Skip to main content Accessibility help
×
Home

Amphiphilic fluorescent copolymers via one-pot synthesis of RAFT polymerization and multicomponent Biginelli reaction and their cells imaging applications

  • Zengfang Huang (a1), Runze Wang (a1), Yali Chen (a1), Xiaobo Liu (a2), Liucheng Mao (a3), Jinying Yuan (a3), Lei Tao (a3), Yen Wei (a3) and Xiaoyong Zhang (a4)...

Abstract

In this contribution, we devoted ourselves to fabricating aggregation-induced emission (AIE) activity copolymers via one-pot combination of RAFT polymerization and Biginelli reaction for the first time. When the feeding ratio of TPB was 33.5%, the molar fraction of TPB was, respectively, about 14.2 and 22.5% in PEG-PTE1 copolymers by two-step strategy and PEG-PTE2 copolymers by one-pot strategy with the similar structure. The Mn of PEG-PTE1 increased to 59,300 from 52,800 of PEG-AE presoma with narrow PDI, which was more than Mn of PEG-PTE2 with 52,300. As compared with PEG-PTE2, when the feeding ratio of TPB was 48.6%, the molar fraction of TPB increased to 32.6% in PEG-PTE3. In aqueous solution, the as-obtained PEG-PTE2 copolymers can self-assemble into fluorescent organic nanoparticles (FONs) with 100–180 nm spherical morphology, the maximal emission peak of which presented at 460 nm with the obvious AIE phenomenon. Moreover, due to the low toxicity and excellent cell dyeing behavior, the as-prepared PEG-PTE2 copolymers displayed great potential for biomedical applications.

  • View HTML
    • Send article to Kindle

      To send this article to your Kindle, first ensure no-reply@cambridge.org is added to your Approved Personal Document E-mail List under your Personal Document Settings on the Manage Your Content and Devices page of your Amazon account. Then enter the ‘name’ part of your Kindle email address below. Find out more about sending to your Kindle. Find out more about sending to your Kindle.

      Note you can select to send to either the @free.kindle.com or @kindle.com variations. ‘@free.kindle.com’ emails are free but can only be sent to your device when it is connected to wi-fi. ‘@kindle.com’ emails can be delivered even when you are not connected to wi-fi, but note that service fees apply.

      Find out more about the Kindle Personal Document Service.

      Amphiphilic fluorescent copolymers via one-pot synthesis of RAFT polymerization and multicomponent Biginelli reaction and their cells imaging applications
      Available formats
      ×

      Send article to Dropbox

      To send this article to your Dropbox account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your <service> account. Find out more about sending content to Dropbox.

      Amphiphilic fluorescent copolymers via one-pot synthesis of RAFT polymerization and multicomponent Biginelli reaction and their cells imaging applications
      Available formats
      ×

      Send article to Google Drive

      To send this article to your Google Drive account, please select one or more formats and confirm that you agree to abide by our usage policies. If this is the first time you use this feature, you will be asked to authorise Cambridge Core to connect with your <service> account. Find out more about sending content to Google Drive.

      Amphiphilic fluorescent copolymers via one-pot synthesis of RAFT polymerization and multicomponent Biginelli reaction and their cells imaging applications
      Available formats
      ×

