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Drug release property of a pH-responsive double-hydrophilic hyperbranched graft copolymer

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Abstract

In this paper, we report the synthesis and self-assembly of double-hydrophilic hyperbranched graft copolymers of HPG-g-PDMAEMA, which consist of a hyperbranched polyglycerol (HPG) core and several grafted poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA) arms. HPG was synthesized by cationic polymerization. Then HPG-Br macroinitiator was obtained by esterification of HPG with 2-bromoisobutyryl bromide, which was subsequently used in the preparation of HPG-g-PDMAEMA graft copolymers through atom transfer radical polymerization (ATRP) of DMAEMA monomers. The molecular structures were studied by 1H NMR and GPC. The pyrene-based fluorescent probe method, 1H NMR and DLS were used to study the self-assembly behavior of HPG-g-PDMAEMA. The drug loading and pH-responsive release properties of HPG-g-PDMAEMA were also investigated by using coumarin 102 as a model drug. The results show that the HPG-g-PDMAEMA micelles can continuously release and re-encapsulate coumarin 102 as the pH continuously changes from 11.5 to 2.5; however, this process is not totally reversible.

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References

  1. Cölfen H. Double-hydrophilic block copolymers: synthesis and application as novel surfactants and crystal growth modifiers. Macromol Rapid Commun, 2001, 22: 219–252

    Article  Google Scholar 

  2. Kabanov A V, Kabanov V A. Interpolyelectrolyte and block ionomer complexes for gene delivery: Physico-chemical aspects. Adv Drug Deliv Rev, 1998, 30: 49–60

    Article  CAS  Google Scholar 

  3. Cölfen H, Antonietti M. Crystal design of calcium carbonate microparticles using double-hydrophilic block copolymers. Langmuir, 1998, 14: 582–589

    Article  Google Scholar 

  4. Qi L, Li J, Ma J. Biomimetic morphogenesis of calcium carbonate in mixed solutions for surfactants and double-hydrophilic block copolymers. Adv Mater, 2002, 14: 300–303

    Article  CAS  Google Scholar 

  5. Martin T J, Prochazka K, Munk P, Webber S E. pH-dependent micellization of poly(2-vinylpyridine)-block-poly(ethylene oxide). Macromolecules, 1996, 29: 6071–6073

    Article  CAS  Google Scholar 

  6. Butun V, Billingham N C, Armes S P. Unusual aggregation behavior of a novel tertiary amine methacrylate-based diblock copolymer: Formation of Micelles and reverse Micelles in aqueous solution. J Am Chem Soc, 1998, 120: 11818–11819

    Article  Google Scholar 

  7. Liu S, Armes S P. Polymeric surfactants for the new millennium: A pH-responsive, zwitterionic, schizophrenic diblock copolymer. Angew Chem Int Ed, 2002, 41: 1413–1416

    Article  CAS  Google Scholar 

  8. Liu S, Billingham N C, Armes S P. A schizophrenic water-soluble diblock copolymer. Angew Chem int Ed, 2001, 40: 2328–2331

    Article  CAS  Google Scholar 

  9. Cai Y, Armes S P. A zwitterionic ABC triblock copolymer that forms a “trinity” of micellar aggregates in aqueous solution. Macromolecules, 2004, 37: 7116–7122

    Article  CAS  Google Scholar 

  10. Gao C, Tang W, Yan D, Zhu P, Tao P. Hyperbranched copolymers made from A2, B2 and BB’2 type monomers (iv) — Copolymerization of divinyl sulfonate with 4, 4′-trimethylenepiperidine and N-ethylethylenediamine. Sci China Ser B, 2001, 44: 207–215

    Article  CAS  Google Scholar 

  11. Zhu X, Chen L, Chen Y, Yan D. Using 2D NMR to determine the degree of branching of complicated hyperbranched polymers. Sci China Ser B. 2008, 51: 1057–1065

    Article  CAS  Google Scholar 

  12. Wurm F, Nieberle J, Frey H. Double-Hydrophilic Linear-Hyper-branched Block Copolymers Based on Poly(ethylene oxide) and Poly(glycerol). Macromolecules, 2008, 41: 1184–1188

    Article  CAS  Google Scholar 

  13. Ranganathan K, Deng R, Kainthan R K, Wu C, Brooks D E, Kizhakkedathu J N. Synthesis of thermoresponsive mixed arm star polymers by combination of RAFT and ATRP from a multifunctional core and its self-assembly in water. Macromolecules, 2008, 41: 4226–4234

