Citation: Li Min, Li Yuntao, Wang Xijing, Cui Xiaoyan, Wang Ting. Synthesis and application of near-infrared substituted rhodamines[J]. Chinese Chemical Letters, ;2019, 30(10): 1682-1688. doi: 10.1016/j.cclet.2019.06.036 shu

Synthesis and application of near-infrared substituted rhodamines

Li Min ^a ,
Li Yuntao ^a ,
Wang Xijing ^a ,
Cui Xiaoyan ^a,*, ,
Wang Ting ^b,*,

a.
Department of Chemistry, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China
b.
Department of Organic Chemistry, College of Pharmacy, Second Military Medical University, Shanghai 200433, China

xycui@chem.ecnu.edu.cn

wangting1983927@gmail.com

Received Date: 4 May 2019
Revised Date: 18 June 2019
Accepted Date: 19 June 2019
Available Online: 20 October 2019

Figures(8)

Near infrared (NIR) fluorescent probes are highly attractive in the field of fluorescent imaging of living organisms for their outstanding signal-to-noise ratio, strong tissue penetration and low biotoxicity. Herein, we summarized some recent progress in the synthesis and application of NIR rhodamines by replacing the bridging oxygen atom with main group elements such as silicon and phosphorus.
- Silicon,
- Rhodamine,
- Probe,
- Near infrared,
- Biological fluorescence imaging
1. [1]
  S.W. Hell, S.J. Sahl, M. Bates, et al., J. Phys. D Appl. Phys. 48(2015) 1-35.
2. [2]
  A.M. Sydor, K.J. Czymmek, E.M. Puchner, et al., Trends Cell Biol. 25(2015) 730-748. doi: 10.1016/j.tcb.2015.10.004
3. [3]
  S. Ma, L. Li, M. She, et al., Chin. Chem. Lett. 28(2017) 2014-2018. doi: 10.1016/j.cclet.2017.09.027
4. [4]
  H.R. Cheng, Y. Qian, Chin. Chem. Lett. 27(2016) 879-886. doi: 10.1016/j.cclet.2016.01.039
5. [5]
  X.M. Li, R.R. Zhao, Y. Yang, et al., Chin. Chem. Lett. 28(2017) 1258-1261. doi: 10.1016/j.cclet.2016.12.029
6. [6]
  Y. Xia, X. Liu, D. Wang, et al., Chin. Chem. Lett. 29(2018) 1517-1520. doi: 10.1016/j.cclet.2018.01.054
7. [7]
  X.M. Li, R.R. Zhao, Y.L. Wei, et al., Chin. Chem. Lett. 27(2016) 813-816. doi: 10.1016/j.cclet.2016.04.001
8. [8]
  X. Luo, L. Qian, Y. Xiao, et al., Nat. Commun. 10(2019) 258. doi: 10.1038/s41467-018-08241-3
9. [9]
  H. He, Z. Ye, Y. Zheng, et al., Chem. Commun. (Camb.) 54(2018) 2842-2845. doi: 10.1039/C7CC08886H
10. [10]
  H. He, T. He, Z. Zhang, et al., Chin. Chem. Lett. 29(2018) 1497-1499. doi: 10.1016/j.cclet.2018.08.019
11. [11]
  M. Fu, Y. Xiao, X. Qian, et al., Chem. Commun. (Camb.) (2008) 1780-1782.
12. [12]
  Y. Koide, Y. Urano, K. Hanaoka, et al., ACS Chem. Biol. 6(2011) 600-608. doi: 10.1021/cb1002416
13. [13]
  Y. Koide, Y. Urano, K. Hanaoka, et al., J. Am. Chem. Soc. 133(2011) 5680-5682. doi: 10.1021/ja111470n
14. [14]
