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One-step preparation of branched PEG functionalized AIE-active luminescent polymeric nanoprobes

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Abstract

The synthesis of amphiphilic aggregation-induced emission (AIE) dyes based organic nanoparticles has recently attracted increasing attention in the biomedical fields. These AIE dyes based nanoparticles could effectively overcome the aggregation caused quenching effect of conventional organic dyes, making them promising candidates for fabrication of ultrabright organic luminescent nanomaterials. In this work, AIE-active luminescent polymeric nanoparticles (4-NH2-PEG-TPE-E LPNs) were facilely fabricated through Michael addition reaction between tetraphenylethene acrylate (TPE-E) and 4-arm-poly(ethylene glycol)-amine (4-NH2-PEG) in rather mild ambient. The 4-NH2-PEG can not only endow these AIE-active LPNs good water dispersibility, but also provide functional groups for further conjugation reaction. The size, morphology and luminescent properties of 4-NH2-PEG-TPE-E LPNs were characterized by a series of techniques in detail. Results suggested that these AIE-active LPNs showed spherical morphology with diameter about 100–200 nm. The obtained 4-NH2-PEG-TPE-E LPNs display high water dispersibility and strong fluorescence intensity because of their self assembly and AIE properties of TPE-E. Biological evaluation results demonstrated that 4-NH2-PEG-TPE-E LPNs showed negative toxicity toward cancer cells and good fluorescent imaging performance. All of these features make 4-NH2-PEG-TPE-E LPNs promising candidates for biological imaging and therapeutic applications.

