Citation: Lina Huang, Yu Chen, Yuqiang Zhao, Yumin Wang, Junwei Xiong, Junfeng Zhang, Xianghua Wu, Ying Zhou. A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe²⁺ in vivo[J]. Chinese Chemical Letters, ;2020, 31(11): 2941-2944. doi: 10.1016/j.cclet.2020.06.006 shu

A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe²⁺ in vivo

Lina Huang ^a ,
Yu Chen ^a ,
Yuqiang Zhao ^b ,
Yumin Wang ^a ,
Junwei Xiong ^a ,
Junfeng Zhang ^{a, *,} ,
Xianghua Wu ^{a, *,} ,
Ying Zhou ^{b, *,}

a.
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China
b.
College of Chemical Science and Technology, Yunnan University, Kunming 650091, China

junfengzhang78@126.com

chxhwu@sina.com

yingzhou@ynu.edu.cn

Received Date: 20 February 2020
Revised Date: 30 May 2020
Accepted Date: 2 June 2020
Available Online: 4 June 2020

Figures(5)

Iron is one of the essential trace elements in the human body. It plays an important role in human biology and pathology. Deregulation of iron levels in cells is associated with disease development. In this work, we synthesized a novel near-infrared intramolecular charge transfer (ICT) based ratiometric fluorescent probe to detect Fe²⁺, by using naphthalimide and indole moieties as building blocks. Our work showed that the radiometric probe has excellent selectivity, sensitivity and rapid response. Moreover, we could successfully perform real-time monitoring of Fe²⁺ in HeLa cells and C. elegans.
- Fluorescent probe,
- Ratiometric,
- Fe²⁺,
- Naphthalimide,
- Near-infrared
1. [1]
  S.A. James, B.R. Roberts, D.J. Hare, et al., Chem. Sci. 6(2015) 2952-2962. doi: 10.1039/C5SC00233H
2. [2]
  S.V. Haehling, E.A. Jankowska, D.J. Veldhuisen, P. Ponikowski, S.D. Anker, Nat. Rev. Cardiol. 12(2015) 659-669. doi: 10.1038/nrcardio.2015.109
3. [3]
  D. Hare, S. Ayton, A. Bush, P.A. Lei, Front. Aging Neurosci. 5(2013) 34.
4. [4]
  S.V. Torti, F.M. Torti, Nat. Rev. Cancer 13(2013) 342-355. doi: 10.1038/nrc3495
5. [5]
  Z.K. Pinnix, L.D. Miller, W. Wang, Sci. Transl. Med. 2(2010) 43-56.
6. [6]
  M.W. Hentze, M.U. Muckenthaler, B. Galy, C. Camaschella, Cell 142(2010) 24-38. doi: 10.1016/j.cell.2010.06.028
7. [7]
  J. Wang, K. Pantopoulos, Biochem. J. 434(2011) 365-381. doi: 10.1042/BJ20101825
8. [8]
  D.C. Johnson, D.R. Dean, A.D. Smith, M.K. Johnson, Annu. Rev. Biochem. 74(2005) 247-281. doi: 10.1146/annurev.biochem.74.082803.133518
9. [9]
  J. Xie, Y.H. Chen, W. Yang, et al., J. Photochem. Photobiol. A:Chem. 223(2011) 111-118. doi: 10.1016/j.jphotochem.2011.08.006
10. [10]
  V.B. Bojinov, D.B. Simeonov, N.I. Georgiev, Dye. Pigment. 76(2008) 41-46. doi: 10.1016/j.dyepig.2006.08.006
