Citation: Wen Jia, Xia Pengyi, Zheng Ziming, Xu Yongqian, Li Hongjuan, Liu Fengyu, Sun Shiguo. Naphthalimide-rhodamine based fluorescent probe for ratiometric sensing of cellular pH[J]. Chinese Chemical Letters, ;2017, 28(10): 2005-2008. doi: 10.1016/j.cclet.2017.09.014 shu

Naphthalimide-rhodamine based fluorescent probe for ratiometric sensing of cellular pH

Wen Jia ^a,1 ,
Xia Pengyi ^a,1 ,
Zheng Ziming ^a ,
Xu Yongqian ^a ,
Li Hongjuan ^a ,
Liu Fengyu ^b,, ,
Sun Shiguo ^a,,

a.
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, China
b.
State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian 116023, China

Corresponding author: Liu Fengyu, liufengyu@dlut.edu.cn Sun Shiguo, sunsg@nwsuaf.edu.cn

Received Date: 11 July 2017
Revised Date: 3 September 2017
Accepted Date: 5 September 2017
Available Online: 8 October 2017

Figures(4)

The pH values of lysosomes in cancer cells is slightly lower than that in normal cells, which can be used to distinguish cancer cells from normal cells. According to this, a naphthalimide-rhodamine based fluorescent probe (hereafter referred to as RBN) with a pK_a of 4.20 was designed and synthesized for ratiometric sensing of cellular pH via fluorescence resonance energy transfer (FRET), which can respond to different pH precisely through ratiometric fluorescence intensity (I₅₇₇/I₅₄₀). RBN can be employed to distinguish cancer cells from normal cells on the basis of different fluorescent response, in particular, RBN showed excellent water solubility and low cell toxicity, all these are quite significant for potential application in cancer diagnose and therapy.
- Naphthalimide-rhodamine derivative,
- Cellular pH,
- Ratiometric detection,
- Imaging,
- Fluorescence resonance energy transfer (FRET)
1. [1]
  J.R. Casey, S. Grinstein, J. Orlowski, Nat. Rev. Mol. Cell Biol. 11(2010) 50-61. doi: 10.1038/nrm2820
2. [2]
  H. Izumi, T. Torigoe, H. Ishiguchi, et al., Cancer Treat. Rev. 29(2003) 541-549. doi: 10.1016/S0305-7372(03)00106-3
3. [3]
  G.K. Vegesna, J. Janjanam, J. Bi, et al., J. Mater. Chem. B 2(2014) 4500-4508. doi: 10.1039/C4TB00475B
4. [4]
  F. Yu, Y. Wang, W. Zhu, et al., RSC Adv. 4(2014) 36849-36853. doi: 10.1039/C4RA06834C
5. [5]
  J. Han, K. Burgess, Chem. Rev. 110(2009) 2709-2728.
6. [6]
  D.D. He, W. Liu, R. Sun, et al., Anal. Chem. 87(2015) 1499-1502. doi: 10.1021/ac5045912
7. [7]
  X.F. Zhang, T. Zhang, S.L. Shen, J.Y. Miao, B.X. Zhao, J. Mater. Chem. B 3(2015) 3260-3266. doi: 10.1039/C4TB02082K
8. [8]
  M.H. Lee, N. Park, C. Yi, et al., J. Am. Chem. Soc. 136(2014) 14136-14142. doi: 10.1021/ja506301n
9. [9]
  J.Y. Han, K. Burgess, Chem. Rev. 110(2010) 2709-2728. doi: 10.1021/cr900249z
10. [10]
  Y. Long, J. Zhou, M.P. Yang, B.Q. Yang, Chin. Chem. Lett. 27(2016) 205-210. doi: 10.1016/j.cclet.2015.09.003
11. [11]
  Q.J. Luo, Y.X. Li, M.Q. Zhang, P. Qiu, Y.H. Deng, Chin. Chem. Lett. 28(2017) 345-349. doi: 10.1016/j.cclet.2016.10.024
12. [12]
  Y. Gao, J.L. Li, Z. Shi, Chin. Chem. Lett. 18(2007) 667-669. doi: 10.1016/j.cclet.2007.04.007
13. [13]
  H.R. Cheng, Y. Qian, Chin. Chem. Lett. 27(2016) 879-886. doi: 10.1016/j.cclet.2016.01.039
14. [14]
  X.M. Li, R.R. Zhao, Y.L. Wei, et al., Chin. Chem. Lett. 27(2016) 813-816. doi: 10.1016/j.cclet.2016.04.001
