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
1. [1]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
2. [2]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
3. [3]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
4. [4]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
5. [5]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769
6. [6]
  Zhimin Sun , Xin-Hui Guo , Yue Zhao , Qing-Yu Meng , Li-Juan Xing , He-Lue Sun . Dynamically switchable porphyrin-based molecular tweezer for on−off fullerene recognition. Chinese Chemical Letters, 2024, 35(6): 109162-. doi: 10.1016/j.cclet.2023.109162
7. [7]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
8. [8]
  Xiaxia Xing , Xiaoyu Chen , Zhenxu Li , Xinhua Zhao , Yingying Tian , Xiaoyan Lang , Dachi Yang . Polyethylene imine functionalized porous carbon framework for selective nitrogen dioxide sensing with smartphone communication. Chinese Chemical Letters, 2024, 35(9): 109230-. doi: 10.1016/j.cclet.2023.109230
9. [9]
  Jichun Li , Zhengren Wang , Yu Deng , Hongxiu Yu , Yonghui Deng , Xiaowei Cheng , Kaiping Yuan . Construction of mesoporous silica-implanted tungsten oxides for selective acetone gas sensing. Chinese Chemical Letters, 2024, 35(11): 110111-. doi: 10.1016/j.cclet.2024.110111
10. [10]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
11. [11]
  Yueyue WEI , Xuehua SUN , Hongmei CHAI , Wanqiao BAI , Yixia REN , Loujun GAO , Gangqiang ZHANG , Jun ZHANG . Two Ln-Co (Ln=Eu, Sm) metal-organic frameworks: Structures, magnetism, and fluorescent sensing sulfasalazine and glutaraldehyde. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2475-2485. doi: 10.11862/CJIC.20240193
12. [12]
  Weixu Li , Yuexin Wang , Lin Li , Xinyi Huang , Mengdi Liu , Bo Gui , Xianjun Lang , Cheng Wang . Promoting energy transfer pathway in porphyrin-based sp2 carbon-conjugated covalent organic frameworks for selective photocatalytic oxidation of sulfide. Chinese Journal of Structural Chemistry, 2024, 43(7): 100299-100299. doi: 10.1016/j.cjsc.2024.100299
13. [13]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879
14. [14]
  Bharathi Natarajan , Palanisamy Kannan , Longhua Guo . Metallic nanoparticles for visual sensing: Design, mechanism, and application. Chinese Journal of Structural Chemistry, 2024, 43(9): 100349-100349. doi: 10.1016/j.cjsc.2024.100349
15. [15]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
16. [16]
  Deshuai Zhen , Chunlin Liu , Qiuhui Deng , Shaoqi Zhang , Ningman Yuan , Le Li , Yu Liu . A review of covalent organic frameworks for metal ion fluorescence sensing. Chinese Chemical Letters, 2024, 35(8): 109249-. doi: 10.1016/j.cclet.2023.109249
17. [17]
  Quan Zhang , Shunjie Xing , Jingqian Han , Li Feng , Jianchun Li , Zhaosheng Qian , Jin Zhou . Organic pollutant sensing for human health based on carbon dots. Chinese Chemical Letters, 2025, 36(1): 110117-. doi: 10.1016/j.cclet.2024.110117
18. [18]
  Huan Yao , Jian Qin , Yan-Fang Wang , Song-Meng Wang , Liu-Huan Yi , Shi-Yao Li , Fangfang Du , Liu-Pan Yang , Li-Li Wang . Ultra-highly selective recognition of nucleosides over nucleotides by rational modification of tetralactam macrocycle and its application in enzyme assay. Chinese Chemical Letters, 2024, 35(6): 109154-. doi: 10.1016/j.cclet.2023.109154
19. [19]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
20. [20]
  Yu Deng , Yan Liu , Yonghui Deng , Jinsheng Cheng , Yidong Zou , Wei Luo . In situ sulfur-doped mesoporous tungsten oxides for gas sensing toward benzene series. Chinese Chemical Letters, 2024, 35(7): 108898-. doi: 10.1016/j.cclet.2023.108898

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(302)
HTML views(11)

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