Copyright

Corresponding author

a)Address all correspondence to this author. e-mail: hzf105@163.com

References

Hide All
1.Nagarajaiah, H., Mukhopadhyay, A., and Moorthy, J.N.: Biginelli reaction: An overview. Tetrahedron Lett. 57, 5135 (2016).
2.Rotstein, B.H., Zaretsky, S., Rai, V., and Yudin, A.K.: Small heterocycles in multicomponent reactions. Chem. Rev. 114, 8323 (2014).
3.Tao, L., Zhao, Y., Yang, B., Wei, Y., and Wu, H.B.: Multicomponent click chemistry in polymer synthesis-new opportunity for polymer chemistry. Acta Polym. Sin., 1482 (2016).
4.Wu, H.B., Yang, L., and Tao, L.: Polymer synthesis by mimicking nature’s strategy: The combination of ultra-fast RAFT and the Biginelli reaction. Polym. Chem. 8, 5679 (2017).
5.Xue, H.D., Zhao, Y., Wu, H.B., Wang, Z.L., Yang, B., Wei, Y., Wang, Z.M., and Tao, L.: Multicomponent combinatorial polymerization via the Biginelli reaction. J. Am. Chem. Soc. 138, 8690 (2016).
6.Dong, J.D., Liu, M.Y., Jiang, R.M., Huang, H.Y., Wan, Q., Wen, Y.Q., Tian, J.W., Dai, Y.F., Zhang, X.Y., and Wei, Y.: Synthesis and biological imaging of cross-linked fluorescent polymeric nanoparticles with aggregation-induced emission characteristics based on the combination of RAFT polymerization and the Biginelli reaction. J. Colloid Interface Sci. 528, 192 (2018).
7.Jiang, R., Liu, H., Liu, M., Tian, J., Huang, Q., Huang, H., Wen, Y., Cao, Q.Y., Zhang, X., and Wei, Y.: A facile one-pot Mannich reaction for the construction of fluorescent polymeric nanoparticles with aggregation-induced emission feature and their biological imaging. Mater. Sci. Eng., C 81, 416 (2017).
8.Zhu, C., Yang, B., Zhao, Y., Fu, C., Tao, L., and Wei, Y.: A new insight into the Biginelli reaction: The dawn of multicomponent click chemistry? Polym. Chem. 4, 5395 (2013).
9.Mao, T.F., Liu, G.Q., Wu, H.B., Wei, Y., Gou, Y.Z., Wang, J., and Tao, L.: High throughput preparation of UV-protective polymers from essential oil extracts via the Biginelli reaction. J. Am. Chem. Soc. 140, 6865 (2018).
10.Wang, S.Q., Fu, C.K., Wei, Y., and Tao, L.: Exploration of multicomponent polymerization system. Prog. Chem. 26, 1099 (2014).
11.Kappe, C.O.: Biologically active dihydropyrimidones of the Biginelli-type-a literature survey. Eur. J. Med. Chem. 35, 1043 (2000).
12.Crespo, A., Maatougui, A.E., Biagini, P., Azuaje, J., Coelho, A., Brea, J., Loza, M.I., Cadavid, M.I., Garcia-Mera, X., Gutierrez-de-Teran, H., and Sotelo, E.: Discovery of 3,4-dihydropyrimidin-2(1H)-ones as a novel class of potent and selective A2B adenosine receptor antagonists. ACS Med. Chem. Lett. 4, 1031 (2013).
13.Kaur, H., Machado, M., Kock, C., Smith, P., Chibale, K., Prudencio, M., and Singh, K.: Primaquine-pyrimidine hybrids: Synthesis and dual-stage antiplasmodial activity. Eur. J. Med. Chem. 101, 266 (2015).
14.Joshi, R.R., Barchha, A., Khedkar, V.M., Pissurlenkar, R.R.S., Sarkar, S., Sarkar, D., Joshi, R.R., Joshi, R.A., Shah, A.K., and Coutinho, E.C.: Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold. Chem. Biol. Drug Des. 85, 201 (2015).
15.Simurova, N. and Maiboroda, O.: Biginelli reaction-an effective method for the synthesis of dihydropyrimidine derivatives. Chem. Heterocycl. Compd. 53, 413 (2017).
16.Akhaja, T.N. and Raval, J.P.: 1,3-Dihydro-2H-indol-2-ones derivatives: Design, synthesis, in vitro antibacterial, antifungal and antitubercular study. Eur. J. Med. Chem. 46, 5573 (2011).
17.Zhao, Y., Wu, H.B., Zhang, Y.Y., Wang, X., Yang, B., Zhang, Q.D., Ren, X., Fu, C.K., Wei, Y., Wang, Z.M., Wang, Y.R., and Tao, L.: Postpolymerization modification of poly(dihydropyrimidin-2(1H)-thione)s via the thiourea–haloalkane reaction to prepare functional polymers. ACS Macro Lett. 4, 843 (2015).
18.Ren, X., Yang, B., Zhao, Y., Zhang, X.Y., Wang, X., Wei, Y., and Tao, L.: One-pot polymer conjugation on carbon nanotubes through simultaneous π–π stacking and the Biginelli reaction. Polymer 64, 210 (2015).
