Citation: Yubin Ding, Jiaxin Wang, Ruinan Wang, Yongshu Xie. Development of porphyrin-based fluorescent sensors and sensor arrays for saccharide recognition[J]. Chinese Chemical Letters, ;2024, 35(2): 109008. doi: 10.1016/j.cclet.2023.109008 shu

Development of porphyrin-based fluorescent sensors and sensor arrays for saccharide recognition

Yubin Ding ^{a, *,} ,
Jiaxin Wang ^a ,
Ruinan Wang ^a ,
Yongshu Xie ^{b, *,}

a.
Department of Chemistry, College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
b.
Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China

ybding@njau.edu.cn

yshxie@ecust.edu.cn

Received Date: 16 June 2023
Revised Date: 22 August 2023
Accepted Date: 28 August 2023
Available Online: 31 August 2023

Figures(7)

Saccharide sensing is a very meaningful research topic as saccharides are involved in many biological activities. However, it is challenging to design molecular sensors for saccharides because this family of compounds is hydromimetic in aqueous solutions and shares a similar chemical structure. In this review, research progress in the development of porphyrin-based saccharide sensors is described with representative examples. We focus on using porphyrin as the signal reporter because porphyrins exhibit unique advantages in high chemical stability, long emission wavelength, and multiple structural modification strategies. Reported literature results have been classified into mainly two sections according to the general working principles of the porphyrin sensor molecules. In the first section, recognition unit, design strategy and sensing performance of traditional porphyrin-based selective saccharide sensors are discussed. While in the second section, development of porphyrin-based sensor arrays for pattern recognition of saccharides has been summarized. Looking through the design strategy and sensing performance of reported achievements, it is reasonable to anticipate a bright future for designing practical porphyrin-based saccharide sensors.
- Porphyrin,
- Saccharide,
- Fluorescent sensing,
- Selective sensing,
- Pattern recognition
1. [1]
  X. Sun, D.J. Tony, Chem. Rev. 115 (2015) 8001–8037. doi: 10.1021/cr500562m
2. [2]
  M. Poudineh, C.L. Maikawa, E.Y. Ma, et al., Nat. Biomed. Eng. 5 (2021) 53–63.
3. [3]
  J. Dai, H. Zhang, C. Huang, Z. Chen, A. Han, Anal. Chem. 92 (2020) 16122–16129. doi: 10.1021/acs.analchem.0c03801
4. [4]
  E.S.F. Berman, K.S. Kulp, M.G. Knize, et al., Anal. Chem. 78 (2006) 6497–6503. doi: 10.1021/ac060865g
5. [5]
  R. Pandey, S.K. Paidi, T.A. Valdez, et al., Acc. Chem. Res. 50 (2017) 264–272. doi: 10.1021/acs.accounts.6b00472
