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A new generation of star polymer: magnetic aromatic polyamides with unique microscopic flower morphology and in vitro hyperthermia of cancer therapy

  • Reza Eivazzadeh-Keihan
  • Fateme Radinekiyan
  • Ali MalekiEmail author
  • Milad Salimi Bani
  • Mojtaba Azizi
Materials for life sciences
  • 4 Downloads

Abstract

In this work, a novel magnetic nanocomposite based on aromatic polyamide as a statistical star polymer was designed, characterized and studied in hyperthermia process of cancer therapy. The polymerization reaction was carried out via surface modification of magnetic nanoparticles (Fe3O4 MNPs) using polymerization process by phenylenediamine derivatives and terephthaloyl chloride. Various analytical techniques such as field-emission scanning electron microscopy (FE-SEM), transmission electron microscopy, energy-dispersive X-ray, thermogravimetric and vibrating-sample magnetometer analyses were used to confirm the structure of the prepared nanocomposite. A unique rose flower and sphere morphologies were observed by FE-SEM images by the result of polymerization process and fabrication of the synthetic polymeric strands on the surface of the modified Fe3O4 magnetic cores. The application of this novel magnetic nanocomposite was evaluated in hyperthermia process as a potential method for cancer therapy and its exposure to an external alternating magnetic field. The highest specific absorption rate measured for 0.5 mg/mL of a sample was 191.97 w g−1, and the saturation magnetization value was 4.3 emu g−1.

Notes

Acknowledgements

The authors gratefully acknowledge the partial support from the Research Council of the Iran University of Science and Technology (IUST) and the Iran National Science Foundation (INSF).

Supplementary material

10853_2019_4005_MOESM1_ESM.docx (737 kb)
Supplementary material 1 (DOCX 737 kb)

