Citation: Guangjie Song, Di Jiang, Lei Wang, Xiangzhong Sun, Hongtian Liu, Yanqing Tian, Meiwan Chen. A series of simple curcumin-derived colorimetric and fluorescent probes for ratiometric-pH sensing and cell imaging[J]. Chinese Chemical Letters, ;2022, 33(1): 339-343. doi: 10.1016/j.cclet.2021.06.076 shu

A series of simple curcumin-derived colorimetric and fluorescent probes for ratiometric-pH sensing and cell imaging

Guangjie Song ^{a, b, 1} ,
Di Jiang ^{a, 1} ,
Lei Wang ^b ,
Xiangzhong Sun ^{b, c} ,
Hongtian Liu ^b ,
Yanqing Tian ^{b, *,} ,
Meiwan Chen ^{a, *,}

a.
State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao, China
b.
Department of Materials Science and Engineering, Southern University of Science and Technology, Shenzhen 518055, China
c.
School of Physics and Technology, Wuhan University, Wuhan 430072, China

tianyq@sustech.edu.cn

mwchen@um.edu.mo

Received Date: 18 March 2021
Revised Date: 23 June 2021
Accepted Date: 28 June 2021
Available Online: 20 July 2021

Figures(5)

Colorimetric and fluorescent probes have emerged as a potent tool for pH sensing due to easy operation and high sensitivity. However, most of the existing bimodal probes require complicated synthesis, which greatly limits their wide applications. Herein, a simple fluorescent dye (called BFCUR) featuring a D-π-A-π-D conjugated system was developed from the natural polyphenol curcumin (CUR). BFCUR exhibited significant red-shift in UV absorption and fluorescence emission as pH increased because of the deprotonation of the phenolic hydroxyl groups, which resulted in the enhanced intramolecular charge transfer (ICT). The ratiometric pH detection of BFCUR was achieved with remarkable accuracy by monitoring both the absorbance ratio A₅₀₀/A₆₅₀ and the fluorescence intensity ratio I₆₂₂/I₇₄₃ under various pH values. In addition, the clear color changes of BFCUR under different pH conditions were visible, which enabled BFCUR to be used in test strips for rapid, visual pH detection. Moreover, BFCUR exhibited low cytotoxicity, and was successfully applied for intracellular pH detection, where the fluorescence intensity was linearly related to pH value. This study highlighted the great potential of CUR-derived BFCUR as colorimetric and fluorescent probes for ratiometric-pH sensing and cell imaging.
- Natural product,
- Fluorescent probe,
- Ratiometric pH sensing,
- Colorimetric response,
- pH Bioimaging
1. [1]
  S. Dong, M. Luo, G. Peng, W. Cheng, Sens. Actuators B129 (2008) 94-98. doi: 10.1016/j.snb.2007.07.078
2. [2]
  T.A. Davies, R.E. Fine, R.J. Johnson, et al., Biochem. Biophys. Res. Commun. 194 (1993) 537-543. doi: 10.1006/bbrc.1993.1853
3. [3]
  M. Schindler, S. Grabski, E. Hoff, S.M. Simon, Biochemistry35 (1996) 2811-2817. doi: 10.1021/bi952234e
4. [4]
  S. Sinharay, M.D. Pagel, Annu. Rev. Anal. Chem. 9 (2016) 95-115. doi: 10.1146/annurev-anchem-071015-041514
5. [5]
  J. Han, K. Burgess, Chem. Rev. 110 (2010) 2709-2728. doi: 10.1021/cr900249z
6. [6]
  S. Takahashi, Y. Kagami, K. Hanaoka, et al., J. Am. Chem. Soc. 140 (2018) 5925-5933. doi: 10.1021/jacs.8b00277
7. [7]
  X. Liu, Y. Su, H. Tian, et al., Anal. Chem. 89 (2017) 7038-7045. doi: 10.1021/acs.analchem.7b00754
8. [8]
  F. Su, S. Agarwal, T. Pan, et al., ACS Appl. Mater. Interfaces10 (2018) 1556-1565. doi: 10.1021/acsami.7b15796
9. [9]
  D. Iacopini, A. Moscardini, F. Lessi, et al., Bioorg. Chem. 105 (2020) 104372. doi: 10.1016/j.bioorg.2020.104372
10. [10]
  M.J. Marin, F. Galindo, P. Thomas, D.A. Russell, Angew. Chem. Int. Ed. 51 (2012) 9657-9661. doi: 10.1002/anie.201203866
11. [11]
  C.B. He, K.D. Lu, W.B. Lin, J. Am. Chem. Soc. 136 (2014) 12253-12256. doi: 10.1021/ja507333c
12. [12]