6. [6]
  M. Qin, Y. Huang, Y. Li, et al., Angew. Chem. Int. Ed. 55 (2016) 6911–6914. doi: 10.1002/anie.201602582
7. [7]
  T. Jin, M. Cui, D. Wu, et al., Chin. Chem. Lett. 32 (2021) 3899–3902. doi: 10.1016/j.cclet.2021.06.033
8. [8]
  J. Li, M. Zhao, J. Huang, et al., Coordin. Chem. Rev. 473 (2022) 214813. doi: 10.1016/j.ccr.2022.214813
9. [9]
  S. Li, F. Huo, Y. Yue, et al., Chin. Chem. Lett. 32 (2021) 3870–3875. doi: 10.1016/j.cclet.2021.05.026
10. [10]
  Y. Wang, J. Nie, W. Fang, et al., Chem. Rev. 120 (2020) 4534–4577. doi: 10.1021/acs.chemrev.9b00814
11. [11]
  W. Zhang, Y. Li, Y. Liang, et al., Chem. Sci. 10 (2019) 6617–6623. doi: 10.1039/C9SC02266J
12. [12]
  Y. Liu, C. Deng, L. Tang, et al., J. Am. Chem. Soc. 133 (2011) 660–663. doi: 10.1021/ja107086y
13. [13]
  W. Liu, Y. Tan, L.O. Jones, et al., J. Am. Chem. Soc. 143 (2021) 15688–15700. doi: 10.1021/jacs.1c06333
14. [14]
  Y. Sasaki, É. Leclerc, V. Hamedpour, et al., Anal. Chem. 91 (2019) 15570–15576. doi: 10.1021/acs.analchem.9b03578
15. [15]
  S. Jiang, J.O. Escobedo, K.K. Kim, et al., J. Am. Chem. Soc. 128 (2006) 12221–12228. doi: 10.1021/ja063651p
16. [16]
  J. Ramos-Soriano, S.J. Benitez-Benitez, A.P. Davis, M.C. Galan, Angew. Chem. Int. Ed. 60 (2021) 16880–16884. doi: 10.1002/anie.202103545
17. [17]
  Y. Ding, W.H. Zhu, Y. Xie, Chem. Rev. 117 (2017) 2203–2256. doi: 10.1021/acs.chemrev.6b00021
18. [18]
  L. Liu, J. Kim, L. Xu, et al., Angew. Chem. Int. Ed. 61 (2022) e202214342. doi: 10.1002/anie.202214342
19. [19]
  F. Wu, Y. Sun, H. Gao, et al., Sci. China Chem. 66 (2023) 164–173. doi: 10.1007/s11426-022-1409-3
20. [20]
  S.P. Wang, W. Lin, X. Wang, et al., Nat. Commun. 10 (2019) 1399. doi: 10.1038/s41467-019-09363-y
21. [21]
  Y. Xie, Y. Tang, W. Wu, et al., J. Am. Chem. Soc. 137 (2015) 14055–14058. doi: 10.1021/jacs.5b09665
22. [22]
  E.R.H. Walter, Y. Ge, J.C. Mason, J.J. Boyle, N.J. Long, J. Am. Chem. Soc. 143 (2021) 6460–6469. doi: 10.1021/jacs.0c12864
23. [23]
  A.P. Davis, Chem. Soc. Rev. 49 (2020) 2531–2545. doi: 10.1039/C9CS00391F
24. [24]
  T.S. Carter, T.J. Mooibroek, P.F.N. Stewart, et al., Angew. Chem. Int. Ed. 55 (2016) 9311–9315. doi: 10.1002/anie.201603082
25. [25]
  E.J. Toone, Curr. Opin. Struc. Biol. 4 (1994) 719–728. doi: 10.1016/S0959-440X(94)90170-8
26. [26]
  H. Teymourian, A. Barfidokht, J. Wang, Chem. Soc. Rev. 49 (2020) 7671–7709. doi: 10.1039/D0CS00304B
27. [27]
  A. Liu, M. Li, J. Wang, et al., Chin. Chem. Lett. 31 (2020) 1133–1136. doi: 10.1016/j.cclet.2019.10.011
28. [28]