References

  1. 1.
    Hadjichristidis N, Pitsikalis M, Pispas S, Iatrou H (2001) Polymers with complex architecture by living anionic polymerization. Chem Rev 101:3747–3792CrossRefGoogle Scholar
  2. 2.
    Rasolonjatovo B, Pitard B, Haudebourg T, Bennevault V, Guégan P (2017) Synthesis of tetraarm star block copolymer based on polytetrahydrofuran and poly (2-methyl-2-oxazoline) for gene delivery applications. Eur Polym J 88:689–700CrossRefGoogle Scholar
  3. 3.
    Ghamkhari A, Sarvari R, Ghorbani M, Hamishehkar H (2018) Novel thermoresponsive star-liked nanomicelles for targeting of anticancer agent. Eur Polym J 107:143–154CrossRefGoogle Scholar
  4. 4.
    Hadjichristidis N, Iatrou H, Pitsikalis M, Mays J (2006) Macromolecular architectures by living and controlled/living polymerizations. Prog Polym Sci 31:1068–1132CrossRefGoogle Scholar
  5. 5.
    Hirao A, Hayashi M, Haraguchi N (200) Synthesis of well‐defined functionalized polymers and star branched polymers by means of living anionic polymerization using specially designed 1,1‐diphenylethylene derivatives, Macromol Rapid Commun 21:1171-1184Google Scholar
  6. 6.
    Kubotera A, Saito R (2016) Synthesis of well-defined 3-arm and 6-arm poly (acrylic acid)s via ATRP of methyl acrylate and hydrolyses of 3-arm and 6-arm poly (methyl acrylate)s. Polym J 48:611–619CrossRefGoogle Scholar
  7. 7.
    Xiao N, Chen Y, Shen X, Zhang C, Yano S, Gottschaldt M, Schubert US, Kakuchi T, Satoh T (2013) Synthesis of miktoarm star copolymer Ru (II) complexes by click-to-chelate approach. Polym J 45:216–225CrossRefGoogle Scholar
  8. 8.
    Rodrigues PR, Vieira RP (2019) Advances in atom-transfer radical polymerization for drug delivery applications. Eur Polym J 115:45–48CrossRefGoogle Scholar
  9. 9.
    Gao H, Matyjaszewski K (2006) Synthesis of star polymers by a combination of ATRP and the “click” coupling method. Macromolecules 39:4960–4965CrossRefGoogle Scholar
  10. 10.
    Hirao A, Yoo H-S (2011) Dendrimer-like star-branched polymers: novel structurally well-defined hyperbranched polymers. Polym J 43:2–17CrossRefGoogle Scholar
  11. 11.
    Terashima T, Ouchi M, Ando T, Kamigaito M, Sawamoto M (2007) Amphiphilic, thermosensitive ruthenium (II)-bearing star polymer catalysts: one-pot synthesis of PEG armed star polymers with ruthenium (II)-enclosed microgel cores via metal-catalyzed living radical polymerization. Macromolecules 40:3581–3588CrossRefGoogle Scholar
  12. 12.
    Giustini AJ, Petryk AA, Cassim SM, Tate JA, Baker I, Hoopes PJ (2010) Magnetic nanoparticle hyperthermia in cancer treatment. Nano Life 1:17–32CrossRefGoogle Scholar
  13. 13.
    Linh PH, Chien NV, Dung DD, Nam PH, Hoa DT, Anh NTN, Hong LV, Phunc NX, Phong PT (2018) Biocompatible nanoclusters of O-carboxymethyl chitosan-coated Fe3O4 nanoparticles: synthesis, characterization and magnetic heating efficiency. J Mater Sci 53:8887–8900.  https://doi.org/10.1007/s10853-018-2180-0 CrossRefGoogle Scholar
  14. 14.
    Le TTH, Bui TQ, Ha TMT, Le MH, Pham HN, Ha PT (2018) Optimizing the alginate coating layer of doxorubicin-loaded iron oxide nanoparticles for cancer hyperthermia and chemotherapy. J Mater Sci 53:13826–13842.  https://doi.org/10.1007/s10853-018-2574-z CrossRefGoogle Scholar
  15. 15.
    Diaz-Bleis D, Vales-Pinzón C, Freile-Pelegrín Y, Alvarado-Gil J (2014) Thermal characterization of magnetically aligned carbonyl iron/agar composites. Carbohydr Polym 99:84–90CrossRefGoogle Scholar
  16. 16.
    Boyer C, Whittaker MR, Bulmus V, Liu J, Davis TP (2010) The design and utility of polymer-stabilized iron-oxide nanoparticles for nanomedicine applications. NPG Asia Mater 2:23–30CrossRefGoogle Scholar
  17. 17.
    Hu H, Sun J, Huang G, Li X, Dai A, Yang H, Yang S (2013) Preparation of amino-functionalized magnetite nanoclusters by ring-opening polymerization and application for targeted magnetic resonance imaging. J Mater Sci 48:7686–7695.  https://doi.org/10.1007/s10853-013-7588-y CrossRefGoogle Scholar
  18. 18.
    Marutani E, Yamamoto S, Ninjbadgar T, Tsujii Y, Fukuda T, Takano M (2004) Surface-initiated atom transfer radical polymerization of methyl methacrylate on magnetite nanoparticles. Polymer 45:2231–2235CrossRefGoogle Scholar
  19. 19.
