Citation: Ji Guang, Yan Lulin, Wang Hui, Ma Lian, Xu Bin, Tian Wenjing. Efficient Near-infrared AIE Nanoparticles for Cell Imaging[J]. Acta Chimica Sinica, ;2016, 74(11): 917-922. doi: 10.6023/A16080430 shu

Efficient Near-infrared AIE Nanoparticles for Cell Imaging

1.
State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012

Corresponding author: Xu Bin, xubin@jlu.edu.cn Tian Wenjing, wjtian@jlu.edu.cn
Received Date: 24 August 2016

Fund Project: the Natural Science Foundation of China 21221063and Program for Chang Jiang Scholars and Innovative Research Team in University IRT101713018the Natural Science Foundation of China 51573068the Natural Science Foundation of China 51373063Project supported by 973 Program 2013CB834701

Figures(8)

Near-infrared fluorescence signals are highly desirable to acheieve high resolution in biological imaging. We encapsulated hydrophobic AIE (aggregation-induced emission) fluorophores into the biocompatible Pluronic F-127 NPs for cellular imaging and efficiently enhance the near-infrared AIE fluorophore emission. AIE molecule 2-(4-bromophenyl)-3-(4-(4-(diphenylamino) styryl) phenyl) fumaronitrile (TPABDFN) with near-infrared emission was synthesized and selected as the fluorescence resonance energy transfer (FRET) acceptor. (2-p-tolylethene-1, 1, 2-triyl) tribenzene (TPE-Me) was a blue-emitting AIE molecule, which spectrum was matching with TPABDFN. TPE-Me@F127 NPs emission was 480 nm, TPABDFN@F127 NPs maximum absorption wavelength was also 480 nm, that the absorption had a large area of overlapping with the TPE-Me@F127 NPs emission spectrum and leaded to efficient energy transfer, so TPE-Me was selected as the FRET donor. By encapsulating both TPE-Me donor and TPABDFN acceptor simultaneously within the NPs, a significant FRET effect was induced. FRET pairs of different ratios was co-encapsulated into the F127 NPs to optimize the fluorescence signals. The maximum of fluorescence quantum yield was 19.9%, energy transfer efficiency was 43.5%. TPABDFN@F127 NPs only had weak fluorescence, but the TPABDFN/TPE-Me@F127 NPs showed bright fluorescence signal. Fluorescence resonance energy transfer contributed to the notable increase of acceptor emission The fluorescence quantum yield had 10-fold enhancement of the TPABDFN. In addition, the obtained TPABDFN/TPE-Me@F127 NPs showed a large Stokes shift of 265 nm, which can be used to avoid the interference between excitation and emission light, as well as the near-infrared emission spectrum away from the organism auto-fluorescence, which was beneficial for the bio-application. Fluorescent probe emission in the far red/near-infrared (FR/NIR) (650~900 nm) region for biological detection also can greatly reduce the damage to living body. And TPABDFN/TPE-Me@F127 NPs had low cytotoxicity, good biocompatibility, stability and anti-photobleaching. The TPABDFN/TPE-Me@F127 NPs achieved good imaging result on HepG2 cell cytoplasm.
- aggregation-induced emission,
- energy transfer,
- self-assembly,
- nanoparticles,
- cell imaging
1. [1]
  Luo, S.; Zhang, E.; Su, Y. Biomaterials 2011, 32, 7127. doi: 10.1016/j.biomaterials.2011.06.024
2. [2]
  Frangioni, J. V. Curr. Opin. Chem. Biol. 2003, 7, 626. doi: 10.1016/j.cbpa.2003.08.007
3. [3]
  Liu, J.; Geng, J.; Liu, B. Chem. Commun. 2013, 49, 1491. doi: 10.1039/C2CC37219C
4. [4]
  Ghoroghchian, P. P.; Frail, P. R.; Susumu, K. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 2922. doi: 10.1073/pnas.0409394102
5. [5]
  Geng, J.; Li, K.; Pu, K. Y. Small 2012, 8, 2421. doi: 10.1002/smll.v8.15
6. [6]
  He, X.; Wang, K.; Cheng, Z. WIRES Nanomed Nano 2010, 2, 349. doi: 10.1002/wnan.85
7. [7]
  Lu, H. G.; Xu, B.; Tian, W. J. Angew. Chem. Int. Ed. 2016, 55, 155. doi: 10.1002/anie.201507031
8. [8]
  Zhang, Y.; Wu, C. F.; Tian, W. J. RSC Adv. 2015, 5, 36837. doi: 10.1039/C5RA04669F
9. [9]
  Gao, G. B.; Gong, D. J.; Zhang, M. X. Acta Chim. Sinica 2016, 74, 363.
10. [10]
  Zrazhevskiy, P.; Sena, M.; Gao, X. Chem. Soc. Rev. 2010, 39, 4326. doi: 10.1039/b915139g
