Skip to main content
Log in

Novel hyperbranched poly (amine-ester)-poly (lactide-co-glycolide) polymeric micelles as amphotericin B carriers

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

A series of amphiphilic hyperbranched poly (amine-ester)-poly (lactide-co-glycolide) (HPAE-co-PLGA) copolymers were synthesized by ring-opening polymerization of dl-lactide, glycolide and a fourth generation hyperbranched poly (amine-ester) (HPAE-OHs4) with Sn(Oct)2 as catalyst. The chemical structure of copolymers was characterized by Fourier transform infrared (FT-IR), nuclear magnetic resonance (1H-NMR, 13C-NMR), thermo gravimetric analysis apparatus (TGA), and different scanning calorimetry (DSC). Formation and characteristics of polymeric micelles of the amphiphilic copolymer were studied by environmental scanning electron microscopy (ESEM), fluorescence spectroscopy, and dynamic light scattering (DLS). In order to estimate the feasibility as novel drug carriers, a lipophilic model drug amphotericin B was incorporated into polymeric micelles and the drug release behavior was investigated. The micelle size and drug-loading content were found increased, and the drug-release rate decreased with the increase of molar ratio of dl-lactide/glycolide to HPAE.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Hans M, Shimoni K, Danino D, Siegel SJ, Lowman A (2005) Synthesis and characterization of mPEG-PLA prodrug micelles. Biomacromolecules 6:2708–2717

    Article  CAS  Google Scholar 

  2. Lin R, Ng LS, Wang CH (2005) In vitro study of anticancer drug doxorubicin in PLGA-based microparticles. Biomaterials 26:4476–4485

    Article  CAS  Google Scholar 

  3. Wang C, Wang C, Hsiue GH (2005) Polymeric micelles with a pH-responsive structure as intracellular drug carriers. J Control Release 108:140–149

    Article  CAS  Google Scholar 

  4. Agrawal SK, Sanabria-DeLong N, Coburn JM, Tew GN, Bhatia SR (2006) Novel drug release profiles from micellar solutions of PLA–PEO–PLA triblock copolymers. J Control Release 112:64–71

    Article  CAS  Google Scholar 

  5. Jiang XZ, Zhang JY, Zhou YM, Xu J, Liu SY (2008) Facile preparation of core-crosslinked micelles from azide-containing thermoresponsive double hydrophilic diblock copolymer via click chemistry. J Polym Sci A Polym Chem 46:860–871

    Article  CAS  Google Scholar 

  6. Riess G (2003) Micellization of block copolymers. Prog Polym Sci 28:1107–1170

    Article  CAS  Google Scholar 

  7. Ryu JG, Jeong YI, Kim IS, Lee JH, Nah JW, Kim SH (2000) Clonazepam release from core–shell type nanoparticles of poly(ε-caprolactone)/poly(ethylene glycol)/poly(ε-caprolactone) triblock copolymers. Int J Pharm 200:231–242

    Article  CAS  Google Scholar 

  8. Lo CL, Huang CK, Lin KM, Hsiue GH (2007) Mixed micelles formed from graft and diblock copolymers for application in intracellular drug delivery. Biomaterials 28:1225–1235

    Article  CAS  Google Scholar 

  9. Han HD, Shin BC, Choi HS (2006) Doxorubicin-encapsulated thermosensitive liposomes modified with poly (N-isopropylacrylamide-co-acrylamide): drug release behavior and stability in the presence of serum. Eur J Pharm Biopharm 62:110–116

    Article  CAS  Google Scholar 

  10. Yoo HS, Park TG (2001) Biodegradable polymeric micelles composed of doxorubicin conjugated PLGA–PEG block copolymer. J Control Release 70:63–70

    Article  CAS  Google Scholar 

  11. Layre A, Couvreur P, Chacun H, Richard J, Passirani C, Requier D, Benoit JP, Gref R (2006) Novel composite core–shell nanoparticles as busulfan carriers. J Control Release 111:271–280

    Article  CAS  Google Scholar 

  12. Li YY, Zhang XZ, Kim GC, Cheng H, Cheng SX, Zhuo RX (2006) Thermosensitive Y-shaped micelles of poly(oleic acid-Y-N-isopropylacrylamide) for drug delivery. Small 2:917–923

    Article  CAS  Google Scholar 

  13. Gao C, Yan D (2004) Hyperbranched polymers: from synthesis to applications. Prog Polym Sci 29:183–275

    Article  CAS  Google Scholar 

  14. Voit B (2000) New developments in hyperbranched polymers. J Polym Sci A Polym Chem 38:2505–2525

    Article  CAS  Google Scholar 

  15. Tian HY, Deng C, Lin H, Sun JR, Deng MX, Chen XS, Jing XB (2005) Biodegradable cationic PEG-PEI-PBLG hyperbranched block copolymer: synthesis and micelle characterization. Biomaterials 26:4209–4217