    Rana S, Jadhav NV, Barick K, Pandey B, Hassan P (2014) Polyaniline shell cross-linked Fe3O4 magnetic nanoparticles for heat activated killing of cancer cells. Dalton Trans 43:12263–12271CrossRefGoogle Scholar
  20. 20.
    Nie C, Yang Y, Peng Z, Cheng C, Ma L, Zhao C (2017) Aramid nanofiber as an emerging nanofibrous modifier to enhance ultrafiltration and biological performances of polymeric membranes. J Membrane Sci 528:251–263CrossRefGoogle Scholar
  21. 21.
    Yang C, Xiang X, Zhang Y, Peng Z, Cao Z, Wang J, Xuan L (2015) Large-scale controlled fabrication of highly roughened flower-like silver nanostructures in liquid crystalline phase. Sci Rep 5:12355CrossRefGoogle Scholar
  22. 22.
    Shen L, Yu L, Wu HB, Yu X-Y, Zhang X, Lou XWD (2015) Formation of nickel cobalt sulfide ball-in-ball hollow spheres with enhanced electrochemical pseudocapacitive properties. Nat Commun 6:6694CrossRefGoogle Scholar
  23. 23.
    Stöber W, Fink A, Bohn E (1968) Controlled growth of monodisperse silica spheres in the micron size range. J Colloid Interface Sci 26:62–69CrossRefGoogle Scholar
  24. 24.
    Ji L, Zhou L, Bai X, Shao Y, Zhao G, Qu Y, Wang C, Li Y (2012) Facile synthesis of multiwall carbon nanotubes/iron oxides for removal of tetrabromobisphenol A and Pb(II). J Mater Chem 22:15853–15862CrossRefGoogle Scholar
  25. 25.
    Villa S, Riani P, Locardi F, Canepa F (2016) Functionalization of Fe3O4 NPs by silanization: use of amine (APTES) and thiol (MPTMS) silanes and their physical characterization. Materials 9:826CrossRefGoogle Scholar
  26. 26.
    Safaiee M, Zolfigol MA, Afsharnadery F, Baghery S (2015) Synthesis of a novel dendrimer core of oxo-vanadium phthalocyanine magnetic nano particles: as an efficient catalyst for the synthesis of 3,4-dihydropyrano [c] chromenes derivatives under green condition. RSC Adv 5:102340–102349CrossRefGoogle Scholar
  27. 27.
    Farahi M, Karami B, Keshavarz R, Khosravian F (2017) Nano-Fe3O4@SiO2-supported boron sulfonic acid as a novel magnetically heterogeneous catalyst for the synthesis of pyrano coumarins. RSC Adv 7:46644–46650CrossRefGoogle Scholar
  28. 28.
    Vieira EG, Soares IV, Da Silva NC, Perujo SD, Do Carmo DR, Dias Filho NL (2013) Synthesis and characterization of 3-[(thiourea)-propyl]-functionalized silica gel and its application in adsorption and catalysis. New J Chem 37:1933–1943CrossRefGoogle Scholar
  29. 29.
    Lu X-w, Wu W, Chen J-f, Zhang P-y, Zhao Y-b (2011) Preparation of polyaniline nanofibers by high gravity chemical oxidative polymerization. Ind Eng Chem Res 50:5589–5595CrossRefGoogle Scholar
  30. 30.
    Du S, Zhang J, Guan Y, Wan X (2014) Sequence effects on properties of the poly (p-phenylene terephthalamide)-based macroinitiators and their comb-like copolymers grafted by polystyrene side chains. Aust J Chem 67:39–48CrossRefGoogle Scholar
  31. 31.
    Yan H, Li J, Tian W, He L, Tuo X, Qiu T (2016) A new approach to the preparation of poly (p-phenylene terephthalamide) nanofibers. RSC Adv 6:26599–26605CrossRefGoogle Scholar
  32. 32.
    Zarchi MAK and Abadi SSADM (2019) Dendron-functionalized Fe3O4 magnetic nanoparticles with palladium catalyzed CN insertion of arylhalide for the synthesis of tetrazoles and benzamide. J Organomet Chem 880:196–212CrossRefGoogle Scholar
  33. 33.
    Mouradzadegun A, Ganjali MR, Mostafavi MA (2018) Design and synthesis of a magnetic hierarchical porous organic polymer: a new platform in heterogeneous phase-transfer catalysis. Appl Organomet Chem 32:e4214CrossRefGoogle Scholar
  34. 34.
    Cai GM, Yu WD (2010) Study on the thermal degradation of high performance fibers by TG/FTIR and Py-GC/MS. J Therm Anal Calorim 104:757–763CrossRefGoogle Scholar
  35. 35.
    Wei S, Wang Q, Zhu J, Sun L, Lin H, Guo Z (2011) Multifunctional composite core–shell nanoparticles. Nanoscale 3:4474–4502CrossRefGoogle Scholar
  36. 36.
    Beyki MH, Miri S, Shemirani F, Bayat M, Ranjbar PR (2016) A new derivative of core-shell magnetic chitosan biopolymer: synthesis, characterization and application for adsorption of lead and copper ions, clean-soil air. Water 6:710–719Google Scholar
  37. 37.