11. [11]
  Gao, J.; Chen, K.; Luong, R. Nano Lett. 2011, 12, 281.
12. [12]
  Michalet, X.; Pinaud, F.; Bentolila, L. Science 2005, 307, 538. doi: 10.1126/science.1104274
13. [13]
  Cui, X. T.; Lv, Y. Y.; Liu, Y. Acta Chim. Sinica 2014, 72, 75.
14. [14]
  Santra, S.; Zhang, P.; Wang, K. Anal. Chem. 2001, 73, 4988. doi: 10.1021/ac010406+
15. [15]
  Wu, X.; Chang, S.; Sun, X. Chem. Sci. 2013, 4, 1221. doi: 10.1039/c2sc22035k
16. [16]
  Shi, C.; Guo, Z.; Yan, Y. ACS Appl. Mater. Interfaces 2012, 5, 192.
17. [17]
  Gao, X.; Yang, L.; Petros, J. A. Curr. Opin. Chem. Biol. 2005, 16, 63.
18. [18]
  Resch-Genger, U.; Grabolle, M.; Cavaliere-Jaricot, S. Nat. Methods 2008, 5, 763. doi: 10.1038/nmeth.1248
19. [19]
  Smith, A.; Duan, H.; Mohs, A. Adv. Drug Deliver. Rev. 2008, 60, 1226. doi: 10.1016/j.addr.2008.03.015
20. [20]
  Jamieson, T.; Bakhshi, R.; Petrova, D. Biomaterials 2007, 28, 4717. doi: 10.1016/j.biomaterials.2007.07.014
21. [21]
  Wang, L.; Tan, W. Nano Lett. 2006, 6, 84. doi: 10.1021/nl052105b
22. [22]
  Schadlich, A.; Caysa, H.; Mueller, T. ACS Nano 2011, 5, 8710. doi: 10.1021/nn2026353
23. [23]
  Lee, C. H. Cheng, S. H.; Wang, Y. J. Adv. Funct. Mater. 2009, 19, 215. doi: 10.1002/adfm.v19:2
24. [24]
  Altınoğlu, E.; Adair, J. H WIRES Nanomed. Nanobi. 2010, 2, 461. doi: 10.1002/wnan.77
25. [25]
  Yan, L. L.; Xu, B.; Tian, W. J. Nanoscale 2016, 8, 2471. doi: 10.1039/C5NR05051K
26. [26]
  Thomas, S.; Joly, G.; Swager, T. Chem. Rev. 2007, 107, 1339. doi: 10.1021/cr0501339
27. [27]
  Brasseur, N.; Nguyen, T.; Langlois, R. J. Med. Chem. 1994, 37, 415. doi: 10.1021/jm00029a014
28. [28]
  Mei, J.; Leung, N.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263
29. [29]
  Luo, J.; Xie, Z.; Lam, J. W. Chem. Commun. 2001, 18, 1740.
30. [30]
  Hong, Y.; Lam, J. W.; Tang, B. Z. Chem. Commun. 2009, 29, 4332.
31. [31]
  Wang, M.; Zhang, D.; Zhang, G. Chem. Commun. 2008, 37, 4469.
32. [32]
  Hong, Y.; Lam, J.; Tang, B. Z. Chem. Soc. Rev. 2011, 40. 5361. doi: 10.1039/c1cs15113d
33. [33]
  Wang, M.; Zhang, G.; Zhang, D. J. Mater. Chem. 2010, 20, 1858. doi: 10.1039/b921610c
34. [34]
  Chen J. L.; Xu, B.; Tian, W. J. ACS Photonics 2015, 2, 313. doi: 10.1021/ph5004384
35. [35]
  Zhang, Y.; Xu, B.; Tian, W. J. Polym. Chem. 2014, 5, 3824. doi: 10.1039/c4py00075g
36. [36]
  Qi, Q. K.; Xu, B.; Tian, W. J. Adv. Funct. Mater. 2015, 25, 4005. doi: 10.1002/adfm.v25.26
37. [37]
  Zhang, J. B.; Xu, B.; Tian, W. J. Adv. Mater. 2014, 26, 739. doi: 10.1002/adma.201303639
38. [38]
  Zhang, J. B.; Xu, B.; Tian, W. J. Chem. Commun. 2013, 49, 3878. doi: 10.1039/c3cc41171k
39. [39]
  Zhao, Z.; Geng, J.; Chang, Z. J. Mater. Chem. 2012, 22, 11018. doi: 10.1039/c2jm31482g
40. [40]
  Qin, W.; Ding, D.; Liu, J. Adv. Funct. Mater. 2012, 22, 771. doi: 10.1002/adfm.201102191
41. [41]
  Geng, J.; Li, K.; Ding, D. Small 2012, 8, 3655. doi: 10.1002/smll.v8.23
42. [42]
  Geng, J.; Li, K.; Qin, W. Small 2013, 9, 2012. doi: 10.1002/smll.v9.11
43. [43]
  Shi, H.; Liu, J.; Geng, J. J. Am. Chem. Soc. 2012, 134, 9569. doi: 10.1021/ja302369e
44. [44]
  Wang, M.; Gu, X.; Zhang, G. Anal. Chem. 2009, 81, 4444. doi: 10.1021/ac9002722
45. [45]
  Liu, L.; Zhang, G.; Xiang, J. Org. Lett. 2008, 10, 4581. doi: 10.1021/ol801855s
46. [46]
  Li, X.; Xu, B.; Tian, W. J. Anal. Chem. 2014, 86, 298. doi: 10.1021/ac403629t
47. [47]
  Ma, K.; Xu, B.; Tian, W. J. Anal. Bioanal. Chem. 2015, 407, 2625. doi: 10.1007/s00216-015-8467-y
48. [48]
  Qian, J.; Zhu, Z. F.; Qin, A. J. Adv. Mater. 2015, 27, 2332. doi: 10.1002/adma.v27.14
49. [49]
  Wang, Y. L.; Hu, R. R.; Xu, W. Biomed. Opt. Express. 2015, 6, 3783. doi: 10.1364/BOE.6.003783
50. [50]
  Jin, Y.; Ye, F.; Zeigler, M. ACS Nano 2011, 5, 1468. doi: 10.1021/nn103304m
51. [51]
  Chung, C. Y.-S.; Yam, V. W.-W. Chem. Sci. 2013, 4, 377. doi: 10.1039/C2SC20897K
52. [52]
  Xu, Y.; Zhang, H.; Li, F. J. Mater. Chem. 2012, 22, 1592. doi: 10.1039/C1JM14815J
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