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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Yijian Zhao , Jvzhe Li , Yunyi Shi , Jie Hu , Meiyi Liu , Yao Shen , Xinglin Hou , Qiuyue Wang , Qi Wang , Zhiyi Yao . A label-free and ratiometric fluorescent sensor based on porphyrin-metal-organic frameworks for sensitive detection of ochratoxin A in cereal. Chinese Chemical Letters, 2025, 36(4): 110132-. doi: 10.1016/j.cclet.2024.110132
14. [14]
  Baoli Yin , Xinlin Liu , Zhe Li , Zhifei Ye , Youjuan Wang , Xia Yin , Sulai Liu , Guosheng Song , Shuangyan Huan , Xiao-Bing Zhang . Ratiometric NIR-Ⅱ fluorescent organic nanoprobe for imaging and monitoring tumor-activated photodynamic therapy. Chinese Chemical Letters, 2025, 36(5): 110119-. doi: 10.1016/j.cclet.2024.110119
15. [15]
  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
16. [16]
  Wenkai Liu , Yanxian Hou , Weijian Liu , Ran Wang , Shan He , Xiang Xia , Chengyuan Lv , Hua Gu , Qichao Yao , Qingze Pan , Zehou Su , Danhong Zhou , Wen Sun , Jiangli Fan , Xiaojun Peng . Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process. Chinese Chemical Letters, 2024, 35(12): 109631-. doi: 10.1016/j.cclet.2024.109631
17. [17]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
18. [18]
  Han Han , Bi-Te Chen , Jia-Rong Ding , Jin-Ming Si , Tian-Jiao Zhou , Yi Wang , Lei Xing , Hu-Lin Jiang . A PDGFRβ-targeting nanodrill system for pancreatic fibrosis therapy. Chinese Chemical Letters, 2024, 35(10): 109583-. doi: 10.1016/j.cclet.2024.109583
19. [19]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
20. [20]
  Zhihui Zhang , Ru Sun , Chong Bian , Hongbo Wang , Zhen Zhao , Panpan Lv , Jianzhong Lu , Haixin Zhang , Hulie Zeng , Yuanyuan Chen , Zhijuan Cao . A dual-protease-triggered chemiluminescent probe for precise tumor imaging. Chinese Chemical Letters, 2025, 36(2): 109784-. doi: 10.1016/j.cclet.2024.109784

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(152)
HTML views(3)

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