Citation: Wang Liulin, Chen Buxiang, Peng Pingping, Hu Wenbo, Liu Zhipeng, Pei Xiaohua, Zhao Weihong, Zhang Chengwu, Li Lin, Huang Wei. Fluorescence imaging mitochondrial copper(Ⅱ) via photocontrollable fluorogenic probe in live cells[J]. Chinese Chemical Letters, ;2017, 28(10): 1965-1968. doi: 10.1016/j.cclet.2017.07.016 shu

Fluorescence imaging mitochondrial copper(Ⅱ) via photocontrollable fluorogenic probe in live cells

Wang Liulin ^a ,
Chen Buxiang ^a ,
Peng Pingping ^a ,
Hu Wenbo ^a ,
Liu Zhipeng ^a ,
Pei Xiaohua ^b ,
Zhao Weihong ^b ,
Zhang Chengwu ^a ,
Li Lin ^a,, ,
Huang Wei ^a,c,,

a.
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University (NanjingTech), Nanjing 211816, China
b.
Division of Nephrology, Department of Geriatrics, The First Affiliated Hospital of Nanjing Medical University, Nanjing 210009, China
c.
Key Laboratory for Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, China

Corresponding author: Li Lin, iamlli@njtech.edu.cn Huang Wei, iamwhuang@njtech.edu.cn
Received Date: 27 April 2017
Revised Date: 10 July 2017
Accepted Date: 12 July 2017
Available Online: 17 October 2017

Figures(4)

