Citation: Tiancong Shi, Xi Chen, Xiao Zhou, Hongyi Zhang, Fuping Han, Lihan Cai, Wen Sun, Jianjun Du, Jiangli Fan, Xiaojun Peng. Azaindole-based asymmetric pentamethine cyanine dye for mitochondrial pH detection and near-infrared ratiometric fluorescence imaging of mitophagy[J]. Chinese Chemical Letters, ;2025, 36(6): 110408. doi: 10.1016/j.cclet.2024.110408 shu

Azaindole-based asymmetric pentamethine cyanine dye for mitochondrial pH detection and near-infrared ratiometric fluorescence imaging of mitophagy

Tiancong Shi ^{a, 1} ,
Xi Chen ^{a, 1} ,
Xiao Zhou ^a ,
Hongyi Zhang ^a ,
Fuping Han ^a ,
Lihan Cai ^a ,
Wen Sun ^{a, b} ,
Jianjun Du ^{a, b, *,} ,
Jiangli Fan ^{a, b, *,} ,
Xiaojun Peng ^a

a.
State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, Dalian University of Technology, Dalian 116024, China
b.
Ningbo Institute of Dalian University of Technology, Ningbo 315016, China

dujj@dlut.edu.cn

fanjl@dlut.edu.cn

Received Date: 8 July 2024
Revised Date: 30 August 2024
Accepted Date: 3 September 2024
Available Online: 3 September 2024

Figures(4)