15. [15]
  X.M. Li, R.R. Zhao, Y. Yang, et al., Chin. Chem. Lett. 28(2017) 1258-1261. doi: 10.1016/j.cclet.2016.12.029
16. [16]
  K.K. Yu, K. Li, J.T. Hou, et al., RSC Adv. 4(2014) 33975-33980. doi: 10.1039/C4RA05215C
17. [17]
  R. Zhang, F. Yan, Y. Huang, et al., RSC Adv. 6(2016) 50732-50760. doi: 10.1039/C6RA06956H
18. [18]
  Y. Yang, C.Y. Gao, J. Liu, D. Dong, Anal. Methods U. K. 8(2016) 2863-2871. doi: 10.1039/C6AY00135A
19. [19]
  X.X. Zhao, X.P. Chen, S.L. Shen, et al., RSC Adv. 4(2014) 50318-50324. doi: 10.1039/C4RA07555B
20. [20]
  Z. Li, S. Wu, J. Han, S. Han, Analyst 136(2011) 3698-3706. doi: 10.1039/c1an15108h
21. [21]
  K.K. Yu, K. Li, J.T. Hou, et al., RSC Adv. 4(2014) 33975-33980. doi: 10.1039/C4RA05215C
22. [22]
  Z. Xue, M. Chen, J. Chen, J. Han, S. Han, RSC Adv. 4(2014) 374-378. doi: 10.1039/C3RA45329D
23. [23]
  X.L. Shi, G.J. Mao, X.B. Zhang, et al., Talanta 130(2014) 356-362. doi: 10.1016/j.talanta.2014.07.030
24. [24]
  X.X. Zhao, X.P. Chen, S.L. Shen, et al., RSC Adv. 4(2014) 50318-50324. doi: 10.1039/C4RA07555B
25. [25]
  S.L. Shen, X.P. Chen, X.F. Zhang, J.Y. Miao, B.X. Zhao, J. Mater. Chem. B 3(2015) 919-925.
26. [26]
  B. Li, G.B. Ge, L.L. Wen, et al., Dyes Pigm. 139(2017) 318-325. doi: 10.1016/j.dyepig.2016.12.043
27. [27]
  N. Lin, Q. Zhang, X. Xia, et al., RSC Adv. 7(2017) 21446-21451. doi: 10.1039/C6RA28551A
28. [28]
  Y. Zhang, B. Li, H. Ma, L. Zhang, W. Zhang, J. Mater. Chem. C 5(2017) 4661-4669. doi: 10.1039/C7TC00936D
29. [29]
  T.F. Brewer, G. Burgos-Barragan, N. Wit, K.J. Patel, C.J. Chang, Chem. Sci. 8(2017) 4073-4081. doi: 10.1039/C7SC00748E
30. [30]
  P.F. Xing, Y.Q. Xu, H.J. Li, et al., Sci. Rep. 5(2015) 16528. doi: 10.1038/srep16528
31. [31]
  S.G. Sun, B. Qiao, N. Jiang, et al., Org. Lett. 16(2014) 1132-1135. doi: 10.1021/ol500284p
32. [32]
  L. Liu, P. Guo, L. Chai, et al., Sens. Actuators B:Chem. 194(2014) 498-502. doi: 10.1016/j.snb.2013.12.023
33. [33]
  X.F. Zhang, T. Zhang, S.L. Shen, J.Y. Miao, B.X. Zhao, RSC Adv. 5(2015) 49115-49121. doi: 10.1039/C5RA06246B
34. [34]
  J.L. Tan, M.X. Zhang, F. Zhang, et al., Spectrochim. Acta A 140(2015) 489-494. doi: 10.1016/j.saa.2014.12.110
35. [35]
  J. Zhang, G. Li, C. Kang, et al., Dyes Pigm. 115(2015) 181-189. doi: 10.1016/j.dyepig.2015.01.002
36. [36]
  N.Z. Xu, M.M. Liu, M.A. Ye, et al., J. Lumin. 188(2017) 135-140. doi: 10.1016/j.jlumin.2017.03.067
37. [37]
  R. de Levie, J. Chem. Educ. 80(2003) 146-146. doi: 10.1021/ed080p146
38. [38]
  P. Wang, J. Liu, X. Lv, et al., Org. Lett. 14(2012) 520-523. doi: 10.1021/ol203123t
1. [1]
  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
2. [2]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
3. [3]
  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
4. [4]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
5. [5]
  Siwei Wang , Wei-Lei Zhou , Yong Chen . Cucurbituril and cyclodextrin co-confinement-based multilevel assembly for single-molecule phosphorescence resonance energy transfer behavior. Chinese Chemical Letters, 2024, 35(12): 110261-. doi: 10.1016/j.cclet.2024.110261
6. [6]