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References

  1. Feng X, Liu L, Wang S, Zhu D. Chem Soc Rev, 2010, 39: 2411–2419

    Article  CAS  Google Scholar 

  2. Hu R, Leung NL, Tang BZ. Chem Soc Rev, 2014, 43: 4494–4562

    Article  CAS  Google Scholar 

  3. Wu W, Tang R, Li Q, Li Z. Chem Soc Rev, 2015, 12: 3997–4022

    Article  Google Scholar 

  4. Breul AM, Hager MD, Schubert US. Chem Soc Rev, 2013, 42: 5366–5407

    Article  CAS  Google Scholar 

  5. Zhang X, Wang S, Xu L, Ji Y, Feng L, Tao L, Li S, Wei Y. Nanoscale, 2012, 4: 5581–5584

    Article  CAS  Google Scholar 

  6. Qin A, Lam JW, Tang BZ. Prog Polym Sci, 2012, 37: 182–209

    Article  CAS  Google Scholar 

  7. Wang K, Zhang X, Zhang X, Fan X, Huang Z, Chen Y, Wei Y. Polym Chem, 2015, 6: 5891–5898

    Article  CAS  Google Scholar 

  8. Chandra S, Pathan SH, Mitra S, Modha BH, Goswami A, Pramanik P. RSC Adv, 2012, 2: 3602–3606

    Article  CAS  Google Scholar 

  9. De B, Karak N. RSC Adv, 2013, 3: 8286–8290

    Article  CAS  Google Scholar 

  10. Liu S, Zhang H, Qiao Y, Su X. RSC Adv, 2012, 2: 819–825

    Article  CAS  Google Scholar 

  11. Luo PG, Yang F, Yang ST, Sonkar SK, Yang L, Broglie JJ, Liu Y, Sun YP. RSC Adv, 2014, 4: 10791–10807

    Article  CAS  Google Scholar 

  12. Hui J, Zhang X, Zhang Z, Wang S, Tao L, Wei Y, Wang X. Nanoscale, 2012, 4: 6967–6970

    Article  CAS  Google Scholar 

  13. Zhang X, Wang S, Liu M, Yang B, Feng L, Ji Y, Tao L, Wei Y. Phys Chem Chem Phys, 2013, 15: 19013–19018

    Article  CAS  Google Scholar 

  14. Zheng X, Liu M, Hui J, Fan D, Ma H, Zhang X, Wang Y, Wei Y. Phys Chem Chem Phys, 2015, 17: 20301–20307

    Article  CAS  Google Scholar 

  15. Zhang X, Hui J, Yang B, Yang Y, Fan D, Liu M, Tao L, Wei Y. Polym Chem, 2013, 4: 4120–4125

    Article  CAS  Google Scholar 

  16. Zhang X, Wang S, Zhu C, Liu M, Ji Y, Feng L, Tao L, Wei Y. J Colloid Interf Sci, 2013, 397: 39–44

    Article  CAS  Google Scholar 

  17. Díez I, Ras RHA. Nanoscale, 2011, 3: 1963–1970

    Article  Google Scholar 

  18. Liu M, Zhang X, Yang B, Deng F, Ji J, Yang Y, Huang Z, Zhang X, Wei Y. RSC Adv, 2014, 4: 22294–22298

    Article  CAS  Google Scholar 

  19. Tang L, Jin J, Zhang S, Mao Y, Sun J, Yuan W, Zhao H, Xu H, Qin A, Tang BZ. Sci China Chem, 2009, 52: 755–759

    Article  CAS  Google Scholar 

  20. Gao Y, Zhang H, Jiang T, Yang J, Li B, Li Z, Hua J. Sci China Chem, 2013, 56: 1204–1212

    Article  CAS  Google Scholar 

  21. Li Q, Li Z. Sci China Chem, 2015, 58: 1800–1809

    Article  CAS  Google Scholar 

  22. Liang J, Feng G, Kwok RTK, Ding D, Tang B, Liu B. Sci China Chem, 2016, 59: 53–61

    Article  CAS  Google Scholar 

  23. Qin A, Zhang Y, Han N, Mei J, Sun J, Fan W, Tang BZ. Sci China Chem, 2012, 55: 772–778

    Article  CAS  Google Scholar 

  24. Hu X, Li Y, Liu T, Zhang G, Liu S. Sci China Chem, 2014, 57: 615–623

    Article  CAS  Google Scholar 

  25. Wang D, Cao W, Fan J. Sci China Chem, 2014, 57: 791–796

    Article  CAS  Google Scholar 

  26. Huang Z, Zhang X, Zhang X, Wang S, Yang B, Wang K, Yuan J, Tao L, Wei Y. RSC Adv, 2015, 5: 65884–65889

    Article  CAS  Google Scholar 

  27. Li K, Qin W, Ding D, Tomczak N, Geng J, Liu R, Liu J, Zhang X, Liu H, Liu B. Sci Rep, 2013, 3: 1150

    Google Scholar 

  28. Hong Y, Lam JWY, Tang BZ. Chem Soc Rev, 2011, 40: 5361–5388

    Article  CAS  Google Scholar 

  29. Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ. Chem Commun, 2001, 37: 1740–1741