Mitochondria are crucial organelles responsible for maintaining cell growth, and their homeostasis is closely linked to pH regulation. Physiologically, mitochondria exhibit a weakly alkaline state (pH~8.0). However, when subjected to stress stimuli that cause damage, cells initiate the process of mitophagy, resulting in mitochondrial acidification. Therefore, monitoring changes in mitochondrial pH to comprehend the physiological processes associated with mitophagy is essential. In this study, we developed an asymmetric pentamethine cyanine dye Cy5.5-H-CyN as a probe for continuous monitoring of mitophagy in living cells. By incorporating an azaindole structure into the dye molecule, a ratiometric fluorescence response was achieved that is specifically responsive to pH variations while preserving its ability to target mitochondria and emit near-infrared fluorescence. Through various methods inducing mitophagy, Cy5.5-H-CyN was employed to determine mitochondrial pH quantitatively, demonstrating its suitability as an ideal probe for continuous monitoring of mitophagy in living cells.
- Asymmetric cyanine dye,
- pH probe,
- Mitochondria-targeting,
- Ratiometric fluorescence,
- Mitophagy
1. [1]
  J. Nunnari, A. Suomalainen, Cell 148 (2012) 1145–1159. doi: 10.1016/j.cell.2012.02.035
2. [2]
  A. Picca, J. Faitg, J. Auwerx, L. Ferrucci, D. D'Amico, Nat. Metab. 5 (2023) 2047–2061. doi: 10.1038/s42255-023-00930-8
3. [3]
  H.M. Ni, J.A. Williams, W.X. Ding, Redox Biol. 4 (2015) 6–13. doi: 10.1016/j.redox.2014.11.006
4. [4]
  R.J. Youle, D.P. Narendra, Nat. Rev. Mol. Cell Biol. 12 (2011) 9–14. doi: 10.1038/nrm3028
5. [5]
  L. Wang, B. Chen, P. Peng, et al., Chin. Chem. Lett. 28 (2017) 1965–1968. doi: 10.1016/j.cclet.2017.07.016
6. [6]
  R. Yadav, S. Munan, M. Ali, K. Mapa, A. Samanta, Chem. Asian J. 18 (2023) e202300308. doi: 10.1002/asia.202300308
7. [7]
  P. Ning, W. Wang, M. Chen, et al., Chin. Chem. Lett. 28 (2017) 1943–1951. doi: 10.1016/j.cclet.2017.09.026
8. [8]
  S. Munan, M. Ali, R. Yadav, K. Mapa, A. Samanta, Anal. Chem. 94 (2022) 11633–11642. doi: 10.1021/acs.analchem.2c02177
9. [9]
  Y. Zhang, Y. Chen, H. Fang, et al., J. Mater. Chem. B 10 (2022) 5422–5429. doi: 10.1039/D2TB00553K
10. [10]
  Y. Zhang, Z. Li, W. Hu, Z. Liu, Anal. Chem. 91 (2019) 10302–10309. doi: 10.1021/acs.analchem.9b02678
11. [11]
  M.H. Lee, N. Park, C. Yi, et al., J. Am. Chem. Soc. 136 (2014) 14136–14142. doi: 10.1021/ja506301n
12. [12]
  W. Shu, J. Yu, Z. Li, et al., Sens. Actuators B: Chem. 369 (2022) 132323. doi: 10.1016/j.snb.2022.132323
13. [13]
  C. Yan, L. Shi, Z. Guo, et al., Chin. Chem. Lett. 30 (2019) 1849–1855. doi: 10.1016/j.cclet.2019.08.038
14. [14]
  F. Han, S.A. Abbas Abedi, S. He, et al., Adv. Sci. 11 (2024) 2305761. doi: 10.1002/advs.202305761
15. [15]
  H. Ma, Y. Lu, Z. Huang, et al., J. Am. Chem. Soc. 144 (2022) 3477–3486. doi: 10.1021/jacs.1c11886
16. [16]
  W. Sun, S. Guo, C. Hu, J. Fan, X. Peng, Chem. Rev. 116 (2016) 7768–7817. doi: 10.1021/acs.chemrev.6b00001
17. [17]
  Y. Ma, Y. Liu, Z. Jiang, et al., Sens. Actuators B: Chem. 349 (2021) 130747. doi: 10.1016/j.snb.2021.130747
18. [18]
  Y. Liu, J. Zhou, L. Wang, et al., J. Am. Chem. Soc. 138 (2016) 12368–12374. doi: 10.1021/jacs.6b04048
19. [19]
  H. Huang, D. Huang, M. Li, et al., Dyes Pigm. 177 (2020) 108284. doi: 10.1016/j.dyepig.2020.108284
20. [20]
  Y. Wang, Z. Lei, C. Wang, et al., RSC Adv. 11 (2021) 17871–17879. doi: 10.1039/d1ra02217b
21. [21]
  J.R. Hou, D. Jin, B. Chen, et al., Chin. Chem. Lett. 28 (2017) 1681–1687. doi: 10.1016/j.cclet.2017.03.037
22. [22]
  R. Wang, Y. Xing, R. Wang, et al., Coord. Chem. Rev. 513 (2024) 215866. doi: 10.1016/j.ccr.2024.215866
23. [23]
  J. Huang, J. Huang, P. Cheng, Y. Jiang, K. Pu, Adv. Funct. Mater. 30 (2020) 2003628. doi: 10.1002/adfm.202003628
24. [24]
  T. Lu, F. Chen, J. Comput. Chem. 33 (2012) 580–592. doi: 10.1002/jcc.22885
25. [25]
  Z. Liu, T. Lu, Q. Chen, Carbon N Y 165 (2020) 468–475. doi: 10.1016/j.carbon.2020.04.099
26. [26]
  X. Li, Y. Hu, X. Li, H. Ma, Anal. Chem. 91 (2019) 11409–11416. doi: 10.1021/acs.analchem.9b02782
27. [27]
  X. Luo, W. Xiang, Y. Lu, et al., Chem. Eng. J. 488 (2024) 151169. doi: 10.1016/j.cej.2024.151169
28. [28]
  Q. Wang, T. Yang, S. Li, et al., Research 6 (2023) 0223. doi: 10.34133/research.0223
29. [29]