  T. Egawa, K. Hanaoka, Y. Koide, et al., J. Am. Chem. Soc.133(2011) 14157-14159. doi: 10.1021/ja205809h
15. [15]
  G. Lukinavicius, K. Umezawa, N. Olivier, et al., Nat. Chem. 5(2013) 1329-139.
16. [16]
  R.S. Erdmann, H. Takakura, A.D. Thompson, et al., Angew. Chem. Int. Ed. 53(2014) 10242-10246. doi: 10.1002/anie.201403349
17. [17]
  P. Shieh, M.S. Siegrist, A.J. Cullen, et al., Proc. Natl. Acad. Sci. U. S. A. 111(2014) 5456-5461. doi: 10.1073/pnas.1322727111
18. [18]
  Y.L. Huang, A.S. Walker, E.W. Miller, J. Am. Chem. Soc. 137(2015) 10767-10776. doi: 10.1021/jacs.5b06644
19. [19]
  X. Chai, X. Cui, B. Wang, et al., Chem.-Eur. J. 21(2015) 16754-16758. doi: 10.1002/chem.201502921
20. [20]
  X. Zhou, R. Lai, J.R. Beck, et al., Chem. Commun. (Camb.) 52(2016) 12290-12293. doi: 10.1039/C6CC05717A
21. [21]
  X. Chai, J. Xiao, M. Li, et al., Chem.-Eur. J. 24(2018) 14506-14512. doi: 10.1002/chem.201802875
22. [22]
  M. Grzybowski, M. Taki, K. Senda, et al., Angew. Chem. Int. Ed. 57(2018) 10137-10141. doi: 10.1002/anie.201804731
23. [23]
  X. Zhou, L. Lesiak, R. Lai, et al., Angew. Chem. Int. Ed. 56(2017) 4197-4200. doi: 10.1002/anie.201612628
24. [24]
  J. Liu, Y.Q. Sun, H. Zhang, et al., Acs Appl. Mater. Inter. 8(2016) 22953-22962. doi: 10.1021/acsami.6b08338
25. [25]
  K. Kolmakov, V.N. Belov, C.A. Wurm, et al., Eur. J. Org. Chem. 2010(2010) 3593-3610. doi: 10.1002/ejoc.201000343
26. [26]
  J. Arden-Jacob, J. Frantzeskos, N.U. Kemnitzer, et al., Spectrochim. Acta A. 57(2001) 2271-2283. doi: 10.1016/S1386-1425(01)00476-0
27. [27]
  J.B. Grimm, A.J. Sung, W.R. Legant, et al., ACS Chem. Biol. 8(2013) 1303-1310. doi: 10.1021/cb4000822
28. [28]
  J.B. Grimm, T.D. Gruber, G. Ortiz, et al., Bioconj. Chem. 27(2016) 474-480. doi: 10.1021/acs.bioconjchem.5b00566
29. [29]
  G. Tombline, D.J. Donnelly, J.J. Holt, et al., Biochemistry 45(2006) 8034-8047. doi: 10.1021/bi0603470
30. [30]
  B. Calitree, D.J. Donnelly, J.J. Holt, et al., Organometallics 26(2007) 6248-6257. doi: 10.1021/om700846m
31. [31]
  P. Shieh, V.T. Dien, B.J. Beahm, et al., J. Am. Chem. Soc. 137(2015) 7145-7151. doi: 10.1021/jacs.5b02383
32. [32]
  L.D. Lavis, Biochemistry 56(2017) 5165-5170. doi: 10.1021/acs.biochem.7b00529
33. [33]
  L.D. Lavis, Annu. Rev. Biochem. 86(2017) 825-843. doi: 10.1146/annurev-biochem-061516-044839
34. [34]
  Y. Kushida, T. Nagano, K. Hanaoka, Analyst 140(2015) 685-695. doi: 10.1039/C4AN01172D
35. [35]
  T. Ikeno, T. Nagano, K. Hanaoka, Chem.-Asia. J 12(2017) 1435-1446. doi: 10.1002/asia.201700385
36. [36]
  F. Deng, Z. Xu, Chin. Chem. Lett. (2018), doi: http://dx.doi.org/10.1016/j.cclet.2018.12.012.
37. [37]
  M. Ceresole, Ger. Pat. 44002, Nov 13, 1887.
38. [38]