19.He, W.W., Jiang, H.J., Zhang, L.F., Cheng, Z.P., and Zhu, X.L.: Atom transfer radical polymerization of hydrophilic monomers and its applications. Polym. Chem. 4, 2919 (2013).
20.Huang, Y.K., Hou, T.T., and Cao, X.Q.: Synthesis of silica-polymer hybrids by combination of RAFT polymerization and azide-alkyne cycloaddition ‘click’ reactions. Polym. Chem. 1, 1615 (2010).
21.Peng, J.Y., Tian, C., Zhang, L.F., Cheng, Z.P., and Zhu, X.L.: The in situ formation of nanoparticles via RAFT polymerization-induced self-assembly in a continuous tubular reactor. Polym. Chem. 8, 1495 (2017).
22.Zhao, G.D., Zhang, P.P., Zhang, C.B., and Zhao, Y.L.: Facile synthesis of highly pure block copolymers by combination of RAFT polymerization, click reaction and de-grafting process. Polym. Chem. 3, 1803 (2012).
23.Jiang, R.M., Liu, M.Y., Huang, Q., Huang, H.Y., Wan, Q., Wen, Y.Q., Tian, J.W., Cao, Q.Y., Zhang, X.Y., and Wei, Y.: Fabrication of multifunctional fluorescent organic nanoparticles with AIE feature through photo-initiated RAFT polymerization. Polym. Chem. 8, 7390 (2017).
24.Banerjee, S.L., Hoskins, R., Swift, T., Rimmer, S., and Singha, N.K.: A self-healable fluorescence active hydrogel based on ionic block copolymers prepared via ring opening polymerization and xanthate mediated RAFT polymerization. Polym. Chem. 9, 1190 (2018).
25.Zeng, G.J., Liu, M.Y., Jiang, R.M., Huang, Q., Huang, L., Wan, Q., Dai, Y.F., Wen, Y.Q., Zhang, X.Y., and Wei, Y.: Self-catalyzed photo-initiated RAFT polymerization for fabrication of fluorescent polymeric nanoparticles with aggregation-induced emission feature. Mater. Sci. Eng., C 83, 154 (2018).
26.Tian, C., Niu, J.Y., Wei, X.R., Xu, Y.J., Zhang, L.F., Cheng, Z.P., and Zhu, X.L.: Construction of dual-functional polymer nanomaterials with near-infrared fluorescence imaging and polymer prodrug by RAFT-mediated aqueous dispersion polymerization. Nanoscale 10, 10277 (2018).
27.Wang, Z.L., Yu, Y., Li, Y.S., Yang, L., Zhao, Y., Liu, G.Q., Wei, Y., Wang, X., and Tao, L.: Post-polymerization modification via the Biginelli reaction to prepare water-soluble polymer adhesives. Polym. Chem. 8, 5490 (2017).
28.Wei, R.B., He, Y.N., and Wang, X.G.: Diblock copolymers composed of a liquid crystalline azo block and a poly(dimethylsiloxane) block: Synthesis, morphology and photoresponsive properties. RSC Adv. 4, 58386 (2014).
29.He, Y.N., He, W., Liu, D., Gu, T.H., Wei, R.B., and Wang, X.G.: Synthesis of block copolymers via the combination of RAFT and a macromolecular azo coupling reaction. Polym. Chem. 4, 402 (2013).
30.Wei, R.B., Wang, X.G., and He, Y.N.: Synthesis of side-on liquid crystalline diblock copolymers through macromolecular azo coupling reaction. Eur. Polym. J. 69, 584 (2015).
31.Wei, R.B., Wang, X.G., and He, Y.N.: Synthesis, self-assembly and photo-responsive behavior of AB2 shaped amphiphilic azo block copolymer. Chin. Chem. Lett. 26, 857 (2015).
32.Zhang, X., Chi, Z., Zhang, J., Li, H., Xu, B., Li, X., Liu, S., Zhang, Y., and Xu, J.: Piezofluorochromic properties and mechanism of an aggregation-induced emission enhancement compound containing N-hexyl-phenothiazine and anthracene moieties. J. Phys. Chem. B 115, 7606 (2011).
33.Hong, Y., Lam, J., and Tang, B.: Aggregation-induced emission: Phenomenon, mechanism and applications. Chem. Commun., 4332 (2009).
34.Tong, H., Dong, Y., Hong, Y., Häussler, M., Lam, J., Sung, H., Yu, X., Sun, J., Williams, I., Kwok, H., and Tang, B.: Aggregation-induced emission: Effects of molecular structure, solid-state conformation, and morphological packing arrangement on light-emitting behaviors of diphenyldibenzofulvene derivatives. J. Phys. Chem. C 111, 2287 (2007).