    Article  CAS  Google Scholar 

  16. Rajesh KK, Muthiah G, Munia G, Tanay G, Donald EB, Souvik M, Jayachandran NK (2006) Blood compatibility of novel water soluble hyperbranched polyglycerol-based multivalent cationic polymers and their interaction with DNA. Biomaterials 27:5377–5390

    Article  Google Scholar 

  17. Karger-Kocsis J, Fröhlich J, Gryshchuk O, Kautz H, Frey H, Mülhaupt R (2004) Synthesis of reactive hyperbranched and star-like polyethers and their use for toughening of vinylester-urethane hybrid resins. Polymer 45:1185–1195

    Article  CAS  Google Scholar 

  18. Gao C, Xu Y, Yan D, Chen W (2003) Water-soluble degradable hyperbranched polyesters: novel candidates for drug delivery? Biomacromolecules 4:704–712

    Article  CAS  Google Scholar 

  19. Kolhe P, Misra E, Kannan RM, Kannan S, Lieh-Lai M (2003) Drug complexation, in vitro release and cellular entry of dendrimers and hyperbranched polymers. Int J Pharm 259:143–160

    Article  CAS  Google Scholar 

  20. Kim HJ, Kwon MS, Choi JS, Kim BH, Yoon JK, Kim K, Park JS (2007) Synthesis and characterization of poly (amino ester) for slow biodegradable gene delivery vector. Bioorg Med Chem 15:1708–1715

    Article  CAS  Google Scholar 

  21. Jeong B, Bae YH, Kim SW (2000) Drug release from biodegradable injectable thermosensitive hydrogel of PEG-PLGA-PEG triblock copolymers. J Control Release 63:155–163

    Article  CAS  Google Scholar 

  22. Blanco MD, Alonso MJ (1997) Development and characterization of protein-loaded poly (lactide-co-glycolide) nanospheres. Eur J Pharm Biopharm 43:287–294

    Article  CAS  Google Scholar 

  23. Yang R, Yang SG, Shim WS, Cui F, Cheng G, Kim IW, Kim DD, Chung SJ, Shim CK (2009) Lung-specific delivery of paclitaxel by chitosan-modified PLGA nanoparticles via transient formation of microaggregates. J Pharm Sci 98:970–984

    Article  CAS  Google Scholar 

  24. Thomas PA (1994) Mycotic keratitis-an underestimated mycosis. J Med Vet Mycol 32:235–256

    Article  CAS  Google Scholar 

  25. Essman TF, Flynn HW Jr, Smiddy WE, Brod RD, Murray TG, Davis JL, Rubsamen PE (1997) Treatment outcomes in a 10-year study of endogenous fungal endophthalmitis. Ophthalmic Surg Lasers 28:185–194

    CAS  Google Scholar 

  26. Zhu BK, Wei XZ, Xiao L, Xu YY, Geckeler KE (2006) Preparation and properties of hyperbranched poly (amine-ester) films using acetal cross-linking units. Polym Int 55:63–70

    Article  CAS  Google Scholar 

  27. Dong YC, Feng SS (2004) Methoxy poly(ethylene glycol)-poly(lactide) (MPEG-PLA) nanoparticles for controlled delivery of anticancer drugs. Biomaterials 25:2843–2849

    Article  CAS  Google Scholar 

  28. Lu Y, Lin D, Wei HY, Shi WF (2001) Synthesis and characterization of hyperbranched poly(amine-ester). Acta Polymer Sin 4:411–414

    Google Scholar 

  29. Karayannidis GP, Roupakias CP, Bikiaris DN, Achilias DS (2003) Study of various catalysts in the synthesis of poly (propylene terephthalate) and mathematical modeling of the esterification reaction. Polymer 44:931–942

    Article  CAS  Google Scholar 

  30. Zhang LM (2001) Cellulosic associative thickeners. Carbohydr Polym 45:1–10

    Article  CAS  Google Scholar 

  31. Shin IG, Kim SY, Lee YM, Cho CS, Sung YK (1998) Methoxy poly(ethylene glycol)/ε-caprolactone amphiphilic block copolymeric micelle containing indomethacin. I. Preparation and characterization. J Control Release 51:1–11

    Article  CAS  Google Scholar 

  32. Niwa T, Takeuchi H, Hino T, Kunou N, Kawashima Y (1993) Preparations of biodegradable nanospheres of water-soluble and insoluble drugs with d, l-lactide/glycolide copolymer by a novel spontaneous emulsification solvent diffusion method, and the drug release behavior. J Control Release 25:89–98

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This project was supported by the major program for fundamental research of the Chinese Academy of Sciences, China (No: KJCX2-YW-M02); the State Key Development Program for Basic Research of China (973) (No: 2009CB930200).)

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yan Wu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, T., Wu, Y. & Li, M. Novel hyperbranched poly (amine-ester)-poly (lactide-co-glycolide) polymeric micelles as amphotericin B carriers. Polym. Bull. 65, 425–442 (2010). https://doi.org/10.1007/s00289-009-0218-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-009-0218-9

Keywords

Navigation