Ma, X.; Fan, J.; Long, S.; Du, J.; Wang, J.; Peng, X. Anal. Chem. 2018, 90, 4641. doi: 10.1021/acs.analchem.7b05172
18. [18]
  Ali, F.; Sreedharan, S.; Ashoka, A. H.; Saeed, H. K.; Smythe, C. G. W.; Thomas, J. A.; Das, A. Anal. Chem. 2017, 89, 12087. doi: 10.1021/acs.analchem.7b02567
19. [19]
  Jiao, C.-P.; Liu, Y.-Y.; Lu, W.-J.; Zhang, P.-P.; Wang, Y.-F. Chin. J. Org. Chem. 2019, 39, 591 (in Chinese).
20. [20]
  Wang, X.-F.; Wei, C.; Li, X.-Y.; Zheng, X.-Y.; Geng, X.-W.; Zhang, P.-Z.; Li, X.-L. Chin. J. Org. Chem. 2019, 39, 469. (in Chinese).
21. [21]
  Cline, M. R.; Toscano, J. P. J. Phys. Org. Chem. 2011, 24, 993. doi: 10.1002/poc.1871
22. [22]
  Zhou, Y.; Liu, K.; Li, J.-Y.; Fang, Y.; Zhao, T.-C.; Yao, C. Org. Lett. 2011, 13, 1290. doi: 10.1021/ol103077q
23. [23]
  Mcquade, L. E.; Lippard, S. J. Curr. Opin. Chem. Biol. 2010, 14, 43. doi: 10.1016/j.cbpa.2009.10.004
24. [24]
  Zheng, W.; Huang, P.; Tu, D.; Ma, E.; Zhu, H.; Chen, X. Chem. Soc. Rev. 2015, 44, 1379. doi: 10.1039/C4CS00178H
25. [25]
  Yang, D.; Ma, P.; Hou, Z.; Cheng, Z.; Li, C.; Lin, J. Chem. Soc. Rev. 2015, 44, 1416. doi: 10.1039/C4CS00155A
26. [26]
  Chen, G.; Qiu, H.; Prasad, P.; Chen, X. Chem. Rev. 2014, 114, 5161. doi: 10.1021/cr400425h
27. [27]
  Zhu, X.; Feng, W.; Chang, J.; Tan, Y.-W.; Li, J.; Chen, M.; Sun, Y.; Li, F. Nat. Commun. 2016, 7, 10437. doi: 10.1038/ncomms10437
28. [28]
  Zhou, L.; Wang, R.; Yao, C.; Li, X.; Wang, C.; Zhang, X.; Xu, C.; Zeng, A.; Zhao, D.; Zhang, F. Nat. Commun. 2015, 6, 7350. doi: 10.1038/ncomms8350
29. [29]
  Gu, B.; Zhang, Q. Adv. Sci. 2018, 5, 1700609. doi: 10.1002/advs.201700609
30. [30]
  Su, Q.; Feng, W.; Yang, D.; Li, F. Acc. Chem. Res. 2017, 50, 32. doi: 10.1021/acs.accounts.6b00382
31. [31]
  Wang, S.; Liu, L.; Fan, Y.; El-Toni, A. M.; Alhoshan, M. S.; Li, D.; Zhang, F. Nano Lett. 2019, 19, 2418. doi: 10.1021/acs.nanolett.8b05148
32. [32]
  Fan, Y.; Liu, L.; Zhang, F. Nano Today 2019, 25, 68. doi: 10.1016/j.nantod.2019.02.009
33. [33]
  Fan, Y.; Zhang, F. Adv. Optical. Mater. 2019, 7, 1801417. doi: 10.1002/adom.201801417
34. [34]
  Li, X.; Guo, Z.; Zhao, T.; Lu, Y.; Zhou, L.; Zhao, D.; Zhang, F. Angew. Chem., Int. Ed. 2016, 55, 2464. doi: 10.1002/anie.201510609
35. [35]
  Liu, L.; Wang, S.; Zhao, B.; Pei, P.; Fan, Y.; Li, X.; Zhang, F. Angew. Chem., Int. Ed. 2018, 57, 7518. doi: 10.1002/anie.201802889
36. [36]
  Lin, R.-Y.; Chen, Y.; Tao, G.-Y.; Pei, X.-J.; Liu, F.; Li, N. Acta Chim. Sinica 2017, 75, 1103 (in Chinese).