  Q. Liu, Y. Yang, H. Li, et al., Biosens. Bioelectron. 64 (2015) 147–153. doi: 10.1016/j.bios.2014.08.062
29. [29]
  S. Hu, Y. Jiang, Y. Wu, et al., ACS Appl. Mater. Interfaces 12 (2020) 55324–55330. doi: 10.1021/acsami.0c12988
30. [30]
  P. Du, Q. Niu, J. Chen, et al., Anal. Chem. 92 (2020) 7980–7986. doi: 10.1021/acs.analchem.0c01651
31. [31]
  B. Sookcharoenpinyo, E. Klein, Y. Ferrand, et al., Angew. Chem. Int. Ed. 51 (2012) 4586–4590. doi: 10.1002/anie.201200447
32. [32]
  R.A. Tromans, T.S. Carter, L. Chabanne, et al., Nat. Chem. 11 (2019) 52–56. doi: 10.1038/s41557-018-0155-z
33. [33]
  T. Wei, Q. Xu, C. Zou, et al., Chin. Chem. Lett. 32 (2021) 1470–1474. doi: 10.1016/j.cclet.2020.10.003
34. [34]
  J.P. Lorand, J.O. Edwards, J. Org. Chem. 24 (1959) 769–774. doi: 10.1021/jo01088a011
35. [35]
  Y.E. Wang, R.X. Rong, H. Chen, et al., Chin. Chem. Lett. 28 (2017) 1262–1267. doi: 10.1016/j.cclet.2017.02.013
36. [36]
  J. Yoon, A.W. Czarnik, J. Am. Chem. Soc. 114 (1992) 5874–5875. doi: 10.1021/ja00040a067
37. [37]
  M. Takeuchi, Y. Chin, T. Imada, S. Shinkai, Chem. Commun. (1996) 1867–1868.
38. [38]
  H. Murakami, T. Nagasaki, I. Hamachi, S. Shinkai, Tetrahedron Lett. 34 (1993) 6273–6276. doi: 10.1016/S0040-4039(00)73730-0
39. [39]
  H. Murakami, T. Nagasaki, I. Hamachi, S. Shinkai, J. Chem. Soc. Perkin Trans. (1994) 975–981.
40. [40]
  T. Imada, H. Kijima, M. Takeuchi, S. Shinkai, Tetrahedron 52 (1996) 2817–2826. doi: 10.1016/0040-4020(96)00003-8
41. [41]
  M. Takeuchi, H. Kijima, I. Hamachi, S. Shinkai, Bull. Chem. Soc. Jpn. 70 (1997) 699–705. doi: 10.1246/bcsj.70.699
42. [42]
  A.E. Hargrove, R.N. Reyes, I. Riddington, E.V. Anslyn, J.L. Sessler, Org. Lett. 12 (2010) 4804–4807. doi: 10.1021/ol1019647
43. [43]
  O. Hirata, Y. Kubo, M. Takeuchi, S. Shinkai, Tetrahedron 60 (2004) 11211–11218. doi: 10.1016/j.tet.2004.08.061
44. [44]
  M. Takeuchi, T. Imada, S. Shinkai, J. Am. Chem. Soc. 118 (1996) 10658–10659. doi: 10.1021/ja961480q
45. [45]
  C.M. Renney, G. Fukuhara, Y. Inoue, A.P. Davis, Chem. Commun. 51 (2015) 9551–9554. doi: 10.1039/C5CC02768C
46. [46]
  V. r. Král, O. Rusin, J. Charvátová, P. Anzenbacher, J. Fogl, Tetrahedron Lett. 41 (2000) 10147–10151. doi: 10.1016/S0040-4039(00)01805-0
47. [47]
  J. Charvátová, O. Rusin, V. r. Král, K. Volka, P. Matějka, Sens. Actuator. B 76 (2001) 366–372. doi: 10.1016/S0925-4005(01)00635-9
48. [48]
  K. Ladomenou, R.P. Bonar-Law, Chem. Commun. (2002) 2108–2109.
49. [49]
  J.D. Lee, Y.H. Kim, J.I. Hong, J. Org. Chem. 75 (2010) 7588–7595. doi: 10.1021/jo101384u
50. [50]
  J.-D. Lee, D.-H. Jang, J.I. Hong, Bull. Korean Chem. Soc. 31 (2010) 2685–2688. doi: 10.5012/bkcs.2010.31.9.2685