  J. Joniak, H. Stankovicova, J. Filo, et al., Sens. Actuators B307 (2020) 127646. doi: 10.1016/j.snb.2019.127646
13. [13]
  X. Zhao, C. Wang, G. Yuan, et al., Sens. Actuators B290 (2019) 79-86. doi: 10.1016/j.snb.2019.03.122
14. [14]
  A.P. de Silva, H.Q. Gunaratne, T. Gunnlaugsson, et al., Chem. Rev. 97 (1997) 1515-1566. doi: 10.1021/cr960386p
15. [15]
  F. Galindo, M.I. Burguete, L. Vigara, et al., Angew. Chem. Int. Ed. 44 (2005) 6504-6508. doi: 10.1002/anie.200501920
16. [16]
  M. Lee, N.G. Gubernator, D. Sulzer, D. Sames, J. Am. Chem. Soc. 132 (2010) 8828-8830. doi: 10.1021/ja101740k
17. [17]
  Y. Yan, X. Zhang, X. Zhang, et al., Chin. Chem. Lett. 31 (2020) 1091-1094. doi: 10.1016/j.cclet.2019.10.025
18. [18]
  X. Liu, Q. Yang, W. Chen, et al., Org. Biomol. Chem. 13 (2015) 8663-8668. doi: 10.1039/C5OB00765H
19. [19]
  M. Wang, G. Meng, Q. Huang, et al., Chem. Commun. (Camb. )47 (2011) 3808-3810. doi: 10.1039/c0cc05371f
20. [20]
  X. Feng, T. Zhang, J.T. Liu, J.Y. Miao, B.X. Zhao, Chem. Commun. (Camb. )52 (2016) 3131-3134. doi: 10.1039/C5CC09267A
21. [21]
  L. Yuan, W. Lin, K. Zheng, L. He, W. Huang, Chem. Soc. Rev. 42 (2013) 622-661. doi: 10.1039/C2CS35313J
22. [22]
  D.S. Koktysh, Mater. Res. Bull. 123 (2020) 110686. doi: 10.1016/j.materresbull.2019.110686
23. [23]
  Z.P. She, Y. Tian, Y.S. Xia, et al., Dyes Pigm. 179 (2020) 108402. doi: 10.1016/j.dyepig.2020.108402
24. [24]
  W. Shen, L. Wang, S. Zhu, et al., Anal. Biochem. 596 (2020) 113609. doi: 10.1016/j.ab.2020.113609
25. [25]
  H.X. Li, H. Dong, M.M. Yu, et al., Anal. Chem. 89 (2017) 8863-8869. doi: 10.1021/acs.analchem.7b01324
26. [26]
  J.F. Yang, M. Li, W.H. Zhu, Res. Chem. Intermed. 44 (2018) 3959-3969. doi: 10.1007/s11164-018-3334-z
27. [27]
  J. Li, X.K. Li, J.B. Jia, et al., Dyes Pigm. 166 (2019) 433-442. doi: 10.1016/j.dyepig.2019.03.060
28. [28]
  F.Y. Su, S. Agarwal, T.T. Pan, et al., ACS Appl. Mater. Interfaces10 (2018) 1556-1565. doi: 10.1021/acsami.7b15796
29. [29]
  X.J. Liu, Y.A. Su, H.H. Tian, et al., Anal. Chem. 89 (2017) 7038-7045. doi: 10.1021/acs.analchem.7b00754
30. [30]
  Y. Gu, Z. Zhao, H. Su, et al., Chem. Sci. 9 (2018) 6497-6502. doi: 10.1039/C8SC01635F
31. [31]
  A. Mars, M. Hamami, L. Bechnak, D. Patra, N. Raouafi, Anal. Chim. Acta1036 (2018) 141-146. doi: 10.1016/j.aca.2018.06.075
32. [32]
  W. Qin, P.F. Zhang, H. Li, et al., Chem. Sci. 9 (2018) 2705-2710. doi: 10.1039/C7SC04820C
33. [33]
  F. Zsila, Z. Bikadi, M. Simonyi, Org. Biomol. Chem. 2 (2004) 2902-2910. doi: 10.1039/B409724F
34. [34]
  M.T. Huang, Y.R. Lou, W. Ma, et al., Cancer Res. 54 (1994) 5841-5847.
35. [35]
  H. Hatcher, R. Planalp, J. Cho, F.M. Tortia, S.V. Torti, Cell. Mol. Life Sci. 65 (2008) 1631-1652. doi: 10.1007/s00018-008-7452-4
36. [36]
  M. Pavai, J. Mihaly, A. Paszternak, Food Anal. Meth. 8 (2015) 2243-2249. doi: 10.1007/s12161-015-0102-1
37. [37]
  B. Kuswandi, Jayus, T.S. Larasati, A. Abdullah, L.Y. Heng, Food Anal. Meth. 5 (2012) 881-889. doi: 10.1007/s12161-011-9326-x
38. [38]
  C.Z. Ran, X.Y. Xu, S.B. Raymond, et al., J. Am. Chem. Soc. 131 (2009) 15257-15261. doi: 10.1021/ja9047043
39. [39]
  X.L. Zhang, Y.L. Tian, Z. Li, et al., J. Am. Chem. Soc. 135 (2013) 16397-16409. doi: 10.1021/ja405239v
40. [40]
  A. Chaicham, S. Kulchat, G. Tumcharern, T. Tuntulani, B. Tomapatanaget, Tetrahedron66 (2010) 6217-6223. doi: 10.1016/j.tet.2010.05.088
41. [41]
  D. Xiang, Q. Meng, H. Liu, M. Lan, G. Wei, Talanta, 146 (2016) 851-856. doi: 10.1016/j.talanta.2015.05.066
42. [42]
  L. Zhou, L. Xie, C. Liu, Y. Xiao, Chin. Chem. Lett. 30 (2019) 1799-1808. doi: 10.1016/j.cclet.2019.07.051
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2. [2]
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4. [4]
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