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
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