Citation: Zhuo Yu, Wenbo Huang, Liqiao Shi, Shaoyong Ke, Shengzhen Xu. Selective probes targeting c-MYC Pu22 G-quadruplex and their application in live mice imaging[J]. Chinese Chemical Letters, ;2022, 33(3): 1627-1631. doi: 10.1016/j.cclet.2021.09.087 shu

Selective probes targeting c-MYC Pu22 G-quadruplex and their application in live mice imaging

Zhuo Yu ^{a, b} ,
Wenbo Huang ^a ,
Liqiao Shi ^a ,
Shaoyong Ke ^{a, *,} ,
Shengzhen Xu ^{b, *,}

a.
National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
b.
College of Science, Huazhong Agricultural University, Wuhan 430070, China

shaoyong.ke@nberc.com

xusz@mail.hzau.edu.cn

Received Date: 30 June 2021
Revised Date: 15 September 2021
Accepted Date: 24 September 2021
Available Online: 30 September 2021

Figures(5)

Several probes containing benzothiazole-guided conjugated systems (BGCS) were designed and synthesized, and two molecules (BGCS5 and BGCS6) of which were discovered as selective probes targeting c-MYC Pu22 G-quadruplex DNA. The fluorescence intensity of BGCS5 and BGCS6 in the presence of c-MYC Pu22 far exceeds that of the typical G4 probe TO1. Especially, the fluorescence of BGCS6 increased almost 193-fold in the presence of c-MYC Pu22 G4 compared to that alone in aqueous buffer condition with almost no fluorescence and 10–30 folds than those in the presence of other DNAs, which will be useful tools for disease detection in mammals.
- Benthiazole,
- Conjugated system,
- Chemosensor,
- G-quadruplex DNA,
- In vivo imaging
1. [1]
  A. Siddiqui-Jain, C.L. Grand, D.J. Bearss, L.H. Hurley, Proc. Natl. Acad. Sci. U. S. A.99 (2002) 11593–11598. doi: 10.1073/pnas.182256799
2. [2]
  M.L. Bochman, K. Paeschke, V.A. Zakian, Nat. Rev. Genet. 13 (2012) 770–780. doi: 10.1038/nrg3296
3. [3]
  S. Cogoi, L.E. Xodo, Nucleic Acids Res. 34 (2006) 2536–2549. doi: 10.1093/nar/gkl286
4. [4]
  H. Fernando, A.P. Reszka, J. Huppert, et al., Biochemistry 45 (2006) 7854–7860. doi: 10.1021/bi0601510
5. [5]
  K. Cao, P. Ryvkin, F.B. Johnson, Methods 57 (2012) 3–10. doi: 10.1016/j.ymeth.2012.05.002
6. [6]
  L.H. Hurley, D.D. Von Hoff, A. Siddiqui-Jain, D. Yang, Semin. Oncol. 33 (2006) 498–512. doi: 10.1053/j.seminoncol.2006.04.012
7. [7]
  R. Rodriguez, K.M. Miller, J.V. Forment, et al., Nat. Chem. Biol. 8 (2012) 301–310. doi: 10.1038/nchembio.780
8. [8]
  K.W. Zheng, S. Xiao, J.Q. Liu, et al., Nucleic Acids Res. 41 (2013) 5533–5541. doi: 10.1093/nar/gkt264
9. [9]
  T. Tian, H. Xiao, Z. Zhang, et al., Chem. Eur. J. 19 (2013) 92–95. doi: 10.1002/chem.201203344
10. [10]
  Y.X. Xiong, Z.S. Huang, J.H. Tan, Eur. J. Med. Chem. 97 (2015) 538–551. doi: 10.1016/j.ejmech.2014.11.021
11. [11]
  D. Zhao, X.W. Dong, N. Jiang, D. Zhang, C.L. Liu, Nucleic Acids Res. 42 (2014) 11612–11621. doi: 10.1093/nar/gku833
12. [12]
  V. Brázda, L. Hároníková, J.C.C. Liao, M. Fojta, Int. J. Mol. Sci. 15 (2014) 17493–17517. doi: 10.3390/ijms151017493
13. [13]
  L. Zhang, D. Duan, Y. Liu, et al., J. Am. Chem. Soc. 136 (2014) 226–233. doi: 10.1021/ja408792k
14. [14]
  P.P. Jia, L. Xu, Y.X. Hu, et al., J. Am. Chem. Soc. 143 (2021) 399–408. doi: 10.1021/jacs.0c11370
15. [15]
  X. Luo, Y. Yang, X. Qian, Chin. Chem. Lett. 31 (2020) 2877–2883. doi: 10.1016/j.cclet.2020.07.009
16. [16]
  Q. Ling, T. Chen, S. Tan, J. Huang, L. Xu, Chin. Chem. Lett. 31 (2020) 2884–2890. doi: 10.1016/j.cclet.2020.08.020
17. [17]
  J. Mohanty, N. Barooah, V. Dhamodharan, et al., J. Am. Chem. Soc. 135 (2013) 367–376. doi: 10.1021/ja309588h
18. [18]
  L.L. Tong, L. Li, Z. Chen, Q. Wang, B. Tang, Biosens. Bioelectron. 49 (2013) 420–425. doi: 10.1016/j.bios.2013.05.051
19. [19]
  V. Gabelica, R. Maeda, T. Fujimoto, et al., Biochemistry 52 (2013) 5620–5628. doi: 10.1021/bi4006072