  M. Ceresole, U.S. Pat. 377349, Jan 31, 1888.
39. [39]
  S.J. Dwight, S. Levin, Org. Lett. 18(2016) 5316-5319. doi: 10.1021/acs.orglett.6b02635
40. [40]
  J.B. Grimm, L.D. Lavis, Org. Lett. 13(2011) 6354-6357. doi: 10.1021/ol202618t
41. [41]
  Y. Koide, Y. Urano, K. Hanaoka, et al., J. Am. Chem. Soc. 134(2012) 5029-5031. doi: 10.1021/ja210375e
42. [42]
  J.L. Bachman, P.R. Escamilla, A.J. Boley, et al., Org. Lett. 21(2019) 206-209. doi: 10.1021/acs.orglett.8b03661
43. [43]
  B.Wang, X.Chai, W.Zhu, etal., Chem.Commun.(Camb.)50(2014)14374-14377. doi: 10.1039/C4CC06178K
44. [44]
  J.B. Grimm, T.A. Brown, A.N. Tkachuk, et al., ACS Cent. Sci. 3(2017) 975-985. doi: 10.1021/acscentsci.7b00247
45. [45]
  C. Fischer, C. Sparr, Angew. Chem. Int. Ed. 57(2018) 2436-2440. doi: 10.1002/anie.201711296
46. [46]
  J.B. Grimm, B.P. English, J.J. Chen, et al., Nat. Methods 12(2015) 244-250. doi: 10.1038/nmeth.3256
47. [47]
  Y. Koide, M. Kawaguchi, Y. Urano, et al., Chem. Commun. (Camb.) 48(2012) 3091-3093. doi: 10.1039/c2cc18011a
48. [48]
  G. Lukinavicius, L. Reymond, E. D 9'Este, et al., Nat. Methods 11(2014) 731-733. doi: 10.1038/nmeth.2972
49. [49]
  J.B. Grimm, T. Klein, B.G. Kopek, et al., Angew. Chem. Int. Ed. 55(2016) 1723-1727. doi: 10.1002/anie.201509649
50. [50]
  G. Lukinavicius, L. Reymond, K. Umezawa, et al., J. Am. Chem. Soc. 138(2016) 99365-9368.
51. [51]
  B. Wang, S. Yu, X. Chai, et al., Chem.-Eur. J. 22(2016) 5649-5656. doi: 10.1002/chem.201505054
52. [52]
  W. Zhu, X. Chai, B. Wang, et al., Chem. Commun. (Camb.) 51(2015) 9608-9611. doi: 10.1039/C5CC02496J
53. [53]
  G. Lukinavicius, C. Blaukopf, E. Pershagen, et al., Nat. Commun. 6(2015) 8497.9 doi: 10.1038/ncomms9497
54. [54]
  K. Kiyose, S. Aizawa, E. Sasaki, et al., Chem.-Eur. J. 15(2009) 9191-9200. doi: 10.1002/chem.200900035
55. [55]
  Y.Q. Sun, J. Liu, X. Lv, et al., Angew. Chem. Int. Ed. 51(2012) 7634-7636. doi: 10.1002/anie.201202264
56. [56]
  J. Miao, Y. Huo, H. Shi, et al., J. Mater. Chem. B Mater. Biol. Med. 6(2018) 4466-4473. doi: 10.1039/C8TB00987B
57. [57]
  M. Albota, D. Beljonne, J.L. Brédas, et al., Science 281(1998) 1653-1656. doi: 10.1126/science.281.5383.1653
58. [58]
  F. Terenziani, C. Katan, E. Badaeva, et al., Adv. Mater. 20(2008) 4641-4678. doi: 10.1002/adma.200800402
59. [59]
  Z. Mao, H. Jiang, X. Song, et al., Anal. Chem. 89(2017) 9620-9624. doi: 10.1021/acs.analchem.7b02697
60. [60]
  H. Zhang, J. Liu, L. Wang, et al., Biomaterials 158(2018) 10-22. doi: 10.1016/j.biomaterials.2017.12.013
61. [61]
  L. Wang, W. Du, Z. Hu, et al., Angew. Chem. Int. Ed 58(2019) 2-20. doi: 10.1002/anie.201813331
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