  Xu Qu , Pengzhao Wu , Kaixuan Duan , Guangwei Wang , Liang-Liang Gao , Yuan Guo , Jianjian Zhang , Donglei Shi . Self-calibrating probes constructed on a unique dual-emissive fluorescence platform for the precise tracking of cellular senescence. Chinese Chemical Letters, 2024, 35(12): 109681-. doi: 10.1016/j.cclet.2024.109681
7. [7]
  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
8. [8]
  Hualei Xu , Manman Han , Haiqiang Liu , Liang Qin , Lulu Chen , Hao Hu , Ran Wu , Chenyu Yang , Hua Guo , Jinrong Li , Jinxiang Fu , Qichen Hao , Yijun Zhou , Jinchao Feng , Xiaodong Wang . 4-Nitrocatechol as a novel matrix for low-molecular-weight compounds in situ detection and imaging in biological tissues by MALDI-MSI. Chinese Chemical Letters, 2024, 35(6): 109095-. doi: 10.1016/j.cclet.2023.109095
9. [9]
  Shuang Li , Jiayu Sun , Guocheng Liu , Shuo Zhang , Zhong Zhang , Xiuli Wang . A new Keggin-type polyoxometallate-based bifunctional catalyst for trace detection and pH-universal photodegradation of phenol. Chinese Chemical Letters, 2024, 35(8): 109148-. doi: 10.1016/j.cclet.2023.109148
10. [10]
  Peide Zhu , Yangjia Liu , Yaoyao Tang , Siqi Zhu , Xinyang Liu , Lei Yin , Quan Liu , Zhiqiang Yu , Quan Xu , Dixian Luo , Juncheng Wang . Bi-doped carbon quantum dots functionalized liposomes with fluorescence visualization imaging for tumor diagnosis and treatment. Chinese Chemical Letters, 2024, 35(4): 108689-. doi: 10.1016/j.cclet.2023.108689
11. [11]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
12. [12]
  Biao Huang , Tao Tang , Fushou Liu , Shi-Hui Chen , Zhi-Ling Zhang , Mingxi Zhang , Ran Cui . Quantum dots boost large-view NIR-Ⅱ imaging with high fidelity for fluorescence-guided tumor surgery. Chinese Chemical Letters, 2024, 35(12): 109694-. doi: 10.1016/j.cclet.2024.109694
13. [13]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
14. [14]
  Xiaoyao Ma , Jinling Zhang , Ge Fang , He Gao , Jie Gao , Li Fu , Yuanyuan Hou , Gang Bai . Förster resonance energy transfer reveals phillygenin and swertiamarin concurrently target AKT on different binding domains to increase the anti-inflammatory effect. Chinese Chemical Letters, 2024, 35(5): 108823-. doi: 10.1016/j.cclet.2023.108823
15. [15]
  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
16. [16]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
17. [17]
  Shihong Wu , Ronghui Zhou , Hang Zhao , Peng Wu . Sonoafterglow luminescence for in vivo deep-tissue imaging. Chinese Chemical Letters, 2024, 35(10): 110026-. doi: 10.1016/j.cclet.2024.110026
18. [18]
  Zhiqiang Liu , Qiang Gao , Wei Shen , Meifeng Xu , Yunxin Li , Weilin Hou , Hai-Wei Shi , Yaozuo Yuan , Erwin Adams , Hian Kee Lee , Sheng Tang . Removal and fluorescence detection of antibiotics from wastewater by layered double oxides/metal-organic frameworks with different topological configurations. Chinese Chemical Letters, 2024, 35(8): 109338-. doi: 10.1016/j.cclet.2023.109338
19. [19]
  Jia-Li Xie , Tian-Jin Xie , Yu-Jie Luo , Kai Mao , Cheng-Zhi Huang , Yuan-Fang Li , Shu-Jun Zhen . Octopus-like DNA nanostructure coupled with graphene oxide enhanced fluorescence anisotropy for hepatitis B virus DNA detection. Chinese Chemical Letters, 2024, 35(6): 109137-. doi: 10.1016/j.cclet.2023.109137
20. [20]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(799)
HTML views(39)

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