20. [20]
  A. Renaud de la Faverie, A. Guedin, A. Bedrat, L.A. Yatsunyk, J.L. Mergny, Nucleic Acids Res. 42 (2014) 1–8. doi: 10.1093/nar/gkt1324
21. [21]
  P.S. Vassar, C.F. Culling, Arch. Pathol. 68 (1959) 487–498.
22. [22]
  L.S. Wolfe, M.F. Calabrese, A. Nath, et al., Proc. Natl. Acad. Sci. U.S.A. 107 (2010) 16863–16868. doi: 10.1073/pnas.1002867107
23. [23]
  M. Biancalana, S. Koide, BBA-Proteins Proteom. 1804 (2010) 1405–1412. doi: 10.1016/j.bbapap.2010.04.001
24. [24]
  E.V. Dolgosheina, S.C.Y. Jeng, S.S.S. Panchapakesan, et al., ACS Chem. Biol. 9 (2014) 2412–2420. doi: 10.1021/cb500499x
25. [25]
  L. Unger-Angel, B. Rout, T. Ilani, et al., Chem. Sci. 6 (2015) 5419–5425. doi: 10.1039/C5SC01038A
26. [26]
  R. Sun, X. Guo, D. Yang, et al., Talanta 226 (2021) 122125. doi: 10.1016/j.talanta.2021.122125
27. [27]
  T.Y. Tseng, W.W. Chen, I.T. Chu, et al., Sci. Rep. 8 (2018) 16082. doi: 10.1038/s41598-018-34378-8
28. [28]
  J. Zhao, Z. Yang, Q. Zhai, D. Wei, Anal. Chim. Acta1132 (2020) 93–100. doi: 10.1016/j.aca.2020.07.017
29. [29]
  Y. Gu, D. Lin, Y. Tang, et al., Spectrochim. Acta A191 (2018) 180–188. doi: 10.1016/j.saa.2017.10.012
30. [30]
  M. Hu, J. Zhou, W.H. Luo, et al., Anal. Chem. 91 (2019) 2480–2487. doi: 10.1021/acs.analchem.8b05298
31. [31]
  H. Chen, H. Sun, S. Zhang, et al., Chem. Commun. 55 (2019) 5060–5063. doi: 10.1039/c9cc01263j
32. [32]
  Z. Yu, W. Luo, X. Chen, et al., Sens. Actuators B: Chem. 324 (2020) 128770. doi: 10.1016/j.snb.2020.128770
33. [33]
  M. Hu, Sens. Actuators B: Chem. 328 (2021) 128990. doi: 10.1016/j.snb.2020.128990
34. [34]
  F. Gao, S. Cao, W. Sun, et al., Dyes Pigments171 (2019) 107749. doi: 10.1016/j.dyepig.2019.107749
35. [35]
  R. Zhang, M. Cheng, L.M. Zhang, L.N. Zhu, D.M. Kong, ACS Appl. Mater. Inter. 10 (2018) 13350–13360. doi: 10.1021/acsami.8b01901
36. [36]
  Y.J. Lu, D.P. Hu, K. Zhang, W.L. Wong, C.F. Chow, Biosens. Bioelectron. 81 (2016) 373–381. doi: 10.1016/j.bios.2016.03.012
37. [37]
  M.D. Antonio, A. Ponjavic, A. Radzevičius, et al., Nat. Chem. 12 (2020) 832–837. doi: 10.1038/s41557-020-0506-4
38. [38]
  V.K. Bhardwaj, P. Saluja, G. Hundal, et al., Tetrahedron 69 (2013) 1606–1610. doi: 10.1016/j.tet.2012.11.090
39. [39]
  W. Wu, J. Li, L. Chen, et al., Anal. Chem. 86 (2014) 9800–9806. doi: 10.1021/ac502396g
40. [40]
  M.J. Peng, X.F. Yang, B. Yin, et al., Chem. Asian J. 9 (2014) 1817–1822. doi: 10.1002/asia.201402113
41. [41]
  L. Liu, Y. Shao, J. Peng, et al., Anal. Chem. 86 (2014) 1622–1631. doi: 10.1021/ac403326m
42. [42]
  D. Li, Y. Xu, N. Zhou, et al., Dyes Pigments136 (2017) 627–632. doi: 10.1016/j.dyepig.2016.09.014
43. [43]
  J. Ming, X. Liu, Z. Xin, et al., ACS Appl. Mater. Inter. 10 (2018) 25166–25173. doi: 10.1021/acsami.8b07869
44. [44]
  J. Wang, S. Qi, J. Du, et al., Chem. J. Chin. Univ. 40 (2019) 1397–1404.
45. [45]
  P. He, L. Tang, K. Zhong, S. Hou, X. Yan, Chin. J. Org. Chem. 37 (2017) 423–428. doi: 10.6023/cjoc201608003
46. [46]
  A. Rouf, C. Tanyeli, Eur. J. Med. Chem. 97 (2015) 911–927. doi: 10.1016/j.ejmech.2014.10.058
47. [47]
  D.C. Liu, H.J. Zhang, C.M. Jin, Z.S. Quan, Molecules 21 (2016) 164. doi: 10.3390/molecules21030164
48. [48]
  A.K. Mora, S. Murudkar, A. Alamelu, et al., Chem. Eur. J. 25 (2016) 16505–16512. doi: 10.1002/chem.201602981
49. [49]
  M.C. Alley, D.A. Scudiero, A. Monks, et al., Cancer Res. 48 (1988) 589–601.
50. [50]
  S. Ke, L. Shi, X. Cao, et al., Eur. J. Med. Chem. 54 (2012) 248–254. doi: 10.1016/j.ejmech.2012.05.003
51. [51]
  T. Xu, L. Shi, Y. Zhang, et al., Eur. J. Med. Chem. 168 (2019) 293–300. doi: 10.1016/j.ejmech.2019.02.060
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