Monitoring mitochondrial derived copper(Ⅱ) in live cells is highly demanded, but accurately detecting is unmet due to the interference with cytoplasmic copper(Ⅱ). Herein, we have reported the design, synthesis and characterization of photocontrollable fluorogenic probe, M_Cu-3, which is equipped with a photo-labile group (nitrobenzyl group) and mitochondria targeting unit (triphenylphosphonium salt). This novel probe showed an intense fluorescence enhancement in response to copper(Ⅱ) without interference from other metal cations in the biological condition (pH 6-9). The detection limit is 1.7×10^-7 mol/L in HEPES buffer. The confocal fluorescence imaging results demonstrated M_Cu-3 can visualize mitochondrial copper(Ⅱ) in live mammalian cells. The clear advantage of our photocontrollable method is successful to avoid the influence of cytoplasmic copper(Ⅱ) during mitochondria specific detection.
- Mitochondria,
- Photocontrollable,
- Fluorogenic probe,
- Fluorescence imaging,
- Copper (Ⅱ)
1. [1]
  R.A. Smith, M.P. Murphy, et al., Trends Pharmacol. Sci. 33(2012) 341-352. doi: 10.1016/j.tips.2012.03.010
2. [2]
  S.R. Jean, S.O. Kelley, et al., Acc. Chem. Res. 49(2016) 1893-1902. doi: 10.1021/acs.accounts.6b00277
3. [3]
  D.C. Wallace, Nat. Rev. Cancer 12(2012) 685-698. doi: 10.1038/nrc3365
4. [4]
  S.R. Jean, D.V. Tulumello, et al., ACS Chem. Biol. 9(2014) 323-333. doi: 10.1021/cb400821p
5. [5]
  G.J. Farrar, N. Chadderton, P.F. Kenna, S. Millington-Ward, Trends Genet. 29(2013) 488-497. doi: 10.1016/j.tig.2013.05.005
6. [6]
  M.R. Duchen, G. Szabadkai, Essays Biochem. 47(2010) 115-137. doi: 10.1042/bse0470115
7. [7]
  A.T. Hoye, J.E. Davoren, et al., Acc. Chem. Res. 41(2008) 87-97. doi: 10.1021/ar700135m
8. [8]
  J. Nunnari, A. Suomalainen, Cell 148(2012) 1145. doi: 10.1016/j.cell.2012.02.035
9. [9]
  K. Henze, W. Martin, Nature 426(2003) 127-128. doi: 10.1038/426127a
10. [10]
  K. Hayakawa, E. Esposito, et al., Nature 535(2016) 551-555. doi: 10.1038/nature18928
11. [11]
  L.M. Gaetke, C.K. Chow, Toxicology 189(2003) 147-163. doi: 10.1016/S0300-483X(03)00159-8
12. [12]
  M.J. Hosseini, F. Shaki, M. Ghazi-Khansari, J. Pourahmad, Cell Biochem. Biophys. 70(2014) 367-381. doi: 10.1007/s12013-014-9922-7
13. [13]
  H. Büeler, Exp. Neurol. 218(2009) 235-246. doi: 10.1016/j.expneurol.2009.03.006
14. [14]
  S.S.Z. Zhang, M.M. Noordin, et al., Toxicology 42(2000) 261-264.
15. [15]
  I. Bremner, Am. J. Clin. Nutr. 67(1998) 1069S-1073S.
16. [16]
  L. Rossi, M.F. Lombardo, et al., Neurochem. Res. 29(2004) 493-504. doi: 10.1023/B:NERE.0000014820.99232.8a
17. [17]
  N.K. Isaev, E.V. Stelmashook, et al., Cell Mol. Neurobiol. 30(2010) 877. doi: 10.1007/s10571-010-9516-x
18. [18]
  G. Masanta, C.H. Heo, et al., Chem. Commun. 48(2012) 3518-3520. doi: 10.1039/c2cc00034b
19. [19]
  Y. Koide, Y. Urano, et al., J. Am. Chem. Soc. 129(2007) 10324-10325. doi: 10.1021/ja073220m
20. [20]
  Z.J. Chen, W. Ren, et al., J. Am. Chem. Soc. 135(2013) 14940-14943. doi: 10.1021/ja408011q
21. [21]
  B.C. Dickinson, C.J. Chang, J. Am. Chem. Soc. 130(2008) 9638-9639. doi: 10.1021/ja802355u
22. [22]
  J. Zhou, L.H. Li, et al., Chem. Sci. 6(2015) 4884-4888. doi: 10.1039/C5SC01562F
23. [23]
  M.D. Hammers, M.J. Taormina, et al., J. Am. Chem. Soc. 137(2015) 10216-10223. doi: 10.1021/jacs.5b04196
24. [24]
  W. Xu, C.L. Teoh, et al., Biomaterials 56(2015) 1. doi: 10.1016/j.biomaterials.2015.03.038
25. [25]
  C.S. Lim, G. Masanta, et al., J. Am. Chem. Soc. 133(2011) 11132-11135. doi: 10.1021/ja205081s
26. [26]
  R.A. Colvin, W.R. Holmes, et al., Metallomics 2(2010) 306-317. doi: 10.1039/b926662c
27. [27]
  M. Taki, K. Akaoka, et al., Org. Biomol. Chem. 12(2014) 4999-5005. doi: 10.1039/C4OB00527A
28. [28]
  W. Lin, L. Long, et al., Anal. Chim. Acta 634(2009) 262. doi: 10.1016/j.aca.2008.12.049
29. [29]
  Y. Shindo, T. Fujii, et al., PLOS One 6(2011) e23684. doi: 10.1371/journal.pone.0023684
30. [30]
  L. Li, C.W. Zhang, S.Q. Yao, et al., Nat. Commun. 5(2014) 3276.
31. [31]
  X.F. Wu, L.H. Li, et al., Anal. Chem. 88(2016) 1440-1446. doi: 10.1021/acs.analchem.5b04303
32. [32]
  M.H. Lee, N. Park, et al., J. Am. Chem. Soc. 136(2014) 14136-14142. doi: 10.1021/ja506301n
33. [33]
  Y. Kurishita, T. Kohira, et al., J. Am. Chem. Soc. 134(2012) 1877918789.
34. [34]
  F. Liu, T. Wu, et al., Chem. Eur. J. 19(2013) 1548-1553. doi: 10.1002/chem.201202646
35. [35]
  H.B. Yu, L.J. Jin, et al., Anal. Chem. 85(2013) 7076-7084. doi: 10.1021/ac401916z
36. [36]
  B.L. Wang, Y. Xiao, et al., Analyst 140(2015) 5488-5494. doi: 10.1039/C5AN01063B
37. [37]
  L. Yuan, W.Y. Lin, et al., Chem. Eur. J. 17(2011) 689-696. doi: 10.1002/chem.201001923
38. [38]
  C. Wu, Q.N. Bian, et al., Org. Lett. 14(2012) 4198-4201. doi: 10.1021/ol3018598
39. [39]
  V. Dujols, F. Ford, A.W. Czarnik, J. Am. Chem. Soc. 119(1997) 7386-7387. doi: 10.1021/ja971221g
40. [40]
