Citation: Jingdong Wang, Fangjun Huo, Yongbin Zhang, Caixia Yin. Spiropyran isomerization triggering ESIPT for visualization of pH fluctuations during oxidative stress in living cells[J]. Chinese Chemical Letters, ;2023, 34(5): 107818. doi: 10.1016/j.cclet.2022.107818 shu

Spiropyran isomerization triggering ESIPT for visualization of pH fluctuations during oxidative stress in living cells

Jingdong Wang ^a ,
Fangjun Huo ^{b, *,} ,
Yongbin Zhang ^b ,
Caixia Yin ^{a, *,}

a.
Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Shanxi University, Taiyuan 030006, China
b.
Research Institute of Applied Chemistry, Shanxi University, Taiyuan 030006, China

huofj@sxu.edu.cn

yincx@sxu.edu.cn

Received Date: 8 June 2022
Revised Date: 5 September 2022
Accepted Date: 9 September 2022
Available Online: 13 September 2022

Figures(7)

Intracellular pH homeostasis is foundation of maintaining normal physiological functions. More and more evidences show that intracellular pH fluctuations were usually associated with many diseases (such as cancer, epilepsy and neurodegenerative diseases). It is very important to develop in situ real-time determination of pH. In recent years, it has been verified that pH can regulate the isomerization process of spiropyran. Thus, we report a pH fluorescent probe BSL, which is a closed loop spiropyran structure by coupling benzothiazole derivatives with indole salts. We utilizes the process of spiropyran isomerization as the trigger of excited state intramolecular proton transfer (ESIPT) effect, and adjust the process of spiropyran isomerization through pH, and then the molecular transformation from enol to ketone (enol: 525 nm, ketone: 677 nm) through the ESIPT effect. This process achieved accurate measurement of pH. The probe BSL showed sensitive and reversible fluorescence response to pH in vitro. Ultimately, BSL was successfully applied to detect pH fluctuations in cell oxidative stress model.
- pH,
- Spiropyran isomerization,
- ESIPT,
- Reversible,
- Oxidative stress
1. [1]
  J.R. Casey, S. Grinstein, J. Orlowski, Nat. Rev. Mol. Cell Biol. 11 (2010) 50–61. doi: 10.1038/nrm2820
2. [2]
  B. Dong, W. Song, Y. Lu, et al., Chem. Commun. 55 (2019) 10776–10779. doi: 10.1039/c9cc03114f
3. [3]
  Y. Wen, N. Jing, F. Huo, C. Yin, Analyst 146 (2021) 7450–7463. doi: 10.1039/d1an01621k
4. [4]
  X. Zhang, F. Huo, Y. Zhang, et al., Analyst 147 (2022) 2470–2476. doi: 10.1039/d2an00547f
5. [5]
  G. Song, D. Jiang, L. Wang, et al., Chin. Chem. Lett. 33 (2022) 339–343. doi: 10.1016/j.cclet.2021.06.076
6. [6]
  B. Feng, Y. Zhu, J. Wu, et al., Chin. Chem. Lett. 32 (2021) 3057–3060. doi: 10.1016/j.cclet.2021.03.074
7. [7]
  T. Zhang, F. Huo, W. Zhang, et al., Sens. Actuat. B 345 (2021) 130393–130400. doi: 10.1016/j.snb.2021.130393
8. [8]
  Y. Wen, W. Zhang, T. Liu, et al., Anal. Chem. 89 (2017) 11869–11874. doi: 10.1021/acs.analchem.7b03612