    Article  CAS  Google Scholar 

  14. Tokar R, Kubisa P, Penczek S, Dworak A. Cationic polymerization of glycidol: coexistence of the activatedmonomer and active chain end mechanism. Macromolecules, 1994, 27: 320–322

    Article  CAS  Google Scholar 

  15. Sunder A, Hanselmann R, Frey H, Mulhaupt R. Controlled synthesis of hyperbranched polyglycerols by ring-opening multibranching polymerization. Macromolecules, 1999, 32: 4240–4246

    Article  CAS  Google Scholar 

  16. Wang S, Chen H, Zhou Y, Yan D. Synthesis and self-assembly of alkyl esterified hyperbranched polyglycerols. J Funct Polym, 2008, 21: 128–132

    CAS  Google Scholar 

  17. Lee H, Wu W, Oh J K, Mueller L, Sherwood G, Peteanu L, Kowalewski T, Matyjaszewski K. Light-induced reversible formation of polymeric micelles. Angew Chem Int Ed, 2007, 46: 2453–2457

    Article  CAS  Google Scholar 

  18. Dai S, Ravi P, Tan C H, Tam K C. Self-assembly behavior of a stimuli-responsive water-soluble [60]fullerene-containing polymer. Langmuir, 2004, 20: 8569–8575

    Article  CAS  Google Scholar 

  19. Muñoz-Bonilla A, Fernández-García M, Haddleton D M. Synthesis and aqueous solution properties of stimuli-responsive triblock copolymers. Soft Matter, 2007, 3: 725–731

    Article  Google Scholar 

  20. Astafieva I, Zhong X F, Eisenberg A. Critical micellization phenomena in block polyelectrolyte solutions. Macromolecules, 1993, 26: 7339–7352

    Article  CAS  Google Scholar 

  21. Kabanov A V, Nazarova I R, Astafieva I V, Batrakova E V, Alakhov V Yu, Yaroslavov A A, Kabanov V A. Micelle formation and solubilization of fluorescent probes in poly(oxyethylene-b-oxypropylene-b-oxyethylene) solutions. Macromolecules, 1995, 28: 2303–2314

    Article  CAS  Google Scholar 

  22. Zhao C L, Winnik M A, Riess G, Croucher M D. Fluorescence probe techniques used to study micelle formation in water-soluble block copolymers. Langmuir, 1990, 6: 514–516

    Article  CAS  Google Scholar 

  23. Astafieva I, Khougaz K, Eisenberg A. Fluorescence study of the critical micelle concentration as a function of soluble block length and salt concentration. Macromolecules, 1995, 28: 7127–7134

    Article  CAS  Google Scholar 

  24. Gohy J F, Creutz S, Garcia M, Mahltig B, Stamm M, Jérôme R. Aggregates formed by amphoteric diblock copolymers in water. Macromolecules, 2000, 33: 6378–6387

    Article  CAS  Google Scholar 

  25. Mai Y, Zhou Y F, Yan D Y. Synthesis and size-controllable self-assembly of a novel amphiphilic hyperbranched multiarm copolyether. Macromolecules, 2005, 38: 8679–8686

    Article  CAS  Google Scholar 

  26. Hong H, Mai Y, Zhou Y F, Yan D Y, Cui J. Self-assembly of large multimolecular micelles from hyperbranched star copolymers. Macromol Rapid Commun, 2007, 28: 591–596

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China

    XiaoYi Sun, YongFeng Zhou & DeYue Yan

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  1. XiaoYi Sun
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  2. YongFeng Zhou
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  3. DeYue Yan
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Corresponding authors

Correspondence to YongFeng Zhou or DeYue Yan.

Additional information

Supported by the National Natural Science Foundation of China (Grant Nos. 20774057 & 50633010), National Basic Research Program (973 Project, Grant No. 2007CB808000), the Basic Research Foundation of Shanghai Science and Technique Committee (Grant No. 07DJ14004), and the Shanghai Leading Academic Discipline Project (Grant No. B202)

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Sun, X., Zhou, Y. & Yan, D. Drug release property of a pH-responsive double-hydrophilic hyperbranched graft copolymer. Sci. China Ser. B-Chem. 52, 1703–1710 (2009). https://doi.org/10.1007/s11426-009-0227-4

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  • DOI: https://doi.org/10.1007/s11426-009-0227-4

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