11. [11]
  D.W. Cui, X.H. Qian, F.Y. Liu, R. Zhang, Org. Lett. 6(2004) 2757-2760. doi: 10.1021/ol049005h
12. [12]
  A. Ajayaghosh, P. Carol, S. Sreejith, J. Am. Chem. Soc. 127(2005) 14962-14963. doi: 10.1021/ja054149s
13. [13]
  S. Atilgan, T. Ozdemir, E.U. Akkaya, Org. Lett. 10(2008) 4065-4067. doi: 10.1021/ol801554t
14. [14]
  J.H. Do, H.N. Kim, J.Y. Yoon, J.S. Kim, H.J. Kim, Org. Lett. 12(2010) 932-934. doi: 10.1021/ol902860f
15. [15]
  I. Takashima, A. Kanegae, M. Sugimoto, et al., Inorg. Chem. 53(2014) 7080-7082. doi: 10.1021/ic500980j
16. [16]
  J. Liu, Y.Q. Sun, Y.Y. Huo, et al., J. Am. Chem. Soc. 136(2014) 574-577. doi: 10.1021/ja409578w
17. [17]
  L.W. He, Q.Y. Xu, Y. Liu, et al., ACS Appl. Mater. Interfaces 7(2016) 12809-12813.
18. [18]
  L.F. Pang, Y.M. Zhou, W.L. Gao, et al., Ind. Eng. Chem. Res. 56(2017) 7650-7655. doi: 10.1021/acs.iecr.7b02133
19. [19]
  X.Y. Zhu, Y. Li, W.Y. Zan, et al., Photochem. Photobiol. Sci. 15(2016) 412-419. doi: 10.1039/C5PP00468C
20. [20]
  N. Pradhan, D. Jana, B.K. Ghorai, et al., ACS Appl. Mater. Interfaces 7(2015) 25813-25820. doi: 10.1021/acsami.5b07751
21. [21]
  Y. Kong, H.Q. Yao, H.J. Ren, et al., Proc. Natl. Acad. Sci. U. S. A. 107(2010) 12239-12244. doi: 10.1073/pnas.1000643107
22. [22]
  C.L. Teoh, D.D. Su, S. Sahu, et al., J. Am. Chem. Soc. 137(2015) 13503-13509. doi: 10.1021/jacs.5b06190
23. [23]
  Q. Jin, L. Feng, D.D. Wang, et al., ACS Appl. Mater. Interfaces 7(2015) 28474-28481. doi: 10.1021/acsami.5b09573
24. [24]
  H. Yu, Y. Xiao, L. Jin, J. Am. Chem. Soc. 134(2012) 17486-17489. doi: 10.1021/ja308967u
25. [25]
  Z.R. Dai, G.B. Ge, L. Feng, J. Am. Chem. Soc. 137(2015) 14488-14495. doi: 10.1021/jacs.5b09854
26. [26]
  (a) M.H. Lee, H.M. Jeon, J.H. Han, et al., J. Am. Chem. Soc. 136 (2014) 8430-8437;
  (b) T. Guo, L. Cui, J. Shen, et al., Chem. Commun. (Camb.) 49 (2013) 1862-1864;
  (c) W. Xuan, R. Pan, Y. Wei, et al., Bioconjugate Chem. 27 (2016) 302-308.
27. [27]
  (a) X. Wu, B. Lin, M. Yu, et al., Chem. Sci. 6 (2015) 2002-2009;
  (b) Q.Q. Wan, S. Chen, W. Shi, L.H. Li, Angew. Chem. Int. Ed. 53 (2014) 10916;
  (c) S. Chen, Y. Hong, Y. Liu, et al., J. Am. Chem. Soc. 135 (2013) 4926-4929;
  (d) X. Jia, Q. Chen, Y. Yang, et al., J. Am. Chem. Soc. 138 (2016) 1065-1077.
28. [28]
  (a) X.M. Li, R.R. Zhao, Y. Yang, et al., Chin. Chem. Lett. 28 (2017) 1258-1261;
  (b) L. Yu, Y.M. Qiao, L.X. Miao, et al., Chin. Chem. Lett. 29 (2018) 1545-1559;
  (c) K.Y. Bi, R. Tan, R.T. Hao, et al., Chin. Chem. Lett. 30 (2019) 545-548;
  (d) Y. Chen, Y.Q. Zhao, P. Xie, et al., Dye. Pigment. 177 (2020) 108308.
