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

Published online by Cambridge University Press:  11 June 2019

Zengfang Huang*
Affiliation:
School of Materials & Food Engineering, Zhongshan Institute, University of Electronic Science & Technology of China, Zhongshan 528402, People’s Republic of China; and School of Materials and Energy, University of Electronic Science & Technology of China, Chengdu 610054, People’s Republic of China
Runze Wang
Affiliation:
School of Materials & Food Engineering, Zhongshan Institute, University of Electronic Science & Technology of China, Zhongshan 528402, People’s Republic of China; and School of Materials and Energy, University of Electronic Science & Technology of China, Chengdu 610054, People’s Republic of China
Yali Chen
Affiliation:
School of Materials & Food Engineering, Zhongshan Institute, University of Electronic Science & Technology of China, Zhongshan 528402, People’s Republic of China; and School of Materials and Energy, University of Electronic Science & Technology of China, Chengdu 610054, People’s Republic of China
Xiaobo Liu
Affiliation:
School of Materials and Energy, University of Electronic Science & Technology of China, Chengdu 610054, People’s Republic of China
Liucheng Mao
Affiliation:
Department of Chemistry, The Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, People’s Republic of China
Jinying Yuan
Affiliation:
Department of Chemistry, The Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, People’s Republic of China
Lei Tao
Affiliation:
Department of Chemistry, The Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, People’s Republic of China
Yen Wei
Affiliation:
Department of Chemistry, The Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, People’s Republic of China
Xiaoyong Zhang
Affiliation:
Department of Chemistry, Nanchang University, Nanchang 330047, People’s Republic of China
*
a)Address all correspondence to this author. e-mail: [email protected]
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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.

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Article
Copyright
Copyright © Materials Research Society 2019 

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References

Nagarajaiah, H., Mukhopadhyay, A., and Moorthy, J.N.: Biginelli reaction: An overview. Tetrahedron Lett. 57, 5135 (2016).CrossRefGoogle Scholar
Rotstein, B.H., Zaretsky, S., Rai, V., and Yudin, A.K.: Small heterocycles in multicomponent reactions. Chem. Rev. 114, 8323 (2014).CrossRefGoogle ScholarPubMed
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).Google Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
Wang, S.Q., Fu, C.K., Wei, Y., and Tao, L.: Exploration of multicomponent polymerization system. Prog. Chem. 26, 1099 (2014).Google Scholar
Kappe, C.O.: Biologically active dihydropyrimidones of the Biginelli-type-a literature survey. Eur. J. Med. Chem. 35, 1043 (2000).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
Simurova, N. and Maiboroda, O.: Biginelli reaction-an effective method for the synthesis of dihydropyrimidine derivatives. Chem. Heterocycl. Compd. 53, 413 (2017).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
Hong, Y., Lam, J., and Tang, B.: Aggregation-induced emission: Phenomenon, mechanism and applications. Chem. Commun., 4332 (2009).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
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).CrossRefGoogle Scholar
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).CrossRefGoogle ScholarPubMed
Tao, L., Liu, J., and Davis, T.: Branched polymer-protein conjugates made from mid-chain-functional P(HPMA). Biomacromolecules 10, 2847 (2009).CrossRefGoogle Scholar
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).CrossRefGoogle Scholar