51. [51]
  M. Dukh, D. Saman, K. Lang, et al., Org. Biomol. Chem. 1 (2003) 3458–3463. doi: 10.1039/B302947F
52. [52]
  J. Kralova, J. Koivukorpi, Z. Kejik, et al., Org. Biomol. Chem. 6 (2008) 1548–1552. doi: 10.1039/b717528k
53. [53]
  E. Kalenius, J. Koivukorpi, E. Kolehmainen, P. Vainiotalo, Eur. J. Org. Chem. 2010 (2010) 1052–1058. doi: 10.1002/ejoc.200901168
54. [54]
  O. Francesconi, A. Ienco, G. Moneti, C. Nativi, S. Roelens, Angew. Chem. Int. Ed. 45 (2006) 6693–6696. doi: 10.1002/anie.200602412
55. [55]
  V. Král, O. Rusin, F.P. Schmidtchen, Org. Lett. 3 (2001) 873–876. doi: 10.1021/ol007069w
56. [56]
  W.B. Lu, L.H. Zhang, X.S. Ye, Sens. Actuator. B 113 (2006) 354–360. doi: 10.1016/j.snb.2005.03.025
57. [57]
  G. Fukuhara, M. Sasaki, M. Numata, T. Mori, Y. Inoue, Chem. Eur. J. 23 (2017) 11272–11278. doi: 10.1002/chem.201701360
58. [58]
  M. Sasaki, Y. Ryoson, M. Numata, G. Fukuhara, J. Org. Chem. 84 (2019) 6017–6027. doi: 10.1021/acs.joc.9b00040
59. [59]
  S.K. Bhaumik, Y.S. Patra, S. Banerjee, Chem. Commun. 56 (2020) 9541–9544. doi: 10.1039/D0CC03644G
60. [60]
  I. Capila, R.J. Linhardt, Angew. Chem. Int. Ed. 41 (2002) 391–412.
61. [61]
  Y. Xu, S. Masuko, M. Takieddin, et al., Science 334 (2011) 498. doi: 10.1126/science.1207478
62. [62]
  S.P. Pandey, P. Jha, P.K. Singh, Sens. Actuator. B 359 (2022) 131613. doi: 10.1016/j.snb.2022.131613
63. [63]
  L. Fan, D. Jia, W. Zhang, Y. Ding, Analyst 145 (2020) 7809–7824. doi: 10.1039/D0AN01562H
64. [64]
  Z. Li, J.R. Askim, K.S. Suslick, Chem. Rev. 119 (2019) 231–292. doi: 10.1021/acs.chemrev.8b00226
65. [65]
  J. Chen, B.L. Hickey, L. Wang, et al., Nat. Chem. 13 (2021) 488–495. doi: 10.1038/s41557-021-00647-9
66. [66]
  D. Jia, C. Yang, W. Zhang, Y. Ding, Dyes Pigments 190 (2021) 109266. doi: 10.1016/j.dyepig.2021.109266
67. [67]
  Z. Zheng, W.C. Geng, J. Gao, Y.J. Mu, D.S. Guo, Org. Chem. Front. 5 (2018) 2685–2691. doi: 10.1039/C8QO00606G
68. [68]
  R.B.C. Jagt, R.F. Gomez-Biagi, M. Nitz, Angew. Chem. Int. Ed. 48 (2009) 1995–1997. doi: 10.1002/anie.200805238
69. [69]
  Z. Yang, X. Fan, W. Cheng, Y. Ding, W. Zhang, Anal. Chem. 91 (2019) 10295–10301. doi: 10.1021/acs.analchem.9b02516
70. [70]
  Z. Yang, L. Fan, X. Fan, et al., Anal. Chem. 92 (2020) 6727–6733. doi: 10.1021/acs.analchem.0c00808
71. [71]
  M. Hou, L. Fan, X. Fan, et al., Anal. Chim. Acta 1141 (2021) 214–220. doi: 10.1016/j.aca.2020.10.052
72. [72]
  D. Jia, Q. Pan, R. Hu, W. Zhang, Y. Ding, Sens. Actuator. B 385 (2023) 133677. doi: 10.1016/j.snb.2023.133677
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