    Article  Google Scholar 

  30. Zhang X, Zhang X, Wang S, Liu M, Tao L, Wei Y. Nanoscale, 2013, 5: 147–150

    Article  CAS  Google Scholar 

  31. Zhang X, Wang K, Liu M, Zhang X, Tao L, Chen Y, Wei Y. Nanoscale, 2015, 7: 11486–11508

    Article  CAS  Google Scholar 

  32. Zhang X, Zhang X, Yang B, Liu L, Hui J, Liu M, Chen Y, Wei Y. RSC Adv, 2014, 4: 10060–10066

    Article  CAS  Google Scholar 

  33. Zhang X, Zhang X, Wang S, Liu M, Zhang Y, Tao L, Wei Y. ACS Appl Mater Interf, 2013, 5: 1943–1947

    Article  CAS  Google Scholar 

  34. Wang K, Zhang X, Zhang X, Yang B, Li Z, Zhang Q, Huang Z, Wei. Polym Chem, 2015, 6: 1360–1366

    Article  CAS  Google Scholar 

  35. Mei J, Leung NL, Kwok RT, Lam JW, Tang BZ. Chem Rev, 2015, 115: 11718–11940

    Article  CAS  Google Scholar 

  36. Yang J, Huang J, Li Q, Li Z. J Mater Chem C, 2016, DOI: 10.1039/C1035TC03262H

    Google Scholar 

  37. Zhang X, Zhang X, Yang B, Liu M, Liu W, Chen Y, Wei Y. Poly Chem, 2014, 5: 399–404

    Article  CAS  Google Scholar 

  38. Feng G, Tay CY, Chui QX, Liu R, Tomczak N, Liu J, Tang BZ, Leong DT, Liu B. Biomaterials, 2014, 35: 8669–8677

    Article  CAS  Google Scholar 

  39. Yuan Y, Kwok RT, Zhang R, Tang BZ, Liu B. Chem Commun, 2014, 50: 11465–11468

    Article  CAS  Google Scholar 

  40. Yuan WZ, Mahtab F, Gong Y, Yu ZQ, Lu P, Tang Y, Lam JW, Zhu C, Tang BZ. J Mater Chem, 2012, 22: 10472–10479

    Article  CAS  Google Scholar 

  41. Li K, Liu B. Chem Soc Rev, 2014, 43: 6570–6597

    Article  CAS  Google Scholar 

  42. Geng J, Li K, Ding D, Zhang X, Qin W, Liu J, Tang BZ, Liu B. Small, 2012, 8: 3655–3663

    Article  CAS  Google Scholar 

  43. Yuan Y, Chen Y, Tang BZ, Liu B. Chem Commun, 2014, 50: 3868–3870

    Article  CAS  Google Scholar 

  44. Liu M, Ji J, Zhang X, Zhang X, Yang B, Deng F, Li Z, Wang K, Yang Y, Wei Y. J Mater Chem B, 2015, 3: 3476–3482

    Article  CAS  Google Scholar 

  45. Wan Q, Wang K, Du H, Huang H, Liu M, Deng F, Dai Y, Zhang X, Wei Y. Polym Chem, 2015, 6: 5288–5294

    Article  CAS  Google Scholar 

  46. Liu Z, Davis C, Cai W, He L, Chen X, Dai H. Proc Natl Acad Sci USA, 2008, 105: 1410–1415

    Article  CAS  Google Scholar 

  47. Greenwald R. J Control Release, 2001, 74: 159–171

    Article  CAS  Google Scholar 

  48. Otsuka H, Nagasaki Y, Kataoka K. Adv Drug Deliver Rev, 2012, 64: 246–255

    Article  Google Scholar 

  49. Zhang X, Wang S, Fu C, Feng L, Ji Y, Tao L, Li S, Wei Y. Polym Chem, 2012, 3: 2716–2719

    Article  CAS  Google Scholar 

  50. Zhang X, Fu C, Feng L, Ji Y, Tao L, Huang Q, Li S, Wei Y. Polymer, 2012, 53: 3178–3184

    Article  CAS  Google Scholar 

  51. Zhang X, Zeng G, Tian J, Wan Q, Huang Q, Wang K, Zhang Q, Liu M, Deng F, Wei Y. Appl Surf Sci, 2015, 351: 425–432

    Article  CAS  Google Scholar 

  52. Wan Q, Liu M, Tian J, Deng F, Zeng G, Li Z, Wang K, Zhang Q, Zhang X, Wei Y. Polym Chem, 2015, 6: 1786–1792

    Article  CAS  Google Scholar 

  53. Wan Q, Mao L, Liu M, Wang K, Zeng G, Xu D, Huang H, Zhang X, Wei Y. Polym Chem, 2015, 6: 7211–7218

    Article  CAS  Google Scholar 

  54. Qin W, Ding D, Liu J, Yuan WZ, Hu Y, Liu B, Tang BZ. Adv Funct Mater, 2012, 22: 771–779

    Article  CAS  Google Scholar 

  55. Qin W, Li K, Feng G, Li M, Yang Z, Liu B, Tang BZ. Adv Funct Mater, 2014, 24: 635–643

    Article  CAS  Google Scholar 

  56. Zhang X, Zhang X, Yang B, Liu M, Liu W, Chen Y, Wei Y. Polym Chem, 2013, 4: 4317–4321

    Article  CAS  Google Scholar 

  57. Zhang X, Zhang X, Yang B, Liu M, Liu W, Chen Y, Wei Y. Polym Chem, 2014, 5: 356–360

    Article  CAS  Google Scholar 

  58. Zhang X, Qi H, Wang S, Feng L, Ji Y, Tao L, Li S, Wei Y. Toxicol Res, 2012, 1: 201–205

    Article  CAS  Google Scholar 

  59. Zhang X, Wang S, Liu M, Hui J, Yang B, Tao L, Wei Y. Toxicol Res, 2013, 2: 335–346

    Article  CAS  Google Scholar 

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Correspondence to Xiaoyong Zhang or Yen Wei.

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Chu, J., Lv, Q., Guo, C. et al. One-step preparation of branched PEG functionalized AIE-active luminescent polymeric nanoprobes. Sci. China Chem. 59, 1003–1009 (2016). https://doi.org/10.1007/s11426-016-5578-z

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  • DOI: https://doi.org/10.1007/s11426-016-5578-z

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