29. [29]
  P. Ning, W. Wang, M. Chen, et al., Chin. Chem. Lett. 28(2017) 1943-1951. doi: 10.1016/j.cclet.2017.09.026
30. [30]
  L. Song, X.D. Sun, Y.H. Yao, et al., Chin. Chem. Lett. 27(2016) 1776-1780. doi: 10.1016/j.cclet.2016.05.007
31. [31]
  C. Duan, M. Won, P. Verwilst, et al., Anal. Chem. 91(2019) 4172-4178. doi: 10.1021/acs.analchem.9b00224
32. [32]
  J.J. Wu, L.R. Jiang, P. Verwilst, et al., Chem. Commun. (Camb.) 55(2019) 9947-9950. doi: 10.1039/C9CC05048E
33. [33]
  J.C. Xu, H.Q. Yuan, L.T. Zeng, G.M. Bao, Chin. Chem. Lett. 29(2018) 1456-1464. doi: 10.1016/j.cclet.2018.08.012
34. [34]
  W. Li, X.Y. Gong, X.P. Fan, et al., Chin. Chem. Lett. 30(2019) 1775-1790. doi: 10.1016/j.cclet.2019.07.056
35. [35]
  Q. Fang, L. Yang, H.Q. Xiong, et al., Chin. Chem. Lett. 31(2020) 129-132. doi: 10.1016/j.cclet.2019.04.021
36. [36]
  Q. Hu, C.Q. Qin, L. Huang, et al., Dye. Pigment. 149(2018) 253-260. doi: 10.1016/j.dyepig.2017.10.002
37. [37]
  M.H. Lee, H. Lee, M.J. Chang, et al., Dye. Pigment. 130(2016) 245-250. doi: 10.1016/j.dyepig.2016.03.032
38. [38]
  C. Wang, D. Zhang, X. Huang, et al., Talanta 128(2014) 69-74. doi: 10.1016/j.talanta.2014.03.073
39. [39]
  S. Maiti, Z. Aydin, Y. Zhang, M. Guo, Dalton Trans. 44(2015) 8942-8949. doi: 10.1039/C4DT03792H
40. [40]
  T. Hirayama, H. Tsuboi, M. Niwa, et al., Chem. Sci. 8(2017) 4858-4866. doi: 10.1039/C6SC05457A
41. [41]
  A.T. Aron, M.O. Loehr, J. Bogena, C.J. Chang, J. Am. Chem. Soc. 138(2016) 14338-14346. doi: 10.1021/jacs.6b08016
42. [42]
  G.G. Hou, C.H. Wang, J.F. Sun, et al., Biochem. Biophys. Res. Commun. 439(2013) 459-463. doi: 10.1016/j.bbrc.2013.08.092
43. [43]
  X.P. Yang, Y.S. Wang, R. Liu, et al., Sens. Actuators B:Chem. 288(2019) 217-224. doi: 10.1016/j.snb.2019.02.123
44. [44]
  H. Chen, Y.H. Tang, H.M. Shang, et al., J. Mater. Chem. B:Mater. Biol. Med. 5(2017) 2436-2444. doi: 10.1039/C7TB00174F
45. [45]
  S. Zhou, Y.F. Rong, H. Wang, et al., Sens. Actuators B:Chem. 276(2018) 136-141. doi: 10.1016/j.snb.2018.08.096
46. [46]
  Z. Mao, H. Jiang, Z. Li, et al., Chem. Sci. 8(2017) 4533-4538. doi: 10.1039/C7SC00416H
47. [47]
  H. Li, Q. Yao, J. Fan, et al., Biosens. Bioelectron. 94(2017) 536-543. doi: 10.1016/j.bios.2017.03.039
48. [48]
  T. Hirayama, K. Okuda, H. Nagasawa, Chem. Sci. 4(2013) 1250. doi: 10.1039/c2sc21649c
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe2+ in vivo

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通讯作者: 陈斌, bchen63@163.com

A ratiometric near-infrared naphthalimide-based fluorescent probe with high sensitivity for detecting Fe²⁺ in vivo