    Zarghani M, Akhlaghinia B (2016) Magnetically separable Fe3O4@chitin as an eco-friendly nanocatalyst with high efficiency for green synthesis of 5-substituted-1 H-tetrazoles under solvent-free conditions. RSC Adv 6:31850–31860CrossRefGoogle Scholar
  38. 38.
    Luo X, Liu S, Zhou J, Zhang L (2009) In situ synthesis of Fe3O4/cellulose microspheres with magnetic-induced protein delivery. J Mater Chem 19:3538–3545CrossRefGoogle Scholar
  39. 39.
    Dung T, Danh T, Hoa L, Chien D, Duc N (2009) Structural and magnetic properties of starch-coated magnetite nanoparticles. J Exp Nanosci 4:259–267CrossRefGoogle Scholar
  40. 40.
    Sari AY, Eko A, Candra K, Hasibuan DP, Ginting M, Sebayang P, et al. Synthesis, Properties and Application of Glucose Coated Fe3O4 Nanoparticles Prepared by Co-precipitation Method. IOP Conference Series: Materials Science and Engineering: IOP Publishing; 2017. p. 012021Google Scholar
  41. 41.
    Ma Y-X, Kou Y-L, Xing D, Jin P-S, Shao W-J, Li X, Du X-Y, La P-Q (2017) Synthesis of magnetic graphene oxide grafted polymaleicamide dendrimer nanohybrids for adsorption of Pb(II) in aqueous solution. J Hazard Mater 340:407–416CrossRefGoogle Scholar
  42. 42.
    Guo H, Jiang Z, Song S, Dai T, Wang X, Sun K, Zhou G, Dou H (2016) Structural regulation of self-assembled iron oxide/polymer microbubbles towards performance-tunable magnetic resonance/ultrasonic dual imaging agents. J Colloid Interface Sci 482:95–104CrossRefGoogle Scholar
  43. 43.
    Nadeem M, Ahmad M, Akhtar MS, Shaari A, Riaz S, Naseem S, Masood M, Saeed MA (2016) Magnetic properties of polyvinyl alcohol and doxorubicine loaded iron oxide nanoparticles for anticancer drug delivery applications. PLoS ONE 11:e0158084CrossRefGoogle Scholar
  44. 44.
    Liu S, Fu J, Wang M, Yan Y, Xin Q, Cai L, Xu Q (2016) Magnetically separable and recyclable Fe3O4–polydopamine hybrid hollow microsphere for highly efficient peroxidase mimetic catalysts. J Colloid Interface Sci 469:69–77CrossRefGoogle Scholar
  45. 45.
    Atila Dinçer C, Yildiz N, Karakeçili A, Aydoğan N, Çalimli A (2017) Synthesis and characterization of Fe3O4-MPTMS-PLGA nanocomposites for anticancer drug loading and release studies. Artif Cell Nanomed B 45:1408–1414CrossRefGoogle Scholar
  46. 46.
    Das B, Mandal M, Upadhyay A, Chattopadhyay P, Karak N (2013) Bio-based hyperbranched polyurethane/Fe3O4 nanocomposites: smart antibacterial biomaterials for biomedical devices and implants. Biomed Mater 8:035003CrossRefGoogle Scholar
  47. 47.
    Nie L, Zhang L, Wu Z (2011) Magnetic/polymer/nanogold complex using as a novel enzyme support. J Nanosci Nanotechnol 11:5223–5227CrossRefGoogle Scholar
  48. 48.
    Pramanik N, De J, Basu RK, Rath T, Kundu PP (2016) Fabrication of magnetite nanoparticle doped reduced graphene oxide grafted polyhydroxyalkanoate nanocomposites for tissue engineering application. RSC Adv 6:46116–46133CrossRefGoogle Scholar
  49. 49.
    Rahmanzadeh L, Ghorbani M, Jahanshahi M (2014) Synthesis and characterization of Fe3O4@ polyrhodanine nanocomposite with core–shell morphology, Adv Polym Tech 33Google Scholar
  50. 50.
    Ray A, Saha N, Sáha P. The dynamic magnetoviscoelastic properties of biomineralized (Fe3O4) PVP-CMC hydrogel. AIP Conference Proceedings: AIP Publishing; 2017. p. 050007Google Scholar
  51. 51.
    Zhang Q, Wang C, Qiao L, Yan H, Liu K (2009) Superparamagnetic iron oxide nanoparticles coated with a folate-conjugated polymer. J Mater Chem 19:8393–8402CrossRefGoogle Scholar
  52. 52.
    Maleki A, Alrezvani Z, Maleki S (2015) Design, preparation and characterization of urea-functionalized Fe3O4/SiO2 magnetic nanocatalyst and application for the one-pot multicomponent synthesis of substituted imidazole derivatives. Catal Commun 69:29–33CrossRefGoogle Scholar
  53. 53.
    Shubitidze F, Kekalo K, Stigliano R, Baker I (2015) Magnetic nanoparticles with high specific absorption rate of electromagnetic energy at low field strength for hyperthermia therapy. J Appl Phys 117:094302CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Catalysts and Organic Synthesis Research Laboratory, Department of ChemistryIran University of Science and TechnologyTehranIran
  2. 2.Department of Biomedical Engineering, Faculty of EngineeringUniversity of IsfahanIsfahanIran

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