37. [37]
  Chen, K.; Han, B.-C.; Ji, S.-X.; Sun, J.; Gao, Z.-Z.; Hou, X.-F. Acta Chim. Sinica 2019, 77, 365 (in Chinese).
38. [38]
  Ma, C.; Xu, X.; Wang, F.; Zhou, Z.; Liu, D.; Zhao, J.; Guan, M.; Lang, C. I.; Jin, D. Nano Lett. 2017, 17, 2858. doi: 10.1021/acs.nanolett.6b05331
39. [39]
  Wen, S.; Zhou, J.; Zheng, K.; Bednarkiewicz, A.; Liu, X.; Jin, D. Nat. Commun. 2018, 9, 2415. doi: 10.1038/s41467-018-04813-5
40. [40]
  Siefe, C.; Mehlenbacher, R. D.; Peng, C. S.; Zhang, Y.; Fischer, S.; Lay, A.; McLellan, C. A.; Alivisatos, A. P.; Chu, S.; Dionne, J. A. J. Am. Chem. Soc. 2019, 141, 16997. doi: 10.1021/jacs.9b09571
41. [41]
  Wang, F.; Han, Y.; Lim, C. S.; Lu, Y.; Wang, J.; Xu, J.; Chen, H.; Zhang, C.; Hong, M.; Liu, X. Nature 2010, 463, 1061. doi: 10.1038/nature08777
42. [42]
  Han, S.; Deng, R.; Xie, X.; Liu, X. Angew. Chem., Int. Ed. 2014, 53, 11702. doi: 10.1002/anie.201403408
43. [43]
  Zhong, Y.; Tian, G.; Gu, Z.; Yang, Y.; Gu, L.; Zhao, Y.; Ma, Y.; Yao, J. Adv. Mater. 2014, 26, 2831. doi: 10.1002/adma.201304903
44. [44]
  Min, Q.; Zhao, L.; Qi, Y.; Lei, J.; Chen, W.; Xu, X.; Zhou, D.; Qiu, J.; Yu, X. Nanoscale 2018, 10, 19031. doi: 10.1039/C8NR05021J
45. [45]
  Maeda, H.; Fukuyasu, Y.; Yoshida, S.; Fukuda, M.; Saeki, K.; Matsuno, H.; Yamauchi, Y.; Yoshida, K.; Hirata, K.; Miyamoto, K.; Angew. Chem., Int. Ed. 2004, 43, 2389. doi: 10.1002/anie.200452381
46. [46]
  Cen, Y.; Wu, Y.-M.; Kong, X.-J.; Wu, S.; Yu, R.-Q.; Chu, X. Anal. Chem. 2014, 86, 7119. doi: 10.1021/ac5016694
47. [47]
  Tao, L.; Li, Z.; Wang, P.; Zhao, F.; Liu, Z. J. Am. Chem. Soc. 2018, 140, 14696. doi: 10.1021/jacs.8b07329
48. [48]
  Zhao, F.; Zhao, Y.; Liu, Y.; Chang, X.; Chen, C.; Zhao, Y. Small 2011, 7, 1322. doi: 10.1002/smll.201100001
49. [49]
  Yang, M.; Fan, J.; Sun, W.; Du, J.; Long, S.; Shao, K.; Peng, X. Chem. Commun. 2019, 55, 8583. doi: 10.1039/C9CC04060A
50. [50]
  Suarez, S. A.; Muñoz, M.; Alvarez, L.; Venâncio, M. F.; Rocha, W. R.; Bikiel, D. E.; Marti, M. A.; Doctorovich, F. J. Am. Chem. Soc. 2017, 139, 14483. doi: 10.1021/jacs.7b06968
51. [51]
  Jing, X.; Yu, F.; Chen, L. Chem. Commun. 2014, 50, 14253. doi: 10.1039/C4CC07561G
52. [52]
  Li, J.-B.; Wang, Q.; Liu, H.-W.; Yin, X.; Hu, X.-X.; Yuan, L.; Zhang, X.-B. Chem. Commun. 2019, 55, 1758. doi: 10.1039/C9CC00211A
53. [53]
  Blanco, E.; Shen, H.; Ferrari, M. Nat. Biotechnol. 2015, 33, 941. doi: 10.1038/nbt.3330
54. [54]
  Liu, Y.; Chen, M.; Cao, T.; Sun, Y.; Li, C.; Liu, Q.; Yang, T.; Yao, L.; Feng, W.; Li, F. J. Am. Chem. Soc. 2013, 135, 9869. doi: 10.1021/ja403798m
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