  Y.R. Zhao, Q. Zheng, et al., J. Am. Chem. Soc. 126(2004) 4653-4663. doi: 10.1021/ja036958m
41. [41]
  S.W. Botchway, M. Charnley, et al., Proc. Natl. Acad. Sci. U. S. A. 105(2008) 16071-16076. doi: 10.1073/pnas.0804071105
42. [42]
  P. Neveu, I. Aujard, et al., Angew. Chem. Int. Ed. 47(2008) 3744-33746. doi: 10.1002/(ISSN)1521-3773
43. [43]
  M.A.H. Fichte, X.M.M. Weyel, et al., Angew. Chem. Int. Ed. 128(2016) 9094-9098. doi: 10.1002/ange.201603281
44. [44]
  A. Momotake, N. Lindegger, et al., Nat. Methods 3(2006) 35-40. doi: 10.1038/nmeth821
45. [45]
  N. Gagey, P. Neveu, L. Jullien, Angew. Chem. Int. Ed. 46(2007) 2467-2469. doi: 10.1002/(ISSN)1521-3773
46. [46]
  R.A.J. Smith, M.P. Murphy, et al., Eur. J. Biochem. 263(1999) 709-716. doi: 10.1046/j.1432-1327.1999.00543.x
47. [47]
  G.F. Kelso, M.P. Murphy, et al., J. Biol. Chem. 276(2001) 4588-4596. doi: 10.1074/jbc.M009093200
48. [48]
  C.W.T. Leung, Y. Hong, et al., J. Am. Chem. Soc. 135(2013) 62-65. doi: 10.1021/ja310324q
49. [49]
  A.R. Sarkar, C.H. Heo, L. Xu, et al., Chem. Sci. 7(2016) 766-773. doi: 10.1039/C5SC03708E
50. [50]
  Y. Dai, Y. Xiao, et al., Chin. Chem. Lett. 25(2014) 1001-1005. doi: 10.1016/j.cclet.2014.05.020
51. [51]
  Q.L. Hu, M. Gao, et al., Angew. Chem. Int. Ed. 53(2014) 14225-14229. doi: 10.1002/anie.v53.51
52. [52]
  T.O. Zaikova, A.V. Rukavishnikov, et al., Bioconjugate Chem.12(2001) 307-313. doi: 10.1021/bc0001138
53. [53]
  R.L. Zhang, J. Zhao, G.M. Han, et al., J. Am. Chem. Soc. 138(2016) 3769-3778. doi: 10.1021/jacs.5b12848
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  Xu Qu , Baohua Ji , Haocheng Gong , Guangwei Wang , Liang-Liang Gao , Jing Zhang , Jianjian Zhang , Yuan Guo . Dual-emissive near-infrared fluorogenic probe with enhanced cellular uptake capability for sensitive tracking of cellular polarity. Chinese Chemical Letters, 2025, 36(10): 110766-. doi: 10.1016/j.cclet.2024.110766
5. [5]
  Jiayu Zeng , Minhui Liu , Ting Yang , Jia Huang , Songjiao Li , Wanting Zhang , Dan Cheng , Longwei He , Jia Zhou . Two-dimensional design strategy to construct smart dual-responsive fluorescent probe for the precise tracking of ischemic stroke. Chinese Chemical Letters, 2025, 36(5): 110166-. doi: 10.1016/j.cclet.2024.110166
6. [6]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
7. [7]
  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
8. [8]
  Sixin Ai , Wenxiu Li , Huayong Zhu , Yang Wan , Weiying Lin . Viscosity-responsive signal amplification dual-modal probe triggered by cysteine/homocysteine for monitoring diabetic liver damages and repair processes. Chinese Chemical Letters, 2025, 36(3): 109904-. doi: 10.1016/j.cclet.2024.109904
9. [9]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
10. [10]
  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
11. [11]
  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
12. [12]
  Lijia Xu , Tong Zhong , Wei Zhao , Bing Yao , Lin Ding , Huangxian Ju . Chemoselective labeling-based spermatozoa glycan imaging reveals abnormal glycosylation in oligoasthenotspermia. Chinese Chemical Letters, 2024, 35(4): 108760-. doi: 10.1016/j.cclet.2023.108760
13. [13]
  Qingyuan Guo , Aojie Liu , Yinghui Huang , Jiayu Ding , Junjie Ding , Limin Wang , Yang Ding , Bo Peng , Lin Li , Bin Fang , Shan Jiang , Hua Bai . Small-molecule fluorescent probes for imaging and diagnosing ischemia-reperfusion injury. Chinese Chemical Letters, 2025, 36(12): 110943-. doi: 10.1016/j.cclet.2025.110943
14. [14]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
15. [15]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295
16. [16]
  Fengkai Zou , Borui Su , Han Leng , Nini Xin , Shichao Jiang , Dan Wei , Mei Yang , Youhua Wang , Hongsong Fan . Red-emissive carbon quantum dots minimize phototoxicity for rapid and long-term lipid droplet monitoring. Chinese Chemical Letters, 2024, 35(10): 109523-. doi: 10.1016/j.cclet.2024.109523
17. [17]
  Zhipeng Li , Qincong Feng , Jianliang Shen . A β-lactamase-activatable photosensitizer for the treatment of resistant bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109602-. doi: 10.1016/j.cclet.2024.109602
18. [18]
  Yaojun Li , Yun Li , Shenglong Liao , Yang Li , Shouchun Yin . Revolutionizing cancer therapies with organic photovoltaic non-fullerene acceptors: A deep dive into molecular engineering for advanced phototheranostics. Chinese Chemical Letters, 2025, 36(8): 110832-. doi: 10.1016/j.cclet.2025.110832
19. [19]
  Dandan Tang , Ningge Xu , Yuyang Fu , Wei Peng , Jinsheng Wu , Heng Liu , Fabiao Yu . Rationally designed an innovative proximity labeling near-infrared fluorogenic probe for imaging of peroxynitrite in acute lung injury. Chinese Chemical Letters, 2025, 36(5): 110082-. doi: 10.1016/j.cclet.2024.110082
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1592)
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