35.Zhang, X., Yin, J., Peng, C., Hu, W., Zhu, Z., Li, W., Fan, C., and Huang, Q.: Distribution and biocompatibility studies of graphene oxide in mice after intravenous administration. Carbon 49, 986 (2011).
36.Zhang, X., Wang, S., Zhu, C., Liu, M., Ji, Y., Feng, L., Tao, L., and Wei, Y.: Carbon-dots derived from nanodiamond: Photoluminescence tunable nanoparticles for cell imaging. J. Colloid Interface Sci. 397, 39 (2013).
37.Zhang, X., Zhang, X., Wang, S., Liu, M., Tao, L., and Wei, Y.: Surfactant modification of aggregation-induced emission material as biocompatible nanoparticles: Facile preparation and cell imaging. Nanoscale 5, 147 (2013).
38.Zhang, X., Hu, W., Li, J., Tao, L., and Wei, Y.: A comparative study of cellular uptake and cytotoxicity of multi-walled carbon nanotubes, graphene oxide, and nanodiamond. Toxicol. Res. 1, 62 (2012).
39.Zhang, X., Qi, H., Wang, S., Feng, L., Ji, Y., Tao, L., Li, S., and Wei, Y.: Cellular responses of aniline oligomers: A preliminary study. Toxicol. Res. 1, 201 (2012).
40.Zhang, X., Hui, J., Yang, B., Yang, Y., Fan, D., Liu, M., Tao, L., and Wei, Y.: PEGylation of fluoridated hydroxyapatite (FAp):Ln3+ nanorods for cell imaging. Polym. Chem. 4, 4120 (2013).
41.Wan, Q., Liu, M.Y., Xu, D.Z., Huang, H.Y., Mao, L.C., Zeng, G.J., Deng, F.J., Zhang, X.Y., and Wei, Y.: Facile fabrication of amphiphilic AIE active glucan via formation of dynamic bonds: Self assembly, stimuli responsiveness and biological imaging. J. Mater. Chem. B 4, 4033 (2016).
42.Wan, Q., Wang, K., He, C.B., Liu, M.Y., Zeng, G.J., Huang, H.Y., Deng, F.J., Zhang, X.Y., and Wei, Y.: Stimulus responsive cross-linked AIE-active polymeric nanoprobes: Fabrication and biological imaging application. Polym. Chem. 6, 8214 (2015).
43.Li, H., Zhang, X., Zhang, X., Yang, B., Yang, Y., and Wei, Y.: Ultra-stable biocompatible cross-linked fluorescent polymeric nanoparticles using AIE chain transfer agent. Polym. Chem. 5, 3758 (2014).
44.Deshmukh, M., Salunkhe, S., Patil, D., and Anbhule, P.: A novel and efficient one step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines and their anti-bacterial activity. Eur. J. Med. Chem. 4, 2651 (2009).
45.Chitra, S., Devanathan, D., and Pandiarajan, K.: Synthesis and in vitro microbiological evaluation of novel 4-aryl-5-isopropoxycarbonyl-6-methyl-3,4-dihydropyrimidinones. Eur. J. Med. Chem. 45, 367 (2010).
46.Zhang, X., Chi, Z., Xu, B., Chen, C., Zhou, X., Zhang, Y., Liu, S., and Xu, J.: End-group effects of piezofluorochromic aggregation-induced enhanced emission compounds containing distyrylanthracene. J. Mater. Chem. 22, 18505 (2012).
47.Zhang, X., Liu, M., Yang, B., Zhang, X., and Wei, Y.: Tetraphenylethene-based aggregation-induced emission fluorescentorganic nanoparticles: Facile preparation and cell imaging application. Colloids Surf., B 112, 81 (2013).
48.Tao, L., Liu, J., and Davis, T.: Branched polymer-protein conjugates made from mid-chain-functional P(HPMA). Biomacromolecules 10, 2847 (2009).
49.Huang, Z., Zhang, X., Zhang, X., Yang, B., Zhang, Y., Wang, K., Yuan, J., Tao, L., and Wei, Y.: One-pot synthesis and biological imaging application of amphiphilic fluorescent copolymer via combination of RAFT polymerization and schiff base reaction. Polym. Chem. 6, 2133 (2015).

Keywords

Amphiphilic fluorescent copolymers via one-pot synthesis of RAFT polymerization and multicomponent Biginelli reaction and their cells imaging applications

  • Zengfang Huang (a1), Runze Wang (a1), Yali Chen (a1), Xiaobo Liu (a2), Liucheng Mao (a3), Jinying Yuan (a3), Lei Tao (a3), Yen Wei (a3) and Xiaoyong Zhang (a4)...

Metrics

Full text views

Total number of HTML views: 0
Total number of PDF views: 0 *
Loading metrics...

Abstract views

Total abstract views: 0 *
Loading metrics...

* Views captured on Cambridge Core between <date>. This data will be updated every 24 hours.

Usage data cannot currently be displayed