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
1. [1]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
2. [2]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
3. [3]
  Haixian Ren , Yuting Du , Xiaojing Yang , Fangjun Huo , Le Zhang , Caixia Yin . Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl. Chinese Chemical Letters, 2025, 36(2): 109867-. doi: 10.1016/j.cclet.2024.109867
4. [4]
  Chuyu Huang , Zhishan Liu , Linping Zhao , Zuxiao Chen , Rongrong Zheng , Xiaona Rao , Yuxuan Wei , Xin Chen , Shiying Li . Metal-coordinated oxidative stress amplifier to suppress tumor growth combined with M2 macrophage elimination. Chinese Chemical Letters, 2024, 35(12): 109696-. doi: 10.1016/j.cclet.2024.109696
5. [5]
  Huiyang Chen , Zibo Li , Xiaoying Li , Chenhong Tang , Xiaoyu Liu , Minyi Nie , Ying Huang , Xiaoyu Chen , Kuncai Liu , Yilan Dai , Qiaoling Zhang , Ling Lin , Siming Zhang , Bingchen Zhang , Zhiqiang Yu . A novel mitochondria-targeted nanoprodrug amplifies oxidative stress to enhance cisplatin chemotherapy for the treatment of hepatocellular carcinoma. Chinese Chemical Letters, 2025, 36(10): 111313-. doi: 10.1016/j.cclet.2025.111313
6. [6]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
7. [7]
  Xingyu Chen , Sihui Zhuang , Weiyao Yan , Zhengli Zeng , Jianguo Feng , Hongen Cao , Lei Yu . Synthesis, antibacterial evaluation, and safety assessment of Se@PLA as a potent bactericide against Xanthomonas oryzae pv. oryzae. Chinese Chemical Letters, 2024, 35(10): 109635-. doi: 10.1016/j.cclet.2024.109635
8. [8]
  Qiang Luo , Jinfeng Sun , Zhibo Li , Bin Liu , Jianxun Ding . Thermo-sensitive poly(amino acid) hydrogel mediates cytoprotection through an antioxidant mechanism. Chinese Chemical Letters, 2025, 36(7): 110433-. doi: 10.1016/j.cclet.2024.110433
9. [9]
  Ruimiao Chang , Xinying Qu , Yuting Ye , Ying Qu , Bingyang Chu , Zhiyong Qian . Current advances in nanomedicine-based therapies for acute kidney injury. Chinese Chemical Letters, 2025, 36(10): 110802-. doi: 10.1016/j.cclet.2024.110802
10. [10]
  Jianye Kang , Xinyu Yang , Xuhao Yang , Jiahui Sun , Yuhang Liu , Shutao Wang , Wenlong Song . Carbon dots-enhanced pH-responsive lubricating hydrogel based on reversible dynamic covalent bondings. Chinese Chemical Letters, 2024, 35(5): 109297-. doi: 10.1016/j.cclet.2023.109297
11. [11]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 2309027-0. doi: 10.3866/PKU.WHXB202309027
12. [12]
  Xiangdong Lai , Tengfei Liu , Zengchao Guo , Yihan Wang , Jiang Xiao , Qingxiu Xia , Xiaohui Liu , Hui Jiang , Xuemei Wang . In situ formed fluorescent gold nanoclusters inhibit hair follicle regeneration in oxidative stress microenvironment via suppressing NFκB signal pathway. Chinese Chemical Letters, 2025, 36(2): 109762-. doi: 10.1016/j.cclet.2024.109762
13. [13]
  Fengyao Cui , Qiaona Zhang , Tangxin Xiao , Zhouyu Wang , Leyong Wang . Reversible phosphorescence in pseudopolyrotaxane elastomer. Chinese Chemical Letters, 2024, 35(10): 110061-. doi: 10.1016/j.cclet.2024.110061
14. [14]
  Faqiong Zhao , Xiaohang Qiu , Yanping Ren , Juanjuan Song , Dongcheng Liu , Xiuqiong Zeng , Wenwei Zhang , Mei Shi , Min Hu , Wan Li , Yongxian Fan , Yiru Wang , Xiuyun Wang , Weihong Li , Yong Fan , Jianrong Zhang , Shuyong Zhang . The Use of pH Indicator Papers and pH Meters. University Chemistry, 2025, 40(5): 32-39. doi: 10.12461/PKU.DXHX202503099
15. [15]
  Min Liu , Bin Feng , Feiyi Chu , Duoyang Fan , Fan Zheng , Fei Chen , Wenbin Zeng . An ESIPT-boosted NIR nanoprobe for ratiometric sensing of carbon monoxide via activatable aggregation-induced dual-color fluorescence. Chinese Chemical Letters, 2025, 36(5): 110043-. doi: 10.1016/j.cclet.2024.110043
16. [16]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
17. [17]
  Chen-Xin Wang , Guang-Lei Li , Yu Hang , Dan-Feng Lu , Jian-Qi Ye , Hao Su , Bing Hou , Tao Suo , Dan Wen . Shock-resistant wearable pH sensor based on tungsten oxide aerogel. Chinese Chemical Letters, 2025, 36(7): 110502-. doi: 10.1016/j.cclet.2024.110502
18. [18]
  Jie Zhou , Quanyu Li , Xiaomeng Hu , Weifeng Wei , Xiaobo Ji , Guichao Kuang , Liangjun Zhou , Libao Chen , Yuejiao Chen . Water molecules regulation for reversible Zn anode in aqueous zinc ion battery: Mini-review. Chinese Chemical Letters, 2024, 35(8): 109143-. doi: 10.1016/j.cclet.2023.109143
19. [19]
  Guoxing Liu , Yixin Li , Changming Tian , Yongmei Xiao , Lijie Liu , Zhanqi Cao , Song Jiang , Xin Zheng , Caoyuan Niu , Yun-Lai Ren , Liangru Yang , Xianfu Zheng , Yong Chen . Highly reversible photomodulated hydrosoluble stiff-stilbene supramolecular luminophor induced by cucurbituril. Chinese Chemical Letters, 2024, 35(8): 109403-. doi: 10.1016/j.cclet.2023.109403
20. [20]
  Yan Wang , Si-Meng Zhai , Peng Luo , Xi-Yan Dong , Jia-Yin Wang , Zhen Han , Shuang-Quan Zang . Vapor- and temperature-triggered reversible optical switching for multi-response Cu₈ cluster supercrystals. Chinese Chemical Letters, 2024, 35(11): 109493-. doi: 10.1016/j.cclet.2024.109493

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(1954)
HTML views(53)

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