9. [9]
  M. Fang, R. Adhikari, J. Bi, et al., J. Mater. Chem. B 5 (2017) 9579–9590. doi: 10.1039/C7TB02583A
10. [10]
  Y. Sun, X. Zhou, L. Sun, et al., Chin. Chem. Lett. 33 (2022) 4229–4232. doi: 10.1016/j.cclet.2022.01.087
11. [11]
  T. Nishi, M. Forgac, Nat. Rev. Mol. Cell Biol. 3 (2002) 94–103. doi: 10.1038/nrm729
12. [12]
  X. Liu, Y. Su, H. Tian, et al., Anal Chem. 89 (2017) 7038–7045. doi: 10.1021/acs.analchem.7b00754
13. [13]
  Y. Yue, F. Huo, S. Lee, et al., Analyst 142 (2017) 30–41. doi: 10.1039/C6AN01942K
14. [14]
  L. Chen, J. Li, Z. Liu, et al., RSC Adv. 3 (2013) 13412–13416. doi: 10.1039/c3ra41898g
15. [15]
  S. Park, J. Hyun, I. Shin, Chem. Sci. 10 (2019) 56–66. doi: 10.1039/C8SC04084B
16. [16]
  C. Chen, L. Zhou, W. Liu, W. Liu, Anal. Chem. 90 (2018) 6138–6143. doi: 10.1021/acs.analchem.8b00434
17. [17]
  Z. Dong, Q. Han, Z. Mou, et al., J. Mater. Chem. B 6 (2018) 1322–1327. doi: 10.1039/c7tb03089d
18. [18]
  P. Swietach, S. Wigfield, P. Cobden, et al., J. Biol. Chem. 283 (2008) 20473–20483. doi: 10.1074/jbc.M801330200
19. [19]
  Q. Wan, S. Chen, W. Shi, et al., Angew. Chem. Int. Ed. 53 (2014) 10916–10920. doi: 10.1002/anie.201405742
20. [20]
  T. Fukuda, L. Ewan, M. Bauer, et al., Ann. Neurol. 59 (2006) 700–708. doi: 10.1002/ana.20807
21. [21]
  R. Balaban, S. Nemoto, T. Finkel, Cell 120 (2005) 483–495. doi: 10.1016/j.cell.2005.02.001
22. [22]
  T. Fukai, M. Ushio-Fukai, Cell 9 (2020) 1849–1865. doi: 10.3390/cells9081849
23. [23]
  M. Reth, Nat. Immunol. 3 (2002) 1129–1134. doi: 10.1038/ni1202-1129
24. [24]
  J. Ge, K. Zhang, L. Fan, et al., Analyst 144 (2019) 4288–4294. doi: 10.1039/c9an00697d
25. [25]
  A. Lieberman, R. Puetollano, N. Raben, et al., Autophagy 8 (2012) 719–730. doi: 10.4161/auto.19469
26. [26]
  J. Han, K. Burgess, Chem. Rev. 110 (2010) 2709–2728. doi: 10.1021/cr900249z
27. [27]
  D. Ellis, R.C. Thomas, Nature 262 (1976) 224–225. doi: 10.1038/262224a0
28. [28]
  B. Lin, L. Fan, J. Ge, et al., Analyst 143 (2018) 5054–5060. doi: 10.1039/c8an01371c
29. [29]
  J. Hou, W. Ren, K. Li, et al., Chem. Soc. Rev. 46 (2017) 2076–2090. doi: 10.1039/C6CS00719H
30. [30]
  C. Benitez-Martin, J. Guadix, J. Pearson, ACS Sens. 5 (2020) 1068–1074. doi: 10.1021/acssensors.9b02590
31. [31]
  B. Lin, L. Fan, Y. Zhou, et al., J. Mater. Chem. B 8 (2020) 10586–10592. doi: 10.1039/d0tb01253j
32. [32]
  L. Shi, S. Yang, H. Hong, et al., Anal. Chim. Acta 1094 (2020) 122–129. doi: 10.1016/j.aca.2019.10.004
33. [33]
  Z. Xu, S. Han, C. Lee, et al., Chem. Commun. 46 (2010) 1679–1681. doi: 10.1039/b924503k
34. [34]
  T. Ren, W. Xu, W. Zhang, et al., J. Am. Chem. Soc. 140 (2018) 7716–7722. doi: 10.1021/jacs.8b04404
35. [35]
  K. Joong, H. Ho, K. Myung, J. Am. Chem. Soc. 135 (2013) 17969–17977. doi: 10.1021/ja409971k
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