  Y. Chen, C. Zhu, J. Cen, et al., Chem. Sci. 6 (2015) 3187–3194. doi: 10.1039/C4SC04021J
30. [30]
  S.K. Dwivedi, D.L. Arachchige, T. Vohs, et al., J. Mater. Chem. B 11 (2023) 2852–2861. doi: 10.1039/d2tb02791g
1. [1]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
2. [2]
  Mingyue Luo , Kehui Zhang , Honghong Rao , Jianying Li , Xin Xue , Panpan Sun , Xiaoquan Lu , Zhonghua Xue . A simplified ratiometric fluorescent sensing strategy for enhanced detection of alkaline phosphatase employing Prussian blue nanozymes and commercially available chromogen. Chinese Chemical Letters, 2025, 36(9): 110703-. doi: 10.1016/j.cclet.2024.110703
3. [3]
  Li Li , Lin-Lin Zhang , Yansha Gao , Lu-Ying Duan , Wuying Yang , Xigen Huang , Yanping Hong , Jiaxin Hong , Lin Yuan , Limin Lu . Target self-calibration ratiometric fluorescent sensor based on facile-synthesized europium metal-organic framework for multi-color visual detection of levofloxacin. Chinese Chemical Letters, 2025, 36(7): 110436-. doi: 10.1016/j.cclet.2024.110436
4. [4]
  Zhoupeng Zheng , Shengyi Gong , Qianhua Li , Shiya Zhang , Guoqiang Feng . Lipid droplets and gallbladder targeted fluorescence probe for ratiometric NO imaging in gallstones disease models. Chinese Chemical Letters, 2025, 36(5): 110191-. doi: 10.1016/j.cclet.2024.110191
5. [5]
  Quan Lu , Lulu Zhang , Zihan Chen , Jiajia Lv , Jie Gao , Xinmin Li , Hongyu Li , Wen Shi , Xiaohua Li , Huimin Ma , Zeli Yuan . A lipid droplet-targeting fluorescence probe for monitoring of lipid peroxidation in ferroptosis and non-alcoholic fatty liver disease. Chinese Chemical Letters, 2025, 36(8): 110620-. doi: 10.1016/j.cclet.2024.110620
6. [6]
  Xianghan Zhang , Yuan Qin , Huaicong Zhang , Yutian Cao , Haixing Zhu , Yingdi Tang , Zimeng Ma , Zehua Li , Jialin Zhou , Qunyan Dong , Peng Yang , Yuqiong Xia , Zhongliang Wang . An aggregation-independent and rotor-specific TPE-cyanine probe for in vivo near-infrared fluorescent imaging. Chinese Chemical Letters, 2025, 36(9): 110715-. doi: 10.1016/j.cclet.2024.110715
7. [7]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
8. [8]
  Meitong Wu , Ke Wu , Shumin Feng , Li Xu , Mi Lei , Jianmei Chen , Shuang Li , Mian Qin , Dahui Liu , Guoqiang Feng . A NIR and ratiometric fluorescent probe for quantitative detection of SO₂ derivatives in Chinese medicinal materials and bioimaging in vivo. Chinese Chemical Letters, 2026, 37(1): 110979-. doi: 10.1016/j.cclet.2025.110979
9. [9]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
10. [10]
  Yu Zhang , Shan Lei , Yuantao Pan , Chao Zhao , Qiang Liu , Yumeng Wu , Yurong Liu , Meng Li , Peng Huang , Jing Lin . In vivo second near-infrared fluorescence and ratiometric photoacoustic dual-modality imaging of glutathione. Chinese Chemical Letters, 2026, 37(2): 110977-. doi: 10.1016/j.cclet.2025.110977
11. [11]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
12. [12]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
13. [13]
  Fengzhi Wang , Ke Hu , Jinquan Chen , Zhubin Hu , Haitao Sun , Tony D. James , Yufang Xu , Xuhong Qian . Meta-amino substituted naphthalimides exhibit large charge transfer and strong N-H vibrations enabling use as ratiometric fluorescent probe. Chinese Chemical Letters, 2026, 37(1): 110971-. doi: 10.1016/j.cclet.2025.110971
14. [14]
  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
15. [15]
  Luolin Wang , Xing Liang , Hanwen Chi , Weiying Lin . A dual-targeted near-infrared fluorescence lifetime probe for detecting viscosity heterogeneity in arthritic mice. Chinese Chemical Letters, 2025, 36(12): 110962-. doi: 10.1016/j.cclet.2025.110962
16. [16]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
17. [17]
  Zhaorui Song , Qiulian Hao , Bing Li , Yuwei Yuan , Shanshan Zhang , Yongkuan Suo , Hai-Hao Han , Zhen Cheng . NIR-Ⅱ fluorescence lateral flow immunosensor based on efficient energy transfer probe for point-of-care testing of tumor biomarkers. Chinese Chemical Letters, 2025, 36(1): 109834-. doi: 10.1016/j.cclet.2024.109834
18. [18]
  Qiuye Wang , Yabing Sun , Liangxue Lai , Haijing Cui , Yonglong Ye , Ming Yang , Weihao Zhu , Bo Yuan , Quanliang Mao , Wenzhi Ren , Aiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212
19. [19]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1135)
HTML views(31)

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